Reproducability and transferability of topological properties; experimental charge density of the hexapeptide cyclo-(d,l-Pro)_2–(l-Ala)_4 monohydrate

Dittrich, B.; Koritsánszky, T.; Grosche, M.; Scherer, W.; Flaig, R.; Wagner, A.; Krane, H.G.; Kessler, H.; Riemer, C.; Schreurs, A.M.M.; Luger, P.

doi:10.1107/S0108768102005839

Reproducability and transferability of topological properties; experimental charge density of the hexapeptide cyclo-(D,L-Pro)-(L-Ala) monohydrate

B. Dittrich, T. Koritsánszky, M. Grosche, W. Scherer, R. Flaig, A. Wagner, H. G. Krane, H. Kessler, C. Riemer, A. M. M. Schreurs and P. Luger

The charge density of a hexapeptide was determined from high-resolution CCD area-detector experiments at 100 K. Two datasets, one from a rotating anode and a second one from synchrotron radiation, were measured and the results are compared. The data are interpreted in terms of the `rigid pseudoatom' model. The topology of the experimental density is analyzed and compared with the topology of the constituting amino acids, and shows good agreement. All critical points of the electron density at the covalent and hydrogen bonds, as well as those of the Laplacian, were located. With respect to the transferability of electronic and bond topological properties the six peptide bonds were compared with values given in the literature.

Keywords: topological properties; hexapeptide; charge density; peptides.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768102005839/lc0050sup1.cif Contains datablocks Global, Berlin, Muenchen
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768102005839/lc0050sup2.hkl Contains datablock merg

CCDC references: 193593; 193594

Computing details top

Data collection: SMART (Siemens, 1996) for Berlin. Cell refinement: SAINT (Siemens, 1996) for Berlin. Data reduction: SAINT (Siemens, 1996) for Berlin; EVAL (Nonius B.V. 2000) for Muenchen. For both compounds, program(s) used to refine structure: Koritsanszky et al., (1995); molecular graphics: Koritsanszky et al., (1995); software used to prepare material for publication: Koritsanszky et al., (1995).

Figures top

(Berlin) top

Crystal data top

C₂₂H₃₆N₆O₇	D_x = 1.337 Mg m⁻³
M_r = 496.57	Synchrotron radiation, λ = 0.5583 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 20246 reflections
a = 10.128 (1) Å	θ = 1.5–47.5°
b = 12.486 (1) Å	µ = 0.06 mm⁻¹
c = 19.507 (1) Å	T = 100 K
V = 2466.8 (4) Å³	Cube, colorless
Z = 4	0.54 × 0.45 × 0.40 mm
F(000) = 1064

Data collection top

Bruker SMART 1000 CCD Detector at DESY HASYLAB beamline D3 on Huber four circle diffractometer	21906 reflections with F > 2.5σF
ω and ϕ scans	R_int = 0.064
Absorption correction: empirical (using intensity measurements) SADABS (Blessing, 1995, Sheldrick, 1997)	θ_max = 47.5°, θ_min = 1.5°
T_min = 0.967, T_max = 0.975	h = 0→26
185339 measured reflections	k = 0→32
24878 independent reflections	l = 0→50

Refinement top

Refinement on F	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.027	Weighting scheme based on measured s.u.'s
wR(F²) = 0.025	(Δ/σ)_max < 0.001
S = 1.41	Δρ_max = 0.20 e Å⁻³
24878 reflections	Δρ_min = −0.30 e Å⁻³
945 parameters

Crystal data top

C₂₂H₃₆N₆O₇	V = 2466.8 (4) Å³
M_r = 496.57	Z = 4
Orthorhombic, P2₁2₁2₁	Synchrotron radiation, λ = 0.5583 Å
a = 10.128 (1) Å	µ = 0.06 mm⁻¹
b = 12.486 (1) Å	T = 100 K
c = 19.507 (1) Å	0.54 × 0.45 × 0.40 mm

Data collection top

Bruker SMART 1000 CCD Detector at DESY HASYLAB beamline D3 on Huber four circle diffractometer	24878 independent reflections
Absorption correction: empirical (using intensity measurements) SADABS (Blessing, 1995, Sheldrick, 1997)	21906 reflections with F > 2.5σF
T_min = 0.967, T_max = 0.975	R_int = 0.064
185339 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	945 parameters
wR(F²) = 0.025	H atoms treated by a mixture of independent and constrained refinement
S = 1.41	Δρ_max = 0.20 e Å⁻³
24878 reflections	Δρ_min = −0.30 e Å⁻³

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O(11)	0.44885 (3)	0.77338 (3)	0.48132 (2)	0.017
O(21)	0.66481 (3)	0.60898 (2)	0.51784 (1)	0.013
O(31)	0.44408 (4)	0.41451 (2)	0.69561 (2)	0.017
O(41)	0.27899 (3)	0.26168 (4)	0.50137 (2)	0.019
O(51)	0.42470 (3)	0.46354 (3)	0.41616 (2)	0.020
O(61)	0.49504 (4)	0.63459 (3)	0.27368 (2)	0.019
O(71)	0.72068 (3)	0.21950 (2)	0.28907 (2)	0.016
N(11)	0.62769 (2)	0.75200 (2)	0.58632 (1)	0.011
N(21)	0.55682 (2)	0.47085 (2)	0.60213 (1)	0.012
N(31)	0.49458 (2)	0.28534 (2)	0.53091 (1)	0.011
N(41)	0.54422 (2)	0.31679 (2)	0.38900 (1)	0.011
N(51)	0.61142 (2)	0.60463 (2)	0.37085 (1)	0.012
N(61)	0.61213 (2)	0.81475 (2)	0.40685 (1)	0.011
C(11)	0.56257 (2)	0.80348 (2)	0.47097 (1)	0.010
C(12)	0.65546 (2)	0.82813 (2)	0.53068 (1)	0.010
C(13)	0.62667 (2)	0.93827 (2)	0.56334 (1)	0.013
C(14)	0.64197 (3)	0.91728 (2)	0.64047 (1)	0.014
C(15)	0.58218 (3)	0.80604 (2)	0.64883 (1)	0.013
C(21)	0.63205 (2)	0.64678 (2)	0.57404 (1)	0.010
C(22)	0.59632 (2)	0.57175 (2)	0.63312 (1)	0.011
C(23)	0.71333 (3)	0.55482 (2)	0.68193 (1)	0.016
C(31)	0.48678 (2)	0.39837 (2)	0.63686 (1)	0.011
C(32)	0.46582 (2)	0.28924 (2)	0.60373 (1)	0.010
C(33)	0.54794 (3)	0.20704 (2)	0.64331 (1)	0.016
C(41)	0.39637 (2)	0.26733 (2)	0.48529 (1)	0.012
C(42)	0.44042 (2)	0.24482 (2)	0.41171 (1)	0.013
C(43)	0.48774 (4)	0.12851 (2)	0.40676 (2)	0.021
C(51)	0.52360 (2)	0.42398 (2)	0.39046 (1)	0.012
C(52)	0.63227 (2)	0.49208 (2)	0.35697 (1)	0.011
C(53)	0.77141 (2)	0.46106 (2)	0.37953 (2)	0.017
C(61)	0.54393 (2)	0.66744 (2)	0.32808 (1)	0.012
C(62)	0.53320 (2)	0.78647 (2)	0.34688 (1)	0.012
C(63)	0.59402 (3)	0.85615 (2)	0.29021 (1)	0.017
C(64)	0.74112 (3)	0.85638 (3)	0.30938 (1)	0.019
C(65)	0.74074 (3)	0.86194 (2)	0.38812 (1)	0.016
H(12)	0.75716	0.81643	0.51581	0.038
H(13A)	0.69379	0.99896	0.54484	0.040
H(13B)	0.52600	0.95977	0.55139	0.032
H(14A)	0.74551	0.91520	0.65366	0.046
H(14B)	0.59231	0.97513	0.67254	0.049
H(15A)	0.61721	0.76397	0.69366	0.042
H(15B)	0.47567	0.81028	0.64868	0.041
H(21)	0.58060	0.45780	0.55309	0.031
H(22)	0.51445	0.60357	0.66217	0.036
H(23A)	0.68835	0.49620	0.72052	0.051
H(23B)	0.73652	0.62876	0.70801	0.047
H(23C)	0.79869	0.52747	0.65374	0.059
H(31)	0.58710	0.27483	0.51434	0.031
H(32)	0.36202	0.27114	0.60889	0.030
H(33A)	0.53033	0.12893	0.62135	0.051
H(33B)	0.51901	0.20508	0.69658	0.053
H(33C)	0.65163	0.22650	0.63983	0.056
H(41)	0.61833	0.28721	0.36092	0.036
H(42)	0.35295	0.25582	0.38084	0.044
H(43A)	0.50493	0.10564	0.35412	0.059
H(43B)	0.41321	0.07678	0.42847	0.052
H(43C)	0.57860	0.12014	0.43524	0.054
H(51)	0.63316	0.63225	0.41762	0.031
H(52)	0.62049	0.48142	0.30237	0.034
H(53A)	0.84153	0.51275	0.35413	0.058
H(53B)	0.79503	0.38017	0.36420	0.059
H(53C)	0.78167	0.47082	0.43428	0.062
H(62)	0.42994	0.80212	0.35640	0.038
H(63A)	0.55806	0.93731	0.29447	0.045
H(63B)	0.57589	0.82534	0.23934	0.040
H(64A)	0.79679	0.92171	0.28744	0.050
H(64B)	0.78672	0.78295	0.29222	0.054
H(65A)	0.82023	0.81640	0.41075	0.045
H(65B)	0.74547	0.94416	0.40516	0.054
H(71A)	0.64832	0.18997	0.26451	0.051
H(71B)	0.78855	0.16698	0.28972	0.049
DUM0	0.71706	0.17729	0.27906	0.000	0.0000

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O(11)	0.00974 (7)	0.02365 (11)	0.01701 (9)	−0.00450 (7)	0.00087 (7)	−0.00097 (9)
O(21)	0.01779 (8)	0.01031 (7)	0.01068 (7)	−0.00062 (6)	0.00257 (6)	−0.00080 (5)
O(31)	0.0249 (1)	0.0144 (1)	0.0128 (1)	−0.0058 (1)	0.0072 (1)	−0.0030 (1)
O(41)	0.00842 (7)	0.03165 (14)	0.01707 (10)	−0.00440 (8)	0.00028 (7)	0.00100 (10)
O(51)	0.01438 (9)	0.01727 (10)	0.02888 (14)	0.00557 (8)	0.00792 (9)	0.00247 (10)
O(61)	0.0247 (1)	0.0153 (1)	0.0173 (1)	0.0033 (1)	−0.0114 (1)	−0.0024 (1)
O(71)	0.01422 (8)	0.01699 (9)	0.01570 (9)	0.00101 (7)	−0.00150 (7)	−0.00382 (7)
N(11)	0.01477 (6)	0.00805 (5)	0.01036 (5)	−0.00055 (5)	0.00151 (5)	−0.00007 (4)
N(21)	0.01682 (7)	0.00976 (5)	0.01028 (5)	−0.00425 (5)	0.00173 (5)	−0.00044 (4)
N(31)	0.00808 (5)	0.01286 (6)	0.01074 (5)	−0.00143 (4)	0.00070 (4)	−0.00160 (4)
N(41)	0.01073 (5)	0.01099 (5)	0.01263 (6)	−0.00023 (4)	0.00124 (4)	−0.00017 (4)
N(51)	0.01606 (7)	0.00992 (5)	0.01053 (5)	0.00279 (5)	−0.00239 (5)	0.00039 (4)
N(61)	0.01050 (5)	0.01175 (6)	0.01057 (6)	−0.00056 (5)	−0.00047 (5)	0.00060 (5)
C(11)	0.00877 (6)	0.01116 (6)	0.01149 (6)	−0.00070 (5)	0.00036 (5)	−0.00016 (5)
C(12)	0.00982 (6)	0.00931 (6)	0.01073 (6)	−0.00041 (4)	0.00028 (5)	0.00049 (5)
C(13)	0.01535 (7)	0.00893 (6)	0.01338 (7)	−0.00010 (5)	−0.00075 (6)	0.00020 (5)
C(14)	0.01904 (9)	0.00983 (6)	0.01286 (7)	−0.00089 (6)	−0.00174 (6)	−0.00132 (5)
C(15)	0.01681 (8)	0.01052 (6)	0.01127 (7)	−0.00059 (6)	0.00189 (6)	−0.00065 (5)
C(21)	0.01267 (7)	0.00845 (6)	0.00995 (6)	−0.00112 (5)	0.00079 (5)	−0.00021 (5)
C(22)	0.01359 (7)	0.00899 (6)	0.01033 (6)	−0.00168 (5)	0.00017 (5)	−0.00006 (4)
C(23)	0.01946 (9)	0.01290 (7)	0.01647 (8)	−0.00134 (6)	−0.00555 (7)	0.00102 (6)
C(31)	0.01333 (7)	0.00951 (6)	0.01045 (6)	−0.00226 (5)	0.00207 (5)	−0.00043 (5)
C(32)	0.01012 (5)	0.00913 (5)	0.01123 (6)	−0.00136 (4)	0.00104 (5)	−0.00005 (4)
C(33)	0.01635 (8)	0.01386 (7)	0.01767 (8)	0.00175 (6)	−0.00052 (6)	0.00324 (6)
C(41)	0.00826 (5)	0.01574 (7)	0.01209 (6)	−0.00258 (5)	0.00002 (5)	−0.00040 (5)
C(42)	0.01240 (6)	0.01653 (8)	0.01153 (6)	−0.00446 (6)	−0.00089 (5)	−0.00105 (5)
C(43)	0.0314 (1)	0.0137 (1)	0.0183 (1)	−0.0071 (1)	0.0057 (1)	−0.0040 (1)
C(51)	0.00992 (6)	0.01187 (6)	0.01350 (6)	0.00213 (5)	0.00101 (5)	0.00087 (5)
C(52)	0.01235 (6)	0.01010 (6)	0.01204 (6)	0.00155 (5)	0.00079 (5)	0.00033 (5)
C(53)	0.01104 (7)	0.01275 (7)	0.02830 (11)	0.00146 (5)	0.00060 (7)	0.00192 (7)
C(61)	0.01295 (7)	0.01043 (6)	0.01170 (7)	0.00126 (5)	−0.00353 (6)	0.00036 (5)
C(62)	0.01273 (7)	0.01066 (6)	0.01262 (7)	0.00176 (5)	−0.00301 (5)	0.00097 (5)
C(63)	0.0238 (1)	0.0138 (1)	0.0135 (1)	−0.0003 (1)	−0.0041 (1)	0.0039 (1)
C(64)	0.0208 (1)	0.0230 (1)	0.0129 (1)	−0.0045 (1)	0.0021 (1)	0.0033 (1)
C(65)	0.01369 (7)	0.02154 (10)	0.01290 (7)	−0.00468 (7)	0.00060 (6)	0.00164 (7)

Geometric parameters (Å, º) top

O(11)—C(11)	1.2281 (3)	C(15)—H(15B)	1.0800 (2)
O(21)—C(21)	1.2388 (3)	C(21)—C(22)	1.5287 (3)
O(31)—C(31)	1.2414 (4)	C(22)—C(23)	1.5349 (4)
O(41)—C(41)	1.2315 (3)	C(22)—H(22)	1.0800 (2)
O(51)—C(51)	1.2242 (4)	C(23)—H(23A)	1.0800 (2)
O(61)—C(61)	1.2409 (4)	C(23)—H(23B)	1.0799 (2)
O(61)—H(71A)ⁱ	1.7724 (3)	C(23)—H(23C)	1.0800 (3)
O(71)—H(71A)	0.9500 (3)	C(31)—C(32)	1.5230 (3)
O(71)—H(71B)	0.9501 (3)	C(32)—C(33)	1.5301 (3)
N(11)—C(12)	1.4699 (3)	C(32)—H(32)	1.0800 (2)
N(11)—C(15)	1.4678 (3)	C(33)—H(33A)	1.0800 (3)
N(11)—C(21)	1.3362 (3)	C(33)—H(33B)	1.0799 (2)
N(21)—C(22)	1.4534 (3)	C(33)—H(33C)	1.0801 (3)
N(21)—C(31)	1.3346 (3)	C(41)—C(42)	1.5291 (3)
N(21)—H(21)	0.9999 (2)	C(42)—C(43)	1.5324 (4)
N(31)—C(32)	1.4507 (3)	C(42)—H(42)	1.0799 (3)
N(31)—C(41)	1.3535 (3)	C(43)—H(43A)	1.0799 (3)
N(31)—H(31)	0.9998 (2)	C(43)—H(43B)	1.0801 (3)
N(41)—C(42)	1.4522 (3)	C(43)—H(43C)	1.0800 (4)
N(41)—C(51)	1.3548 (3)	C(51)—C(52)	1.5367 (3)
N(41)—H(41)	0.9999 (2)	C(52)—C(53)	1.5263 (3)
N(51)—C(52)	1.4466 (3)	C(52)—H(52)	1.0800 (2)
N(51)—C(61)	1.3335 (3)	C(53)—H(53A)	1.0799 (3)
N(51)—H(51)	0.9999 (2)	C(53)—H(53B)	1.0800 (3)
N(61)—C(11)	1.3550 (3)	C(53)—H(53C)	1.0800 (3)
N(61)—C(62)	1.4602 (3)	C(61)—C(62)	1.5346 (3)
N(61)—C(65)	1.4756 (3)	C(62)—C(63)	1.5358 (4)
C(11)—C(12)	1.5286 (3)	C(62)—H(62)	1.0800 (2)
C(12)—C(13)	1.5435 (3)	C(63)—C(64)	1.5361 (4)
C(12)—H(12)	1.0800 (2)	C(63)—H(63A)	1.0800 (3)
C(13)—C(14)	1.5349 (3)	C(63)—H(63B)	1.0799 (3)
C(13)—H(13A)	1.0800 (2)	C(64)—C(65)	1.5375 (4)
C(13)—H(13B)	1.0798 (2)	C(64)—H(64A)	1.0800 (3)
C(14)—C(15)	1.5239 (3)	C(64)—H(64B)	1.0798 (4)
C(14)—H(14A)	1.0800 (3)	C(65)—H(65A)	1.0800 (3)
C(14)—H(14B)	1.0799 (3)	C(65)—H(65B)	1.0801 (3)
C(15)—H(15A)	1.0801 (2)

C(61)—O(61)—H(71A)ⁱ	123.9 (1)	C(42)—C(43)—H(43B)	108.9 (1)
H(71A)—O(71)—H(71B)	107.3 (1)	C(42)—C(43)—H(43C)	109.0 (1)
C(12)—N(11)—C(15)	112.1 (1)	H(43A)—C(43)—H(43B)	109.1 (1)
C(12)—N(11)—C(21)	119.8 (1)	H(43A)—C(43)—H(43C)	109.0 (1)
C(15)—N(11)—C(21)	127.7 (1)	H(43B)—C(43)—H(43C)	109.6 (1)
C(22)—N(21)—C(31)	121.5 (1)	O(51)—C(51)—N(41)	122.2 (1)
C(22)—N(21)—H(21)	118.2 (1)	O(51)—C(51)—C(52)	122.5 (1)
C(31)—N(21)—H(21)	120.2 (1)	N(41)—C(51)—C(52)	115.3 (1)
C(32)—N(31)—C(41)	120.1 (1)	N(51)—C(52)—C(51)	110.7 (1)
C(32)—N(31)—H(31)	120.6 (1)	N(51)—C(52)—C(53)	109.1 (1)
C(41)—N(31)—H(31)	117.0 (1)	N(51)—C(52)—H(52)	106.8 (1)
C(42)—N(41)—C(51)	119.6 (1)	C(51)—C(52)—C(53)	113.5 (1)
C(42)—N(41)—H(41)	118.8 (1)	C(51)—C(52)—H(52)	105.8 (1)
C(51)—N(41)—H(41)	119.5 (1)	C(53)—C(52)—H(52)	110.8 (1)
C(52)—N(51)—C(61)	121.9 (1)	C(52)—C(53)—H(53A)	108.9 (1)
C(52)—N(51)—H(51)	118.3 (1)	C(52)—C(53)—H(53B)	111.2 (1)
C(61)—N(51)—H(51)	118.7 (1)	C(52)—C(53)—H(53C)	110.2 (1)
C(11)—N(61)—C(62)	120.8 (1)	H(53A)—C(53)—H(53B)	106.6 (1)
C(11)—N(61)—C(65)	126.7 (1)	H(53A)—C(53)—H(53C)	108.8 (1)
C(62)—N(61)—C(65)	112.4 (1)	H(53B)—C(53)—H(53C)	111.0 (1)
O(11)—C(11)—N(61)	122.1 (1)	O(61)—C(61)—N(51)	123.0 (1)
O(11)—C(11)—C(12)	120.9 (1)	O(61)—C(61)—C(62)	119.8 (1)
N(61)—C(11)—C(12)	117.0 (1)	N(51)—C(61)—C(62)	117.2 (1)
N(11)—C(12)—C(11)	108.3 (1)	N(61)—C(62)—C(61)	112.8 (1)
N(11)—C(12)—C(13)	103.6 (1)	N(61)—C(62)—C(63)	102.7 (1)
N(11)—C(12)—H(12)	107.1 (1)	N(61)—C(62)—H(62)	110.4 (1)
C(11)—C(12)—C(13)	112.2 (1)	C(61)—C(62)—C(63)	110.4 (1)
C(11)—C(12)—H(12)	110.8 (1)	C(61)—C(62)—H(62)	106.6 (1)
C(13)—C(12)—H(12)	114.3 (1)	C(63)—C(62)—H(62)	114.2 (1)
C(12)—C(13)—C(14)	103.5 (1)	C(62)—C(63)—C(64)	102.4 (1)
C(12)—C(13)—H(13A)	111.6 (1)	C(62)—C(63)—H(63A)	109.9 (1)
C(12)—C(13)—H(13B)	108.1 (1)	C(62)—C(63)—H(63B)	113.0 (1)
C(14)—C(13)—H(13A)	112.6 (1)	C(64)—C(63)—H(63A)	107.8 (1)
C(14)—C(13)—H(13B)	110.5 (1)	C(64)—C(63)—H(63B)	112.9 (1)
H(13A)—C(13)—H(13B)	110.3 (1)	H(63A)—C(63)—H(63B)	110.3 (1)
C(13)—C(14)—C(15)	102.7 (1)	C(63)—C(64)—C(65)	103.9 (1)
C(13)—C(14)—H(14A)	109.6 (1)	C(63)—C(64)—H(64A)	114.3 (1)
C(13)—C(14)—H(14B)	114.0 (1)	C(63)—C(64)—H(64B)	109.7 (1)
C(15)—C(14)—H(14A)	109.8 (1)	C(65)—C(64)—H(64A)	111.3 (1)
C(15)—C(14)—H(14B)	111.2 (1)	C(65)—C(64)—H(64B)	110.4 (1)
H(14A)—C(14)—H(14B)	109.3 (1)	H(64A)—C(64)—H(64B)	107.2 (1)
N(11)—C(15)—C(14)	101.8 (1)	N(61)—C(65)—C(64)	103.4 (1)
N(11)—C(15)—H(15A)	110.2 (1)	N(61)—C(65)—H(65A)	110.3 (1)
N(11)—C(15)—H(15B)	109.5 (1)	N(61)—C(65)—H(65B)	110.0 (1)
C(14)—C(15)—H(15A)	113.5 (1)	C(64)—C(65)—H(65A)	112.5 (1)
C(14)—C(15)—H(15B)	110.6 (1)	C(64)—C(65)—H(65B)	110.5 (1)
H(15A)—C(15)—H(15B)	110.7 (1)	H(65A)—C(65)—H(65B)	110.0 (1)
O(21)—C(21)—N(11)	122.8 (1)	C(13)—H(13A)—H(13B)	34.8 (1)
O(21)—C(21)—C(22)	119.8 (1)	C(13)—H(13B)—H(13A)	34.8 (1)
N(11)—C(21)—C(22)	117.4 (1)	C(14)—H(14A)—H(14B)	35.4 (1)
N(21)—C(22)—C(21)	106.4 (1)	C(14)—H(14B)—H(14A)	35.4 (1)
N(21)—C(22)—C(23)	110.6 (1)	C(15)—H(15A)—H(15B)	34.6 (1)
N(21)—C(22)—H(22)	109.0 (1)	C(15)—H(15B)—H(15A)	34.6 (1)
C(21)—C(22)—C(23)	111.7 (1)	C(23)—H(23A)—H(23B)	36.2 (1)
C(21)—C(22)—H(22)	110.6 (1)	C(23)—H(23A)—H(23C)	35.4 (1)
C(23)—C(22)—H(22)	108.5 (1)	C(23)—H(23B)—H(23A)	36.2 (1)
C(22)—C(23)—H(23A)	110.2 (1)	C(23)—H(23B)—H(23C)	35.2 (1)
C(22)—C(23)—H(23B)	110.0 (1)	C(23)—H(23C)—H(23A)	35.4 (1)
C(22)—C(23)—H(23C)	110.2 (1)	C(23)—H(23C)—H(23B)	35.2 (1)
H(23A)—C(23)—H(23B)	107.6 (1)	C(33)—H(33A)—H(33B)	35.8 (1)
H(23A)—C(23)—H(23C)	109.2 (1)	C(33)—H(33A)—H(33C)	35.1 (1)
H(23B)—C(23)—H(23C)	109.6 (1)	C(33)—H(33B)—H(33A)	35.8 (1)
O(31)—C(31)—N(21)	122.9 (1)	C(33)—H(33B)—H(33C)	35.4 (1)
O(31)—C(31)—C(32)	119.2 (1)	C(33)—H(33C)—H(33A)	35.1 (1)
N(21)—C(31)—C(32)	117.7 (1)	C(33)—H(33C)—H(33B)	35.4 (1)
N(31)—C(32)—C(31)	114.7 (1)	C(43)—H(43A)—H(43B)	35.4 (1)
N(31)—C(32)—C(33)	111.2 (1)	C(43)—H(43A)—H(43C)	35.5 (1)
N(31)—C(32)—H(32)	106.2 (1)	C(43)—H(43B)—H(43A)	35.4 (1)
C(31)—C(32)—C(33)	108.1 (1)	C(43)—H(43B)—H(43C)	35.2 (1)
C(31)—C(32)—H(32)	106.5 (1)	C(43)—H(43C)—H(43A)	35.5 (1)
C(33)—C(32)—H(32)	110.0 (1)	C(43)—H(43C)—H(43B)	35.2 (1)
C(32)—C(33)—H(33A)	108.4 (1)	C(53)—H(53A)—H(53B)	36.7 (1)
C(32)—C(33)—H(33B)	110.7 (1)	C(53)—H(53A)—H(53C)	35.6 (1)
C(32)—C(33)—H(33C)	110.2 (1)	C(53)—H(53B)—H(53A)	36.7 (1)
H(33A)—C(33)—H(33B)	108.4 (1)	C(53)—H(53B)—H(53C)	34.5 (1)
H(33A)—C(33)—H(33C)	109.8 (1)	C(53)—H(53C)—H(53A)	35.6 (1)
H(33B)—C(33)—H(33C)	109.2 (1)	C(53)—H(53C)—H(53B)	34.5 (1)
O(41)—C(41)—N(31)	123.5 (1)	C(63)—H(63A)—H(63B)	34.8 (1)
O(41)—C(41)—C(42)	120.7 (1)	C(63)—H(63B)—H(63A)	34.8 (1)
N(31)—C(41)—C(42)	115.7 (1)	C(64)—H(64A)—H(64B)	36.4 (1)
N(41)—C(42)—C(41)	112.6 (1)	C(64)—H(64B)—H(64A)	36.4 (1)
N(41)—C(42)—C(43)	109.9 (1)	C(65)—H(65A)—H(65B)	35.0 (1)
N(41)—C(42)—H(42)	110.2 (1)	C(65)—H(65B)—H(65A)	35.0 (1)
C(41)—C(42)—C(43)	108.9 (1)	O(61)ⁱⁱ—H(71A)—O(71)	174.5 (1)
C(41)—C(42)—H(42)	105.1 (1)	O(61)ⁱⁱ—H(71A)—H(71B)	145.3 (1)
C(43)—C(42)—H(42)	110.0 (1)	O(71)—H(71A)—H(71B)	36.4 (1)
C(42)—C(43)—H(43A)	111.2 (1)	O(71)—H(71B)—H(71A)	36.4 (1)

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

(Muenchen) top

Crystal data top

C₂₂H₃₆N₆O₇	F(000) = 1064
M_r = 496.57	D_x = 1.336 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.7107 Å
a = 10.127 (1) Å	µ = 0.10 mm⁻¹
b = 12.501 (1) Å	T = 100 K
c = 19.495 (1) Å	Prism, colorless
V = 2467.8 (4) Å³	0.7 × 0.7 × 0.4 mm
Z = 4

Data collection top

Nonius Kappa CCD diffractometer	27338 reflections with F > 2.5σF
rotation in ω and ϕ scans	R_int = 0.036
Absorption correction: empirical (using intensity measurements) Blessing, 1995	θ_max = 53.6°, θ_min = 1.9°
T_min = 0.948, T_max = 0.961	h = 0→22
293943 measured reflections	k = 0→28
29731 independent reflections	l = −44→44

Refinement top

Refinement on F	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.020	Weighting scheme based on measured s.u.'s
wR(F²) = 0.030	(Δ/σ)_max < 0.001
S = 1.62	Δρ_max = 0.12 e Å⁻³
27338 reflections	Δρ_min = −0.21 e Å⁻³
945 parameters

Crystal data top

C₂₂H₃₆N₆O₇	V = 2467.8 (4) Å³
M_r = 496.57	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 10.127 (1) Å	µ = 0.10 mm⁻¹
b = 12.501 (1) Å	T = 100 K
c = 19.495 (1) Å	0.7 × 0.7 × 0.4 mm

Data collection top

Nonius Kappa CCD diffractometer	29731 independent reflections
Absorption correction: empirical (using intensity measurements) Blessing, 1995	27338 reflections with F > 2.5σF
T_min = 0.948, T_max = 0.961	R_int = 0.036
293943 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.020	945 parameters
wR(F²) = 0.030	H atoms treated by a mixture of independent and constrained refinement
S = 1.62	Δρ_max = 0.12 e Å⁻³
27338 reflections	Δρ_min = −0.21 e Å⁻³

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O(11)	0.44888 (3)	0.77334 (3)	0.48135 (2)	0.017
O(21)	0.66467 (3)	0.60890 (2)	0.51789 (1)	0.013
O(31)	0.44414 (4)	0.41450 (3)	0.69563 (2)	0.018
O(41)	0.27911 (3)	0.26178 (4)	0.50154 (2)	0.020
O(51)	0.42481 (4)	0.46362 (3)	0.41627 (3)	0.021
O(61)	0.49502 (5)	0.63446 (3)	0.27380 (2)	0.020
O(71)	0.72048 (3)	0.21947 (3)	0.28908 (2)	0.016
N(11)	0.62756 (3)	0.75199 (2)	0.58635 (1)	0.011
N(21)	0.55685 (3)	0.47088 (2)	0.60221 (1)	0.012
N(31)	0.49454 (2)	0.28537 (2)	0.53099 (1)	0.010
N(41)	0.54410 (2)	0.31688 (2)	0.38912 (1)	0.011
N(51)	0.61142 (3)	0.60461 (2)	0.37085 (1)	0.012
N(61)	0.61206 (2)	0.81470 (2)	0.40691 (1)	0.011
C(11)	0.56249 (2)	0.80340 (2)	0.47093 (1)	0.010
C(12)	0.65536 (2)	0.82807 (2)	0.53067 (1)	0.010
C(13)	0.62678 (3)	0.93814 (2)	0.56336 (1)	0.013
C(14)	0.64199 (3)	0.91726 (2)	0.64042 (1)	0.014
C(15)	0.58221 (3)	0.80607 (2)	0.64881 (1)	0.013
C(21)	0.63194 (3)	0.64679 (2)	0.57408 (1)	0.010
C(22)	0.59626 (3)	0.57174 (2)	0.63315 (1)	0.011
C(23)	0.71332 (4)	0.55487 (2)	0.68190 (2)	0.017
C(31)	0.48684 (3)	0.39840 (2)	0.63690 (1)	0.011
C(32)	0.46590 (2)	0.28928 (2)	0.60379 (1)	0.010
C(33)	0.54807 (3)	0.20713 (2)	0.64337 (2)	0.016
C(41)	0.39637 (2)	0.26739 (2)	0.48546 (1)	0.012
C(42)	0.44033 (3)	0.24491 (2)	0.41184 (1)	0.014
C(43)	0.48769 (5)	0.12860 (3)	0.40686 (2)	0.022
C(51)	0.52356 (2)	0.42396 (2)	0.39056 (1)	0.012
C(52)	0.63223 (3)	0.49211 (2)	0.35705 (1)	0.011
C(53)	0.77127 (3)	0.46105 (2)	0.37961 (2)	0.018
C(61)	0.54406 (3)	0.66742 (2)	0.32814 (1)	0.012
C(62)	0.53328 (3)	0.78635 (2)	0.34690 (1)	0.012
C(63)	0.59399 (4)	0.85609 (3)	0.29033 (2)	0.018
C(64)	0.74107 (4)	0.85652 (3)	0.30955 (2)	0.019
C(65)	0.74060 (3)	0.86187 (3)	0.38822 (2)	0.016
H(12)	0.75765	0.81842	0.51626	0.023
H(13A)	0.69370	0.99882	0.54473	0.033
H(13B)	0.52660	0.96163	0.55180	0.029
H(14A)	0.74567	0.91530	0.65332	0.040
H(14B)	0.59175	0.97490	0.67239	0.037
H(15A)	0.61736	0.76515	0.69406	0.034
H(15B)	0.47567	0.81011	0.64902	0.035
H(21)	0.58293	0.45753	0.55348	0.028
H(22)	0.51419	0.60409	0.66182	0.023
H(23A)	0.68688	0.49547	0.71971	0.051
H(23B)	0.73921	0.62868	0.70735	0.042
H(23C)	0.79711	0.52618	0.65297	0.049
H(31)	0.58821	0.27569	0.51600	0.026
H(32)	0.36189	0.27214	0.60923	0.021
H(33A)	0.53176	0.12888	0.62146	0.045
H(33B)	0.51615	0.20725	0.69623	0.049
H(33C)	0.65128	0.22771	0.63896	0.056
H(41)	0.61872	0.28565	0.36214	0.028
H(42)	0.35278	0.25604	0.38102	0.029
H(43A)	0.50175	0.10694	0.35373	0.055
H(43B)	0.41237	0.07707	0.42799	0.054
H(43C)	0.57943	0.11963	0.43453	0.050
H(51)	0.63682	0.63216	0.41716	0.029
H(52)	0.62256	0.48184	0.30227	0.023
H(53A)	0.84116	0.51280	0.35413	0.050
H(53B)	0.79181	0.37952	0.36471	0.058
H(53C)	0.77790	0.47105	0.43453	0.052
H(62)	0.42976	0.80054	0.35662	0.025
H(63A)	0.55415	0.93619	0.29190	0.041
H(63B)	0.57499	0.82252	0.24024	0.038
H(64A)	0.79606	0.92192	0.28733	0.050
H(64B)	0.78447	0.78157	0.29369	0.043
H(65A)	0.82133	0.81716	0.41032	0.042
H(65B)	0.74521	0.94328	0.40661	0.047
H(71A)	0.65008	0.18653	0.26478	0.044
H(71B)	0.78784	0.16659	0.28924	0.041

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O(11)	0.00919 (8)	0.0243 (2)	0.0184 (1)	−0.00485 (8)	0.00104 (7)	−0.00123 (10)
O(21)	0.01827 (9)	0.00975 (7)	0.01074 (7)	−0.00074 (7)	0.00280 (7)	−0.00094 (6)
O(31)	0.0261 (1)	0.0140 (1)	0.0134 (1)	−0.0058 (1)	0.0080 (1)	−0.0033 (1)
O(41)	0.00790 (7)	0.0325 (2)	0.0182 (2)	−0.00451 (9)	0.00024 (7)	0.00108 (12)
O(51)	0.0139 (1)	0.0173 (1)	0.0320 (2)	0.0060 (1)	0.0088 (1)	0.0027 (1)
O(61)	0.0253 (1)	0.0153 (1)	0.0185 (1)	0.0037 (1)	−0.0126 (1)	−0.0032 (1)
O(71)	0.01405 (9)	0.0171 (1)	0.01640 (9)	0.00132 (8)	−0.00174 (8)	−0.00421 (8)
N(11)	0.01507 (7)	0.00746 (5)	0.01029 (6)	−0.00063 (5)	0.00161 (5)	−0.00017 (5)
N(21)	0.01740 (8)	0.00916 (6)	0.01001 (6)	−0.00438 (5)	0.00201 (5)	−0.00067 (5)
N(31)	0.00777 (5)	0.01244 (6)	0.01113 (6)	−0.00148 (5)	0.00083 (4)	−0.00203 (5)
N(41)	0.01091 (6)	0.01062 (6)	0.01233 (6)	−0.00012 (5)	0.00119 (5)	−0.00028 (5)
N(51)	0.01662 (8)	0.00947 (6)	0.01022 (6)	0.00290 (5)	−0.00255 (5)	0.00037 (5)
N(61)	0.01046 (6)	0.01127 (6)	0.01087 (6)	−0.00053 (5)	−0.00054 (5)	0.00060 (5)
C(11)	0.00862 (6)	0.01072 (7)	0.01194 (7)	−0.00075 (5)	0.00044 (5)	−0.00026 (6)
C(12)	0.00956 (6)	0.00900 (6)	0.01083 (6)	−0.00044 (5)	0.00047 (5)	0.00041 (5)
C(13)	0.01578 (9)	0.00851 (6)	0.01357 (8)	−0.00021 (6)	−0.00066 (7)	0.00008 (6)
C(14)	0.0198 (1)	0.0094 (1)	0.0133 (1)	−0.0010 (1)	−0.0018 (1)	−0.0014 (1)
C(15)	0.01750 (9)	0.01031 (7)	0.01117 (7)	−0.00066 (6)	0.00215 (7)	−0.00073 (6)
C(21)	0.01281 (7)	0.00776 (6)	0.00981 (6)	−0.00131 (6)	0.00077 (6)	−0.00013 (5)
C(22)	0.01400 (8)	0.00863 (6)	0.00995 (6)	−0.00197 (5)	0.00024 (5)	−0.00019 (5)
C(23)	0.0202 (1)	0.0128 (1)	0.0170 (1)	−0.0013 (1)	−0.0062 (1)	0.0009 (1)
C(31)	0.01357 (8)	0.00893 (6)	0.01032 (6)	−0.00241 (5)	0.00227 (5)	−0.00046 (5)
C(32)	0.00991 (6)	0.00868 (6)	0.01132 (6)	−0.00148 (5)	0.00117 (5)	−0.00021 (5)
C(33)	0.01664 (9)	0.01388 (8)	0.01841 (9)	0.00191 (7)	−0.00069 (8)	0.00359 (7)
C(41)	0.00813 (6)	0.01580 (8)	0.01248 (7)	−0.00272 (6)	0.00001 (5)	−0.00054 (6)
C(42)	0.01263 (8)	0.01666 (9)	0.01187 (7)	−0.00461 (7)	−0.00105 (6)	−0.00133 (6)
C(43)	0.0335 (2)	0.0133 (1)	0.0194 (1)	−0.0077 (1)	0.0062 (1)	−0.0047 (1)
C(51)	0.00967 (7)	0.01167 (7)	0.01382 (7)	0.00236 (5)	0.00113 (6)	0.00113 (6)
C(52)	0.01276 (7)	0.00970 (6)	0.01189 (7)	0.00164 (6)	0.00103 (6)	0.00046 (5)
C(53)	0.01076 (8)	0.01265 (8)	0.0304 (2)	0.00161 (6)	0.00061 (8)	0.00202 (8)
C(61)	0.01296 (8)	0.01043 (7)	0.01186 (7)	0.00131 (6)	−0.00356 (6)	0.00045 (6)
C(62)	0.01298 (8)	0.01026 (7)	0.01309 (7)	0.00190 (6)	−0.00324 (6)	0.00096 (6)
C(63)	0.0252 (1)	0.0138 (1)	0.0140 (1)	−0.0003 (1)	−0.0045 (1)	0.0047 (1)
C(64)	0.0214 (1)	0.0232 (1)	0.0135 (1)	−0.0048 (1)	0.0023 (1)	0.0039 (1)
C(65)	0.01395 (9)	0.0220 (2)	0.01351 (8)	−0.00487 (8)	0.00076 (7)	0.00179 (8)

Geometric parameters (Å, º) top

O(11)—C(11)	1.2273 (4)	C(15)—H(15B)	1.0801 (3)
O(21)—C(21)	1.2386 (3)	C(21)—C(22)	1.5286 (3)
O(31)—C(31)	1.2403 (4)	C(22)—C(23)	1.5339 (4)
O(41)—C(41)	1.2301 (4)	C(22)—H(22)	1.0800 (2)
O(51)—C(51)	1.2235 (4)	C(23)—H(23A)	1.0800 (3)
O(61)—C(61)	1.2403 (4)	C(23)—H(23B)	1.0799 (3)
O(61)—H(71A)ⁱ	1.7743 (4)	C(23)—H(23C)	1.0801 (4)
O(71)—H(71A)	0.9500 (3)	C(31)—C(32)	1.5239 (3)
O(71)—H(71B)	0.9499 (3)	C(32)—C(33)	1.5304 (4)
N(11)—C(12)	1.4703 (3)	C(32)—H(32)	1.0800 (2)
N(11)—C(15)	1.4665 (3)	C(33)—H(33A)	1.0801 (3)
N(11)—C(21)	1.3373 (3)	C(33)—H(33B)	1.0800 (3)
N(21)—C(22)	1.4537 (3)	C(33)—H(33C)	1.0798 (3)
N(21)—C(31)	1.3344 (3)	C(41)—C(42)	1.5287 (4)
N(21)—H(21)	0.9999 (2)	C(42)—C(43)	1.5341 (5)
N(31)—C(32)	1.4493 (3)	C(42)—H(42)	1.0800 (3)
N(31)—C(41)	1.3516 (3)	C(43)—H(43A)	1.0800 (4)
N(31)—H(31)	0.9999 (2)	C(43)—H(43B)	1.0799 (4)
N(41)—C(42)	1.4526 (4)	C(43)—H(43C)	1.0802 (5)
N(41)—C(51)	1.3550 (3)	C(51)—C(52)	1.5374 (4)
N(41)—H(41)	0.9999 (2)	C(52)—C(53)	1.5253 (4)
N(51)—C(52)	1.4472 (3)	C(52)—H(52)	1.0800 (2)
N(51)—C(61)	1.3323 (3)	C(53)—H(53A)	1.0799 (3)
N(51)—H(51)	0.9999 (2)	C(53)—H(53B)	1.0800 (3)
N(61)—C(11)	1.3527 (4)	C(53)—H(53C)	1.0801 (4)
N(61)—C(62)	1.4597 (4)	C(61)—C(62)	1.5349 (4)
N(61)—C(65)	1.4748 (4)	C(62)—C(63)	1.5343 (4)
C(11)—C(12)	1.5283 (4)	C(62)—H(62)	1.0800 (3)
C(12)—C(13)	1.5436 (3)	C(63)—C(64)	1.5359 (6)
C(12)—H(12)	1.0801 (2)	C(63)—H(63A)	1.0799 (3)
C(13)—C(14)	1.5325 (4)	C(63)—H(63B)	1.0800 (4)
C(13)—H(13A)	1.0800 (3)	C(64)—C(65)	1.5351 (5)
C(13)—H(13B)	1.0799 (3)	C(64)—H(64A)	1.0799 (4)
C(14)—C(15)	1.5250 (4)	C(64)—H(64B)	1.0801 (5)
C(14)—H(14A)	1.0799 (3)	C(65)—H(65A)	1.0800 (3)
C(14)—H(14B)	1.0801 (3)	C(65)—H(65B)	1.0800 (4)
C(15)—H(15A)	1.0800 (3)

C(61)—O(61)—H(71A)ⁱ	124.9 (1)	C(42)—C(43)—H(43B)	108.7 (1)
H(71A)—O(71)—H(71B)	103.8 (1)	C(42)—C(43)—H(43C)	109.6 (1)
C(12)—N(11)—C(15)	112.0 (1)	H(43A)—C(43)—H(43B)	108.0 (1)
C(12)—N(11)—C(21)	119.9 (1)	H(43A)—C(43)—H(43C)	109.8 (1)
C(15)—N(11)—C(21)	127.7 (1)	H(43B)—C(43)—H(43C)	110.8 (1)
C(22)—N(21)—C(31)	121.6 (1)	O(51)—C(51)—N(41)	122.3 (1)
C(22)—N(21)—H(21)	117.8 (1)	O(51)—C(51)—C(52)	122.3 (1)
C(31)—N(21)—H(21)	120.6 (1)	N(41)—C(51)—C(52)	115.4 (1)
C(32)—N(31)—C(41)	120.1 (1)	N(51)—C(52)—C(51)	110.8 (1)
C(32)—N(31)—H(31)	118.7 (1)	N(51)—C(52)—C(53)	109.2 (1)
C(41)—N(31)—H(31)	119.1 (1)	N(51)—C(52)—H(52)	106.6 (1)
C(42)—N(41)—C(51)	119.6 (1)	C(51)—C(52)—C(53)	113.4 (1)
C(42)—N(41)—H(41)	117.7 (1)	C(51)—C(52)—H(52)	106.8 (1)
C(51)—N(41)—H(41)	120.8 (1)	C(53)—C(52)—H(52)	109.8 (1)
C(52)—N(51)—C(61)	122.1 (1)	C(52)—C(53)—H(53A)	108.7 (1)
C(52)—N(51)—H(51)	117.7 (1)	C(52)—C(53)—H(53B)	109.9 (1)
C(61)—N(51)—H(51)	119.5 (1)	C(52)—C(53)—H(53C)	108.3 (1)
C(11)—N(61)—C(62)	120.8 (1)	H(53A)—C(53)—H(53B)	108.4 (1)
C(11)—N(61)—C(65)	126.7 (1)	H(53A)—C(53)—H(53C)	110.2 (1)
C(62)—N(61)—C(65)	112.4 (1)	H(53B)—C(53)—H(53C)	111.3 (1)
O(11)—C(11)—N(61)	122.2 (1)	O(61)—C(61)—N(51)	122.9 (1)
O(11)—C(11)—C(12)	120.8 (1)	O(61)—C(61)—C(62)	119.8 (1)
N(61)—C(11)—C(12)	117.0 (1)	N(51)—C(61)—C(62)	117.3 (1)
N(11)—C(12)—C(11)	108.3 (1)	N(61)—C(62)—C(61)	112.8 (1)
N(11)—C(12)—C(13)	103.7 (1)	N(61)—C(62)—C(63)	102.7 (1)
N(11)—C(12)—H(12)	107.7 (1)	N(61)—C(62)—H(62)	110.5 (1)
C(11)—C(12)—C(13)	112.3 (1)	C(61)—C(62)—C(63)	110.5 (1)
C(11)—C(12)—H(12)	111.7 (1)	C(61)—C(62)—H(62)	105.7 (1)
C(13)—C(12)—H(12)	112.8 (1)	C(63)—C(62)—H(62)	114.9 (1)
C(12)—C(13)—C(14)	103.5 (1)	C(62)—C(63)—C(64)	102.4 (1)
C(12)—C(13)—H(13A)	111.7 (1)	C(62)—C(63)—H(63A)	110.9 (1)
C(12)—C(13)—H(13B)	109.4 (1)	C(62)—C(63)—H(63B)	111.0 (1)
C(14)—C(13)—H(13A)	112.7 (1)	C(64)—C(63)—H(63A)	110.6 (1)
C(14)—C(13)—H(13B)	110.2 (1)	C(64)—C(63)—H(63B)	113.2 (1)
H(13A)—C(13)—H(13B)	109.2 (1)	H(63A)—C(63)—H(63B)	108.6 (1)
C(13)—C(14)—C(15)	102.7 (1)	C(63)—C(64)—C(65)	103.9 (1)
C(13)—C(14)—H(14A)	109.3 (1)	C(63)—C(64)—H(64A)	113.9 (1)
C(13)—C(14)—H(14B)	113.9 (1)	C(63)—C(64)—H(64B)	108.8 (1)
C(15)—C(14)—H(14A)	109.9 (1)	C(65)—C(64)—H(64A)	111.7 (1)
C(15)—C(14)—H(14B)	111.0 (1)	C(65)—C(64)—H(64B)	109.0 (1)
H(14A)—C(14)—H(14B)	109.8 (1)	H(64A)—C(64)—H(64B)	109.4 (1)
N(11)—C(15)—C(14)	101.9 (1)	N(61)—C(65)—C(64)	103.4 (1)
N(11)—C(15)—H(15A)	110.9 (1)	N(61)—C(65)—H(65A)	111.3 (1)
N(11)—C(15)—H(15B)	109.7 (1)	N(61)—C(65)—H(65B)	109.4 (1)
C(14)—C(15)—H(15A)	112.9 (1)	C(64)—C(65)—H(65A)	111.9 (1)
C(14)—C(15)—H(15B)	110.8 (1)	C(64)—C(65)—H(65B)	111.9 (1)
H(15A)—C(15)—H(15B)	110.4 (1)	H(65A)—C(65)—H(65B)	108.8 (1)
O(21)—C(21)—N(11)	122.9 (1)	C(13)—H(13A)—H(13B)	35.4 (1)
O(21)—C(21)—C(22)	119.7 (1)	C(13)—H(13B)—H(13A)	35.4 (1)
N(11)—C(21)—C(22)	117.5 (1)	C(14)—H(14A)—H(14B)	35.1 (1)
N(21)—C(22)—C(21)	106.5 (1)	C(14)—H(14B)—H(14A)	35.1 (1)
N(21)—C(22)—C(23)	110.5 (1)	C(15)—H(15A)—H(15B)	34.8 (1)
N(21)—C(22)—H(22)	109.2 (1)	C(15)—H(15B)—H(15A)	34.8 (1)
C(21)—C(22)—C(23)	111.6 (1)	C(23)—H(23A)—H(23B)	35.2 (1)
C(21)—C(22)—H(22)	110.0 (1)	C(23)—H(23A)—H(23C)	35.6 (1)
C(23)—C(22)—H(22)	109.0 (1)	C(23)—H(23B)—H(23A)	35.2 (1)
C(22)—C(23)—H(23A)	109.0 (1)	C(23)—H(23B)—H(23C)	35.3 (1)
C(22)—C(23)—H(23B)	110.8 (1)	C(23)—H(23C)—H(23A)	35.6 (1)
C(22)—C(23)—H(23C)	109.2 (1)	C(23)—H(23C)—H(23B)	35.3 (1)
H(23A)—C(23)—H(23B)	109.5 (1)	C(33)—H(33A)—H(33B)	35.3 (1)
H(23A)—C(23)—H(23C)	108.8 (1)	C(33)—H(33A)—H(33C)	35.3 (1)
H(23B)—C(23)—H(23C)	109.4 (1)	C(33)—H(33B)—H(33A)	35.3 (1)
O(31)—C(31)—N(21)	122.9 (1)	C(33)—H(33B)—H(33C)	34.3 (1)
O(31)—C(31)—C(32)	119.2 (1)	C(33)—H(33C)—H(33A)	35.3 (1)
N(21)—C(31)—C(32)	117.8 (1)	C(33)—H(33C)—H(33B)	34.3 (1)
N(31)—C(32)—C(31)	114.7 (1)	C(43)—H(43A)—H(43B)	36.0 (1)
N(31)—C(32)—C(33)	111.2 (1)	C(43)—H(43A)—H(43C)	35.1 (1)
N(31)—C(32)—H(32)	106.5 (1)	C(43)—H(43B)—H(43A)	36.0 (1)
C(31)—C(32)—C(33)	108.1 (1)	C(43)—H(43B)—H(43C)	34.6 (1)
C(31)—C(32)—H(32)	105.8 (1)	C(43)—H(43C)—H(43A)	35.1 (1)
C(33)—C(32)—H(32)	110.3 (1)	C(43)—H(43C)—H(43B)	34.6 (1)
C(32)—C(33)—H(33A)	109.0 (1)	C(53)—H(53A)—H(53B)	35.8 (1)
C(32)—C(33)—H(33B)	108.5 (1)	C(53)—H(53A)—H(53C)	34.9 (1)
C(32)—C(33)—H(33C)	109.0 (1)	C(53)—H(53B)—H(53A)	35.8 (1)
H(33A)—C(33)—H(33B)	109.4 (1)	C(53)—H(53B)—H(53C)	34.3 (1)
H(33A)—C(33)—H(33C)	109.4 (1)	C(53)—H(53C)—H(53A)	34.9 (1)
H(33B)—C(33)—H(33C)	111.4 (1)	C(53)—H(53C)—H(53B)	34.3 (1)
O(41)—C(41)—N(31)	123.5 (1)	C(63)—H(63A)—H(63B)	35.7 (1)
O(41)—C(41)—C(42)	120.7 (1)	C(63)—H(63B)—H(63A)	35.7 (1)
N(31)—C(41)—C(42)	115.7 (1)	C(64)—H(64A)—H(64B)	35.3 (1)
N(41)—C(42)—C(41)	112.5 (1)	C(64)—H(64B)—H(64A)	35.3 (1)
N(41)—C(42)—C(43)	110.0 (1)	C(65)—H(65A)—H(65B)	35.6 (1)
N(41)—C(42)—H(42)	110.2 (1)	C(65)—H(65B)—H(65A)	35.6 (1)
C(41)—C(42)—C(43)	108.9 (1)	O(61)ⁱⁱ—H(71A)—O(71)	172.7 (1)
C(41)—C(42)—H(42)	105.0 (1)	O(61)ⁱⁱ—H(71A)—H(71B)	147.9 (1)
C(43)—C(42)—H(42)	110.1 (1)	O(71)—H(71A)—H(71B)	38.1 (1)
C(42)—C(43)—H(43A)	109.8 (1)	O(71)—H(71B)—H(71A)	38.1 (1)

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

Experimental details

	(Berlin)	(Muenchen)
Crystal data
Chemical formula	C₂₂H₃₆N₆O₇	C₂₂H₃₆N₆O₇
M_r	496.57	496.57
Crystal system, space group	Orthorhombic, P2₁2₁2₁	Orthorhombic, P2₁2₁2₁
Temperature (K)	100	100
a, b, c (Å)	10.128 (1), 12.486 (1), 19.507 (1)	10.127 (1), 12.501 (1), 19.495 (1)
V (Å³)	2466.8 (4)	2467.8 (4)
Z	4	4
Radiation type	Synchrotron, λ = 0.5583 Å	Mo Kα
µ (mm⁻¹)	0.06	0.10
Crystal size (mm)	0.54 × 0.45 × 0.40	0.7 × 0.7 × 0.4

Data collection
Diffractometer	Bruker SMART 1000 CCD Detector at DESY HASYLAB beamline D3 on Huber four circle diffractometer	Nonius Kappa CCD diffractometer
Absorption correction	Empirical (using intensity measurements) SADABS (Blessing, 1995, Sheldrick, 1997)	Empirical (using intensity measurements) Blessing, 1995
T_min, T_max	0.967, 0.975	0.948, 0.961
No. of measured, independent and observed (F > 2.5σF) reflections	185339, 24878, 21906	293943, 29731, 27338
R_int	0.064	0.036
(sin θ/λ)_max (Å⁻¹)	1.320	1.133

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.025, 1.41	0.020, 0.030, 1.62
No. of reflections	24878	27338
No. of parameters	945	945
No. of restraints	?	?
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.30	0.12, −0.21

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), EVAL (Nonius B.V. 2000), Koritsanszky et al., (1995).

Selected geometric parameters (Å, º) for (Berlin) top

O(11)—C(11)	1.2281 (3)	C(15)—H(15B)	1.0800 (2)
O(21)—C(21)	1.2388 (3)	C(21)—C(22)	1.5287 (3)
O(31)—C(31)	1.2414 (4)	C(22)—C(23)	1.5349 (4)
O(41)—C(41)	1.2315 (3)	C(22)—H(22)	1.0800 (2)
O(51)—C(51)	1.2242 (4)	C(23)—H(23A)	1.0800 (2)
O(61)—C(61)	1.2409 (4)	C(23)—H(23B)	1.0799 (2)
O(61)—H(71A)ⁱ	1.7724 (3)	C(23)—H(23C)	1.0800 (3)
O(71)—H(71A)	0.9500 (3)	C(31)—C(32)	1.5230 (3)
O(71)—H(71B)	0.9501 (3)	C(32)—C(33)	1.5301 (3)
N(11)—C(12)	1.4699 (3)	C(32)—H(32)	1.0800 (2)
N(11)—C(15)	1.4678 (3)	C(33)—H(33A)	1.0800 (3)
N(11)—C(21)	1.3362 (3)	C(33)—H(33B)	1.0799 (2)
N(21)—C(22)	1.4534 (3)	C(33)—H(33C)	1.0801 (3)
N(21)—C(31)	1.3346 (3)	C(41)—C(42)	1.5291 (3)
N(21)—H(21)	0.9999 (2)	C(42)—C(43)	1.5324 (4)
N(31)—C(32)	1.4507 (3)	C(42)—H(42)	1.0799 (3)
N(31)—C(41)	1.3535 (3)	C(43)—H(43A)	1.0799 (3)
N(31)—H(31)	0.9998 (2)	C(43)—H(43B)	1.0801 (3)
N(41)—C(42)	1.4522 (3)	C(43)—H(43C)	1.0800 (4)
N(41)—C(51)	1.3548 (3)	C(51)—C(52)	1.5367 (3)
N(41)—H(41)	0.9999 (2)	C(52)—C(53)	1.5263 (3)
N(51)—C(52)	1.4466 (3)	C(52)—H(52)	1.0800 (2)
N(51)—C(61)	1.3335 (3)	C(53)—H(53A)	1.0799 (3)
N(51)—H(51)	0.9999 (2)	C(53)—H(53B)	1.0800 (3)
N(61)—C(11)	1.3550 (3)	C(53)—H(53C)	1.0800 (3)
N(61)—C(62)	1.4602 (3)	C(61)—C(62)	1.5346 (3)
N(61)—C(65)	1.4756 (3)	C(62)—C(63)	1.5358 (4)
C(11)—C(12)	1.5286 (3)	C(62)—H(62)	1.0800 (2)
C(12)—C(13)	1.5435 (3)	C(63)—C(64)	1.5361 (4)
C(12)—H(12)	1.0800 (2)	C(63)—H(63A)	1.0800 (3)
C(13)—C(14)	1.5349 (3)	C(63)—H(63B)	1.0799 (3)
C(13)—H(13A)	1.0800 (2)	C(64)—C(65)	1.5375 (4)
C(13)—H(13B)	1.0798 (2)	C(64)—H(64A)	1.0800 (3)
C(14)—C(15)	1.5239 (3)	C(64)—H(64B)	1.0798 (4)
C(14)—H(14A)	1.0800 (3)	C(65)—H(65A)	1.0800 (3)
C(14)—H(14B)	1.0799 (3)	C(65)—H(65B)	1.0801 (3)
C(15)—H(15A)	1.0801 (2)

C(61)—O(61)—H(71A)ⁱ	123.9 (1)	C(42)—C(43)—H(43B)	108.9 (1)
H(71A)—O(71)—H(71B)	107.3 (1)	C(42)—C(43)—H(43C)	109.0 (1)
C(12)—N(11)—C(15)	112.1 (1)	H(43A)—C(43)—H(43B)	109.1 (1)
C(12)—N(11)—C(21)	119.8 (1)	H(43A)—C(43)—H(43C)	109.0 (1)
C(15)—N(11)—C(21)	127.7 (1)	H(43B)—C(43)—H(43C)	109.6 (1)
C(22)—N(21)—C(31)	121.5 (1)	O(51)—C(51)—N(41)	122.2 (1)
C(22)—N(21)—H(21)	118.2 (1)	O(51)—C(51)—C(52)	122.5 (1)
C(31)—N(21)—H(21)	120.2 (1)	N(41)—C(51)—C(52)	115.3 (1)
C(32)—N(31)—C(41)	120.1 (1)	N(51)—C(52)—C(51)	110.7 (1)
C(32)—N(31)—H(31)	120.6 (1)	N(51)—C(52)—C(53)	109.1 (1)
C(41)—N(31)—H(31)	117.0 (1)	N(51)—C(52)—H(52)	106.8 (1)
C(42)—N(41)—C(51)	119.6 (1)	C(51)—C(52)—C(53)	113.5 (1)
C(42)—N(41)—H(41)	118.8 (1)	C(51)—C(52)—H(52)	105.8 (1)
C(51)—N(41)—H(41)	119.5 (1)	C(53)—C(52)—H(52)	110.8 (1)
C(52)—N(51)—C(61)	121.9 (1)	C(52)—C(53)—H(53A)	108.9 (1)
C(52)—N(51)—H(51)	118.3 (1)	C(52)—C(53)—H(53B)	111.2 (1)
C(61)—N(51)—H(51)	118.7 (1)	C(52)—C(53)—H(53C)	110.2 (1)
C(11)—N(61)—C(62)	120.8 (1)	H(53A)—C(53)—H(53B)	106.6 (1)
C(11)—N(61)—C(65)	126.7 (1)	H(53A)—C(53)—H(53C)	108.8 (1)
C(62)—N(61)—C(65)	112.4 (1)	H(53B)—C(53)—H(53C)	111.0 (1)
O(11)—C(11)—N(61)	122.1 (1)	O(61)—C(61)—N(51)	123.0 (1)
O(11)—C(11)—C(12)	120.9 (1)	O(61)—C(61)—C(62)	119.8 (1)
N(61)—C(11)—C(12)	117.0 (1)	N(51)—C(61)—C(62)	117.2 (1)
N(11)—C(12)—C(11)	108.3 (1)	N(61)—C(62)—C(61)	112.8 (1)
N(11)—C(12)—C(13)	103.6 (1)	N(61)—C(62)—C(63)	102.7 (1)
N(11)—C(12)—H(12)	107.1 (1)	N(61)—C(62)—H(62)	110.4 (1)
C(11)—C(12)—C(13)	112.2 (1)	C(61)—C(62)—C(63)	110.4 (1)
C(11)—C(12)—H(12)	110.8 (1)	C(61)—C(62)—H(62)	106.6 (1)
C(13)—C(12)—H(12)	114.3 (1)	C(63)—C(62)—H(62)	114.2 (1)
C(12)—C(13)—C(14)	103.5 (1)	C(62)—C(63)—C(64)	102.4 (1)
C(12)—C(13)—H(13A)	111.6 (1)	C(62)—C(63)—H(63A)	109.9 (1)
C(12)—C(13)—H(13B)	108.1 (1)	C(62)—C(63)—H(63B)	113.0 (1)
C(14)—C(13)—H(13A)	112.6 (1)	C(64)—C(63)—H(63A)	107.8 (1)
C(14)—C(13)—H(13B)	110.5 (1)	C(64)—C(63)—H(63B)	112.9 (1)
H(13A)—C(13)—H(13B)	110.3 (1)	H(63A)—C(63)—H(63B)	110.3 (1)
C(13)—C(14)—C(15)	102.7 (1)	C(63)—C(64)—C(65)	103.9 (1)
C(13)—C(14)—H(14A)	109.6 (1)	C(63)—C(64)—H(64A)	114.3 (1)
C(13)—C(14)—H(14B)	114.0 (1)	C(63)—C(64)—H(64B)	109.7 (1)
C(15)—C(14)—H(14A)	109.8 (1)	C(65)—C(64)—H(64A)	111.3 (1)
C(15)—C(14)—H(14B)	111.2 (1)	C(65)—C(64)—H(64B)	110.4 (1)
H(14A)—C(14)—H(14B)	109.3 (1)	H(64A)—C(64)—H(64B)	107.2 (1)
N(11)—C(15)—C(14)	101.8 (1)	N(61)—C(65)—C(64)	103.4 (1)
N(11)—C(15)—H(15A)	110.2 (1)	N(61)—C(65)—H(65A)	110.3 (1)
N(11)—C(15)—H(15B)	109.5 (1)	N(61)—C(65)—H(65B)	110.0 (1)
C(14)—C(15)—H(15A)	113.5 (1)	C(64)—C(65)—H(65A)	112.5 (1)
C(14)—C(15)—H(15B)	110.6 (1)	C(64)—C(65)—H(65B)	110.5 (1)
H(15A)—C(15)—H(15B)	110.7 (1)	H(65A)—C(65)—H(65B)	110.0 (1)
O(21)—C(21)—N(11)	122.8 (1)	C(13)—H(13A)—H(13B)	34.8 (1)
O(21)—C(21)—C(22)	119.8 (1)	C(13)—H(13B)—H(13A)	34.8 (1)
N(11)—C(21)—C(22)	117.4 (1)	C(14)—H(14A)—H(14B)	35.4 (1)
N(21)—C(22)—C(21)	106.4 (1)	C(14)—H(14B)—H(14A)	35.4 (1)
N(21)—C(22)—C(23)	110.6 (1)	C(15)—H(15A)—H(15B)	34.6 (1)
N(21)—C(22)—H(22)	109.0 (1)	C(15)—H(15B)—H(15A)	34.6 (1)
C(21)—C(22)—C(23)	111.7 (1)	C(23)—H(23A)—H(23B)	36.2 (1)
C(21)—C(22)—H(22)	110.6 (1)	C(23)—H(23A)—H(23C)	35.4 (1)
C(23)—C(22)—H(22)	108.5 (1)	C(23)—H(23B)—H(23A)	36.2 (1)
C(22)—C(23)—H(23A)	110.2 (1)	C(23)—H(23B)—H(23C)	35.2 (1)
C(22)—C(23)—H(23B)	110.0 (1)	C(23)—H(23C)—H(23A)	35.4 (1)
C(22)—C(23)—H(23C)	110.2 (1)	C(23)—H(23C)—H(23B)	35.2 (1)
H(23A)—C(23)—H(23B)	107.6 (1)	C(33)—H(33A)—H(33B)	35.8 (1)
H(23A)—C(23)—H(23C)	109.2 (1)	C(33)—H(33A)—H(33C)	35.1 (1)
H(23B)—C(23)—H(23C)	109.6 (1)	C(33)—H(33B)—H(33A)	35.8 (1)
O(31)—C(31)—N(21)	122.9 (1)	C(33)—H(33B)—H(33C)	35.4 (1)
O(31)—C(31)—C(32)	119.2 (1)	C(33)—H(33C)—H(33A)	35.1 (1)
N(21)—C(31)—C(32)	117.7 (1)	C(33)—H(33C)—H(33B)	35.4 (1)
N(31)—C(32)—C(31)	114.7 (1)	C(43)—H(43A)—H(43B)	35.4 (1)
N(31)—C(32)—C(33)	111.2 (1)	C(43)—H(43A)—H(43C)	35.5 (1)
N(31)—C(32)—H(32)	106.2 (1)	C(43)—H(43B)—H(43A)	35.4 (1)
C(31)—C(32)—C(33)	108.1 (1)	C(43)—H(43B)—H(43C)	35.2 (1)
C(31)—C(32)—H(32)	106.5 (1)	C(43)—H(43C)—H(43A)	35.5 (1)
C(33)—C(32)—H(32)	110.0 (1)	C(43)—H(43C)—H(43B)	35.2 (1)
C(32)—C(33)—H(33A)	108.4 (1)	C(53)—H(53A)—H(53B)	36.7 (1)
C(32)—C(33)—H(33B)	110.7 (1)	C(53)—H(53A)—H(53C)	35.6 (1)
C(32)—C(33)—H(33C)	110.2 (1)	C(53)—H(53B)—H(53A)	36.7 (1)
H(33A)—C(33)—H(33B)	108.4 (1)	C(53)—H(53B)—H(53C)	34.5 (1)
H(33A)—C(33)—H(33C)	109.8 (1)	C(53)—H(53C)—H(53A)	35.6 (1)
H(33B)—C(33)—H(33C)	109.2 (1)	C(53)—H(53C)—H(53B)	34.5 (1)
O(41)—C(41)—N(31)	123.5 (1)	C(63)—H(63A)—H(63B)	34.8 (1)
O(41)—C(41)—C(42)	120.7 (1)	C(63)—H(63B)—H(63A)	34.8 (1)
N(31)—C(41)—C(42)	115.7 (1)	C(64)—H(64A)—H(64B)	36.4 (1)
N(41)—C(42)—C(41)	112.6 (1)	C(64)—H(64B)—H(64A)	36.4 (1)
N(41)—C(42)—C(43)	109.9 (1)	C(65)—H(65A)—H(65B)	35.0 (1)
N(41)—C(42)—H(42)	110.2 (1)	C(65)—H(65B)—H(65A)	35.0 (1)
C(41)—C(42)—C(43)	108.9 (1)	O(61)ⁱⁱ—H(71A)—O(71)	174.5 (1)
C(41)—C(42)—H(42)	105.1 (1)	O(61)ⁱⁱ—H(71A)—H(71B)	145.3 (1)
C(43)—C(42)—H(42)	110.0 (1)	O(71)—H(71A)—H(71B)	36.4 (1)
C(42)—C(43)—H(43A)	111.2 (1)	O(71)—H(71B)—H(71A)	36.4 (1)

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

Selected geometric parameters (Å, º) for (Muenchen) top

O(11)—C(11)	1.2273 (4)	C(15)—H(15B)	1.0801 (3)
O(21)—C(21)	1.2386 (3)	C(21)—C(22)	1.5286 (3)
O(31)—C(31)	1.2403 (4)	C(22)—C(23)	1.5339 (4)
O(41)—C(41)	1.2301 (4)	C(22)—H(22)	1.0800 (2)
O(51)—C(51)	1.2235 (4)	C(23)—H(23A)	1.0800 (3)
O(61)—C(61)	1.2403 (4)	C(23)—H(23B)	1.0799 (3)
O(61)—H(71A)ⁱ	1.7743 (4)	C(23)—H(23C)	1.0801 (4)
O(71)—H(71A)	0.9500 (3)	C(31)—C(32)	1.5239 (3)
O(71)—H(71B)	0.9499 (3)	C(32)—C(33)	1.5304 (4)
N(11)—C(12)	1.4703 (3)	C(32)—H(32)	1.0800 (2)
N(11)—C(15)	1.4665 (3)	C(33)—H(33A)	1.0801 (3)
N(11)—C(21)	1.3373 (3)	C(33)—H(33B)	1.0800 (3)
N(21)—C(22)	1.4537 (3)	C(33)—H(33C)	1.0798 (3)
N(21)—C(31)	1.3344 (3)	C(41)—C(42)	1.5287 (4)
N(21)—H(21)	0.9999 (2)	C(42)—C(43)	1.5341 (5)
N(31)—C(32)	1.4493 (3)	C(42)—H(42)	1.0800 (3)
N(31)—C(41)	1.3516 (3)	C(43)—H(43A)	1.0800 (4)
N(31)—H(31)	0.9999 (2)	C(43)—H(43B)	1.0799 (4)
N(41)—C(42)	1.4526 (4)	C(43)—H(43C)	1.0802 (5)
N(41)—C(51)	1.3550 (3)	C(51)—C(52)	1.5374 (4)
N(41)—H(41)	0.9999 (2)	C(52)—C(53)	1.5253 (4)
N(51)—C(52)	1.4472 (3)	C(52)—H(52)	1.0800 (2)
N(51)—C(61)	1.3323 (3)	C(53)—H(53A)	1.0799 (3)
N(51)—H(51)	0.9999 (2)	C(53)—H(53B)	1.0800 (3)
N(61)—C(11)	1.3527 (4)	C(53)—H(53C)	1.0801 (4)
N(61)—C(62)	1.4597 (4)	C(61)—C(62)	1.5349 (4)
N(61)—C(65)	1.4748 (4)	C(62)—C(63)	1.5343 (4)
C(11)—C(12)	1.5283 (4)	C(62)—H(62)	1.0800 (3)
C(12)—C(13)	1.5436 (3)	C(63)—C(64)	1.5359 (6)
C(12)—H(12)	1.0801 (2)	C(63)—H(63A)	1.0799 (3)
C(13)—C(14)	1.5325 (4)	C(63)—H(63B)	1.0800 (4)
C(13)—H(13A)	1.0800 (3)	C(64)—C(65)	1.5351 (5)
C(13)—H(13B)	1.0799 (3)	C(64)—H(64A)	1.0799 (4)
C(14)—C(15)	1.5250 (4)	C(64)—H(64B)	1.0801 (5)
C(14)—H(14A)	1.0799 (3)	C(65)—H(65A)	1.0800 (3)
C(14)—H(14B)	1.0801 (3)	C(65)—H(65B)	1.0800 (4)
C(15)—H(15A)	1.0800 (3)

C(61)—O(61)—H(71A)ⁱ	124.9 (1)	C(42)—C(43)—H(43B)	108.7 (1)
H(71A)—O(71)—H(71B)	103.8 (1)	C(42)—C(43)—H(43C)	109.6 (1)
C(12)—N(11)—C(15)	112.0 (1)	H(43A)—C(43)—H(43B)	108.0 (1)
C(12)—N(11)—C(21)	119.9 (1)	H(43A)—C(43)—H(43C)	109.8 (1)
C(15)—N(11)—C(21)	127.7 (1)	H(43B)—C(43)—H(43C)	110.8 (1)
C(22)—N(21)—C(31)	121.6 (1)	O(51)—C(51)—N(41)	122.3 (1)
C(22)—N(21)—H(21)	117.8 (1)	O(51)—C(51)—C(52)	122.3 (1)
C(31)—N(21)—H(21)	120.6 (1)	N(41)—C(51)—C(52)	115.4 (1)
C(32)—N(31)—C(41)	120.1 (1)	N(51)—C(52)—C(51)	110.8 (1)
C(32)—N(31)—H(31)	118.7 (1)	N(51)—C(52)—C(53)	109.2 (1)
C(41)—N(31)—H(31)	119.1 (1)	N(51)—C(52)—H(52)	106.6 (1)
C(42)—N(41)—C(51)	119.6 (1)	C(51)—C(52)—C(53)	113.4 (1)
C(42)—N(41)—H(41)	117.7 (1)	C(51)—C(52)—H(52)	106.8 (1)
C(51)—N(41)—H(41)	120.8 (1)	C(53)—C(52)—H(52)	109.8 (1)
C(52)—N(51)—C(61)	122.1 (1)	C(52)—C(53)—H(53A)	108.7 (1)
C(52)—N(51)—H(51)	117.7 (1)	C(52)—C(53)—H(53B)	109.9 (1)
C(61)—N(51)—H(51)	119.5 (1)	C(52)—C(53)—H(53C)	108.3 (1)
C(11)—N(61)—C(62)	120.8 (1)	H(53A)—C(53)—H(53B)	108.4 (1)
C(11)—N(61)—C(65)	126.7 (1)	H(53A)—C(53)—H(53C)	110.2 (1)
C(62)—N(61)—C(65)	112.4 (1)	H(53B)—C(53)—H(53C)	111.3 (1)
O(11)—C(11)—N(61)	122.2 (1)	O(61)—C(61)—N(51)	122.9 (1)
O(11)—C(11)—C(12)	120.8 (1)	O(61)—C(61)—C(62)	119.8 (1)
N(61)—C(11)—C(12)	117.0 (1)	N(51)—C(61)—C(62)	117.3 (1)
N(11)—C(12)—C(11)	108.3 (1)	N(61)—C(62)—C(61)	112.8 (1)
N(11)—C(12)—C(13)	103.7 (1)	N(61)—C(62)—C(63)	102.7 (1)
N(11)—C(12)—H(12)	107.7 (1)	N(61)—C(62)—H(62)	110.5 (1)
C(11)—C(12)—C(13)	112.3 (1)	C(61)—C(62)—C(63)	110.5 (1)
C(11)—C(12)—H(12)	111.7 (1)	C(61)—C(62)—H(62)	105.7 (1)
C(13)—C(12)—H(12)	112.8 (1)	C(63)—C(62)—H(62)	114.9 (1)
C(12)—C(13)—C(14)	103.5 (1)	C(62)—C(63)—C(64)	102.4 (1)
C(12)—C(13)—H(13A)	111.7 (1)	C(62)—C(63)—H(63A)	110.9 (1)
C(12)—C(13)—H(13B)	109.4 (1)	C(62)—C(63)—H(63B)	111.0 (1)
C(14)—C(13)—H(13A)	112.7 (1)	C(64)—C(63)—H(63A)	110.6 (1)
C(14)—C(13)—H(13B)	110.2 (1)	C(64)—C(63)—H(63B)	113.2 (1)
H(13A)—C(13)—H(13B)	109.2 (1)	H(63A)—C(63)—H(63B)	108.6 (1)
C(13)—C(14)—C(15)	102.7 (1)	C(63)—C(64)—C(65)	103.9 (1)
C(13)—C(14)—H(14A)	109.3 (1)	C(63)—C(64)—H(64A)	113.9 (1)
C(13)—C(14)—H(14B)	113.9 (1)	C(63)—C(64)—H(64B)	108.8 (1)
C(15)—C(14)—H(14A)	109.9 (1)	C(65)—C(64)—H(64A)	111.7 (1)
C(15)—C(14)—H(14B)	111.0 (1)	C(65)—C(64)—H(64B)	109.0 (1)
H(14A)—C(14)—H(14B)	109.8 (1)	H(64A)—C(64)—H(64B)	109.4 (1)
N(11)—C(15)—C(14)	101.9 (1)	N(61)—C(65)—C(64)	103.4 (1)
N(11)—C(15)—H(15A)	110.9 (1)	N(61)—C(65)—H(65A)	111.3 (1)
N(11)—C(15)—H(15B)	109.7 (1)	N(61)—C(65)—H(65B)	109.4 (1)
C(14)—C(15)—H(15A)	112.9 (1)	C(64)—C(65)—H(65A)	111.9 (1)
C(14)—C(15)—H(15B)	110.8 (1)	C(64)—C(65)—H(65B)	111.9 (1)
H(15A)—C(15)—H(15B)	110.4 (1)	H(65A)—C(65)—H(65B)	108.8 (1)
O(21)—C(21)—N(11)	122.9 (1)	C(13)—H(13A)—H(13B)	35.4 (1)
O(21)—C(21)—C(22)	119.7 (1)	C(13)—H(13B)—H(13A)	35.4 (1)
N(11)—C(21)—C(22)	117.5 (1)	C(14)—H(14A)—H(14B)	35.1 (1)
N(21)—C(22)—C(21)	106.5 (1)	C(14)—H(14B)—H(14A)	35.1 (1)
N(21)—C(22)—C(23)	110.5 (1)	C(15)—H(15A)—H(15B)	34.8 (1)
N(21)—C(22)—H(22)	109.2 (1)	C(15)—H(15B)—H(15A)	34.8 (1)
C(21)—C(22)—C(23)	111.6 (1)	C(23)—H(23A)—H(23B)	35.2 (1)
C(21)—C(22)—H(22)	110.0 (1)	C(23)—H(23A)—H(23C)	35.6 (1)
C(23)—C(22)—H(22)	109.0 (1)	C(23)—H(23B)—H(23A)	35.2 (1)
C(22)—C(23)—H(23A)	109.0 (1)	C(23)—H(23B)—H(23C)	35.3 (1)
C(22)—C(23)—H(23B)	110.8 (1)	C(23)—H(23C)—H(23A)	35.6 (1)
C(22)—C(23)—H(23C)	109.2 (1)	C(23)—H(23C)—H(23B)	35.3 (1)
H(23A)—C(23)—H(23B)	109.5 (1)	C(33)—H(33A)—H(33B)	35.3 (1)
H(23A)—C(23)—H(23C)	108.8 (1)	C(33)—H(33A)—H(33C)	35.3 (1)
H(23B)—C(23)—H(23C)	109.4 (1)	C(33)—H(33B)—H(33A)	35.3 (1)
O(31)—C(31)—N(21)	122.9 (1)	C(33)—H(33B)—H(33C)	34.3 (1)
O(31)—C(31)—C(32)	119.2 (1)	C(33)—H(33C)—H(33A)	35.3 (1)
N(21)—C(31)—C(32)	117.8 (1)	C(33)—H(33C)—H(33B)	34.3 (1)
N(31)—C(32)—C(31)	114.7 (1)	C(43)—H(43A)—H(43B)	36.0 (1)
N(31)—C(32)—C(33)	111.2 (1)	C(43)—H(43A)—H(43C)	35.1 (1)
N(31)—C(32)—H(32)	106.5 (1)	C(43)—H(43B)—H(43A)	36.0 (1)
C(31)—C(32)—C(33)	108.1 (1)	C(43)—H(43B)—H(43C)	34.6 (1)
C(31)—C(32)—H(32)	105.8 (1)	C(43)—H(43C)—H(43A)	35.1 (1)
C(33)—C(32)—H(32)	110.3 (1)	C(43)—H(43C)—H(43B)	34.6 (1)
C(32)—C(33)—H(33A)	109.0 (1)	C(53)—H(53A)—H(53B)	35.8 (1)
C(32)—C(33)—H(33B)	108.5 (1)	C(53)—H(53A)—H(53C)	34.9 (1)
C(32)—C(33)—H(33C)	109.0 (1)	C(53)—H(53B)—H(53A)	35.8 (1)
H(33A)—C(33)—H(33B)	109.4 (1)	C(53)—H(53B)—H(53C)	34.3 (1)
H(33A)—C(33)—H(33C)	109.4 (1)	C(53)—H(53C)—H(53A)	34.9 (1)
H(33B)—C(33)—H(33C)	111.4 (1)	C(53)—H(53C)—H(53B)	34.3 (1)
O(41)—C(41)—N(31)	123.5 (1)	C(63)—H(63A)—H(63B)	35.7 (1)
O(41)—C(41)—C(42)	120.7 (1)	C(63)—H(63B)—H(63A)	35.7 (1)
N(31)—C(41)—C(42)	115.7 (1)	C(64)—H(64A)—H(64B)	35.3 (1)
N(41)—C(42)—C(41)	112.5 (1)	C(64)—H(64B)—H(64A)	35.3 (1)
N(41)—C(42)—C(43)	110.0 (1)	C(65)—H(65A)—H(65B)	35.6 (1)
N(41)—C(42)—H(42)	110.2 (1)	C(65)—H(65B)—H(65A)	35.6 (1)
C(41)—C(42)—C(43)	108.9 (1)	O(61)ⁱⁱ—H(71A)—O(71)	172.7 (1)
C(41)—C(42)—H(42)	105.0 (1)	O(61)ⁱⁱ—H(71A)—H(71B)	147.9 (1)
C(43)—C(42)—H(42)	110.1 (1)	O(71)—H(71A)—H(71B)	38.1 (1)
C(42)—C(43)—H(43A)	109.8 (1)	O(71)—H(71B)—H(71A)	38.1 (1)

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

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