Trimethyl 2,2',2''-[1,3,5-triazine-2,4,6-tri-yltris-(aza-nedi-yl)]triacetate.

The title compound, C(12)H(18)N(6)O(6), was synthesized via nucleophilic substitution by reacting 2,4,6-trichloro-1,3,5-triazine with glycine methyl ester hydro-chloride in reflux (dried toluene) under anhydrous atmosphere. Individual mol-ecules self-assemble via strong N-H⋯O hydrogen bonds into supra-molecular double tapes running parallel to the [010] crystallographic direction. The close packing of supra-molecular tapes is mediated by geometrical reasons in tandem with a number of weaker N-H⋯O and C-H⋯N hydrogen-bonding inter-actions.

Related literature

For background to nucleophilic reactions of 1,3,5-triazine, see: Blotny (2006 ▶); Giacomelli et al. (2004 ▶). For coordination polymers based on N,N′,N′′-1,3,5-triazine-2,4,6-triyltrisglycine, see: Wang et al. (2007a ▶,b ▶,c ▶). For previous work from our research group on the synthesis of derivatives of 2,4,6-trichloro-1,3,5-triazine from reactions with glycine methyl ester hydro­chloride, see: Vilela et al. (2009 ▶).

Experimental

Crystal data

C12H18N6O6

M = 342.32

Monoclinic,

a = 24.0808 (11) Å

b = 9.4111 (4) Å

c = 15.5791 (7) Å

β = 116.018 (3)°

V = 3172.8 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.12 mm−1

T = 150 K

0.19 × 0.16 × 0.06 mm

Data collection

Bruker X8 Kappa CCD APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1998) ▶ T min = 0.978, T max = 0.993

27764 measured reflections

4182 independent reflections

2794 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.112

S = 1.03

4182 reflections

229 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT-Plus (Bruker, 2005 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2009 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810047604/gk2317sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810047604/gk2317Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C12H18N6O6	F(000) = 1440
Mr = 342.32	Dx = 1.433 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5859 reflections
a = 24.0808 (11) Å	θ = 2.4–27.5°
b = 9.4111 (4) Å	µ = 0.12 mm−1
c = 15.5791 (7) Å	T = 150 K
β = 116.018 (3)°	Plate, colourless
V = 3172.8 (3) Å3	0.19 × 0.16 × 0.06 mm
Z = 8

Bruker X8 Kappa CCD APEXII diffractometer	4182 independent reflections
Radiation source: fine-focus sealed tube	2794 reflections with I > 2σ(I)
graphite	Rint = 0.043
ω and φ scans	θmax = 29.1°, θmin = 3.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −32→32
Tmin = 0.978, Tmax = 0.993	k = −12→12
27764 measured reflections	l = −21→21

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0517P)2 + 1.3693P] where P = (Fo2 + 2Fc2)/3
4182 reflections	(Δ/σ)max < 0.001
229 parameters	Δρmax = 0.24 e Å−3
3 restraints	Δρmin = −0.23 e Å−3

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.

	x	y	z	Uiso*/Ueq
N1	−0.02089 (6)	0.95185 (13)	0.62956 (8)	0.0207 (3)
N2	0.05790 (6)	0.82777 (12)	0.60540 (8)	0.0205 (3)
N3	−0.02269 (6)	0.69671 (12)	0.62052 (8)	0.0215 (3)
N4	0.05746 (6)	1.07016 (13)	0.61287 (9)	0.0230 (3)
H4	0.0395 (8)	1.1562 (13)	0.6156 (13)	0.034*
N5	0.05373 (6)	0.58500 (13)	0.59451 (9)	0.0232 (3)
H5	0.0322 (7)	0.4997 (13)	0.5904 (13)	0.035*
N6	−0.09379 (6)	0.82321 (14)	0.65212 (9)	0.0247 (3)
H6	−0.1074 (8)	0.9110 (13)	0.6648 (13)	0.037*
C1	0.03017 (7)	0.94590 (15)	0.61581 (9)	0.0193 (3)
C2	0.02848 (7)	0.70791 (15)	0.60707 (9)	0.0198 (3)
C3	−0.04387 (7)	0.82330 (15)	0.63353 (9)	0.0198 (3)
C4	0.11497 (7)	1.06968 (16)	0.60499 (10)	0.0243 (3)
H4A	0.1266	1.1685	0.5981	0.029*
H4B	0.1097	1.0161	0.5472	0.029*
C5	0.16599 (7)	1.00236 (16)	0.69218 (11)	0.0249 (3)
C6	0.26088 (9)	0.8795 (3)	0.74867 (15)	0.0550 (6)
H6A	0.2837	0.9527	0.7956	0.083*
H6B	0.2881	0.8356	0.7243	0.083*
H6C	0.2463	0.8067	0.7790	0.083*
C7	0.09765 (7)	0.58905 (16)	0.55491 (11)	0.0255 (3)
H7A	0.1119	0.4912	0.5522	0.031*
H7B	0.1340	0.6456	0.5974	0.031*
C8	0.07052 (7)	0.65318 (15)	0.45528 (11)	0.0243 (3)
C9	0.09384 (10)	0.7424 (2)	0.33368 (14)	0.0436 (5)
H9A	0.0706	0.6681	0.2880	0.065*
H9B	0.1297	0.7701	0.3233	0.065*
H9C	0.0672	0.8253	0.3246	0.065*
C10	−0.12386 (7)	0.69593 (17)	0.66106 (10)	0.0257 (3)
H10A	−0.1432	0.7149	0.7044	0.031*
H10B	−0.0923	0.6210	0.6907	0.031*
C11	−0.17285 (7)	0.64147 (16)	0.56692 (10)	0.0234 (3)
C12	−0.25262 (8)	0.47226 (18)	0.49934 (12)	0.0335 (4)
H12A	−0.2835	0.5442	0.4632	0.050*
H12B	−0.2724	0.3961	0.5188	0.050*
H12C	−0.2345	0.4327	0.4591	0.050*
O1	0.20846 (5)	0.94345 (14)	0.67039 (8)	0.0397 (3)
O2	0.16898 (5)	1.00247 (12)	0.77126 (8)	0.0325 (3)
O3	0.11481 (5)	0.68883 (13)	0.43052 (8)	0.0362 (3)
O4	0.01591 (5)	0.66684 (10)	0.40391 (7)	0.0255 (2)
O5	−0.20447 (5)	0.53693 (12)	0.58329 (7)	0.0282 (3)
O6	−0.18196 (6)	0.68287 (12)	0.48864 (8)	0.0336 (3)

	U11	U22	U33	U12	U13	U23
N1	0.0204 (7)	0.0224 (6)	0.0187 (6)	0.0007 (5)	0.0080 (5)	−0.0003 (5)
N2	0.0225 (7)	0.0194 (6)	0.0188 (6)	0.0006 (5)	0.0085 (5)	0.0002 (5)
N3	0.0245 (7)	0.0217 (7)	0.0190 (6)	−0.0017 (5)	0.0103 (5)	−0.0005 (5)
N4	0.0217 (7)	0.0186 (7)	0.0272 (7)	0.0015 (5)	0.0094 (6)	0.0020 (5)
N5	0.0293 (7)	0.0189 (7)	0.0236 (6)	0.0018 (5)	0.0137 (6)	0.0004 (5)
N6	0.0241 (7)	0.0270 (7)	0.0255 (6)	−0.0025 (6)	0.0132 (6)	−0.0051 (5)
C1	0.0205 (8)	0.0209 (7)	0.0126 (6)	−0.0002 (6)	0.0037 (6)	0.0005 (5)
C2	0.0238 (8)	0.0206 (7)	0.0129 (6)	0.0004 (6)	0.0061 (6)	0.0003 (5)
C3	0.0201 (7)	0.0242 (8)	0.0127 (6)	−0.0006 (6)	0.0051 (6)	−0.0018 (5)
C4	0.0245 (8)	0.0252 (8)	0.0229 (7)	−0.0024 (6)	0.0099 (7)	0.0042 (6)
C5	0.0227 (8)	0.0286 (8)	0.0226 (7)	−0.0042 (6)	0.0093 (7)	−0.0005 (6)
C6	0.0332 (11)	0.0885 (17)	0.0407 (11)	0.0262 (11)	0.0137 (9)	0.0179 (11)
C7	0.0275 (8)	0.0248 (8)	0.0269 (8)	0.0048 (7)	0.0145 (7)	0.0000 (6)
C8	0.0315 (9)	0.0175 (8)	0.0285 (8)	0.0028 (6)	0.0174 (7)	−0.0018 (6)
C9	0.0574 (12)	0.0458 (11)	0.0437 (11)	0.0095 (10)	0.0371 (10)	0.0135 (9)
C10	0.0265 (8)	0.0320 (9)	0.0215 (7)	−0.0045 (7)	0.0130 (7)	−0.0016 (6)
C11	0.0243 (8)	0.0257 (8)	0.0235 (7)	0.0007 (6)	0.0135 (7)	−0.0013 (6)
C12	0.0309 (9)	0.0375 (10)	0.0277 (8)	−0.0100 (8)	0.0089 (7)	−0.0075 (7)
O1	0.0268 (6)	0.0666 (9)	0.0275 (6)	0.0153 (6)	0.0137 (5)	0.0104 (6)
O2	0.0323 (7)	0.0442 (7)	0.0191 (5)	0.0018 (5)	0.0095 (5)	0.0001 (5)
O3	0.0351 (7)	0.0434 (7)	0.0386 (7)	0.0067 (6)	0.0241 (6)	0.0092 (5)
O4	0.0300 (6)	0.0202 (6)	0.0261 (6)	0.0024 (5)	0.0122 (5)	0.0008 (4)
O5	0.0279 (6)	0.0334 (6)	0.0229 (5)	−0.0075 (5)	0.0109 (5)	−0.0018 (4)
O6	0.0390 (7)	0.0393 (7)	0.0218 (5)	−0.0073 (5)	0.0128 (5)	0.0007 (5)

N1—C1	1.3387 (18)	C6—H6A	0.9800
N1—C3	1.3430 (18)	C6—H6B	0.9800
N2—C2	1.3383 (18)	C6—H6C	0.9800
N2—C1	1.3428 (18)	C7—C8	1.520 (2)
N3—C2	1.3417 (18)	C7—H7A	0.9900
N3—C3	1.3458 (18)	C7—H7B	0.9900
N4—C1	1.3519 (19)	C8—O4	1.2096 (19)
N4—C4	1.4430 (18)	C8—O3	1.3266 (18)
N4—H4	0.927 (9)	C9—O3	1.455 (2)
N5—C2	1.3603 (18)	C9—H9A	0.9800
N5—C7	1.4399 (17)	C9—H9B	0.9800
N5—H5	0.943 (9)	C9—H9C	0.9800
N6—C3	1.3545 (18)	C10—C11	1.512 (2)
N6—C10	1.4377 (19)	C10—H10A	0.9900
N6—H6	0.941 (9)	C10—H10B	0.9900
C4—C5	1.514 (2)	C11—O6	1.2052 (18)
C4—H4A	0.9900	C11—O5	1.3355 (18)
C4—H4B	0.9900	C12—O5	1.447 (2)
C5—O2	1.2021 (18)	C12—H12A	0.9800
C5—O1	1.3316 (19)	C12—H12B	0.9800
C6—O1	1.447 (2)	C12—H12C	0.9800
C1—N1—C3	113.31 (12)	H6B—C6—H6C	109.5
C2—N2—C1	113.58 (12)	N5—C7—C8	112.37 (13)
C2—N3—C3	112.87 (12)	N5—C7—H7A	109.1
C1—N4—C4	119.93 (12)	C8—C7—H7A	109.1
C1—N4—H4	120.7 (11)	N5—C7—H7B	109.1
C4—N4—H4	119.4 (11)	C8—C7—H7B	109.1
C2—N5—C7	119.85 (12)	H7A—C7—H7B	107.9
C2—N5—H5	117.8 (11)	O4—C8—O3	124.06 (14)
C7—N5—H5	118.6 (11)	O4—C8—C7	124.99 (13)
C3—N6—C10	123.59 (12)	O3—C8—C7	110.92 (13)
C3—N6—H6	117.9 (11)	O3—C9—H9A	109.5
C10—N6—H6	118.3 (11)	O3—C9—H9B	109.5
N1—C1—N2	126.46 (13)	H9A—C9—H9B	109.5
N1—C1—N4	117.61 (13)	O3—C9—H9C	109.5
N2—C1—N4	115.93 (12)	H9A—C9—H9C	109.5
N2—C2—N3	126.84 (13)	H9B—C9—H9C	109.5
N2—C2—N5	116.12 (12)	N6—C10—C11	113.58 (12)
N3—C2—N5	117.05 (13)	N6—C10—H10A	108.8
N1—C3—N3	126.83 (12)	C11—C10—H10A	108.8
N1—C3—N6	115.64 (12)	N6—C10—H10B	108.8
N3—C3—N6	117.53 (12)	C11—C10—H10B	108.8
N4—C4—C5	110.88 (11)	H10A—C10—H10B	107.7
N4—C4—H4A	109.5	O6—C11—O5	124.43 (14)
C5—C4—H4A	109.5	O6—C11—C10	126.17 (14)
N4—C4—H4B	109.5	O5—C11—C10	109.39 (12)
C5—C4—H4B	109.5	O5—C12—H12A	109.5
H4A—C4—H4B	108.1	O5—C12—H12B	109.5
O2—C5—O1	123.66 (15)	H12A—C12—H12B	109.5
O2—C5—C4	125.40 (14)	O5—C12—H12C	109.5
O1—C5—C4	110.93 (12)	H12A—C12—H12C	109.5
O1—C6—H6A	109.5	H12B—C12—H12C	109.5
O1—C6—H6B	109.5	C5—O1—C6	116.24 (13)
H6A—C6—H6B	109.5	C8—O3—C9	115.57 (14)
O1—C6—H6C	109.5	C11—O5—C12	115.80 (12)
H6A—C6—H6C	109.5
C3—N1—C1—N2	0.7 (2)	C10—N6—C3—N3	1.7 (2)
C3—N1—C1—N4	−178.61 (12)	C1—N4—C4—C5	−63.99 (17)
C2—N2—C1—N1	1.9 (2)	N4—C4—C5—O2	−29.1 (2)
C2—N2—C1—N4	−178.83 (12)	N4—C4—C5—O1	151.76 (13)
C4—N4—C1—N1	175.63 (12)	C2—N5—C7—C8	−60.15 (18)
C4—N4—C1—N2	−3.74 (19)	N5—C7—C8—O4	−17.7 (2)
C1—N2—C2—N3	−2.1 (2)	N5—C7—C8—O3	164.11 (12)
C1—N2—C2—N5	178.47 (12)	C3—N6—C10—C11	−86.95 (18)
C3—N3—C2—N2	−0.3 (2)	N6—C10—C11—O6	10.5 (2)
C3—N3—C2—N5	179.17 (12)	N6—C10—C11—O5	−170.70 (12)
C7—N5—C2—N2	−17.1 (2)	O2—C5—O1—C6	−1.1 (2)
C7—N5—C2—N3	163.40 (13)	C4—C5—O1—C6	178.03 (16)
C1—N1—C3—N3	−3.6 (2)	O4—C8—O3—C9	−2.2 (2)
C1—N1—C3—N6	176.83 (12)	C7—C8—O3—C9	175.96 (13)
C2—N3—C3—N1	3.4 (2)	O6—C11—O5—C12	−0.2 (2)
C2—N3—C3—N6	−177.03 (12)	C10—C11—O5—C12	−179.05 (13)
C10—N6—C3—N1	−178.64 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O4i	0.93 (1)	2.07 (1)	2.9851 (16)	168 (2)
N5—H5···O4ii	0.94 (1)	1.97 (1)	2.9097 (16)	172 (2)
N6—H6···O2iii	0.94 (1)	2.29 (1)	3.0733 (17)	141 (1)
C9—H9C···N1i	0.98	2.62	3.546 (3)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯O4i	0.93 (1)	2.07 (1)	2.9851 (16)	168 (2)
N5—H5⋯O4ii	0.94 (1)	1.97 (1)	2.9097 (16)	172 (2)
N6—H6⋯O2iii	0.94 (1)	2.29 (1)	3.0733 (17)	141 (1)
C9—H9C⋯N1i	0.98	2.62	3.546 (3)	158

Symmetry codes: (i) ; (ii) ; (iii) .