In the non-planar molecule of the title compound, C
12H
12N
6O
4, one azide group lies almost in the plane of the benzene ring, while the other is inclined above this plane. In the crystal structure, the molecules are linked into chains along the
a axis by C—H
N hydrogen bonds. The packing is further stabilized by dipole–dipole and van der Waals interactions.
Supporting information
CCDC reference: 601236
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.053
- wR factor = 0.142
- Data-to-parameter ratio = 13.1
checkCIF/PLATON results
No syntax errors found
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
PLAT230_ALERT_2_C Hirshfeld Test Diff for N4 - N5 .. 6.61 su
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
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1
C12 H12 N6 O4
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
7 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
3 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
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).
Bis(2-azidoethyl) isophthalate
top
Crystal data top
C12H12N6O4 | F(000) = 632 |
Mr = 304.28 | Dx = 1.394 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1426 reflections |
a = 10.616 (3) Å | θ = 3.0–21.4° |
b = 7.2262 (19) Å | µ = 0.11 mm−1 |
c = 21.640 (5) Å | T = 293 K |
β = 119.164 (10)° | Needle, colourless |
V = 1449.6 (7) Å3 | 0.30 × 0.06 × 0.06 mm |
Z = 4 | |
Data collection top
Siemens SMART 1000 CCD area-detector diffractometer | 2756 independent reflections |
Radiation source: fine-focus sealed tube | 1767 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
Detector resolution: 8.33 pixels mm-1 | θmax = 25.8°, θmin = 2.2° |
ω scans | h = −10→12 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −7→8 |
Tmin = 0.968, Tmax = 0.994 | l = −26→26 |
8307 measured reflections | |
Refinement top
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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.142 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0614P)2 + 0.2657P] where P = (Fo2 + 2Fc2)/3 |
2756 reflections | (Δ/σ)max < 0.001 |
211 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
Special details top
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.47069 (16) | −0.3537 (2) | −0.12170 (7) | 0.0575 (5) | |
O2 | 0.23135 (18) | −0.3548 (3) | −0.16842 (9) | 0.0809 (6) | |
O3 | 0.70533 (19) | −0.0966 (3) | 0.19206 (8) | 0.0786 (6) | |
O4 | 0.78910 (16) | −0.2251 (2) | 0.12540 (7) | 0.0577 (5) | |
N1 | 0.8921 (3) | −0.1779 (4) | −0.14579 (19) | 0.1210 (11) | |
N2 | 0.7776 (3) | −0.2100 (3) | −0.15997 (11) | 0.0716 (6) | |
N3 | 0.6510 (2) | −0.2255 (3) | −0.17660 (11) | 0.0657 (6) | |
N4 | 1.0498 (3) | −0.2841 (4) | 0.11207 (14) | 0.0952 (8) | |
N5 | 0.9523 (3) | −0.3200 (4) | 0.05241 (16) | 0.0977 (9) | |
N6 | 0.8699 (4) | −0.3471 (6) | −0.00540 (16) | 0.1541 (16) | |
C1 | 0.5993 (3) | −0.4182 (4) | −0.18273 (13) | 0.0651 (7) | |
H1A | 0.5948 | −0.4766 | −0.2241 | 0.066 (7)* | |
H1B | 0.6648 | −0.4888 | −0.1413 | 0.078 (8)* | |
C2 | 0.4539 (3) | −0.4135 (4) | −0.18909 (12) | 0.0678 (7) | |
H2A | 0.4104 | −0.5355 | −0.2009 | 0.075 (8)* | |
H2B | 0.3921 | −0.3282 | −0.2262 | 0.072 (8)* | |
C3 | 0.3497 (2) | −0.3285 (3) | −0.11872 (12) | 0.0527 (6) | |
C4 | 0.3784 (2) | −0.2632 (3) | −0.04763 (11) | 0.0483 (5) | |
C5 | 0.2617 (3) | −0.2129 (4) | −0.03903 (14) | 0.0650 (7) | |
H5A | 0.1686 | −0.2238 | −0.0769 | 0.075 (8)* | |
C6 | 0.2824 (3) | −0.1472 (4) | 0.02484 (15) | 0.0737 (8) | |
H6A | 0.2036 | −0.1134 | 0.0301 | 0.080 (8)* | |
C7 | 0.4191 (3) | −0.1316 (3) | 0.08072 (14) | 0.0631 (7) | |
H7A | 0.4326 | −0.0860 | 0.1237 | 0.079 (8)* | |
C8 | 0.5382 (2) | −0.1829 (3) | 0.07405 (11) | 0.0471 (5) | |
C9 | 0.5170 (2) | −0.2492 (3) | 0.00925 (10) | 0.0439 (5) | |
H9A | 0.5956 | −0.2843 | 0.0041 | 0.043 (6)* | |
C10 | 0.6838 (3) | −0.1622 (3) | 0.13653 (11) | 0.0521 (6) | |
C11 | 0.9336 (3) | −0.2180 (4) | 0.18482 (11) | 0.0668 (7) | |
H11A | 0.9713 | −0.0930 | 0.1911 | 0.075 (8)* | |
H11B | 0.9332 | −0.2549 | 0.2278 | 0.083 (8)* | |
C12 | 1.0251 (3) | −0.3468 (4) | 0.16984 (13) | 0.0736 (8) | |
H12A | 0.9792 | −0.4674 | 0.1578 | 0.089 (10)* | |
H12B | 1.1175 | −0.3607 | 0.2124 | 0.094 (9)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0509 (10) | 0.0761 (12) | 0.0418 (8) | −0.0084 (8) | 0.0197 (7) | −0.0055 (7) |
O2 | 0.0491 (11) | 0.1178 (17) | 0.0572 (11) | −0.0186 (10) | 0.0113 (9) | 0.0004 (10) |
O3 | 0.0769 (13) | 0.1092 (15) | 0.0528 (10) | −0.0053 (11) | 0.0340 (9) | −0.0208 (10) |
O4 | 0.0480 (9) | 0.0796 (12) | 0.0397 (8) | 0.0049 (8) | 0.0167 (7) | −0.0027 (7) |
N1 | 0.0649 (18) | 0.119 (3) | 0.168 (3) | −0.0097 (17) | 0.048 (2) | 0.001 (2) |
N2 | 0.0611 (16) | 0.0766 (17) | 0.0740 (15) | 0.0006 (13) | 0.0305 (12) | 0.0038 (12) |
N3 | 0.0570 (14) | 0.0704 (15) | 0.0741 (14) | 0.0019 (11) | 0.0354 (11) | 0.0078 (11) |
N4 | 0.0772 (18) | 0.139 (2) | 0.0771 (17) | −0.0139 (17) | 0.0439 (15) | −0.0144 (16) |
N5 | 0.095 (2) | 0.137 (3) | 0.0738 (18) | 0.0258 (18) | 0.0509 (17) | 0.0120 (18) |
N6 | 0.148 (3) | 0.238 (4) | 0.0628 (18) | 0.038 (3) | 0.041 (2) | 0.008 (2) |
C1 | 0.0785 (18) | 0.0686 (18) | 0.0537 (15) | −0.0073 (14) | 0.0364 (14) | −0.0064 (13) |
C2 | 0.0729 (18) | 0.086 (2) | 0.0426 (13) | −0.0217 (16) | 0.0265 (13) | −0.0091 (13) |
C3 | 0.0449 (14) | 0.0566 (15) | 0.0495 (13) | −0.0096 (11) | 0.0174 (11) | 0.0082 (10) |
C4 | 0.0448 (13) | 0.0456 (13) | 0.0526 (13) | −0.0051 (10) | 0.0223 (11) | 0.0050 (10) |
C5 | 0.0444 (15) | 0.0724 (18) | 0.0753 (17) | −0.0013 (12) | 0.0269 (14) | 0.0036 (14) |
C6 | 0.0546 (17) | 0.086 (2) | 0.093 (2) | 0.0059 (14) | 0.0458 (16) | −0.0061 (16) |
C7 | 0.0692 (18) | 0.0648 (17) | 0.0715 (17) | −0.0018 (13) | 0.0469 (15) | −0.0042 (13) |
C8 | 0.0521 (13) | 0.0432 (13) | 0.0510 (13) | 0.0003 (10) | 0.0290 (11) | 0.0034 (9) |
C9 | 0.0437 (12) | 0.0418 (12) | 0.0490 (12) | 0.0022 (10) | 0.0248 (10) | 0.0062 (9) |
C10 | 0.0607 (15) | 0.0534 (15) | 0.0482 (13) | −0.0026 (11) | 0.0311 (12) | 0.0020 (10) |
C11 | 0.0530 (15) | 0.094 (2) | 0.0418 (13) | −0.0046 (14) | 0.0142 (11) | −0.0070 (12) |
C12 | 0.0517 (15) | 0.100 (2) | 0.0528 (15) | 0.0034 (16) | 0.0123 (13) | −0.0012 (14) |
Geometric parameters (Å, º) top
O1—C3 | 1.330 (3) | C3—C4 | 1.492 (3) |
O1—C2 | 1.446 (3) | C4—C5 | 1.387 (3) |
O2—C3 | 1.206 (3) | C4—C9 | 1.388 (3) |
O3—C10 | 1.206 (2) | C5—C6 | 1.374 (4) |
O4—C10 | 1.333 (3) | C5—H5A | 0.9300 |
O4—C11 | 1.445 (3) | C6—C7 | 1.368 (3) |
N1—N2 | 1.123 (3) | C6—H6A | 0.9300 |
N2—N3 | 1.215 (3) | C7—C8 | 1.391 (3) |
N3—C1 | 1.479 (3) | C7—H7A | 0.9300 |
N4—N5 | 1.226 (3) | C8—C9 | 1.392 (3) |
N4—C12 | 1.469 (3) | C8—C10 | 1.484 (3) |
N5—N6 | 1.141 (4) | C9—H9A | 0.9299 |
C1—C2 | 1.482 (3) | C11—C12 | 1.491 (3) |
C1—H1A | 0.9698 | C11—H11A | 0.9700 |
C1—H1B | 0.9700 | C11—H11B | 0.9699 |
C2—H2A | 0.9700 | C12—H12A | 0.9700 |
C2—H2B | 0.9700 | C12—H12B | 0.9700 |
| | | |
C3—O1—C2 | 116.26 (17) | C7—C6—C5 | 119.9 (2) |
C10—O4—C11 | 116.58 (17) | C7—C6—H6A | 120.0 |
N1—N2—N3 | 173.3 (3) | C5—C6—H6A | 120.1 |
N2—N3—C1 | 115.0 (2) | C6—C7—C8 | 120.8 (2) |
N5—N4—C12 | 114.9 (2) | C6—C7—H7A | 119.6 |
N6—N5—N4 | 173.5 (3) | C8—C7—H7A | 119.6 |
N3—C1—C2 | 108.1 (2) | C7—C8—C9 | 119.1 (2) |
N3—C1—H1A | 110.0 | C7—C8—C10 | 118.3 (2) |
C2—C1—H1A | 110.1 | C9—C8—C10 | 122.55 (19) |
N3—C1—H1B | 110.2 | C4—C9—C8 | 120.0 (2) |
C2—C1—H1B | 110.0 | C4—C9—H9A | 120.0 |
H1A—C1—H1B | 108.4 | C8—C9—H9A | 120.0 |
O1—C2—C1 | 107.58 (19) | O3—C10—O4 | 123.1 (2) |
O1—C2—H2A | 110.2 | O3—C10—C8 | 123.7 (2) |
C1—C2—H2A | 110.2 | O4—C10—C8 | 113.19 (18) |
O1—C2—H2B | 110.2 | O4—C11—C12 | 107.83 (19) |
C1—C2—H2B | 110.2 | O4—C11—H11A | 110.1 |
H2A—C2—H2B | 108.5 | C12—C11—H11A | 110.1 |
O2—C3—O1 | 123.1 (2) | O4—C11—H11B | 110.2 |
O2—C3—C4 | 124.7 (2) | C12—C11—H11B | 110.2 |
O1—C3—C4 | 112.15 (18) | H11A—C11—H11B | 108.4 |
C5—C4—C9 | 119.5 (2) | N4—C12—C11 | 113.5 (2) |
C5—C4—C3 | 118.3 (2) | N4—C12—H12A | 108.9 |
C9—C4—C3 | 122.2 (2) | C11—C12—H12A | 108.9 |
C6—C5—C4 | 120.6 (2) | N4—C12—H12B | 108.9 |
C6—C5—H5A | 119.7 | C11—C12—H12B | 108.8 |
C4—C5—H5A | 119.7 | H12A—C12—H12B | 107.7 |
| | | |
N2—N3—C1—C2 | 169.0 (2) | C6—C7—C8—C10 | 179.9 (2) |
C3—O1—C2—C1 | 175.4 (2) | C5—C4—C9—C8 | −0.8 (3) |
N3—C1—C2—O1 | −69.0 (3) | C3—C4—C9—C8 | 178.32 (19) |
C2—O1—C3—O2 | 0.7 (3) | C7—C8—C9—C4 | 0.1 (3) |
C2—O1—C3—C4 | −178.80 (19) | C10—C8—C9—C4 | −179.1 (2) |
O2—C3—C4—C5 | −6.0 (3) | C11—O4—C10—O3 | 2.4 (3) |
O1—C3—C4—C5 | 173.5 (2) | C11—O4—C10—C8 | −177.1 (2) |
O2—C3—C4—C9 | 174.8 (2) | C7—C8—C10—O3 | −3.0 (4) |
O1—C3—C4—C9 | −5.7 (3) | C9—C8—C10—O3 | 176.2 (2) |
C9—C4—C5—C6 | 0.9 (4) | C7—C8—C10—O4 | 176.45 (19) |
C3—C4—C5—C6 | −178.3 (2) | C9—C8—C10—O4 | −4.3 (3) |
C4—C5—C6—C7 | −0.2 (4) | C10—O4—C11—C12 | 161.6 (2) |
C5—C6—C7—C8 | −0.5 (4) | N5—N4—C12—C11 | −82.3 (3) |
C6—C7—C8—C9 | 0.6 (3) | O4—C11—C12—N4 | 68.8 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5A···N1i | 0.93 | 2.58 | 3.459 (5) | 157 |
Symmetry code: (i) x−1, y, z. |