Tris(2-azido­ethyl) benzene-1,3,5-tricarboxyl­ate

In the title mol­ecule, C₁₅H₁₅N₉O₆, all bond lengths and angles are within normal ranges. In the crystal structure, mol­ecules are linked into centrosymmetric dimers by weak C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.065
• wR factor = 0.191
• Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    N4     -   C15     ..       7.63 su
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for         N8

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.15 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.15 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         N7
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C15
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N2
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N5

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Tris(2-azidoethyl) benzene-1,3,5-tricarboxylate

Crystal data

C15H15N9O6	Z = 2
Mr = 417.36	F(000) = 432
Triclinic, P1	Dx = 1.436 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.7391 (9) Å	Cell parameters from 1412 reflections
b = 10.6986 (14) Å	θ = 2.2–24.5°
c = 14.5075 (19) Å	µ = 0.12 mm^−1
α = 100.108 (2)°	T = 293 K
β = 98.961 (2)°	Block, colourless
γ = 106.181 (2)°	0.21 × 0.11 × 0.09 mm
V = 965.5 (2) Å^3

Data collection

Siemens SMART 1000 CCD area-detector diffractometer	3718 independent reflections
Radiation source: fine-focus sealed tube	2672 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.015
Detector resolution: 8.33 pixels mm^-1	θmax = 26.0°, θmin = 1.5°
ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −8→13
Tmin = 0.976, Tmax = 0.990	l = −17→13
5138 measured reflections

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.191	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0947P)^2 + 0.3141P] where P = (Fo^2 + 2Fc^2)/3
3718 reflections	(Δ/σ)max < 0.001
271 parameters	Δρmax = 0.46 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3

Special details

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
O1	0.4043 (3)	0.35240 (17)	1.08876 (12)	0.0641 (5)
O2	0.2973 (3)	0.22495 (15)	0.93944 (11)	0.0512 (4)
O3	0.1639 (4)	−0.35735 (18)	1.00675 (15)	0.0757 (6)
O4	0.0914 (3)	−0.26362 (16)	0.88516 (12)	0.0607 (5)
O5	0.4287 (4)	−0.0745 (2)	1.33694 (13)	0.0760 (6)
O6	0.4424 (4)	0.14001 (19)	1.35797 (12)	0.0734 (6)
N1	0.0943 (4)	0.2595 (3)	0.74960 (19)	0.0811 (8)
N2	0.0634 (5)	0.2071 (3)	0.6650 (2)	0.0953 (10)
N3	0.0183 (7)	0.1553 (6)	0.5861 (3)	0.1521 (18)
N4	0.6850 (6)	0.3943 (3)	1.4998 (2)	0.1101 (12)
N5	0.6702 (5)	0.4337 (3)	1.4266 (2)	0.0867 (9)
N6	0.6734 (7)	0.4794 (4)	1.3626 (3)	0.1184 (13)
N7	0.0222 (8)	−0.2955 (5)	0.6790 (3)	0.1299 (15)
N8	0.0528 (6)	−0.1777 (5)	0.7082 (2)	0.0992 (10)
N9	0.0962 (7)	−0.0641 (5)	0.7294 (4)	0.1300 (14)
C1	0.3196 (3)	0.1168 (2)	1.06683 (15)	0.0387 (5)
C2	0.2461 (3)	−0.0083 (2)	1.00376 (16)	0.0383 (5)
H2A	0.2080	−0.0157	0.9381	0.046*
C3	0.2298 (3)	−0.1222 (2)	1.03959 (16)	0.0411 (5)
C4	0.2855 (4)	−0.1110 (2)	1.13758 (16)	0.0446 (5)
H4B	0.2741	−0.1875	1.1611	0.054*
C5	0.3579 (4)	0.0135 (2)	1.20051 (16)	0.0456 (5)
C6	0.3757 (4)	0.1278 (2)	1.16463 (16)	0.0440 (5)
H6A	0.4253	0.2118	1.2065	0.053*
C7	0.3449 (4)	0.2440 (2)	1.03419 (16)	0.0441 (5)
C8	0.3381 (5)	0.3470 (2)	0.90398 (18)	0.0589 (7)
H8A	0.4794	0.4065	0.9346	0.071*
H8B	0.2372	0.3927	0.9188	0.071*
C9	0.3179 (5)	0.3107 (3)	0.79820 (19)	0.0631 (7)
H9A	0.3884	0.3889	0.7766	0.076*
H9B	0.3855	0.2432	0.7824	0.076*
C10	0.1584 (4)	−0.2598 (2)	0.97702 (18)	0.0502 (6)
C11	0.0275 (6)	−0.3938 (3)	0.8200 (2)	0.0759 (9)
H11A	−0.0593	−0.4606	0.8469	0.091*
H11B	0.1511	−0.4190	0.8095	0.091*
C12	−0.0931 (7)	−0.3860 (4)	0.7293 (3)	0.1005 (12)
H12A	−0.1470	−0.4748	0.6873	0.121*
H12B	−0.2141	−0.3591	0.7420	0.121*
C13	0.4131 (4)	0.0192 (3)	1.30457 (18)	0.0559 (6)
C14	0.4904 (7)	0.1520 (3)	1.4607 (2)	0.0924 (12)
H14A	0.3780	0.0886	1.4787	0.111*
H14B	0.6213	0.1327	1.4794	0.111*
C15	0.5111 (9)	0.2868 (4)	1.5087 (3)	0.1207 (18)
H15A	0.3814	0.3048	1.4852	0.145*
H15B	0.5207	0.2895	1.5765	0.145*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0993 (15)	0.0379 (9)	0.0484 (10)	0.0137 (9)	0.0116 (9)	0.0095 (8)
O2	0.0706 (11)	0.0371 (8)	0.0405 (9)	0.0099 (8)	0.0031 (8)	0.0145 (7)
O3	0.1087 (17)	0.0382 (10)	0.0737 (13)	0.0189 (10)	0.0078 (11)	0.0136 (9)
O4	0.0827 (13)	0.0403 (9)	0.0485 (10)	0.0141 (8)	0.0043 (9)	0.0007 (8)
O5	0.1164 (18)	0.0589 (12)	0.0522 (11)	0.0259 (11)	0.0058 (11)	0.0255 (9)
O6	0.1220 (18)	0.0541 (11)	0.0358 (10)	0.0188 (11)	0.0057 (10)	0.0133 (8)
N1	0.0801 (18)	0.102 (2)	0.0534 (16)	0.0183 (15)	0.0067 (13)	0.0207 (14)
N2	0.090 (2)	0.114 (3)	0.062 (2)	0.0091 (17)	0.0008 (15)	0.0218 (17)
N3	0.135 (3)	0.205 (5)	0.066 (2)	0.007 (3)	−0.002 (2)	−0.003 (3)
N4	0.171 (3)	0.077 (2)	0.0499 (16)	0.000 (2)	0.0057 (18)	0.0096 (14)
N5	0.134 (3)	0.0624 (16)	0.0679 (18)	0.0335 (16)	0.0280 (17)	0.0146 (14)
N6	0.179 (4)	0.102 (3)	0.110 (3)	0.063 (3)	0.061 (3)	0.059 (2)
N7	0.217 (5)	0.118 (3)	0.073 (2)	0.078 (3)	0.046 (3)	0.015 (2)
N8	0.112 (3)	0.116 (3)	0.082 (2)	0.051 (2)	0.0213 (18)	0.031 (2)
N9	0.128 (3)	0.110 (3)	0.159 (4)	0.034 (3)	0.039 (3)	0.048 (3)
C1	0.0400 (11)	0.0367 (11)	0.0410 (12)	0.0115 (9)	0.0098 (9)	0.0129 (9)
C2	0.0373 (11)	0.0401 (11)	0.0364 (11)	0.0105 (9)	0.0058 (8)	0.0107 (9)
C3	0.0406 (12)	0.0364 (11)	0.0461 (13)	0.0112 (9)	0.0101 (9)	0.0102 (9)
C4	0.0495 (13)	0.0404 (12)	0.0468 (13)	0.0137 (10)	0.0107 (10)	0.0177 (10)
C5	0.0497 (13)	0.0456 (13)	0.0406 (12)	0.0126 (10)	0.0077 (10)	0.0138 (10)
C6	0.0521 (13)	0.0369 (11)	0.0408 (12)	0.0107 (10)	0.0090 (10)	0.0096 (9)
C7	0.0519 (13)	0.0369 (12)	0.0415 (13)	0.0101 (10)	0.0083 (10)	0.0118 (10)
C8	0.0810 (19)	0.0417 (13)	0.0516 (15)	0.0132 (12)	0.0066 (13)	0.0215 (11)
C9	0.0737 (18)	0.0604 (16)	0.0558 (16)	0.0151 (14)	0.0106 (13)	0.0277 (13)
C10	0.0531 (14)	0.0381 (13)	0.0568 (15)	0.0108 (11)	0.0126 (11)	0.0097 (11)
C11	0.102 (2)	0.0480 (16)	0.0624 (18)	0.0183 (15)	0.0076 (17)	−0.0091 (13)
C12	0.119 (3)	0.086 (3)	0.070 (2)	0.026 (2)	−0.004 (2)	−0.023 (2)
C13	0.0709 (17)	0.0474 (14)	0.0452 (14)	0.0115 (12)	0.0065 (12)	0.0166 (11)
C14	0.158 (4)	0.067 (2)	0.0364 (15)	0.017 (2)	0.0055 (17)	0.0133 (14)
C15	0.221 (5)	0.075 (2)	0.0489 (19)	0.023 (3)	0.025 (2)	0.0123 (17)

Geometric parameters (Å, º)

O1—C7	1.205 (3)	C3—C4	1.387 (3)
O2—C7	1.327 (3)	C3—C10	1.491 (3)
O2—C8	1.458 (3)	C4—C5	1.385 (3)
O3—C10	1.204 (3)	C4—H4B	0.9300
O4—C10	1.329 (3)	C5—C6	1.393 (3)
O4—C11	1.448 (3)	C5—C13	1.484 (3)
O5—C13	1.202 (3)	C6—H6A	0.9300
O6—C13	1.330 (3)	C8—C9	1.490 (4)
O6—C14	1.450 (3)	C8—H8A	0.9700
N1—N2	1.216 (4)	C8—H8B	0.9700
N1—C9	1.463 (4)	C9—H9A	0.9700
N2—N3	1.133 (4)	C9—H9B	0.9700
N4—N5	1.210 (4)	C11—C12	1.464 (5)
N4—C15	1.436 (6)	C11—H11A	0.9700
N5—N6	1.123 (4)	C11—H11B	0.9700
N7—N8	1.205 (5)	C12—H12A	0.9700
N7—C12	1.441 (6)	C12—H12B	0.9700
N8—N9	1.140 (5)	C14—C15	1.445 (5)
C1—C6	1.385 (3)	C14—H14A	0.9700
C1—C2	1.390 (3)	C14—H14B	0.9700
C1—C7	1.492 (3)	C15—H15A	0.9700
C2—C3	1.390 (3)	C15—H15B	0.9700
C2—H2A	0.9300
C7—O2—C8	114.90 (18)	N1—C9—C8	110.0 (2)
C10—O4—C11	116.0 (2)	N1—C9—H9A	109.7
C13—O6—C14	115.2 (2)	C8—C9—H9A	109.7
N2—N1—C9	113.9 (3)	N1—C9—H9B	109.7
N3—N2—N1	174.7 (4)	C8—C9—H9B	109.7
N5—N4—C15	118.0 (4)	H9A—C9—H9B	108.2
N6—N5—N4	173.6 (5)	O3—C10—O4	123.5 (2)
N8—N7—C12	117.6 (4)	O3—C10—C3	123.3 (2)
N9—N8—N7	172.7 (5)	O4—C10—C3	113.2 (2)
C6—C1—C2	120.2 (2)	O4—C11—C12	108.1 (3)
C6—C1—C7	116.89 (19)	O4—C11—H11A	110.1
C2—C1—C7	122.87 (19)	C12—C11—H11A	110.1
C1—C2—C3	119.5 (2)	O4—C11—H11B	110.1
C1—C2—H2A	120.3	C12—C11—H11B	110.1
C3—C2—H2A	120.3	H11A—C11—H11B	108.4
C4—C3—C2	120.2 (2)	N7—C12—C11	115.6 (4)
C4—C3—C10	116.8 (2)	N7—C12—H12A	108.4
C2—C3—C10	123.1 (2)	C11—C12—H12A	108.4
C5—C4—C3	120.4 (2)	N7—C12—H12B	108.4
C5—C4—H4B	119.8	C11—C12—H12B	108.4
C3—C4—H4B	119.8	H12A—C12—H12B	107.4
C4—C5—C6	119.5 (2)	O5—C13—O6	123.9 (2)
C4—C5—C13	118.0 (2)	O5—C13—C5	124.1 (2)
C6—C5—C13	122.6 (2)	O6—C13—C5	112.1 (2)
C1—C6—C5	120.2 (2)	C15—C14—O6	108.7 (3)
C1—C6—H6A	119.9	C15—C14—H14A	109.9
C5—C6—H6A	119.9	O6—C14—H14A	109.9
O1—C7—O2	124.0 (2)	C15—C14—H14B	109.9
O1—C7—C1	123.0 (2)	O6—C14—H14B	109.9
O2—C7—C1	113.00 (18)	H14A—C14—H14B	108.3
O2—C8—C9	108.7 (2)	N4—C15—C14	118.3 (4)
O2—C8—H8A	109.9	N4—C15—H15A	107.7
C9—C8—H8A	109.9	C14—C15—H15A	107.7
O2—C8—H8B	109.9	N4—C15—H15B	107.7
C9—C8—H8B	109.9	C14—C15—H15B	107.7
H8A—C8—H8B	108.3	H15A—C15—H15B	107.1
C6—C1—C2—C3	−0.2 (3)	O2—C8—C9—N1	78.2 (3)
C7—C1—C2—C3	179.0 (2)	C11—O4—C10—O3	−1.3 (4)
C1—C2—C3—C4	0.4 (3)	C11—O4—C10—C3	177.7 (2)
C1—C2—C3—C10	−178.2 (2)	C4—C3—C10—O3	−6.3 (4)
C2—C3—C4—C5	−0.1 (3)	C2—C3—C10—O3	172.4 (2)
C10—C3—C4—C5	178.6 (2)	C4—C3—C10—O4	174.8 (2)
C3—C4—C5—C6	−0.4 (3)	C2—C3—C10—O4	−6.6 (3)
C3—C4—C5—C13	179.5 (2)	C10—O4—C11—C12	164.8 (3)
C2—C1—C6—C5	−0.3 (3)	N8—N7—C12—C11	−77.2 (5)
C7—C1—C6—C5	−179.6 (2)	O4—C11—C12—N7	63.2 (4)
C4—C5—C6—C1	0.6 (3)	C14—O6—C13—O5	−1.5 (5)
C13—C5—C6—C1	−179.3 (2)	C14—O6—C13—C5	178.1 (3)
C8—O2—C7—O1	4.7 (4)	C4—C5—C13—O5	11.3 (4)
C8—O2—C7—C1	−174.7 (2)	C6—C5—C13—O5	−168.9 (3)
C6—C1—C7—O1	−2.4 (3)	C4—C5—C13—O6	−168.4 (2)
C2—C1—C7—O1	178.4 (2)	C6—C5—C13—O6	11.5 (4)
C6—C1—C7—O2	177.0 (2)	C13—O6—C14—C15	−178.2 (3)
C2—C1—C7—O2	−2.3 (3)	N5—N4—C15—C14	79.0 (6)
C7—O2—C8—C9	169.1 (2)	O6—C14—C15—N4	−66.5 (5)
N2—N1—C9—C8	−168.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O1^i	0.97	2.58	3.175 (3)	120

Symmetry code: (i) −x+1, −y+1, −z+2.