(S)-1,4,7-Tris(2-hydroxy­prop­yl)-1,4,7,10-tetra­azacyclo­dodecane

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.

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

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

Crystal data

C17H38N4O3	Z = 1
Mr = 346.51	F(000) = 192
Triclinic, P1	Dx = 1.117 Mg m^−3
Hall symbol: P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8231 (11) Å	Cell parameters from 2473 reflections
b = 9.0594 (13) Å	θ = 2.6–27.3°
c = 9.2040 (13) Å	µ = 0.08 mm^−1
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) Å^3

Data collection

Bruker APEX CCD area-detector diffractometer	2200 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.041
Graphite monochromator	θmax = 28.3°, θmin = 2.6°
ω scans	h = −10→10
6008 measured reflections	k = −11→12
2380 independent reflections	l = −12→12

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0489P)^2] where P = (Fo^2 + 2Fc^2)/3
2380 reflections	(Δ/σ)max < 0.001
221 parameters	Δρmax = 0.21 e Å^−3
3 restraints	Δρmin = −0.16 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.4382 (2)	0.8920 (2)	0.8273 (2)	0.0178 (4)
C2	0.4994 (3)	1.0296 (3)	0.7927 (3)	0.0244 (5)
H2A	0.5817	1.1439	0.9103	0.029*
H2B	0.3870	1.0508	0.7363	0.029*
C3	0.6067 (3)	0.9766 (3)	0.6682 (3)	0.0249 (5)
H3A	0.6203	1.0615	0.6304	0.030*
H3B	0.7351	0.9888	0.7381	0.030*
N4	0.5153 (2)	0.7949 (2)	0.5071 (2)	0.0222 (4)
C5	0.6434 (3)	0.7189 (3)	0.4262 (3)	0.0235 (5)
H5A	0.7429	0.8160	0.4448	0.028*
H5B	0.5722	0.6302	0.2937	0.028*
C6	0.7339 (3)	0.6284 (3)	0.5108 (3)	0.0219 (4)
H6B	0.8225	0.5806	0.4571	0.026*
H6A	0.8058	0.7165	0.6433	0.026*
N7	0.5857 (2)	0.4819 (2)	0.4767 (2)	0.0196 (4)
H7	0.501 (3)	0.521 (3)	0.507 (3)	0.023*
C8	0.6501 (3)	0.4019 (3)	0.5775 (3)	0.0226 (4)
H8A	0.7698	0.3833	0.5704	0.027*
H8B	0.5551	0.2827	0.5195	0.027*
C9	0.6809 (3)	0.5182 (3)	0.7755 (3)	0.0222 (4)
H9A	0.7223	0.4576	0.8367	0.027*
H9B	0.7822	0.6344	0.8362	0.027*
N10	0.5070 (2)	0.5517 (2)	0.7940 (2)	0.0186 (4)
C11	0.5515 (3)	0.7254 (3)	0.9634 (3)	0.0221 (4)
H11A	0.6599	0.7415	1.0621	0.027*
H11B	0.4419	0.7236	0.9974	0.027*
C12	0.5990 (3)	0.8840 (3)	0.9469 (3)	0.0213 (4)
H12A	0.6500	0.9966	1.0697	0.026*
H12B	0.6996	0.8778	0.9002	0.026*
C13	0.2812 (3)	0.9091 (3)	0.8871 (3)	0.0200 (4)
H13A	0.2205	0.7932	0.8677	0.024*
H13B	0.1865	0.9264	0.8059	0.024*
C14	0.3259 (3)	1.0585 (3)	1.0830 (3)	0.0225 (4)
H14A	0.4199	1.0426	1.1677	0.027*
O15	0.4063 (2)	1.22515 (19)	1.1085 (2)	0.0276 (4)
H15A	0.4643	1.3049	1.2202	0.033*
C16	0.1471 (3)	1.0499 (3)	1.1185 (3)	0.0343 (6)
H16B	0.1771	1.1457	1.2446	0.052*
H16A	0.0942	0.9328	1.0979	0.052*
H16C	0.0548	1.0657	1.0359	0.052*
C17	0.3333 (3)	0.7604 (3)	0.3772 (3)	0.0274 (5)
H17B	0.3474	0.7493	0.2690	0.033*
H17A	0.2874	0.8620	0.4334	0.033*
C18	0.1916 (3)	0.5876 (3)	0.3204 (3)	0.0259 (5)
H18A	0.2378	0.4856	0.2606	0.031*
O19	0.1752 (2)	0.60241 (19)	0.47721 (19)	0.0241 (3)
H19A	0.2729	0.6810	0.5700	0.029*
C20	−0.0020 (3)	0.5474 (4)	0.1889 (3)	0.0397 (6)
H20C	−0.0890	0.4353	0.1554	0.060*
H20A	0.0068	0.5348	0.0794	0.060*
H20B	−0.0491	0.6463	0.2468	0.060*
C21	0.3880 (3)	0.4023 (3)	0.7842 (3)	0.0232 (5)
H21B	0.4348	0.4208	0.9052	0.028*
H21A	0.4016	0.2890	0.6974	0.028*
C22	0.1808 (3)	0.3815 (3)	0.7259 (3)	0.0253 (5)
H22A	0.1662	0.4977	0.8086	0.030*
O23	0.0974 (2)	0.3313 (2)	0.5434 (2)	0.0325 (4)
H23A	0.1540	0.4098	0.5329	0.039*
C24	0.0730 (3)	0.2348 (3)	0.7349 (4)	0.0355 (6)
H24B	−0.0609	0.2227	0.6968	0.053*
H24C	0.1233	0.2660	0.8599	0.053*
H24A	0.0868	0.1207	0.6538	0.053*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0196 (8)	0.0168 (8)	0.0193 (9)	0.0077 (7)	0.0093 (7)	0.0105 (7)
C2	0.0286 (12)	0.0180 (10)	0.0307 (12)	0.0091 (9)	0.0158 (10)	0.0140 (10)
C3	0.0268 (12)	0.0234 (11)	0.0344 (12)	0.0096 (9)	0.0166 (10)	0.0204 (10)
N4	0.0232 (9)	0.0266 (10)	0.0252 (10)	0.0125 (8)	0.0139 (8)	0.0168 (8)
C5	0.0233 (11)	0.0284 (11)	0.0261 (11)	0.0099 (9)	0.0155 (9)	0.0168 (10)
C6	0.0186 (10)	0.0260 (11)	0.0239 (11)	0.0092 (9)	0.0120 (9)	0.0136 (10)
N7	0.0163 (8)	0.0235 (9)	0.0212 (9)	0.0102 (7)	0.0088 (7)	0.0125 (8)
C8	0.0201 (10)	0.0234 (11)	0.0286 (12)	0.0118 (9)	0.0102 (9)	0.0161 (10)
C9	0.0197 (10)	0.0237 (11)	0.0256 (11)	0.0102 (9)	0.0064 (9)	0.0160 (10)
N10	0.0193 (8)	0.0179 (8)	0.0199 (9)	0.0075 (7)	0.0080 (7)	0.0109 (7)
C11	0.0216 (11)	0.0257 (11)	0.0192 (10)	0.0090 (9)	0.0072 (9)	0.0128 (9)
C12	0.0177 (10)	0.0198 (10)	0.0201 (11)	0.0051 (8)	0.0065 (9)	0.0077 (9)
C13	0.0196 (10)	0.0178 (10)	0.0203 (11)	0.0058 (8)	0.0083 (8)	0.0091 (9)
C14	0.0248 (11)	0.0214 (11)	0.0210 (11)	0.0089 (9)	0.0105 (9)	0.0107 (9)
O15	0.0375 (9)	0.0173 (7)	0.0197 (8)	0.0066 (7)	0.0109 (7)	0.0059 (6)
C16	0.0326 (13)	0.0352 (13)	0.0301 (13)	0.0114 (11)	0.0198 (11)	0.0113 (11)
C17	0.0341 (12)	0.0399 (13)	0.0274 (12)	0.0231 (11)	0.0183 (10)	0.0257 (11)
C18	0.0240 (11)	0.0358 (12)	0.0195 (11)	0.0158 (10)	0.0084 (9)	0.0152 (10)
O19	0.0211 (7)	0.0280 (8)	0.0178 (8)	0.0042 (6)	0.0052 (6)	0.0115 (7)
C20	0.0283 (13)	0.0642 (18)	0.0254 (13)	0.0231 (13)	0.0087 (10)	0.0232 (13)
C21	0.0282 (11)	0.0226 (11)	0.0285 (11)	0.0115 (9)	0.0138 (9)	0.0187 (10)
C22	0.0262 (11)	0.0234 (11)	0.0360 (13)	0.0115 (9)	0.0163 (10)	0.0204 (10)
O23	0.0261 (8)	0.0324 (9)	0.0392 (10)	0.0035 (7)	0.0079 (7)	0.0244 (8)
C24	0.0307 (13)	0.0355 (14)	0.0555 (17)	0.0142 (11)	0.0234 (12)	0.0316 (14)

Geometric parameters (Å, º)

N1—C12	1.468 (2)	C12—H12B	0.9900
N1—C2	1.474 (3)	C13—C14	1.527 (3)
N1—C13	1.476 (2)	C13—H13A	0.9900
C2—C3	1.535 (3)	C13—H13B	0.9900
C2—H2A	0.9900	C14—O15	1.420 (3)
C2—H2B	0.9900	C14—C16	1.520 (3)
C3—N4	1.449 (3)	C14—H14A	1.0000
C3—H3A	0.9900	O15—H15A	0.8400
C3—H3B	0.9900	C16—H16B	0.9800
N4—C17	1.459 (3)	C16—H16A	0.9800
N4—C5	1.465 (3)	C16—H16C	0.9800
C5—C6	1.510 (3)	C17—C18	1.519 (3)
C5—H5A	0.9900	C17—H17B	0.9900
C5—H5B	0.9900	C17—H17A	0.9900
C6—N7	1.460 (3)	C18—O19	1.426 (3)
C6—H6B	0.9900	C18—C20	1.516 (3)
C6—H6A	0.9900	C18—H18A	1.0000
N7—C8	1.468 (3)	O19—H19A	0.8400
N7—H7	0.84 (2)	C20—H20C	0.9800
C8—C9	1.515 (3)	C20—H20A	0.9800
C8—H8A	0.9900	C20—H20B	0.9800
C8—H8B	0.9900	C21—C22	1.513 (3)
C9—N10	1.474 (3)	C21—H21B	0.9900
C9—H9A	0.9900	C21—H21A	0.9900
C9—H9B	0.9900	C22—O23	1.422 (3)
N10—C21	1.468 (3)	C22—C24	1.513 (3)
N10—C11	1.472 (3)	C22—H22A	1.0000
C11—C12	1.519 (3)	O23—H23A	0.8400
C11—H11A	0.9900	C24—H24B	0.9800
C11—H11B	0.9900	C24—H24C	0.9800
C12—H12A	0.9900	C24—H24A	0.9800
C12—N1—C2	111.39 (16)	H12A—C12—H12B	107.6
C12—N1—C13	113.92 (15)	N1—C13—C14	118.20 (17)
C2—N1—C13	112.66 (16)	N1—C13—H13A	107.8
N1—C2—C3	113.17 (16)	C14—C13—H13A	107.8
N1—C2—H2A	108.9	N1—C13—H13B	107.8
C3—C2—H2A	108.9	C14—C13—H13B	107.8
N1—C2—H2B	108.9	H13A—C13—H13B	107.1
C3—C2—H2B	108.9	O15—C14—C16	111.49 (18)
H2A—C2—H2B	107.8	O15—C14—C13	107.70 (16)
N4—C3—C2	113.62 (17)	C16—C14—C13	109.97 (18)
N4—C3—H3A	108.8	O15—C14—H14A	109.2
C2—C3—H3A	108.8	C16—C14—H14A	109.2
N4—C3—H3B	108.8	C13—C14—H14A	109.2
C2—C3—H3B	108.8	C14—O15—H15A	109.5
H3A—C3—H3B	107.7	C14—C16—H16B	109.5
C3—N4—C17	115.84 (16)	C14—C16—H16A	109.5
C3—N4—C5	113.79 (17)	H16B—C16—H16A	109.5
C17—N4—C5	114.97 (17)	C14—C16—H16C	109.5
N4—C5—C6	110.87 (17)	H16B—C16—H16C	109.5
N4—C5—H5A	109.5	H16A—C16—H16C	109.5
C6—C5—H5A	109.5	N4—C17—C18	109.65 (17)
N4—C5—H5B	109.5	N4—C17—H17B	109.7
C6—C5—H5B	109.5	C18—C17—H17B	109.7
H5A—C5—H5B	108.1	N4—C17—H17A	109.7
N7—C6—C5	108.70 (17)	C18—C17—H17A	109.7
N7—C6—H6B	109.9	H17B—C17—H17A	108.2
C5—C6—H6B	109.9	O19—C18—C20	108.60 (18)
N7—C6—H6A	109.9	O19—C18—C17	109.56 (18)
C5—C6—H6A	109.9	C20—C18—C17	111.97 (19)
H6B—C6—H6A	108.3	O19—C18—H18A	108.9
C6—N7—C8	114.45 (17)	C20—C18—H18A	108.9
C6—N7—H7	109.3 (16)	C17—C18—H18A	108.9
C8—N7—H7	106.9 (16)	C18—O19—H19A	109.5
N7—C8—C9	112.57 (17)	C18—C20—H20C	109.5
N7—C8—H8A	109.1	C18—C20—H20A	109.5
C9—C8—H8A	109.1	H20C—C20—H20A	109.5
N7—C8—H8B	109.1	C18—C20—H20B	109.5
C9—C8—H8B	109.1	H20C—C20—H20B	109.5
H8A—C8—H8B	107.8	H20A—C20—H20B	109.5
N10—C9—C8	111.35 (17)	N10—C21—C22	114.27 (16)
N10—C9—H9A	109.4	N10—C21—H21B	108.7
C8—C9—H9A	109.4	C22—C21—H21B	108.7
N10—C9—H9B	109.4	N10—C21—H21A	108.7
C8—C9—H9B	109.4	C22—C21—H21A	108.7
H9A—C9—H9B	108.0	H21B—C21—H21A	107.6
C21—N10—C11	111.65 (16)	O23—C22—C21	111.97 (18)
C21—N10—C9	109.95 (15)	O23—C22—C24	106.68 (18)
C11—N10—C9	110.95 (16)	C21—C22—C24	110.30 (17)
N10—C11—C12	112.86 (16)	O23—C22—H22A	109.3
N10—C11—H11A	109.0	C21—C22—H22A	109.3
C12—C11—H11A	109.0	C24—C22—H22A	109.3
N10—C11—H11B	109.0	C22—O23—H23A	109.5
C12—C11—H11B	109.0	C22—C24—H24B	109.5
H11A—C11—H11B	107.8	C22—C24—H24C	109.5
N1—C12—C11	114.18 (16)	H24B—C24—H24C	109.5
N1—C12—H12A	108.7	C22—C24—H24A	109.5
C11—C12—H12A	108.7	H24B—C24—H24A	109.5
N1—C12—H12B	108.7	H24C—C24—H24A	109.5
C11—C12—H12B	108.7
C12—N1—C2—C3	71.5 (2)	C2—N1—C12—C11	−170.43 (16)
C13—N1—C2—C3	−159.04 (18)	C13—N1—C12—C11	60.8 (2)
N1—C2—C3—N4	47.1 (3)	N10—C11—C12—N1	68.8 (2)
C2—C3—N4—C17	65.8 (2)	C12—N1—C13—C14	51.8 (2)
C2—C3—N4—C5	−157.65 (18)	C2—N1—C13—C14	−76.4 (2)
C3—N4—C5—C6	87.9 (2)	N1—C13—C14—O15	59.9 (2)
C17—N4—C5—C6	−135.16 (19)	N1—C13—C14—C16	−178.46 (18)
N4—C5—C6—N7	61.1 (2)	C3—N4—C17—C18	−132.93 (19)
C5—C6—N7—C8	−170.04 (17)	C5—N4—C17—C18	91.0 (2)
C6—N7—C8—C9	76.7 (2)	N4—C17—C18—O19	57.9 (2)
N7—C8—C9—N10	58.2 (2)	N4—C17—C18—C20	178.50 (17)
C8—C9—N10—C21	84.9 (2)	C11—N10—C21—C22	79.8 (2)
C8—C9—N10—C11	−151.08 (17)	C9—N10—C21—C22	−156.55 (18)
C21—N10—C11—C12	−155.85 (16)	N10—C21—C22—O23	66.0 (2)
C9—N10—C11—C12	81.1 (2)	N10—C21—C22—C24	−175.32 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O23—H23A···O19	0.84	2.04	2.826 (3)	155
O19—H19A···N1	0.84	2.02	2.826 (2)	160
O15—H15A···N7^i	0.84	1.91	2.751 (2)	178

Symmetry code: (i) x, y+1, z+1.