Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807024567/rn2025sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807024567/rn2025Isup2.hkl |
CCDC reference: 651467
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.042
- wR factor = 0.104
- Data-to-parameter ratio = 15.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for N4 - C30 .. 6.22 su
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT793_ALERT_1_G Check the Absolute Configuration of C7 = ... S PLAT793_ALERT_1_G Check the Absolute Configuration of C9 = ... R PLAT793_ALERT_1_G Check the Absolute Configuration of C26 = ... S PLAT793_ALERT_1_G Check the Absolute Configuration of C28 = ... R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 6 ALERT level G = General alerts; check 6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Bromine (1.92 g, 24 mmol) was added dropwise to a solution of 4-methoxyacetophenone (3.00 g, 20 mmol) in anhydrous diethyl ether (50 ml) in an ice-bath. The reaction proceeded for 6 h to give w-bromine-4-methoxyacetophenone. Anhydrous 3-chloro-1,2-propanediol (3.33 g, 30 mmol), 1-butanol (10 ml) and toluene-p-sulfonic acid(0.1 g, 0.2 mmol) were then added. The reaction mixture was refluxed for 7 h and then cooled to room temperature. The organic layer was washed with saturated sodium bicarbonate solution and dried over anhydrous sodium sulfate. A white solid was obtained by recrystallization from methanol. A solution of this compound (7.70 g, 24 mmol) in dimethylformamide (15 ml) was added to a solution of benzimidazole (2.81 g, 24 mmol) and dried KI (0.5 g, 3 mmol) in dimethylformamide (50 ml). The mixture was heated to reflux for 5 h and then the solution was washed with water and extracted with chloroform. Single crystals of (I) were obtained by slow evaporation of a solution of the product in petroleum ether-ethyl acetate (3:1 v/v) at room temperature over a period of 3 d.
All H atoms were located in difference Fourier map. Water H atoms were refined with O1W-H1W1 and O1W-H2W1 distance restrains of 0.85±0.01 Å. The remaining H atoms were placed in idealized positions and constrained to ride on their parent atoms, with C—H distances in the range 0.93–0.97 Å, and with Uiso(H) = 1.2 Ueq(C).
Benzimidazole compounds containing 1,3-dioxolane have the ability to prevent plant diseases (Chai, 1985). In the present study, a novel benzimidazole compound, (I), containing 1,3-dioxolane, has been synthesized from cheap 3-chloropropane-1,2-diol instead of expensive pentane-1,2-diol.
There are two molecules, A and B, in the asymmetric unit (Fig. 1). The bond lengths and angles in A and B are within normal ranges (Allen et al., 1987). The benzimidazole units, C11—C17/N1/N2 and C30—C36/N3/N4, are essentially planar with dihedral angles of 0.77 (2)° and 0.90 (2)° in A and B, respectively. Intramolecular C20—H20A···O6 interactions (Table 2) result in the formation of a five-numbered ring.
As can be seen from the packing diagram (Fig. 2), intermolecular C15—H15A···O1i hydrogen bonds (Table 1) link the molecules, forming infinite chains along the b axis (Fig. 2). The packing is further stabilized by C—H···π interactions (Table 1),where Cg denotes the centroid of C1—C6 benzene ring. The distance of 3.523 Å between the centroids of the rings C30/C31/C36/N3/N4 related by the symmetry operation (2 - x, -y, 1 - z) suggests a π-π interaction.
For related literature, see: Allen et al. (1987); Chai (1985).
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
C19H19BrN2O3 | F(000) = 1648 |
Mr = 403.26 | Dx = 1.473 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 12.683 (4) Å | Cell parameters from 3621 reflections |
b = 10.967 (4) Å | θ = 2.5–20.6° |
c = 26.530 (8) Å | µ = 2.28 mm−1 |
β = 99.677 (7)° | T = 293 K |
V = 3638 (2) Å3 | Column, colourless |
Z = 8 | 0.41 × 0.21 × 0.14 mm |
Siemens SMART 1000 CCD area-detector diffractometer | 7191 independent reflections |
Radiation source: fine-focus sealed tube | 4269 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
Detector resolution: 8.33 pixels mm-1 | θmax = 26.1°, θmin = 1.6° |
ω scans | h = −15→9 |
Absorption correction: multi-scan SADABS (Sheldrick, 1996) | k = −13→13 |
Tmin = 0.455, Tmax = 0.741 | l = −31→32 |
19950 measured reflections |
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) = 0.104 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0485P)2 + 0.1464P] where P = (Fo2 + 2Fc2)/3 |
7191 reflections | (Δ/σ)max = 0.001 |
451 parameters | Δρmax = 0.53 e Å−3 |
0 restraints | Δρmin = −0.32 e Å−3 |
C19H19BrN2O3 | V = 3638 (2) Å3 |
Mr = 403.26 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.683 (4) Å | µ = 2.28 mm−1 |
b = 10.967 (4) Å | T = 293 K |
c = 26.530 (8) Å | 0.41 × 0.21 × 0.14 mm |
β = 99.677 (7)° |
Siemens SMART 1000 CCD area-detector diffractometer | 7191 independent reflections |
Absorption correction: multi-scan SADABS (Sheldrick, 1996) | 4269 reflections with I > 2σ(I) |
Tmin = 0.455, Tmax = 0.741 | Rint = 0.036 |
19950 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.104 | H-atom parameters constrained |
S = 0.99 | Δρmax = 0.53 e Å−3 |
7191 reflections | Δρmin = −0.32 e Å−3 |
451 parameters |
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 | ||
Br1 | 0.78726 (3) | 0.28198 (4) | 0.167855 (14) | 0.07979 (15) | |
Br2 | 0.57291 (3) | 0.11064 (3) | 0.456477 (18) | 0.09666 (18) | |
O3 | 0.76388 (15) | 0.33379 (15) | 0.28135 (7) | 0.0483 (5) | |
O6 | 0.75670 (15) | 0.31159 (16) | 0.44731 (6) | 0.0475 (5) | |
O5 | 0.65429 (16) | 0.36202 (18) | 0.50601 (7) | 0.0541 (5) | |
N1 | 0.95774 (17) | 0.42740 (19) | 0.34591 (8) | 0.0441 (6) | |
C7 | 0.6796 (2) | 0.2610 (2) | 0.25541 (11) | 0.0467 (7) | |
O2 | 0.71432 (16) | 0.13815 (16) | 0.26158 (8) | 0.0545 (5) | |
O1 | 0.29443 (17) | 0.3243 (2) | 0.33276 (9) | 0.0697 (6) | |
O4 | 0.58098 (17) | 0.83370 (18) | 0.37021 (9) | 0.0681 (6) | |
N3 | 0.9258 (2) | 0.1434 (2) | 0.47892 (9) | 0.0519 (6) | |
C6 | 0.5772 (2) | 0.2786 (2) | 0.27646 (10) | 0.0437 (7) | |
C11 | 0.9950 (2) | 0.4562 (3) | 0.39540 (11) | 0.0523 (8) | |
H11A | 1.0158 | 0.3975 | 0.4204 | 0.063* | |
C22 | 0.6035 (2) | 0.7177 (3) | 0.38762 (11) | 0.0495 (7) | |
C20 | 0.7035 (2) | 0.5328 (3) | 0.39791 (11) | 0.0491 (7) | |
H20A | 0.7605 | 0.4865 | 0.3907 | 0.059* | |
C10 | 0.9432 (2) | 0.3058 (2) | 0.32409 (11) | 0.0498 (7) | |
H10A | 0.9895 | 0.2497 | 0.3458 | 0.060* | |
H10B | 0.9653 | 0.3062 | 0.2908 | 0.060* | |
C26 | 0.6549 (2) | 0.3585 (2) | 0.45304 (10) | 0.0469 (7) | |
C18 | 0.6593 (3) | 0.2961 (3) | 0.19921 (12) | 0.0620 (8) | |
H18A | 0.6336 | 0.3795 | 0.1959 | 0.074* | |
H18B | 0.6038 | 0.2440 | 0.1810 | 0.074* | |
C23 | 0.5348 (2) | 0.6716 (3) | 0.41814 (11) | 0.0531 (8) | |
H23A | 0.4775 | 0.7180 | 0.4250 | 0.064* | |
C5 | 0.5499 (2) | 0.3928 (2) | 0.29164 (10) | 0.0483 (7) | |
H5A | 0.5961 | 0.4578 | 0.2896 | 0.058* | |
C25 | 0.6379 (2) | 0.4852 (2) | 0.42916 (10) | 0.0424 (7) | |
C1 | 0.5066 (2) | 0.1839 (3) | 0.27949 (11) | 0.0555 (8) | |
H1A | 0.5228 | 0.1063 | 0.2689 | 0.067* | |
N2 | 0.9992 (2) | 0.5726 (2) | 0.40511 (9) | 0.0585 (7) | |
C14 | 0.8955 (2) | 0.5644 (3) | 0.26991 (11) | 0.0544 (8) | |
H14A | 0.8794 | 0.5037 | 0.2453 | 0.065* | |
C4 | 0.4555 (2) | 0.4132 (2) | 0.30981 (10) | 0.0496 (7) | |
H4A | 0.4382 | 0.4912 | 0.3195 | 0.060* | |
C13 | 0.9350 (2) | 0.5368 (2) | 0.32053 (10) | 0.0428 (7) | |
C28 | 0.8287 (2) | 0.3282 (2) | 0.49474 (10) | 0.0445 (7) | |
H28A | 0.8888 | 0.3801 | 0.4895 | 0.053* | |
C21 | 0.6867 (2) | 0.6487 (3) | 0.37683 (11) | 0.0518 (7) | |
H21A | 0.7317 | 0.6791 | 0.3555 | 0.062* | |
N4 | 0.9507 (3) | 0.0307 (2) | 0.41143 (10) | 0.0699 (8) | |
C32 | 1.0312 (3) | 0.1611 (3) | 0.47307 (11) | 0.0518 (8) | |
C9 | 0.8295 (2) | 0.2592 (2) | 0.31804 (11) | 0.0461 (7) | |
H9A | 0.8037 | 0.2596 | 0.3508 | 0.055* | |
C24 | 0.5520 (2) | 0.5564 (3) | 0.43830 (10) | 0.0531 (8) | |
H24A | 0.5052 | 0.5252 | 0.4585 | 0.064* | |
C12 | 0.9611 (2) | 0.6265 (3) | 0.35794 (11) | 0.0488 (7) | |
C17 | 0.9458 (3) | 0.7485 (3) | 0.34484 (15) | 0.0641 (9) | |
H17A | 0.9623 | 0.8099 | 0.3691 | 0.077* | |
C2 | 0.4127 (3) | 0.2027 (3) | 0.29789 (12) | 0.0613 (9) | |
H2B | 0.3664 | 0.1377 | 0.2998 | 0.074* | |
C33 | 1.1130 (3) | 0.2305 (3) | 0.50087 (13) | 0.0649 (9) | |
H33A | 1.1023 | 0.2780 | 0.5286 | 0.078* | |
C30 | 0.8832 (3) | 0.0654 (3) | 0.44097 (12) | 0.0656 (9) | |
H30A | 0.8125 | 0.0392 | 0.4364 | 0.079* | |
C27 | 0.7613 (2) | 0.3925 (3) | 0.52859 (11) | 0.0530 (8) | |
H27A | 0.7777 | 0.3631 | 0.5635 | 0.064* | |
H27B | 0.7725 | 0.4800 | 0.5284 | 0.064* | |
C8 | 0.8164 (3) | 0.1342 (2) | 0.29330 (12) | 0.0569 (8) | |
H8A | 0.8722 | 0.1190 | 0.2732 | 0.068* | |
H8B | 0.8189 | 0.0708 | 0.3190 | 0.068* | |
C29 | 0.8691 (2) | 0.2051 (3) | 0.51457 (11) | 0.0539 (8) | |
H29A | 0.9165 | 0.2153 | 0.5470 | 0.065* | |
H29B | 0.8091 | 0.1553 | 0.5204 | 0.065* | |
C3 | 0.3870 (2) | 0.3165 (3) | 0.31343 (11) | 0.0502 (7) | |
C15 | 0.8816 (2) | 0.6849 (3) | 0.25791 (13) | 0.0649 (9) | |
H15A | 0.8555 | 0.7070 | 0.2243 | 0.078* | |
C37 | 0.5676 (3) | 0.2741 (3) | 0.42735 (13) | 0.0655 (9) | |
H37A | 0.5729 | 0.2677 | 0.3914 | 0.079* | |
H37B | 0.4987 | 0.3101 | 0.4297 | 0.079* | |
C31 | 1.0450 (3) | 0.0900 (3) | 0.43109 (12) | 0.0600 (9) | |
C16 | 0.9053 (3) | 0.7754 (3) | 0.29473 (16) | 0.0705 (10) | |
H16A | 0.8935 | 0.8565 | 0.2852 | 0.085* | |
C36 | 1.1447 (4) | 0.0868 (3) | 0.41568 (14) | 0.0819 (11) | |
H36A | 1.1557 | 0.0400 | 0.3878 | 0.098* | |
C19 | 0.2627 (3) | 0.4400 (3) | 0.34839 (14) | 0.0859 (11) | |
H19A | 0.1964 | 0.4324 | 0.3611 | 0.129* | |
H19B | 0.2534 | 0.4948 | 0.3198 | 0.129* | |
H19C | 0.3167 | 0.4714 | 0.3749 | 0.129* | |
C34 | 1.2100 (3) | 0.2246 (4) | 0.48492 (17) | 0.0868 (11) | |
H34A | 1.2672 | 0.2685 | 0.5026 | 0.104* | |
C38 | 0.6542 (3) | 0.8897 (3) | 0.34226 (14) | 0.0837 (11) | |
H38A | 0.6295 | 0.9701 | 0.3320 | 0.125* | |
H38B | 0.6593 | 0.8418 | 0.3125 | 0.125* | |
H38C | 0.7234 | 0.8948 | 0.3634 | 0.125* | |
C35 | 1.2257 (4) | 0.1541 (4) | 0.44256 (19) | 0.0967 (13) | |
H35A | 1.2926 | 0.1532 | 0.4327 | 0.116* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0835 (3) | 0.0932 (3) | 0.0707 (3) | −0.0159 (2) | 0.0360 (2) | −0.00961 (19) |
Br2 | 0.0870 (3) | 0.0610 (2) | 0.1373 (4) | −0.0144 (2) | 0.0053 (3) | 0.0236 (2) |
O3 | 0.0438 (12) | 0.0378 (10) | 0.0612 (13) | −0.0029 (9) | 0.0027 (10) | −0.0005 (9) |
O6 | 0.0492 (12) | 0.0533 (11) | 0.0394 (11) | 0.0115 (9) | 0.0054 (9) | −0.0002 (9) |
O5 | 0.0516 (13) | 0.0695 (13) | 0.0438 (12) | 0.0080 (10) | 0.0158 (10) | 0.0097 (10) |
N1 | 0.0421 (14) | 0.0436 (13) | 0.0450 (14) | −0.0011 (11) | 0.0027 (11) | −0.0011 (11) |
C7 | 0.0458 (18) | 0.0403 (15) | 0.0527 (19) | −0.0047 (13) | 0.0048 (14) | −0.0043 (13) |
O2 | 0.0483 (13) | 0.0421 (11) | 0.0715 (14) | −0.0002 (9) | 0.0053 (11) | −0.0120 (10) |
O1 | 0.0551 (14) | 0.0748 (15) | 0.0847 (16) | −0.0046 (12) | 0.0280 (12) | −0.0170 (12) |
O4 | 0.0647 (15) | 0.0530 (12) | 0.0869 (16) | 0.0094 (11) | 0.0140 (12) | 0.0155 (12) |
N3 | 0.0592 (18) | 0.0472 (14) | 0.0467 (15) | 0.0145 (13) | 0.0012 (13) | −0.0014 (12) |
C6 | 0.0439 (17) | 0.0407 (15) | 0.0441 (17) | −0.0025 (14) | 0.0006 (13) | −0.0030 (13) |
C11 | 0.0461 (19) | 0.062 (2) | 0.0464 (19) | −0.0042 (15) | 0.0020 (14) | 0.0052 (15) |
C22 | 0.0470 (19) | 0.0467 (17) | 0.0524 (19) | 0.0010 (15) | 0.0015 (15) | 0.0027 (14) |
C20 | 0.0443 (18) | 0.0499 (17) | 0.0563 (19) | 0.0037 (14) | 0.0176 (14) | −0.0023 (14) |
C10 | 0.0475 (19) | 0.0474 (16) | 0.0536 (18) | 0.0049 (14) | 0.0061 (14) | 0.0001 (14) |
C26 | 0.0456 (19) | 0.0514 (17) | 0.0443 (18) | 0.0040 (14) | 0.0091 (14) | 0.0056 (13) |
C18 | 0.056 (2) | 0.072 (2) | 0.059 (2) | −0.0019 (17) | 0.0093 (16) | −0.0008 (16) |
C23 | 0.0484 (19) | 0.0570 (19) | 0.0555 (19) | 0.0168 (15) | 0.0139 (15) | 0.0053 (15) |
C5 | 0.0512 (19) | 0.0421 (16) | 0.0514 (18) | −0.0026 (14) | 0.0078 (14) | 0.0025 (13) |
C25 | 0.0377 (16) | 0.0492 (16) | 0.0398 (16) | 0.0025 (13) | 0.0050 (13) | −0.0011 (13) |
C1 | 0.054 (2) | 0.0441 (17) | 0.069 (2) | −0.0031 (15) | 0.0117 (16) | −0.0111 (15) |
N2 | 0.0551 (17) | 0.0638 (17) | 0.0552 (16) | −0.0059 (14) | 0.0051 (13) | −0.0098 (14) |
C14 | 0.055 (2) | 0.0559 (19) | 0.052 (2) | −0.0095 (15) | 0.0081 (15) | 0.0048 (15) |
C4 | 0.058 (2) | 0.0401 (15) | 0.0506 (18) | 0.0059 (15) | 0.0082 (15) | −0.0033 (13) |
C13 | 0.0356 (16) | 0.0451 (16) | 0.0486 (18) | −0.0033 (13) | 0.0093 (13) | 0.0038 (14) |
C28 | 0.0470 (18) | 0.0471 (16) | 0.0385 (16) | 0.0028 (14) | 0.0041 (13) | −0.0030 (13) |
C21 | 0.0473 (19) | 0.0535 (18) | 0.0576 (19) | −0.0047 (15) | 0.0176 (15) | 0.0075 (15) |
N4 | 0.093 (2) | 0.0568 (16) | 0.0565 (18) | 0.0188 (17) | 0.0036 (17) | −0.0117 (13) |
C32 | 0.067 (2) | 0.0425 (16) | 0.0447 (18) | 0.0194 (16) | 0.0062 (16) | 0.0063 (14) |
C9 | 0.0510 (19) | 0.0432 (15) | 0.0437 (17) | 0.0011 (14) | 0.0067 (14) | 0.0024 (13) |
C24 | 0.0443 (19) | 0.069 (2) | 0.0486 (18) | 0.0007 (16) | 0.0157 (14) | 0.0067 (15) |
C12 | 0.0402 (18) | 0.0482 (18) | 0.059 (2) | −0.0062 (13) | 0.0105 (15) | −0.0053 (15) |
C17 | 0.052 (2) | 0.054 (2) | 0.089 (3) | −0.0063 (16) | 0.0194 (19) | −0.0116 (18) |
C2 | 0.055 (2) | 0.0499 (18) | 0.080 (2) | −0.0143 (16) | 0.0147 (17) | −0.0096 (16) |
C33 | 0.069 (3) | 0.061 (2) | 0.062 (2) | 0.0053 (19) | 0.0019 (19) | 0.0013 (17) |
C30 | 0.080 (3) | 0.0473 (17) | 0.061 (2) | 0.0081 (18) | −0.0121 (19) | −0.0066 (16) |
C27 | 0.058 (2) | 0.0592 (18) | 0.0424 (17) | 0.0102 (16) | 0.0096 (15) | −0.0020 (14) |
C8 | 0.059 (2) | 0.0398 (16) | 0.070 (2) | −0.0016 (15) | 0.0057 (17) | 0.0015 (14) |
C29 | 0.060 (2) | 0.0574 (18) | 0.0435 (17) | 0.0101 (16) | 0.0060 (15) | 0.0000 (14) |
C3 | 0.0467 (19) | 0.0559 (19) | 0.0478 (18) | −0.0010 (15) | 0.0069 (14) | −0.0065 (14) |
C15 | 0.053 (2) | 0.067 (2) | 0.075 (2) | −0.0106 (17) | 0.0108 (17) | 0.0244 (19) |
C37 | 0.054 (2) | 0.0583 (19) | 0.080 (2) | −0.0057 (16) | −0.0011 (18) | 0.0133 (17) |
C31 | 0.076 (3) | 0.0487 (18) | 0.054 (2) | 0.0194 (18) | 0.0079 (19) | 0.0075 (16) |
C16 | 0.059 (2) | 0.0464 (19) | 0.108 (3) | −0.0020 (17) | 0.020 (2) | 0.017 (2) |
C36 | 0.103 (3) | 0.078 (3) | 0.070 (3) | 0.028 (3) | 0.028 (2) | 0.003 (2) |
C19 | 0.071 (3) | 0.088 (3) | 0.106 (3) | 0.013 (2) | 0.036 (2) | −0.022 (2) |
C34 | 0.077 (3) | 0.090 (3) | 0.093 (3) | −0.007 (2) | 0.012 (2) | 0.004 (2) |
C38 | 0.093 (3) | 0.062 (2) | 0.098 (3) | −0.006 (2) | 0.021 (2) | 0.025 (2) |
C35 | 0.076 (3) | 0.109 (3) | 0.111 (4) | 0.018 (3) | 0.033 (3) | 0.017 (3) |
Br1—C18 | 1.950 (3) | C14—C13 | 1.385 (4) |
Br2—C37 | 1.949 (3) | C14—H14A | 0.9300 |
O3—C7 | 1.416 (3) | C4—C3 | 1.385 (4) |
O3—C9 | 1.427 (3) | C4—H4A | 0.9300 |
O6—C26 | 1.421 (3) | C13—C12 | 1.397 (4) |
O6—C28 | 1.437 (3) | C28—C29 | 1.506 (4) |
O5—C26 | 1.407 (3) | C28—C27 | 1.514 (4) |
O5—C27 | 1.428 (3) | C28—H28A | 0.9800 |
N1—C11 | 1.356 (3) | C21—H21A | 0.9300 |
N1—C13 | 1.383 (3) | N4—C30 | 1.311 (4) |
N1—C10 | 1.454 (3) | N4—C31 | 1.385 (4) |
C7—O2 | 1.418 (3) | C32—C33 | 1.394 (4) |
C7—C6 | 1.510 (4) | C32—C31 | 1.395 (4) |
C7—C18 | 1.519 (4) | C9—C8 | 1.518 (4) |
O2—C8 | 1.422 (3) | C9—H9A | 0.9800 |
O1—C3 | 1.360 (4) | C24—H24A | 0.9300 |
O1—C19 | 1.414 (4) | C12—C17 | 1.388 (4) |
O4—C22 | 1.367 (3) | C17—C16 | 1.374 (5) |
O4—C38 | 1.422 (4) | C17—H17A | 0.9300 |
N3—C30 | 1.361 (4) | C2—C3 | 1.371 (4) |
N3—C32 | 1.385 (4) | C2—H2B | 0.9300 |
N3—C29 | 1.449 (4) | C33—C34 | 1.368 (5) |
C6—C5 | 1.378 (4) | C33—H33A | 0.9300 |
C6—C1 | 1.382 (4) | C30—H30A | 0.9300 |
C11—N2 | 1.301 (4) | C27—H27A | 0.9700 |
C11—H11A | 0.9300 | C27—H27B | 0.9700 |
C22—C21 | 1.366 (4) | C8—H8A | 0.9700 |
C22—C23 | 1.382 (4) | C8—H8B | 0.9700 |
C20—C25 | 1.373 (4) | C29—H29A | 0.9700 |
C20—C21 | 1.391 (4) | C29—H29B | 0.9700 |
C20—H20A | 0.9300 | C15—C16 | 1.390 (5) |
C10—C9 | 1.512 (4) | C15—H15A | 0.9300 |
C10—H10A | 0.9700 | C37—H37A | 0.9700 |
C10—H10B | 0.9700 | C37—H37B | 0.9700 |
C26—C37 | 1.515 (4) | C31—C36 | 1.392 (5) |
C26—C25 | 1.528 (4) | C16—H16A | 0.9300 |
C18—H18A | 0.9700 | C36—C35 | 1.365 (5) |
C18—H18B | 0.9700 | C36—H36A | 0.9300 |
C23—C24 | 1.375 (4) | C19—H19A | 0.9600 |
C23—H23A | 0.9300 | C19—H19B | 0.9600 |
C5—C4 | 1.382 (4) | C19—H19C | 0.9600 |
C5—H5A | 0.9300 | C34—C35 | 1.406 (6) |
C25—C24 | 1.394 (4) | C34—H34A | 0.9300 |
C1—C2 | 1.376 (4) | C38—H38A | 0.9600 |
C1—H1A | 0.9300 | C38—H38B | 0.9600 |
N2—C12 | 1.395 (4) | C38—H38C | 0.9600 |
C14—C15 | 1.364 (4) | C35—H35A | 0.9300 |
C7—O3—C9 | 108.34 (19) | C33—C32—C31 | 123.1 (3) |
C26—O6—C28 | 108.4 (2) | O3—C9—C10 | 108.4 (2) |
C26—O5—C27 | 105.1 (2) | O3—C9—C8 | 102.4 (2) |
C11—N1—C13 | 106.2 (2) | C10—C9—C8 | 112.6 (2) |
C11—N1—C10 | 126.9 (2) | O3—C9—H9A | 111.1 |
C13—N1—C10 | 126.9 (2) | C10—C9—H9A | 111.1 |
O3—C7—O2 | 106.6 (2) | C8—C9—H9A | 111.1 |
O3—C7—C6 | 112.0 (2) | C23—C24—C25 | 121.6 (3) |
O2—C7—C6 | 110.4 (2) | C23—C24—H24A | 119.2 |
O3—C7—C18 | 108.9 (2) | C25—C24—H24A | 119.2 |
O2—C7—C18 | 110.6 (2) | C17—C12—N2 | 130.2 (3) |
C6—C7—C18 | 108.4 (2) | C17—C12—C13 | 119.6 (3) |
C7—O2—C8 | 109.38 (19) | N2—C12—C13 | 110.1 (2) |
C3—O1—C19 | 118.2 (2) | C16—C17—C12 | 117.5 (3) |
C22—O4—C38 | 117.4 (2) | C16—C17—H17A | 121.2 |
C30—N3—C32 | 106.0 (3) | C12—C17—H17A | 121.2 |
C30—N3—C29 | 126.6 (3) | C3—C2—C1 | 120.5 (3) |
C32—N3—C29 | 127.0 (3) | C3—C2—H2B | 119.8 |
C5—C6—C1 | 118.0 (3) | C1—C2—H2B | 119.8 |
C5—C6—C7 | 119.9 (2) | C34—C33—C32 | 116.0 (3) |
C1—C6—C7 | 122.1 (2) | C34—C33—H33A | 122.0 |
N2—C11—N1 | 114.6 (3) | C32—C33—H33A | 122.0 |
N2—C11—H11A | 122.7 | N4—C30—N3 | 114.0 (3) |
N1—C11—H11A | 122.7 | N4—C30—H30A | 123.0 |
C21—C22—O4 | 124.7 (3) | N3—C30—H30A | 123.0 |
C21—C22—C23 | 120.4 (3) | O5—C27—C28 | 103.5 (2) |
O4—C22—C23 | 114.9 (3) | O5—C27—H27A | 111.1 |
C25—C20—C21 | 121.5 (3) | C28—C27—H27A | 111.1 |
C25—C20—H20A | 119.2 | O5—C27—H27B | 111.1 |
C21—C20—H20A | 119.2 | C28—C27—H27B | 111.1 |
N1—C10—C9 | 114.0 (2) | H27A—C27—H27B | 109.0 |
N1—C10—H10A | 108.7 | O2—C8—C9 | 104.5 (2) |
C9—C10—H10A | 108.7 | O2—C8—H8A | 110.8 |
N1—C10—H10B | 108.7 | C9—C8—H8A | 110.8 |
C9—C10—H10B | 108.7 | O2—C8—H8B | 110.8 |
H10A—C10—H10B | 107.6 | C9—C8—H8B | 110.8 |
O5—C26—O6 | 105.9 (2) | H8A—C8—H8B | 108.9 |
O5—C26—C37 | 109.9 (2) | N3—C29—C28 | 111.6 (2) |
O6—C26—C37 | 109.8 (2) | N3—C29—H29A | 109.3 |
O5—C26—C25 | 111.4 (2) | C28—C29—H29A | 109.3 |
O6—C26—C25 | 110.7 (2) | N3—C29—H29B | 109.3 |
C37—C26—C25 | 109.1 (2) | C28—C29—H29B | 109.3 |
C7—C18—Br1 | 112.5 (2) | H29A—C29—H29B | 108.0 |
C7—C18—H18A | 109.1 | O1—C3—C2 | 115.8 (3) |
Br1—C18—H18A | 109.1 | O1—C3—C4 | 124.7 (3) |
C7—C18—H18B | 109.1 | C2—C3—C4 | 119.5 (3) |
Br1—C18—H18B | 109.1 | C14—C15—C16 | 121.6 (3) |
H18A—C18—H18B | 107.8 | C14—C15—H15A | 119.2 |
C24—C23—C22 | 119.3 (3) | C16—C15—H15A | 119.2 |
C24—C23—H23A | 120.3 | C26—C37—Br2 | 114.2 (2) |
C22—C23—H23A | 120.3 | C26—C37—H37A | 108.7 |
C6—C5—C4 | 121.6 (3) | Br2—C37—H37A | 108.7 |
C6—C5—H5A | 119.2 | C26—C37—H37B | 108.7 |
C4—C5—H5A | 119.2 | Br2—C37—H37B | 108.7 |
C20—C25—C24 | 117.6 (3) | H37A—C37—H37B | 107.6 |
C20—C25—C26 | 122.6 (2) | N4—C31—C36 | 130.3 (3) |
C24—C25—C26 | 119.8 (3) | N4—C31—C32 | 110.3 (3) |
C2—C1—C6 | 121.0 (3) | C36—C31—C32 | 119.4 (4) |
C2—C1—H1A | 119.5 | C17—C16—C15 | 121.9 (3) |
C6—C1—H1A | 119.5 | C17—C16—H16A | 119.0 |
C11—N2—C12 | 104.0 (2) | C15—C16—H16A | 119.0 |
C15—C14—C13 | 116.7 (3) | C35—C36—C31 | 118.3 (4) |
C15—C14—H14A | 121.7 | C35—C36—H36A | 120.9 |
C13—C14—H14A | 121.7 | C31—C36—H36A | 120.9 |
C5—C4—C3 | 119.4 (3) | O1—C19—H19A | 109.5 |
C5—C4—H4A | 120.3 | O1—C19—H19B | 109.5 |
C3—C4—H4A | 120.3 | H19A—C19—H19B | 109.5 |
N1—C13—C14 | 132.3 (3) | O1—C19—H19C | 109.5 |
N1—C13—C12 | 105.1 (2) | H19A—C19—H19C | 109.5 |
C14—C13—C12 | 122.6 (3) | H19B—C19—H19C | 109.5 |
O6—C28—C29 | 108.7 (2) | C33—C34—C35 | 121.9 (4) |
O6—C28—C27 | 103.8 (2) | C33—C34—H34A | 119.0 |
C29—C28—C27 | 113.8 (2) | C35—C34—H34A | 119.0 |
O6—C28—H28A | 110.1 | O4—C38—H38A | 109.5 |
C29—C28—H28A | 110.1 | O4—C38—H38B | 109.5 |
C27—C28—H28A | 110.1 | H38A—C38—H38B | 109.5 |
C22—C21—C20 | 119.6 (3) | O4—C38—H38C | 109.5 |
C22—C21—H21A | 120.2 | H38A—C38—H38C | 109.5 |
C20—C21—H21A | 120.2 | H38B—C38—H38C | 109.5 |
C30—N4—C31 | 104.4 (3) | C36—C35—C34 | 121.3 (4) |
N3—C32—C33 | 131.6 (3) | C36—C35—H35A | 119.3 |
N3—C32—C31 | 105.3 (3) | C34—C35—H35A | 119.3 |
C9—O3—C7—O2 | −21.4 (3) | C30—N3—C32—C31 | −0.4 (3) |
C9—O3—C7—C6 | 99.3 (2) | C29—N3—C32—C31 | −174.4 (2) |
C9—O3—C7—C18 | −140.8 (2) | C7—O3—C9—C10 | 148.8 (2) |
O3—C7—O2—C8 | 3.1 (3) | C7—O3—C9—C8 | 29.7 (3) |
C6—C7—O2—C8 | −118.7 (3) | N1—C10—C9—O3 | 65.3 (3) |
C18—C7—O2—C8 | 121.3 (3) | N1—C10—C9—C8 | 177.8 (2) |
O3—C7—C6—C5 | 37.9 (3) | C22—C23—C24—C25 | 0.7 (4) |
O2—C7—C6—C5 | 156.4 (2) | C20—C25—C24—C23 | −1.9 (4) |
C18—C7—C6—C5 | −82.3 (3) | C26—C25—C24—C23 | 179.0 (3) |
O3—C7—C6—C1 | −144.5 (3) | C11—N2—C12—C17 | 178.9 (3) |
O2—C7—C6—C1 | −25.9 (4) | C11—N2—C12—C13 | −0.2 (3) |
C18—C7—C6—C1 | 95.4 (3) | N1—C13—C12—C17 | −179.0 (3) |
C13—N1—C11—N2 | −0.1 (3) | C14—C13—C12—C17 | 1.1 (4) |
C10—N1—C11—N2 | −179.3 (3) | N1—C13—C12—N2 | 0.2 (3) |
C38—O4—C22—C21 | −5.2 (4) | C14—C13—C12—N2 | −179.7 (3) |
C38—O4—C22—C23 | 174.8 (3) | N2—C12—C17—C16 | −179.2 (3) |
C11—N1—C10—C9 | 98.5 (3) | C13—C12—C17—C16 | −0.2 (4) |
C13—N1—C10—C9 | −80.5 (3) | C6—C1—C2—C3 | 0.3 (5) |
C27—O5—C26—O6 | 35.2 (3) | N3—C32—C33—C34 | 178.4 (3) |
C27—O5—C26—C37 | 153.8 (2) | C31—C32—C33—C34 | −0.5 (5) |
C27—O5—C26—C25 | −85.2 (3) | C31—N4—C30—N3 | −0.1 (3) |
C28—O6—C26—O5 | −20.4 (3) | C32—N3—C30—N4 | 0.4 (3) |
C28—O6—C26—C37 | −139.0 (2) | C29—N3—C30—N4 | 174.3 (3) |
C28—O6—C26—C25 | 100.5 (2) | C26—O5—C27—C28 | −35.5 (3) |
O3—C7—C18—Br1 | 56.3 (3) | O6—C28—C27—O5 | 22.5 (3) |
O2—C7—C18—Br1 | −60.5 (3) | C29—C28—C27—O5 | −95.5 (3) |
C6—C7—C18—Br1 | 178.31 (18) | C7—O2—C8—C9 | 14.9 (3) |
C21—C22—C23—C24 | 1.1 (4) | O3—C9—C8—O2 | −26.8 (3) |
O4—C22—C23—C24 | −178.8 (3) | C10—C9—C8—O2 | −143.0 (2) |
C1—C6—C5—C4 | 0.5 (4) | C30—N3—C29—C28 | −91.2 (3) |
C7—C6—C5—C4 | 178.3 (3) | C32—N3—C29—C28 | 81.6 (3) |
C21—C20—C25—C24 | 1.2 (4) | O6—C28—C29—N3 | 60.3 (3) |
C21—C20—C25—C26 | −179.7 (3) | C27—C28—C29—N3 | 175.4 (2) |
O5—C26—C25—C20 | 129.8 (3) | C19—O1—C3—C2 | −178.7 (3) |
O6—C26—C25—C20 | 12.2 (4) | C19—O1—C3—C4 | 2.9 (4) |
C37—C26—C25—C20 | −108.7 (3) | C1—C2—C3—O1 | −177.6 (3) |
O5—C26—C25—C24 | −51.2 (3) | C1—C2—C3—C4 | 0.9 (5) |
O6—C26—C25—C24 | −168.7 (2) | C5—C4—C3—O1 | 177.0 (3) |
C37—C26—C25—C24 | 70.3 (3) | C5—C4—C3—C2 | −1.4 (4) |
C5—C6—C1—C2 | −1.0 (4) | C13—C14—C15—C16 | −0.3 (5) |
C7—C6—C1—C2 | −178.7 (3) | O5—C26—C37—Br2 | −54.0 (3) |
N1—C11—N2—C12 | 0.2 (3) | O6—C26—C37—Br2 | 62.2 (3) |
C6—C5—C4—C3 | 0.7 (4) | C25—C26—C37—Br2 | −176.4 (2) |
C11—N1—C13—C14 | 179.8 (3) | C30—N4—C31—C36 | 179.2 (3) |
C10—N1—C13—C14 | −1.0 (5) | C30—N4—C31—C32 | −0.2 (3) |
C11—N1—C13—C12 | 0.0 (3) | N3—C32—C31—N4 | 0.4 (3) |
C10—N1—C13—C12 | 179.1 (2) | C33—C32—C31—N4 | 179.5 (3) |
C15—C14—C13—N1 | 179.3 (3) | N3—C32—C31—C36 | −179.0 (3) |
C15—C14—C13—C12 | −0.8 (4) | C33—C32—C31—C36 | 0.1 (4) |
C26—O6—C28—C29 | 119.8 (2) | C12—C17—C16—C15 | −0.9 (5) |
C26—O6—C28—C27 | −1.6 (3) | C14—C15—C16—C17 | 1.2 (5) |
O4—C22—C21—C20 | 178.2 (3) | N4—C31—C36—C35 | −179.3 (3) |
C23—C22—C21—C20 | −1.7 (4) | C32—C31—C36—C35 | 0.0 (5) |
C25—C20—C21—C22 | 0.5 (4) | C32—C33—C34—C35 | 0.9 (5) |
C30—N3—C32—C33 | −179.5 (3) | C31—C36—C35—C34 | 0.3 (6) |
C29—N3—C32—C33 | 6.6 (5) | C33—C34—C35—C36 | −0.8 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
C37—H37A···Cg | 0.97 | 2.65 | 3.515 | 148 |
C15—H15A···O1i | 0.93 | 2.56 | 3.362 (5) | 144 |
C20—H20A···O6 | 0.93 | 2.44 | 2.788 (4) | 102 |
Symmetry code: (i) −x+1, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C19H19BrN2O3 |
Mr | 403.26 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 12.683 (4), 10.967 (4), 26.530 (8) |
β (°) | 99.677 (7) |
V (Å3) | 3638 (2) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 2.28 |
Crystal size (mm) | 0.41 × 0.21 × 0.14 |
Data collection | |
Diffractometer | Siemens SMART 1000 CCD area-detector diffractometer |
Absorption correction | Multi-scan SADABS (Sheldrick, 1996) |
Tmin, Tmax | 0.455, 0.741 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 19950, 7191, 4269 |
Rint | 0.036 |
(sin θ/λ)max (Å−1) | 0.619 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.104, 0.99 |
No. of reflections | 7191 |
No. of parameters | 451 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.53, −0.32 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997, SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
C37—H37A···Cg | 0.97 | 2.653 | 3.515 | 148.37 |
C15—H15A···O1i | 0.93 | 2.560 | 3.362 (5) | 143.80 |
C20—H20A···O6 | 0.93 | 2.444 | 2.788 (4) | 101.83 |
Symmetry code: (i) −x+1, y+1/2, −z+1/2. |
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Benzimidazole compounds containing 1,3-dioxolane have the ability to prevent plant diseases (Chai, 1985). In the present study, a novel benzimidazole compound, (I), containing 1,3-dioxolane, has been synthesized from cheap 3-chloropropane-1,2-diol instead of expensive pentane-1,2-diol.
There are two molecules, A and B, in the asymmetric unit (Fig. 1). The bond lengths and angles in A and B are within normal ranges (Allen et al., 1987). The benzimidazole units, C11—C17/N1/N2 and C30—C36/N3/N4, are essentially planar with dihedral angles of 0.77 (2)° and 0.90 (2)° in A and B, respectively. Intramolecular C20—H20A···O6 interactions (Table 2) result in the formation of a five-numbered ring.
As can be seen from the packing diagram (Fig. 2), intermolecular C15—H15A···O1i hydrogen bonds (Table 1) link the molecules, forming infinite chains along the b axis (Fig. 2). The packing is further stabilized by C—H···π interactions (Table 1),where Cg denotes the centroid of C1—C6 benzene ring. The distance of 3.523 Å between the centroids of the rings C30/C31/C36/N3/N4 related by the symmetry operation (2 - x, -y, 1 - z) suggests a π-π interaction.