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The title compound, C26H45N3O8, is a bicyclic mol­ecule; the seven-membered diazepane ring has a twisted-chair conformation and the six-membered morpholine ring has a boat conformation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270109049361/fn3037sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270109049361/fn3037Isup2.hkl
Contains datablock I

CCDC reference: 774897

Comment top

The chemistry of 1,4-diazepane-based ligands is attracting increasing attention since these ligands have strong binding capabilities with different metal ions, including main group metals, transition metals and lanthanides (Comba et al., 2009, Ge et al., 2007, 2009; Peralta et al., 2005; Rey et al., 2007). In particular, it has been proposed that gadolinium(III) complexes of 6-amino-6-methylperhydro-1,4-diazepinetetraaceticacid (AAZTA) ligands are good candidates as MRI contrast agents due to their good thermodynamic stability, kinetic inertness and high relaxivity at neutral pH (Aime et al., 2004).

Recently, we reported the syntheses and characterization of new bifunctional AAZTA ligands with hyroxy side chains, and the crystal structures of gadolinium and europium complexes (Sengar et al., 2008, 2009). The title compound, (I), was used as a precursor for one of the bifunctional ligands with a hydroxy arm and the complete synthesis and spectroscopic characterization of (I) was provided (Sengar et al., 2009). Herein we report the molecular structure of compound (I) determined by X-ray crystallography (Fig. 1).

Compound (I) crystallizes with two independent molecules in the asymmetric cell unit, having nearly similar [change to: identical?] conformations . As expected, compound (I) contains two cyclic rings: a seven-membered 1,4-diazepane ring with a twisted-chair conformation and a six-membered oxomorpholine ring which adopts a boat conformation (Fig. 1). Both rings are connected to each other via one C atom in such a way that the mean planes of both rings are nearly orthogonal to each other. The diazepane and morpholine rings in both structures have slightly different puckering parameters (Cremer & Pople, 1975) as given in Table 1. The puckering parameters for the seven-membered ring in (I) are different to the values for the AAZTA chelate (Table 1) or the protonated diazepane (daza-3HCl-3H2O) chelate (Romba et al., 2005). This shows that the large flexibility is associated with the diazepane ring, and gives rise to the different puckering constants for non-coordinated ligands. However, upon metal coordination, the diazepane ring adopts a pseudo-chair conformation and all three N atoms coordinate to the metal ion in facial mode.

The C—N bond distances (N6—C43, N5—C30, N5—C29, N4—C27, N4—C28) in (I) are very similar [average distance ~1.465 (3) Å] for the exocyclic and endocyclic N atoms with respect to the diazepane ring. Interestingly, in the crystal structures of the metal complexes with such ligands, the exocyclic Nexo—C(ring) bond length becomes slightly longer compared with the endocyclic Nendo—C(ring) bond length. This may be due to the geometric constraint imposed by the coordinated metal ion.

Related literature top

For related literature, see: Aime et al. (2004); Comba et al. (2009); Cremer & Pople (1975); Ge et al. (2007); Peralta et al. (2005); Rey et al. (2007); Sengar et al. (2008, 2009).

Experimental top

Compound (I) was synthesized according to the literature procedure (Sengar et al., 2009). Colorless crystals suitable for X-ray analysis were obtained by slow evaporation of a methylene chloride solution of (I) in air.

Refinement top

H atoms were placed in calculated positions and refined using a riding model [Cmethyl—H = 0.97 Å, Cmethylene—H = 0.98 Å and Uiso(H) = 1.2Ueq(C)].

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SMART (Bruker, 2003); data reduction: SAINT-Plus (Bruker, 2003); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing one of the molecules in the unit cell, with displacement ellipsoids drawn at the 50% probability level. H atoms have been omitted.
Tri-tert-butyl 3-oxo-4-oxa-1,8,11-triazaspiro[5.6]dodecane-1,8,11-triacetate top
Crystal data top
C26H45N3O8Z = 4
Mr = 527.65F(000) = 1144
Triclinic, P1Dx = 1.175 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.1304 (17) ÅCell parameters from 4387 reflections
b = 15.250 (2) Åθ = 2.3–24.7°
c = 18.098 (3) ŵ = 0.09 mm1
α = 99.305 (4)°T = 203 K
β = 90.010 (3)°Block, colorless
γ = 100.168 (3)°0.24 × 0.18 × 0.13 mm
V = 2982.5 (8) Å3
Data collection top
Bruker SMART APEX CCD
diffractometer
11582 independent reflections
Radiation source: sealed tube7769 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.052
ω scansθmax = 26.0°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2003)
h = 1313
Tmin = 0.962, Tmax = 0.980k = 1818
21467 measured reflectionsl = 2222
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.170H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.078P)2]
where P = (Fo2 + 2Fc2)/3
11582 reflections(Δ/σ)max = 0.001
667 parametersΔρmax = 0.58 e Å3
0 restraintsΔρmin = 0.22 e Å3
Crystal data top
C26H45N3O8γ = 100.168 (3)°
Mr = 527.65V = 2982.5 (8) Å3
Triclinic, P1Z = 4
a = 11.1304 (17) ÅMo Kα radiation
b = 15.250 (2) ŵ = 0.09 mm1
c = 18.098 (3) ÅT = 203 K
α = 99.305 (4)°0.24 × 0.18 × 0.13 mm
β = 90.010 (3)°
Data collection top
Bruker SMART APEX CCD
diffractometer
11582 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2003)
7769 reflections with I > 2σ(I)
Tmin = 0.962, Tmax = 0.980Rint = 0.052
21467 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0610 restraints
wR(F2) = 0.170H-atom parameters constrained
S = 1.04Δρmax = 0.58 e Å3
11582 reflectionsΔρmin = 0.22 e Å3
667 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.39731 (16)0.67232 (12)0.09461 (9)0.0377 (4)
O10.40064 (15)0.92475 (12)0.15327 (10)0.0543 (5)
C10.45976 (19)0.75264 (14)0.06693 (11)0.0347 (5)
H1A0.39870.78430.04940.042*
H1B0.50850.73400.02400.042*
N20.66007 (15)0.68993 (12)0.12598 (9)0.0350 (4)
C20.4616 (2)0.59587 (15)0.07647 (13)0.0452 (6)
H2A0.48650.59140.02430.054*
H2B0.40590.53990.08150.054*
O20.42055 (18)1.04161 (13)0.09357 (13)0.0813 (7)
O30.10887 (13)0.63734 (11)0.00927 (7)0.0422 (4)
N30.61348 (15)0.88656 (12)0.08799 (10)0.0386 (4)
C30.5738 (2)0.60575 (15)0.12716 (13)0.0445 (6)
H3A0.54770.60340.17860.053*
H3B0.61550.55460.11150.053*
C40.62026 (18)0.76784 (14)0.17081 (11)0.0333 (5)
H4A0.69260.81040.19280.040*
H4B0.57200.74730.21210.040*
O40.29145 (15)0.61343 (14)0.05496 (9)0.0609 (5)
N40.82517 (18)0.32138 (13)0.39869 (10)0.0437 (5)
O50.93958 (13)0.68547 (10)0.22990 (7)0.0386 (4)
C50.26748 (19)0.65231 (17)0.07875 (11)0.0418 (5)
H5A0.23220.70380.10280.050*
H5B0.23270.60030.10220.050*
N51.08196 (17)0.29854 (13)0.37395 (9)0.0397 (4)
O60.74587 (15)0.66414 (14)0.26987 (9)0.0579 (5)
C60.2270 (2)0.63181 (16)0.00387 (12)0.0395 (5)
N60.91778 (16)0.09754 (12)0.39427 (10)0.0384 (4)
O70.93936 (12)0.89762 (10)0.06443 (8)0.0381 (4)
C70.0418 (2)0.61897 (17)0.08259 (12)0.0438 (6)
O80.84142 (13)0.94627 (11)0.16839 (8)0.0464 (4)
C80.0965 (3)0.6853 (2)0.13176 (14)0.0663 (8)
H8A0.09500.74630.10650.099*
H8B0.04960.67390.17860.099*
H8C0.18030.67860.14190.099*
C90.0851 (2)0.6317 (2)0.05938 (14)0.0697 (9)
H9A0.08310.69390.03590.104*
H9B0.11430.59170.02410.104*
H9C0.13950.61780.10320.104*
O90.70047 (14)0.07270 (12)0.31403 (9)0.0505 (4)
C100.0413 (3)0.52294 (19)0.11932 (14)0.0612 (7)
H10A0.00390.48200.08660.092*
H10B0.12450.51420.12860.092*
H10C0.00490.51070.16640.092*
O100.64781 (17)0.05877 (14)0.35089 (11)0.0709 (6)
C110.78597 (19)0.68381 (16)0.14172 (11)0.0377 (5)
H11A0.83860.73740.12860.045*
H11B0.80570.63110.10850.045*
O110.55671 (15)0.35867 (12)0.50508 (8)0.0510 (4)
C120.8186 (2)0.67609 (15)0.22217 (12)0.0378 (5)
O120.74806 (17)0.36860 (17)0.54955 (9)0.0754 (6)
C130.9998 (2)0.68940 (16)0.30409 (11)0.0423 (5)
O131.36652 (14)0.30534 (12)0.27335 (8)0.0475 (4)
C140.9752 (3)0.7712 (2)0.35646 (14)0.0627 (7)
H14A0.88940.76280.36840.094*
H14B0.99590.82420.33260.094*
H14C1.02430.77930.40210.094*
O141.19095 (17)0.34162 (14)0.23709 (9)0.0601 (5)
C150.9594 (2)0.60264 (18)0.33431 (13)0.0553 (7)
H15A0.87380.59690.34630.083*
H15B1.00750.60330.37920.083*
H15C0.97100.55190.29690.083*
O151.23757 (14)0.08603 (11)0.42575 (8)0.0462 (4)
C161.1340 (2)0.7000 (2)0.28449 (14)0.0618 (7)
H16A1.14770.64640.25100.093*
H16B1.18370.70780.32990.093*
H16C1.15600.75240.26000.093*
O161.11896 (16)0.02944 (15)0.32270 (10)0.0677 (6)
C170.54374 (18)0.81800 (14)0.12679 (11)0.0328 (5)
C180.4664 (2)0.86554 (17)0.18453 (13)0.0457 (6)
H18A0.40810.82000.20480.055*
H18B0.51970.90060.22610.055*
C190.4689 (2)0.98670 (18)0.11756 (16)0.0564 (7)
C200.6003 (2)0.97978 (16)0.11063 (14)0.0480 (6)
H20A0.63691.01580.07350.058*
H20B0.64341.00400.15880.058*
C210.72624 (18)0.87247 (15)0.05463 (11)0.0365 (5)
H21A0.73400.89980.00900.044*
H21B0.72260.80740.03950.044*
C220.84106 (18)0.91027 (15)0.10394 (12)0.0350 (5)
C231.06572 (18)0.92773 (16)0.09735 (12)0.0382 (5)
C241.0815 (2)0.87568 (17)0.16025 (13)0.0480 (6)
H24A1.03150.89430.20180.072*
H24B1.16650.88790.17680.072*
H24C1.05640.81150.14240.072*
C251.1422 (2)0.89998 (19)0.03137 (13)0.0518 (6)
H25A1.13070.93400.00820.078*
H25B1.11720.83600.01290.078*
H25C1.22760.91220.04710.078*
C261.0907 (2)1.02814 (16)0.12306 (14)0.0497 (6)
H26A1.07931.05850.08110.075*
H26B1.17411.04690.14260.075*
H26C1.03481.04380.16210.075*
C270.8389 (2)0.23513 (16)0.41999 (11)0.0395 (5)
H27A0.75860.20340.43180.047*
H27B0.89090.24690.46550.047*
C280.9290 (2)0.39283 (17)0.42381 (13)0.0520 (6)
H28A0.95060.39060.47590.062*
H28B0.90530.45150.42240.062*
C291.0401 (2)0.38505 (17)0.37607 (13)0.0514 (6)
H29A1.02030.39210.32490.062*
H29B1.10690.43430.39590.062*
C301.00556 (19)0.22506 (15)0.32323 (11)0.0373 (5)
H30A1.05680.18170.30200.045*
H30B0.97580.25030.28170.045*
C310.7064 (2)0.34530 (19)0.41613 (12)0.0513 (7)
H31A0.64350.29770.38910.062*
H31B0.70180.40120.39690.062*
C320.6758 (2)0.35875 (18)0.49879 (13)0.0475 (6)
C330.4989 (2)0.3720 (2)0.57917 (12)0.0539 (7)
C340.5486 (4)0.4646 (2)0.61952 (18)0.0978 (12)
H34A0.63380.46840.63320.147*
H34B0.50280.47710.66440.147*
H34C0.54140.50840.58720.147*
C350.5158 (3)0.2981 (2)0.62185 (15)0.0715 (8)
H35A0.60110.30510.63660.107*
H35B0.49030.23990.59030.107*
H35C0.46670.30160.66620.107*
C360.3653 (3)0.3629 (3)0.55614 (16)0.0994 (14)
H36A0.33560.30210.53020.149*
H36B0.35720.40590.52320.149*
H36C0.31790.37490.60040.149*
C371.2114 (2)0.30377 (17)0.36034 (12)0.0448 (6)
H37A1.23480.24740.36960.054*
H37B1.25650.35270.39720.054*
C381.2529 (2)0.31952 (16)0.28246 (12)0.0415 (5)
C391.4270 (2)0.30619 (17)0.19957 (12)0.0457 (6)
C401.4436 (3)0.3985 (2)0.17940 (16)0.0782 (10)
H40A1.49250.44120.21820.117*
H40B1.36440.41570.17470.117*
H40C1.48460.39870.13210.117*
C411.5463 (3)0.2778 (3)0.21366 (17)0.0913 (12)
H41A1.59420.32270.25150.137*
H41B1.59090.27230.16760.137*
H41C1.53090.22000.23100.137*
C421.3514 (3)0.23747 (19)0.14101 (14)0.0624 (7)
H42A1.39020.23780.09300.094*
H42B1.27060.25230.13730.094*
H42C1.34470.17800.15490.094*
C430.89467 (19)0.17349 (15)0.35899 (11)0.0355 (5)
C440.8031 (2)0.13555 (17)0.29429 (12)0.0441 (6)
H44A0.77320.18560.27690.053*
H44B0.84470.10510.25270.053*
C450.7287 (2)0.00207 (18)0.34212 (14)0.0500 (6)
C460.8608 (2)0.00678 (16)0.36005 (14)0.0484 (6)
H46A0.86930.03550.39440.058*
H46B0.90270.01140.31400.058*
C471.0343 (2)0.10550 (16)0.43226 (11)0.0383 (5)
H47A1.02120.07440.47570.046*
H47B1.06440.16960.45120.046*
C481.1329 (2)0.06838 (17)0.38605 (13)0.0428 (6)
C491.3481 (2)0.05074 (17)0.39551 (13)0.0479 (6)
C501.3835 (2)0.0824 (2)0.32272 (15)0.0701 (8)
H50A1.32180.05390.28430.105*
H50B1.46160.06620.30800.105*
H50C1.39000.14740.32890.105*
C511.4440 (2)0.0938 (2)0.45603 (16)0.0694 (8)
H51A1.42030.07270.50260.104*
H51B1.45120.15890.46300.104*
H51C1.52190.07730.44130.104*
C521.3227 (3)0.0507 (2)0.38867 (19)0.0770 (9)
H52A1.26110.07600.34950.116*
H52B1.29360.06740.43590.116*
H52C1.39720.07390.37630.116*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0293 (10)0.0433 (11)0.0378 (9)0.0026 (8)0.0058 (7)0.0091 (8)
O10.0310 (9)0.0551 (11)0.0763 (11)0.0155 (8)0.0008 (8)0.0004 (9)
C10.0283 (11)0.0390 (12)0.0364 (11)0.0042 (9)0.0033 (8)0.0072 (9)
N20.0289 (9)0.0374 (10)0.0403 (9)0.0059 (8)0.0035 (7)0.0113 (8)
C20.0447 (14)0.0357 (13)0.0533 (13)0.0006 (11)0.0073 (11)0.0093 (11)
O20.0545 (12)0.0533 (12)0.1420 (19)0.0251 (10)0.0150 (12)0.0167 (12)
O30.0335 (8)0.0585 (10)0.0337 (8)0.0078 (7)0.0031 (6)0.0058 (7)
N30.0249 (9)0.0374 (10)0.0557 (11)0.0060 (8)0.0013 (8)0.0136 (9)
C30.0440 (14)0.0372 (13)0.0541 (14)0.0054 (11)0.0050 (11)0.0152 (11)
C40.0260 (11)0.0400 (12)0.0342 (11)0.0045 (9)0.0000 (8)0.0087 (9)
O40.0372 (9)0.1012 (15)0.0413 (9)0.0130 (10)0.0009 (7)0.0023 (9)
N40.0486 (12)0.0486 (12)0.0404 (10)0.0202 (10)0.0133 (8)0.0141 (9)
O50.0334 (8)0.0515 (10)0.0342 (8)0.0109 (7)0.0017 (6)0.0131 (7)
C50.0314 (12)0.0531 (15)0.0374 (11)0.0026 (10)0.0007 (9)0.0081 (10)
N50.0398 (11)0.0419 (11)0.0378 (10)0.0041 (9)0.0076 (8)0.0106 (8)
O60.0398 (10)0.0997 (15)0.0435 (9)0.0195 (10)0.0085 (8)0.0318 (10)
C60.0308 (12)0.0469 (14)0.0385 (12)0.0003 (10)0.0020 (9)0.0073 (10)
N60.0325 (10)0.0396 (11)0.0448 (10)0.0072 (8)0.0015 (8)0.0113 (8)
O70.0240 (8)0.0496 (9)0.0402 (8)0.0041 (7)0.0003 (6)0.0081 (7)
C70.0377 (13)0.0598 (16)0.0341 (11)0.0095 (11)0.0080 (9)0.0077 (11)
O80.0321 (9)0.0606 (11)0.0427 (9)0.0066 (8)0.0000 (7)0.0008 (8)
C80.076 (2)0.076 (2)0.0474 (14)0.0078 (16)0.0093 (13)0.0191 (14)
C90.0455 (16)0.119 (3)0.0474 (15)0.0267 (17)0.0081 (12)0.0088 (16)
O90.0294 (9)0.0610 (11)0.0599 (10)0.0073 (8)0.0033 (7)0.0070 (9)
C100.0570 (17)0.0648 (18)0.0543 (15)0.0009 (14)0.0162 (12)0.0012 (13)
O100.0470 (11)0.0708 (14)0.0859 (14)0.0124 (10)0.0013 (10)0.0111 (11)
C110.0328 (12)0.0476 (13)0.0376 (11)0.0141 (10)0.0016 (9)0.0141 (10)
O110.0502 (10)0.0751 (12)0.0342 (8)0.0263 (9)0.0113 (7)0.0115 (8)
C120.0344 (12)0.0424 (13)0.0405 (12)0.0138 (10)0.0011 (10)0.0110 (10)
O120.0523 (12)0.138 (2)0.0380 (9)0.0244 (12)0.0040 (8)0.0126 (11)
C130.0435 (13)0.0520 (14)0.0353 (11)0.0142 (11)0.0074 (9)0.0123 (10)
O130.0367 (9)0.0681 (11)0.0368 (8)0.0008 (8)0.0046 (6)0.0155 (8)
C140.0730 (19)0.0679 (19)0.0470 (14)0.0199 (15)0.0097 (13)0.0009 (13)
O140.0583 (11)0.0885 (14)0.0449 (9)0.0266 (10)0.0100 (8)0.0300 (9)
C150.0607 (17)0.0639 (17)0.0503 (14)0.0200 (14)0.0025 (12)0.0268 (13)
O150.0361 (9)0.0564 (10)0.0484 (9)0.0157 (8)0.0065 (7)0.0068 (8)
C160.0430 (15)0.093 (2)0.0542 (15)0.0152 (15)0.0095 (12)0.0222 (15)
O160.0440 (10)0.1041 (16)0.0517 (11)0.0274 (10)0.0084 (8)0.0131 (10)
C170.0228 (10)0.0376 (12)0.0377 (11)0.0045 (9)0.0011 (8)0.0067 (9)
C180.0328 (12)0.0548 (15)0.0486 (13)0.0106 (11)0.0019 (10)0.0026 (11)
C190.0392 (14)0.0414 (15)0.0855 (19)0.0120 (12)0.0116 (13)0.0040 (14)
C200.0373 (13)0.0413 (14)0.0660 (15)0.0096 (11)0.0072 (11)0.0076 (12)
C210.0302 (11)0.0445 (13)0.0371 (11)0.0059 (10)0.0025 (9)0.0146 (10)
C220.0275 (11)0.0385 (12)0.0409 (12)0.0063 (9)0.0026 (9)0.0116 (10)
C230.0207 (10)0.0470 (14)0.0477 (12)0.0016 (9)0.0025 (9)0.0148 (11)
C240.0302 (12)0.0612 (16)0.0551 (14)0.0043 (11)0.0051 (10)0.0211 (12)
C250.0320 (13)0.0714 (18)0.0518 (14)0.0078 (12)0.0008 (10)0.0112 (13)
C260.0330 (13)0.0488 (15)0.0653 (15)0.0020 (11)0.0023 (11)0.0136 (12)
C270.0374 (12)0.0486 (14)0.0364 (11)0.0117 (10)0.0054 (9)0.0142 (10)
C280.0703 (18)0.0411 (14)0.0484 (14)0.0178 (13)0.0177 (12)0.0096 (11)
C290.0601 (16)0.0441 (14)0.0506 (14)0.0065 (12)0.0172 (12)0.0126 (12)
C300.0374 (12)0.0449 (13)0.0330 (11)0.0106 (10)0.0044 (9)0.0125 (10)
C310.0598 (16)0.0668 (17)0.0374 (12)0.0347 (14)0.0124 (11)0.0133 (12)
C320.0485 (15)0.0592 (16)0.0402 (13)0.0223 (12)0.0091 (11)0.0099 (11)
C330.0551 (16)0.0779 (19)0.0341 (12)0.0248 (14)0.0151 (11)0.0105 (12)
C340.128 (3)0.089 (3)0.068 (2)0.019 (2)0.043 (2)0.0113 (19)
C350.073 (2)0.095 (2)0.0537 (16)0.0204 (18)0.0146 (14)0.0265 (16)
C360.0568 (19)0.203 (4)0.0563 (17)0.052 (2)0.0207 (14)0.041 (2)
C370.0384 (13)0.0559 (15)0.0389 (12)0.0007 (11)0.0038 (10)0.0140 (11)
C380.0396 (13)0.0456 (14)0.0375 (12)0.0003 (11)0.0043 (10)0.0092 (10)
C390.0396 (13)0.0582 (16)0.0366 (12)0.0014 (11)0.0089 (9)0.0115 (11)
C400.107 (3)0.0531 (18)0.0632 (17)0.0160 (17)0.0390 (17)0.0081 (15)
C410.0455 (18)0.171 (4)0.0659 (19)0.023 (2)0.0157 (14)0.042 (2)
C420.0606 (18)0.0602 (18)0.0596 (16)0.0055 (14)0.0125 (13)0.0049 (14)
C430.0324 (11)0.0420 (13)0.0350 (11)0.0103 (10)0.0032 (9)0.0111 (10)
C440.0365 (13)0.0543 (15)0.0441 (12)0.0129 (11)0.0005 (10)0.0105 (11)
C450.0396 (14)0.0531 (16)0.0534 (14)0.0037 (13)0.0018 (11)0.0023 (12)
C460.0397 (14)0.0426 (14)0.0640 (15)0.0057 (11)0.0001 (11)0.0137 (12)
C470.0384 (12)0.0456 (13)0.0342 (11)0.0102 (10)0.0013 (9)0.0129 (10)
C480.0367 (13)0.0521 (15)0.0419 (13)0.0121 (11)0.0053 (10)0.0097 (11)
C490.0315 (12)0.0575 (16)0.0586 (14)0.0188 (11)0.0037 (10)0.0093 (12)
C500.0436 (16)0.103 (2)0.0724 (18)0.0328 (16)0.0083 (13)0.0194 (17)
C510.0416 (15)0.088 (2)0.0769 (19)0.0185 (15)0.0125 (13)0.0017 (16)
C520.0497 (17)0.063 (2)0.121 (3)0.0215 (15)0.0053 (17)0.0126 (18)
Geometric parameters (Å, º) top
N1—C51.442 (3)C17—C181.527 (3)
N1—C11.460 (3)C18—H18A0.9800
N1—C21.467 (3)C18—H18B0.9800
O1—C191.353 (3)C19—C201.488 (3)
O1—C181.439 (3)C20—H20A0.9800
C1—C171.537 (3)C20—H20B0.9800
C1—H1A0.9800C21—C221.528 (3)
C1—H1B0.9800C21—H21A0.9800
N2—C111.452 (3)C21—H21B0.9800
N2—C31.464 (3)C23—C261.503 (3)
N2—C41.463 (3)C23—C241.516 (3)
C2—C31.520 (3)C23—C251.514 (3)
C2—H2A0.9800C24—H24A0.9700
C2—H2B0.9800C24—H24B0.9700
O2—C191.207 (3)C24—H24C0.9700
O3—C61.337 (2)C25—H25A0.9700
O3—C71.484 (2)C25—H25B0.9700
N3—C211.428 (3)C25—H25C0.9700
N3—C201.448 (3)C26—H26A0.9700
N3—C171.463 (3)C26—H26B0.9700
C3—H3A0.9800C26—H26C0.9700
C3—H3B0.9800C27—C431.536 (3)
C4—C171.540 (3)C27—H27A0.9800
C4—H4A0.9800C27—H27B0.9800
C4—H4B0.9800C28—C291.520 (3)
O4—C61.198 (3)C28—H28A0.9800
N4—C311.454 (3)C28—H28B0.9800
N4—C281.457 (3)C29—H29A0.9800
N4—C271.462 (3)C29—H29B0.9800
O5—C121.334 (2)C30—C431.544 (3)
O5—C131.488 (2)C30—H30A0.9800
C5—C61.528 (3)C30—H30B0.9800
C5—H5A0.9800C31—C321.523 (3)
C5—H5B0.9800C31—H31A0.9800
N5—C371.452 (3)C31—H31B0.9800
N5—C301.467 (3)C33—C341.491 (4)
N5—C291.469 (3)C33—C351.503 (4)
O6—C121.197 (3)C33—C361.520 (4)
N6—C471.444 (3)C34—H34A0.9700
N6—C461.454 (3)C34—H34B0.9700
N6—C431.469 (3)C34—H34C0.9700
O7—C221.333 (2)C35—H35A0.9700
O7—C231.492 (2)C35—H35B0.9700
C7—C81.503 (4)C35—H35C0.9700
C7—C101.506 (4)C36—H36A0.9700
C7—C91.510 (3)C36—H36B0.9700
O8—C221.206 (2)C36—H36C0.9700
C8—H8A0.9700C37—C381.526 (3)
C8—H8B0.9700C37—H37A0.9800
C8—H8C0.9700C37—H37B0.9800
C9—H9A0.9700C39—C401.491 (4)
C9—H9B0.9700C39—C421.503 (3)
C9—H9C0.9700C39—C411.502 (4)
O9—C451.347 (3)C40—H40A0.9700
O9—C441.441 (3)C40—H40B0.9700
C10—H10A0.9700C40—H40C0.9700
C10—H10B0.9700C41—H41A0.9700
C10—H10C0.9700C41—H41B0.9700
O10—C451.204 (3)C41—H41C0.9700
C11—C121.528 (3)C42—H42A0.9700
C11—H11A0.9800C42—H42B0.9700
C11—H11B0.9800C42—H42C0.9700
O11—C321.330 (3)C43—C441.522 (3)
O11—C331.487 (3)C44—H44A0.9800
O12—C321.194 (3)C44—H44B0.9800
C13—C141.506 (3)C45—C461.493 (3)
C13—C151.509 (3)C46—H46A0.9800
C13—C161.522 (3)C46—H46B0.9800
O13—C381.326 (3)C47—C481.514 (3)
O13—C391.497 (3)C47—H47A0.9800
C14—H14A0.9700C47—H47B0.9800
C14—H14B0.9700C49—C501.504 (4)
C14—H14C0.9700C49—C521.507 (4)
O14—C381.198 (3)C49—C511.513 (3)
C15—H15A0.9700C50—H50A0.9700
C15—H15B0.9700C50—H50B0.9700
C15—H15C0.9700C50—H50C0.9700
O15—C481.331 (3)C51—H51A0.9700
O15—C491.497 (3)C51—H51B0.9700
C16—H16A0.9700C51—H51C0.9700
C16—H16B0.9700C52—H52A0.9700
C16—H16C0.9700C52—H52B0.9700
O16—C481.199 (3)C52—H52C0.9700
C5—N1—C1113.88 (17)H24B—C24—H24C109.5
C5—N1—C2115.61 (18)C23—C25—H25A109.5
C1—N1—C2112.13 (17)C23—C25—H25B109.5
C19—O1—C18115.68 (18)H25A—C25—H25B109.5
N1—C1—C17112.80 (16)C23—C25—H25C109.5
N1—C1—H1A109.0H25A—C25—H25C109.5
C17—C1—H1A109.0H25B—C25—H25C109.5
N1—C1—H1B109.0C23—C26—H26A109.5
C17—C1—H1B109.0C23—C26—H26B109.5
H1A—C1—H1B107.8H26A—C26—H26B109.5
C11—N2—C3113.80 (17)C23—C26—H26C109.5
C11—N2—C4113.43 (16)H26A—C26—H26C109.5
C3—N2—C4112.42 (17)H26B—C26—H26C109.5
N1—C2—C3112.03 (18)N4—C27—C43113.62 (16)
N1—C2—H2A109.2N4—C27—H27A108.8
C3—C2—H2A109.2C43—C27—H27A108.8
N1—C2—H2B109.2N4—C27—H27B108.8
C3—C2—H2B109.2C43—C27—H27B108.8
H2A—C2—H2B107.9H27A—C27—H27B107.7
C6—O3—C7121.86 (16)N4—C28—C29112.69 (19)
C21—N3—C20115.96 (18)N4—C28—H28A109.1
C21—N3—C17120.15 (17)C29—C28—H28A109.1
C20—N3—C17118.45 (18)N4—C28—H28B109.1
N2—C3—C2113.11 (18)C29—C28—H28B109.1
N2—C3—H3A109.0H28A—C28—H28B107.8
C2—C3—H3A109.0N5—C29—C28113.17 (19)
N2—C3—H3B109.0N5—C29—H29A108.9
C2—C3—H3B109.0C28—C29—H29A108.9
H3A—C3—H3B107.8N5—C29—H29B108.9
N2—C4—C17114.40 (15)C28—C29—H29B108.9
N2—C4—H4A108.7H29A—C29—H29B107.8
C17—C4—H4A108.7N5—C30—C43115.51 (16)
N2—C4—H4B108.7N5—C30—H30A108.4
C17—C4—H4B108.7C43—C30—H30A108.4
H4A—C4—H4B107.6N5—C30—H30B108.4
C31—N4—C28114.8 (2)C43—C30—H30B108.4
C31—N4—C27113.08 (19)H30A—C30—H30B107.5
C28—N4—C27112.45 (18)N4—C31—C32115.91 (19)
C12—O5—C13121.42 (16)N4—C31—H31A108.3
N1—C5—C6116.49 (17)C32—C31—H31A108.3
N1—C5—H5A108.2N4—C31—H31B108.3
C6—C5—H5A108.2C32—C31—H31B108.3
N1—C5—H5B108.2H31A—C31—H31B107.4
C6—C5—H5B108.2O12—C32—O11125.8 (2)
H5A—C5—H5B107.3O12—C32—C31125.0 (2)
C37—N5—C30112.76 (17)O11—C32—C31109.2 (2)
C37—N5—C29113.53 (19)O11—C33—C34109.0 (2)
C30—N5—C29112.04 (18)O11—C33—C35110.2 (2)
O4—C6—O3126.13 (19)C34—C33—C35113.8 (2)
O4—C6—C5125.0 (2)O11—C33—C36101.52 (19)
O3—C6—C5108.90 (17)C34—C33—C36111.4 (3)
C47—N6—C46115.95 (17)C35—C33—C36110.3 (3)
C47—N6—C43118.34 (18)C33—C34—H34A109.5
C46—N6—C43118.06 (17)C33—C34—H34B109.5
C22—O7—C23122.05 (16)H34A—C34—H34B109.5
O3—C7—C8110.53 (19)C33—C34—H34C109.5
O3—C7—C10109.85 (19)H34A—C34—H34C109.5
C8—C7—C10111.7 (2)H34B—C34—H34C109.5
O3—C7—C9101.82 (17)C33—C35—H35A109.5
C8—C7—C9111.9 (2)C33—C35—H35B109.5
C10—C7—C9110.6 (2)H35A—C35—H35B109.5
C7—C8—H8A109.5C33—C35—H35C109.5
C7—C8—H8B109.5H35A—C35—H35C109.5
H8A—C8—H8B109.5H35B—C35—H35C109.5
C7—C8—H8C109.5C33—C36—H36A109.5
H8A—C8—H8C109.5C33—C36—H36B109.5
H8B—C8—H8C109.5H36A—C36—H36B109.5
C7—C9—H9A109.5C33—C36—H36C109.5
C7—C9—H9B109.5H36A—C36—H36C109.5
H9A—C9—H9B109.5H36B—C36—H36C109.5
C7—C9—H9C109.5N5—C37—C38116.59 (18)
H9A—C9—H9C109.5N5—C37—H37A108.1
H9B—C9—H9C109.5C38—C37—H37A108.1
C45—O9—C44115.40 (18)N5—C37—H37B108.1
C7—C10—H10A109.5C38—C37—H37B108.1
C7—C10—H10B109.5H37A—C37—H37B107.3
H10A—C10—H10B109.5O14—C38—O13125.9 (2)
C7—C10—H10C109.5O14—C38—C37124.3 (2)
H10A—C10—H10C109.5O13—C38—C37109.80 (19)
H10B—C10—H10C109.5C40—C39—O13110.1 (2)
N2—C11—C12116.68 (17)C40—C39—C42111.5 (2)
N2—C11—H11A108.1O13—C39—C42109.13 (19)
C12—C11—H11A108.1C40—C39—C41112.5 (3)
N2—C11—H11B108.1O13—C39—C41102.93 (18)
C12—C11—H11B108.1C42—C39—C41110.3 (2)
H11A—C11—H11B107.3C39—C40—H40A109.5
C32—O11—C33122.05 (18)C39—C40—H40B109.5
O6—C12—O5126.41 (19)H40A—C40—H40B109.5
O6—C12—C11124.6 (2)C39—C40—H40C109.5
O5—C12—C11108.99 (17)H40A—C40—H40C109.5
O5—C13—C14109.27 (18)H40B—C40—H40C109.5
O5—C13—C15110.80 (19)C39—C41—H41A109.5
C14—C13—C15112.8 (2)C39—C41—H41B109.5
O5—C13—C16101.91 (17)H41A—C41—H41B109.5
C14—C13—C16110.9 (2)C39—C41—H41C109.5
C15—C13—C16110.6 (2)H41A—C41—H41C109.5
C38—O13—C39121.81 (17)H41B—C41—H41C109.5
C13—C14—H14A109.5C39—C42—H42A109.5
C13—C14—H14B109.5C39—C42—H42B109.5
H14A—C14—H14B109.5H42A—C42—H42B109.5
C13—C14—H14C109.5C39—C42—H42C109.5
H14A—C14—H14C109.5H42A—C42—H42C109.5
H14B—C14—H14C109.5H42B—C42—H42C109.5
C13—C15—H15A109.5N6—C43—C44107.73 (18)
C13—C15—H15B109.5N6—C43—C27105.51 (15)
H15A—C15—H15B109.5C44—C43—C27110.47 (17)
C13—C15—H15C109.5N6—C43—C30115.95 (16)
H15A—C15—H15C109.5C44—C43—C30104.77 (16)
H15B—C15—H15C109.5C27—C43—C30112.36 (18)
C48—O15—C49121.24 (17)O9—C44—C43113.18 (17)
C13—C16—H16A109.5O9—C44—H44A108.9
C13—C16—H16B109.5C43—C44—H44A108.9
H16A—C16—H16B109.5O9—C44—H44B108.9
C13—C16—H16C109.5C43—C44—H44B108.9
H16A—C16—H16C109.5H44A—C44—H44B107.8
H16B—C16—H16C109.5O10—C45—O9118.8 (2)
N3—C17—C18107.69 (18)O10—C45—C46125.4 (3)
N3—C17—C1106.21 (16)O9—C45—C46115.8 (2)
C18—C17—C1109.58 (17)N6—C46—C45111.20 (19)
N3—C17—C4115.56 (16)N6—C46—H46A109.4
C18—C17—C4105.89 (16)C45—C46—H46A109.4
C1—C17—C4111.79 (17)N6—C46—H46B109.4
O1—C18—C17112.43 (18)C45—C46—H46B109.4
O1—C18—H18A109.1H46A—C46—H46B108.0
C17—C18—H18A109.1N6—C47—C48116.20 (17)
O1—C18—H18B109.1N6—C47—H47A108.2
C17—C18—H18B109.1C48—C47—H47A108.2
H18A—C18—H18B107.9N6—C47—H47B108.2
O2—C19—O1119.1 (2)C48—C47—H47B108.2
O2—C19—C20125.3 (3)H47A—C47—H47B107.4
O1—C19—C20115.6 (2)O16—C48—O15125.0 (2)
N3—C20—C19110.4 (2)O16—C48—C47124.9 (2)
N3—C20—H20A109.6O15—C48—C47110.09 (19)
C19—C20—H20A109.6O15—C49—C50111.02 (18)
N3—C20—H20B109.6O15—C49—C52108.5 (2)
C19—C20—H20B109.6C50—C49—C52112.9 (2)
H20A—C20—H20B108.1O15—C49—C51102.05 (19)
N3—C21—C22115.78 (17)C50—C49—C51110.2 (2)
N3—C21—H21A108.3C52—C49—C51111.6 (2)
C22—C21—H21A108.3C49—C50—H50A109.5
N3—C21—H21B108.3C49—C50—H50B109.5
C22—C21—H21B108.3H50A—C50—H50B109.5
H21A—C21—H21B107.4C49—C50—H50C109.5
O8—C22—O7125.89 (19)H50A—C50—H50C109.5
O8—C22—C21124.74 (18)H50B—C50—H50C109.5
O7—C22—C21109.37 (17)C49—C51—H51A109.5
O7—C23—C26110.53 (17)C49—C51—H51B109.5
O7—C23—C24108.95 (17)H51A—C51—H51B109.5
C26—C23—C24112.4 (2)C49—C51—H51C109.5
O7—C23—C25101.67 (17)H51A—C51—H51C109.5
C26—C23—C25111.9 (2)H51B—C51—H51C109.5
C24—C23—C25110.86 (19)C49—C52—H52A109.5
C23—C24—H24A109.5C49—C52—H52B109.5
C23—C24—H24B109.5H52A—C52—H52B109.5
H24A—C24—H24B109.5C49—C52—H52C109.5
C23—C24—H24C109.5H52A—C52—H52C109.5
H24A—C24—H24C109.5H52B—C52—H52C109.5

Experimental details

Crystal data
Chemical formulaC26H45N3O8
Mr527.65
Crystal system, space groupTriclinic, P1
Temperature (K)203
a, b, c (Å)11.1304 (17), 15.250 (2), 18.098 (3)
α, β, γ (°)99.305 (4), 90.010 (3), 100.168 (3)
V3)2982.5 (8)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.24 × 0.18 × 0.13
Data collection
DiffractometerBruker SMART APEX CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2003)
Tmin, Tmax0.962, 0.980
No. of measured, independent and
observed [I > 2σ(I)] reflections
21467, 11582, 7769
Rint0.052
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.061, 0.170, 1.04
No. of reflections11582
No. of parameters667
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.58, 0.22

Computer programs: SMART (Bruker, 2003), SAINT-Plus (Bruker, 2003), SHELXTL (Sheldrick, 2008).

Puckering parameters for two independent molecules in (I) calculated using PLATON (Spek, 2009) top
Similar calculation for AAZTA chelate gave values for comparison.
diazepane ringmorpholine ringAAZTA
q20.5100.5370.6380.6530.641
q30.6760.6750.0310.0260.633
θ269.067.255.159.365.7
θ3323.7323.516.2
X-ray cif was obtained from Cambridge Crystal Data Centre #650378 (Aime et al., 2008).
 

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