Bis(2-azido­ethyl) terephthalate

The molecule of the title compound, C₁₂H₁₂N₆O₄, is arranged around an inversion center located at the mid-point of the benzene ring. In the crystal structure, mol­ecules are linked into ribbons along the a axis by weak C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.045
• wR factor = 0.123
• Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for         N2

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.96
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
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         N3

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   5 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
   2 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: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON.

Bis(2-azidoethyl) terephthalate

Crystal data

C12H12N6O4	Z = 1
Mr = 304.28	F(000) = 158
Triclinic, P1	Dx = 1.407 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.2833 (8) Å	Cell parameters from 824 reflections
b = 5.7039 (8) Å	θ = 3.6–25.9°
c = 12.0883 (18) Å	µ = 0.11 mm^−1
α = 88.052 (2)°	T = 293 K
β = 85.975 (2)°	Column, colourless
γ = 81.389 (2)°	0.26 × 0.15 × 0.12 mm
V = 359.19 (9) Å^3

Data collection

Siemens SMART 1000 CCD area-detector diffractometer	1366 independent reflections
Radiation source: fine-focus sealed tube	1104 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.007
Detector resolution: 8.33 pixels mm^-1	θmax = 26.0°, θmin = 1.7°
ω scans	h = −6→6
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −7→6
Tmin = 0.972, Tmax = 0.987	l = −14→9
2001 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.123	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0609P)^2 + 0.0623P] where P = (Fo^2 + 2Fc^2)/3
1366 reflections	(Δ/σ)max < 0.001
100 parameters	Δρmax = 0.12 e Å^−3
0 restraints	Δρmin = −0.19 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	0.4205 (2)	0.52724 (18)	0.72197 (9)	0.0591 (3)
O2	0.5223 (3)	0.1655 (2)	0.65231 (10)	0.0770 (4)
N1	0.1169 (4)	1.0794 (5)	0.8717 (2)	0.1252 (9)
N2	0.2659 (3)	0.9298 (3)	0.89324 (14)	0.0752 (5)
N3	0.4133 (4)	0.7682 (3)	0.92911 (13)	0.0914 (6)
C1	0.6427 (4)	0.6857 (3)	0.85774 (17)	0.0745 (5)
H1A	0.7902	0.6559	0.9024	0.089*
H1B	0.6722	0.8090	0.8032	0.089*
C2	0.6175 (3)	0.4650 (3)	0.79954 (14)	0.0616 (5)
H2A	0.7790	0.4029	0.7605	0.074*
H2B	0.5696	0.3450	0.8525	0.074*
C3	0.3946 (3)	0.3584 (3)	0.65108 (12)	0.0530 (4)
C4	0.1910 (3)	0.4366 (2)	0.57324 (11)	0.0486 (4)
C5	0.0434 (3)	0.6598 (3)	0.57757 (13)	0.0554 (4)
H5A	0.0732	0.7673	0.6296	0.066*
C6	0.1463 (3)	0.2779 (3)	0.49470 (13)	0.0561 (4)
H6A	0.2453	0.1288	0.4910	0.067*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0717 (7)	0.0483 (6)	0.0550 (6)	0.0043 (5)	−0.0138 (5)	−0.0056 (5)
O2	0.0983 (10)	0.0549 (7)	0.0706 (8)	0.0212 (6)	−0.0207 (7)	−0.0120 (6)
N1	0.0815 (14)	0.131 (2)	0.152 (2)	0.0091 (13)	−0.0085 (13)	0.0488 (17)
N2	0.0807 (11)	0.0737 (11)	0.0742 (10)	−0.0164 (9)	−0.0184 (9)	0.0027 (8)
N3	0.1335 (16)	0.0744 (11)	0.0574 (9)	0.0179 (11)	−0.0125 (10)	−0.0062 (8)
C1	0.0851 (13)	0.0652 (11)	0.0760 (12)	−0.0104 (9)	−0.0272 (10)	−0.0002 (9)
C2	0.0670 (10)	0.0574 (10)	0.0577 (9)	0.0022 (8)	−0.0118 (8)	0.0019 (7)
C3	0.0650 (10)	0.0454 (8)	0.0449 (8)	0.0010 (7)	0.0030 (7)	−0.0032 (6)
C4	0.0596 (9)	0.0409 (8)	0.0425 (8)	−0.0014 (6)	0.0035 (6)	−0.0015 (6)
C5	0.0724 (10)	0.0419 (8)	0.0495 (8)	0.0008 (7)	−0.0033 (7)	−0.0101 (6)
C6	0.0711 (10)	0.0392 (8)	0.0536 (9)	0.0063 (7)	−0.0028 (7)	−0.0066 (6)

Geometric parameters (Å, º)

O1—C3	1.3388 (19)	C2—H2A	0.9700
O1—C2	1.4464 (19)	C2—H2B	0.9700
O2—C3	1.2019 (18)	C3—C4	1.487 (2)
N1—N2	1.108 (2)	C4—C6	1.389 (2)
N2—N3	1.204 (2)	C4—C5	1.390 (2)
N3—C1	1.465 (3)	C5—C6^i	1.375 (2)
C1—C2	1.490 (3)	C5—H5A	0.9300
C1—H1A	0.9700	C6—C5^i	1.375 (2)
C1—H1B	0.9700	C6—H6A	0.9300
C3—O1—C2	115.68 (12)	H2A—C2—H2B	108.6
N1—N2—N3	172.2 (2)	O2—C3—O1	122.76 (15)
N2—N3—C1	116.67 (17)	O2—C3—C4	124.73 (15)
N3—C1—C2	111.95 (17)	O1—C3—C4	112.51 (12)
N3—C1—H1A	109.2	C6—C4—C5	119.42 (15)
C2—C1—H1A	109.2	C6—C4—C3	118.19 (13)
N3—C1—H1B	109.2	C5—C4—C3	122.39 (14)
C2—C1—H1B	109.2	C6^i—C5—C4	120.25 (14)
H1A—C1—H1B	107.9	C6^i—C5—H5A	119.9
O1—C2—C1	107.06 (13)	C4—C5—H5A	119.9
O1—C2—H2A	110.3	C5^i—C6—C4	120.33 (14)
C1—C2—H2A	110.3	C5^i—C6—H6A	119.8
O1—C2—H2B	110.3	C4—C6—H6A	119.8
C1—C2—H2B	110.3
N2—N3—C1—C2	−101.0 (2)	O2—C3—C4—C5	178.01 (16)
C3—O1—C2—C1	171.27 (15)	O1—C3—C4—C5	−1.4 (2)
N3—C1—C2—O1	67.26 (19)	C6—C4—C5—C6^i	0.5 (3)
C2—O1—C3—O2	1.3 (2)	C3—C4—C5—C6^i	−178.62 (14)
C2—O1—C3—C4	−179.29 (12)	C5—C4—C6—C5^i	−0.5 (3)
O2—C3—C4—C6	−1.1 (2)	C3—C4—C6—C5^i	178.66 (14)
O1—C3—C4—C6	179.50 (13)

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O2^ii	0.93	2.57	3.341 (2)	140

Symmetry code: (ii) −x+1, −y, −z+1.