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The title compound, C17H38N4O3, is an asymmetric tetra­azacyclo­dodecane macrocycle with three pendant hydroxy­isopropyl arms. Two of these arms are involved in hydrogen bonding inter­nal to the macrocyclic ring while the third forms an inter­molecular O—H...N hydrogen bond, leading to chains of mol­ecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806043030/tk2085sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806043030/tk2085Isup2.hkl
Contains datablock I

CCDC reference: 628415

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.040
  • wR factor = 0.087
  • Data-to-parameter ratio = 10.8

checkCIF/PLATON results

No syntax errors found



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 28.30 From the CIF: _reflns_number_total 2380 Count of symmetry unique reflns 2565 Completeness (_total/calc) 92.79% 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 PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C18 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C22 = . S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour 2001; Atwood & Barbour,2003); software used to prepare material for publication: X-SEED.

(S)-1,4,7-Tris(2-hydroxypropyl)-1,4,7,10-tetraazacyclododecane top
Crystal data top
C17H38N4O3Z = 1
Mr = 346.51F(000) = 192
Triclinic, P1Dx = 1.117 Mg m3
Hall symbol: P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.8231 (11) ÅCell parameters from 2473 reflections
b = 9.0594 (13) Åθ = 2.6–27.3°
c = 9.2040 (13) ŵ = 0.08 mm1
α = 119.287 (2)°T = 100 K
β = 105.764 (2)°Block, colorless
γ = 98.734 (2)°0.35 × 0.32 × 0.27 mm
V = 515.07 (13) Å3
Data collection top
Bruker APEX CCD area-detector
diffractometer
2200 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.041
Graphite monochromatorθmax = 28.3°, θmin = 2.6°
ω scansh = 1010
6008 measured reflectionsk = 1112
2380 independent reflectionsl = 1212
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)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087H atoms treated by a mixture of independent and constrained refinement
S = 0.99 w = 1/[σ2(Fo2) + (0.0489P)2]
where P = (Fo2 + 2Fc2)/3
2380 reflections(Δ/σ)max < 0.001
221 parametersΔρmax = 0.21 e Å3
3 restraintsΔρmin = 0.16 e Å3
Special details top

Experimental. 1H NMR (deuterated chloroform, p.p.m.): 1.10 (9H, d, CH3), 2.0–3.0 (22H, m, all H next to N), 3.9 (3H, m, H on asymmetric C), 5.10 (3H, s, br, OH).

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
N10.4382 (2)0.8920 (2)0.8273 (2)0.0178 (4)
C20.4994 (3)1.0296 (3)0.7927 (3)0.0244 (5)
H2A0.58171.14390.91030.029*
H2B0.38701.05080.73630.029*
C30.6067 (3)0.9766 (3)0.6682 (3)0.0249 (5)
H3A0.62031.06150.63040.030*
H3B0.73510.98880.73810.030*
N40.5153 (2)0.7949 (2)0.5071 (2)0.0222 (4)
C50.6434 (3)0.7189 (3)0.4262 (3)0.0235 (5)
H5A0.74290.81600.44480.028*
H5B0.57220.63020.29370.028*
C60.7339 (3)0.6284 (3)0.5108 (3)0.0219 (4)
H6B0.82250.58060.45710.026*
H6A0.80580.71650.64330.026*
N70.5857 (2)0.4819 (2)0.4767 (2)0.0196 (4)
H70.501 (3)0.521 (3)0.507 (3)0.023*
C80.6501 (3)0.4019 (3)0.5775 (3)0.0226 (4)
H8A0.76980.38330.57040.027*
H8B0.55510.28270.51950.027*
C90.6809 (3)0.5182 (3)0.7755 (3)0.0222 (4)
H9A0.72230.45760.83670.027*
H9B0.78220.63440.83620.027*
N100.5070 (2)0.5517 (2)0.7940 (2)0.0186 (4)
C110.5515 (3)0.7254 (3)0.9634 (3)0.0221 (4)
H11A0.65990.74151.06210.027*
H11B0.44190.72360.99740.027*
C120.5990 (3)0.8840 (3)0.9469 (3)0.0213 (4)
H12A0.65000.99661.06970.026*
H12B0.69960.87780.90020.026*
C130.2812 (3)0.9091 (3)0.8871 (3)0.0200 (4)
H13A0.22050.79320.86770.024*
H13B0.18650.92640.80590.024*
C140.3259 (3)1.0585 (3)1.0830 (3)0.0225 (4)
H14A0.41991.04261.16770.027*
O150.4063 (2)1.22515 (19)1.1085 (2)0.0276 (4)
H15A0.46431.30491.22020.033*
C160.1471 (3)1.0499 (3)1.1185 (3)0.0343 (6)
H16B0.17711.14571.24460.052*
H16A0.09420.93281.09790.052*
H16C0.05481.06571.03590.052*
C170.3333 (3)0.7604 (3)0.3772 (3)0.0274 (5)
H17B0.34740.74930.26900.033*
H17A0.28740.86200.43340.033*
C180.1916 (3)0.5876 (3)0.3204 (3)0.0259 (5)
H18A0.23780.48560.26060.031*
O190.1752 (2)0.60241 (19)0.47721 (19)0.0241 (3)
H19A0.27290.68100.57000.029*
C200.0020 (3)0.5474 (4)0.1889 (3)0.0397 (6)
H20C0.08900.43530.15540.060*
H20A0.00680.53480.07940.060*
H20B0.04910.64630.24680.060*
C210.3880 (3)0.4023 (3)0.7842 (3)0.0232 (5)
H21B0.43480.42080.90520.028*
H21A0.40160.28900.69740.028*
C220.1808 (3)0.3815 (3)0.7259 (3)0.0253 (5)
H22A0.16620.49770.80860.030*
O230.0974 (2)0.3313 (2)0.5434 (2)0.0325 (4)
H23A0.15400.40980.53290.039*
C240.0730 (3)0.2348 (3)0.7349 (4)0.0355 (6)
H24B0.06090.22270.69680.053*
H24C0.12330.26600.85990.053*
H24A0.08680.12070.65380.053*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0196 (8)0.0168 (8)0.0193 (9)0.0077 (7)0.0093 (7)0.0105 (7)
C20.0286 (12)0.0180 (10)0.0307 (12)0.0091 (9)0.0158 (10)0.0140 (10)
C30.0268 (12)0.0234 (11)0.0344 (12)0.0096 (9)0.0166 (10)0.0204 (10)
N40.0232 (9)0.0266 (10)0.0252 (10)0.0125 (8)0.0139 (8)0.0168 (8)
C50.0233 (11)0.0284 (11)0.0261 (11)0.0099 (9)0.0155 (9)0.0168 (10)
C60.0186 (10)0.0260 (11)0.0239 (11)0.0092 (9)0.0120 (9)0.0136 (10)
N70.0163 (8)0.0235 (9)0.0212 (9)0.0102 (7)0.0088 (7)0.0125 (8)
C80.0201 (10)0.0234 (11)0.0286 (12)0.0118 (9)0.0102 (9)0.0161 (10)
C90.0197 (10)0.0237 (11)0.0256 (11)0.0102 (9)0.0064 (9)0.0160 (10)
N100.0193 (8)0.0179 (8)0.0199 (9)0.0075 (7)0.0080 (7)0.0109 (7)
C110.0216 (11)0.0257 (11)0.0192 (10)0.0090 (9)0.0072 (9)0.0128 (9)
C120.0177 (10)0.0198 (10)0.0201 (11)0.0051 (8)0.0065 (9)0.0077 (9)
C130.0196 (10)0.0178 (10)0.0203 (11)0.0058 (8)0.0083 (8)0.0091 (9)
C140.0248 (11)0.0214 (11)0.0210 (11)0.0089 (9)0.0105 (9)0.0107 (9)
O150.0375 (9)0.0173 (7)0.0197 (8)0.0066 (7)0.0109 (7)0.0059 (6)
C160.0326 (13)0.0352 (13)0.0301 (13)0.0114 (11)0.0198 (11)0.0113 (11)
C170.0341 (12)0.0399 (13)0.0274 (12)0.0231 (11)0.0183 (10)0.0257 (11)
C180.0240 (11)0.0358 (12)0.0195 (11)0.0158 (10)0.0084 (9)0.0152 (10)
O190.0211 (7)0.0280 (8)0.0178 (8)0.0042 (6)0.0052 (6)0.0115 (7)
C200.0283 (13)0.0642 (18)0.0254 (13)0.0231 (13)0.0087 (10)0.0232 (13)
C210.0282 (11)0.0226 (11)0.0285 (11)0.0115 (9)0.0138 (9)0.0187 (10)
C220.0262 (11)0.0234 (11)0.0360 (13)0.0115 (9)0.0163 (10)0.0204 (10)
O230.0261 (8)0.0324 (9)0.0392 (10)0.0035 (7)0.0079 (7)0.0244 (8)
C240.0307 (13)0.0355 (14)0.0555 (17)0.0142 (11)0.0234 (12)0.0316 (14)
Geometric parameters (Å, º) top
N1—C121.468 (2)C12—H12B0.9900
N1—C21.474 (3)C13—C141.527 (3)
N1—C131.476 (2)C13—H13A0.9900
C2—C31.535 (3)C13—H13B0.9900
C2—H2A0.9900C14—O151.420 (3)
C2—H2B0.9900C14—C161.520 (3)
C3—N41.449 (3)C14—H14A1.0000
C3—H3A0.9900O15—H15A0.8400
C3—H3B0.9900C16—H16B0.9800
N4—C171.459 (3)C16—H16A0.9800
N4—C51.465 (3)C16—H16C0.9800
C5—C61.510 (3)C17—C181.519 (3)
C5—H5A0.9900C17—H17B0.9900
C5—H5B0.9900C17—H17A0.9900
C6—N71.460 (3)C18—O191.426 (3)
C6—H6B0.9900C18—C201.516 (3)
C6—H6A0.9900C18—H18A1.0000
N7—C81.468 (3)O19—H19A0.8400
N7—H70.84 (2)C20—H20C0.9800
C8—C91.515 (3)C20—H20A0.9800
C8—H8A0.9900C20—H20B0.9800
C8—H8B0.9900C21—C221.513 (3)
C9—N101.474 (3)C21—H21B0.9900
C9—H9A0.9900C21—H21A0.9900
C9—H9B0.9900C22—O231.422 (3)
N10—C211.468 (3)C22—C241.513 (3)
N10—C111.472 (3)C22—H22A1.0000
C11—C121.519 (3)O23—H23A0.8400
C11—H11A0.9900C24—H24B0.9800
C11—H11B0.9900C24—H24C0.9800
C12—H12A0.9900C24—H24A0.9800
C12—N1—C2111.39 (16)H12A—C12—H12B107.6
C12—N1—C13113.92 (15)N1—C13—C14118.20 (17)
C2—N1—C13112.66 (16)N1—C13—H13A107.8
N1—C2—C3113.17 (16)C14—C13—H13A107.8
N1—C2—H2A108.9N1—C13—H13B107.8
C3—C2—H2A108.9C14—C13—H13B107.8
N1—C2—H2B108.9H13A—C13—H13B107.1
C3—C2—H2B108.9O15—C14—C16111.49 (18)
H2A—C2—H2B107.8O15—C14—C13107.70 (16)
N4—C3—C2113.62 (17)C16—C14—C13109.97 (18)
N4—C3—H3A108.8O15—C14—H14A109.2
C2—C3—H3A108.8C16—C14—H14A109.2
N4—C3—H3B108.8C13—C14—H14A109.2
C2—C3—H3B108.8C14—O15—H15A109.5
H3A—C3—H3B107.7C14—C16—H16B109.5
C3—N4—C17115.84 (16)C14—C16—H16A109.5
C3—N4—C5113.79 (17)H16B—C16—H16A109.5
C17—N4—C5114.97 (17)C14—C16—H16C109.5
N4—C5—C6110.87 (17)H16B—C16—H16C109.5
N4—C5—H5A109.5H16A—C16—H16C109.5
C6—C5—H5A109.5N4—C17—C18109.65 (17)
N4—C5—H5B109.5N4—C17—H17B109.7
C6—C5—H5B109.5C18—C17—H17B109.7
H5A—C5—H5B108.1N4—C17—H17A109.7
N7—C6—C5108.70 (17)C18—C17—H17A109.7
N7—C6—H6B109.9H17B—C17—H17A108.2
C5—C6—H6B109.9O19—C18—C20108.60 (18)
N7—C6—H6A109.9O19—C18—C17109.56 (18)
C5—C6—H6A109.9C20—C18—C17111.97 (19)
H6B—C6—H6A108.3O19—C18—H18A108.9
C6—N7—C8114.45 (17)C20—C18—H18A108.9
C6—N7—H7109.3 (16)C17—C18—H18A108.9
C8—N7—H7106.9 (16)C18—O19—H19A109.5
N7—C8—C9112.57 (17)C18—C20—H20C109.5
N7—C8—H8A109.1C18—C20—H20A109.5
C9—C8—H8A109.1H20C—C20—H20A109.5
N7—C8—H8B109.1C18—C20—H20B109.5
C9—C8—H8B109.1H20C—C20—H20B109.5
H8A—C8—H8B107.8H20A—C20—H20B109.5
N10—C9—C8111.35 (17)N10—C21—C22114.27 (16)
N10—C9—H9A109.4N10—C21—H21B108.7
C8—C9—H9A109.4C22—C21—H21B108.7
N10—C9—H9B109.4N10—C21—H21A108.7
C8—C9—H9B109.4C22—C21—H21A108.7
H9A—C9—H9B108.0H21B—C21—H21A107.6
C21—N10—C11111.65 (16)O23—C22—C21111.97 (18)
C21—N10—C9109.95 (15)O23—C22—C24106.68 (18)
C11—N10—C9110.95 (16)C21—C22—C24110.30 (17)
N10—C11—C12112.86 (16)O23—C22—H22A109.3
N10—C11—H11A109.0C21—C22—H22A109.3
C12—C11—H11A109.0C24—C22—H22A109.3
N10—C11—H11B109.0C22—O23—H23A109.5
C12—C11—H11B109.0C22—C24—H24B109.5
H11A—C11—H11B107.8C22—C24—H24C109.5
N1—C12—C11114.18 (16)H24B—C24—H24C109.5
N1—C12—H12A108.7C22—C24—H24A109.5
C11—C12—H12A108.7H24B—C24—H24A109.5
N1—C12—H12B108.7H24C—C24—H24A109.5
C11—C12—H12B108.7
C12—N1—C2—C371.5 (2)C2—N1—C12—C11170.43 (16)
C13—N1—C2—C3159.04 (18)C13—N1—C12—C1160.8 (2)
N1—C2—C3—N447.1 (3)N10—C11—C12—N168.8 (2)
C2—C3—N4—C1765.8 (2)C12—N1—C13—C1451.8 (2)
C2—C3—N4—C5157.65 (18)C2—N1—C13—C1476.4 (2)
C3—N4—C5—C687.9 (2)N1—C13—C14—O1559.9 (2)
C17—N4—C5—C6135.16 (19)N1—C13—C14—C16178.46 (18)
N4—C5—C6—N761.1 (2)C3—N4—C17—C18132.93 (19)
C5—C6—N7—C8170.04 (17)C5—N4—C17—C1891.0 (2)
C6—N7—C8—C976.7 (2)N4—C17—C18—O1957.9 (2)
N7—C8—C9—N1058.2 (2)N4—C17—C18—C20178.50 (17)
C8—C9—N10—C2184.9 (2)C11—N10—C21—C2279.8 (2)
C8—C9—N10—C11151.08 (17)C9—N10—C21—C22156.55 (18)
C21—N10—C11—C12155.85 (16)N10—C21—C22—O2366.0 (2)
C9—N10—C11—C1281.1 (2)N10—C21—C22—C24175.32 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O23—H23A···O190.842.042.826 (3)155
O19—H19A···N10.842.022.826 (2)160
O15—H15A···N7i0.841.912.751 (2)178
Symmetry code: (i) x, y+1, z+1.
 

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