Download citation
Download citation
link to html
The title compound, C19H19BrN2O3, forms an intra­molecular C—H...O hydrogen bond which results in the formation of a five-membered ring. In the crystal structure, inter­molecular C—H...O hydrogen bonds link the mol­ecules into infinite chains along the b axis. The packing is further stabilized by C—H...π and π-π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807024567/rn2025sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807024567/rn2025Isup2.hkl
Contains datablock I

CCDC reference: 651467

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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

Comment top

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.

Related literature top

For related literature, see: Allen et al. (1987); Chai (1985).

Experimental top

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.

Refinement top

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).

Structure description top

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).

Computing details top

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).

Figures top
[Figure 1] Fig. 1. The structure of the compound (I) showing 50% probability displacement ellipsoids and the atom numbering scheme.
[Figure 2] Fig. 2. Packing diagram of (I) showing the intermolecular hydrogen bonds (dished lines), viewed down the a axis,
1-{[2-(Bromomethyl)-2-(4-methoxyphenyl)-1,3-dioxolan-4- yl]methyl}benzo[d]imidazole top
Crystal data top
C19H19BrN2O3F(000) = 1648
Mr = 403.26Dx = 1.473 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 12.683 (4) ÅCell parameters from 3621 reflections
b = 10.967 (4) Åθ = 2.5–20.6°
c = 26.530 (8) ŵ = 2.28 mm1
β = 99.677 (7)°T = 293 K
V = 3638 (2) Å3Column, colourless
Z = 80.41 × 0.21 × 0.14 mm
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer
7191 independent reflections
Radiation source: fine-focus sealed tube4269 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
Detector resolution: 8.33 pixels mm-1θmax = 26.1°, θmin = 1.6°
ω scansh = 159
Absorption correction: multi-scan
SADABS (Sheldrick, 1996)
k = 1313
Tmin = 0.455, Tmax = 0.741l = 3132
19950 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H-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 parametersΔρmax = 0.53 e Å3
0 restraintsΔρmin = 0.32 e Å3
Crystal data top
C19H19BrN2O3V = 3638 (2) Å3
Mr = 403.26Z = 8
Monoclinic, P21/cMo Kα radiation
a = 12.683 (4) ŵ = 2.28 mm1
b = 10.967 (4) ÅT = 293 K
c = 26.530 (8) Å0.41 × 0.21 × 0.14 mm
β = 99.677 (7)°
Data collection top
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 = 0.741Rint = 0.036
19950 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.104H-atom parameters constrained
S = 0.99Δρmax = 0.53 e Å3
7191 reflectionsΔρmin = 0.32 e Å3
451 parameters
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
xyzUiso*/Ueq
Br10.78726 (3)0.28198 (4)0.167855 (14)0.07979 (15)
Br20.57291 (3)0.11064 (3)0.456477 (18)0.09666 (18)
O30.76388 (15)0.33379 (15)0.28135 (7)0.0483 (5)
O60.75670 (15)0.31159 (16)0.44731 (6)0.0475 (5)
O50.65429 (16)0.36202 (18)0.50601 (7)0.0541 (5)
N10.95774 (17)0.42740 (19)0.34591 (8)0.0441 (6)
C70.6796 (2)0.2610 (2)0.25541 (11)0.0467 (7)
O20.71432 (16)0.13815 (16)0.26158 (8)0.0545 (5)
O10.29443 (17)0.3243 (2)0.33276 (9)0.0697 (6)
O40.58098 (17)0.83370 (18)0.37021 (9)0.0681 (6)
N30.9258 (2)0.1434 (2)0.47892 (9)0.0519 (6)
C60.5772 (2)0.2786 (2)0.27646 (10)0.0437 (7)
C110.9950 (2)0.4562 (3)0.39540 (11)0.0523 (8)
H11A1.01580.39750.42040.063*
C220.6035 (2)0.7177 (3)0.38762 (11)0.0495 (7)
C200.7035 (2)0.5328 (3)0.39791 (11)0.0491 (7)
H20A0.76050.48650.39070.059*
C100.9432 (2)0.3058 (2)0.32409 (11)0.0498 (7)
H10A0.98950.24970.34580.060*
H10B0.96530.30620.29080.060*
C260.6549 (2)0.3585 (2)0.45304 (10)0.0469 (7)
C180.6593 (3)0.2961 (3)0.19921 (12)0.0620 (8)
H18A0.63360.37950.19590.074*
H18B0.60380.24400.18100.074*
C230.5348 (2)0.6716 (3)0.41814 (11)0.0531 (8)
H23A0.47750.71800.42500.064*
C50.5499 (2)0.3928 (2)0.29164 (10)0.0483 (7)
H5A0.59610.45780.28960.058*
C250.6379 (2)0.4852 (2)0.42916 (10)0.0424 (7)
C10.5066 (2)0.1839 (3)0.27949 (11)0.0555 (8)
H1A0.52280.10630.26890.067*
N20.9992 (2)0.5726 (2)0.40511 (9)0.0585 (7)
C140.8955 (2)0.5644 (3)0.26991 (11)0.0544 (8)
H14A0.87940.50370.24530.065*
C40.4555 (2)0.4132 (2)0.30981 (10)0.0496 (7)
H4A0.43820.49120.31950.060*
C130.9350 (2)0.5368 (2)0.32053 (10)0.0428 (7)
C280.8287 (2)0.3282 (2)0.49474 (10)0.0445 (7)
H28A0.88880.38010.48950.053*
C210.6867 (2)0.6487 (3)0.37683 (11)0.0518 (7)
H21A0.73170.67910.35550.062*
N40.9507 (3)0.0307 (2)0.41143 (10)0.0699 (8)
C321.0312 (3)0.1611 (3)0.47307 (11)0.0518 (8)
C90.8295 (2)0.2592 (2)0.31804 (11)0.0461 (7)
H9A0.80370.25960.35080.055*
C240.5520 (2)0.5564 (3)0.43830 (10)0.0531 (8)
H24A0.50520.52520.45850.064*
C120.9611 (2)0.6265 (3)0.35794 (11)0.0488 (7)
C170.9458 (3)0.7485 (3)0.34484 (15)0.0641 (9)
H17A0.96230.80990.36910.077*
C20.4127 (3)0.2027 (3)0.29789 (12)0.0613 (9)
H2B0.36640.13770.29980.074*
C331.1130 (3)0.2305 (3)0.50087 (13)0.0649 (9)
H33A1.10230.27800.52860.078*
C300.8832 (3)0.0654 (3)0.44097 (12)0.0656 (9)
H30A0.81250.03920.43640.079*
C270.7613 (2)0.3925 (3)0.52859 (11)0.0530 (8)
H27A0.77770.36310.56350.064*
H27B0.77250.48000.52840.064*
C80.8164 (3)0.1342 (2)0.29330 (12)0.0569 (8)
H8A0.87220.11900.27320.068*
H8B0.81890.07080.31900.068*
C290.8691 (2)0.2051 (3)0.51457 (11)0.0539 (8)
H29A0.91650.21530.54700.065*
H29B0.80910.15530.52040.065*
C30.3870 (2)0.3165 (3)0.31343 (11)0.0502 (7)
C150.8816 (2)0.6849 (3)0.25791 (13)0.0649 (9)
H15A0.85550.70700.22430.078*
C370.5676 (3)0.2741 (3)0.42735 (13)0.0655 (9)
H37A0.57290.26770.39140.079*
H37B0.49870.31010.42970.079*
C311.0450 (3)0.0900 (3)0.43109 (12)0.0600 (9)
C160.9053 (3)0.7754 (3)0.29473 (16)0.0705 (10)
H16A0.89350.85650.28520.085*
C361.1447 (4)0.0868 (3)0.41568 (14)0.0819 (11)
H36A1.15570.04000.38780.098*
C190.2627 (3)0.4400 (3)0.34839 (14)0.0859 (11)
H19A0.19640.43240.36110.129*
H19B0.25340.49480.31980.129*
H19C0.31670.47140.37490.129*
C341.2100 (3)0.2246 (4)0.48492 (17)0.0868 (11)
H34A1.26720.26850.50260.104*
C380.6542 (3)0.8897 (3)0.34226 (14)0.0837 (11)
H38A0.62950.97010.33200.125*
H38B0.65930.84180.31250.125*
H38C0.72340.89480.36340.125*
C351.2257 (4)0.1541 (4)0.44256 (19)0.0967 (13)
H35A1.29260.15320.43270.116*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0835 (3)0.0932 (3)0.0707 (3)0.0159 (2)0.0360 (2)0.00961 (19)
Br20.0870 (3)0.0610 (2)0.1373 (4)0.0144 (2)0.0053 (3)0.0236 (2)
O30.0438 (12)0.0378 (10)0.0612 (13)0.0029 (9)0.0027 (10)0.0005 (9)
O60.0492 (12)0.0533 (11)0.0394 (11)0.0115 (9)0.0054 (9)0.0002 (9)
O50.0516 (13)0.0695 (13)0.0438 (12)0.0080 (10)0.0158 (10)0.0097 (10)
N10.0421 (14)0.0436 (13)0.0450 (14)0.0011 (11)0.0027 (11)0.0011 (11)
C70.0458 (18)0.0403 (15)0.0527 (19)0.0047 (13)0.0048 (14)0.0043 (13)
O20.0483 (13)0.0421 (11)0.0715 (14)0.0002 (9)0.0053 (11)0.0120 (10)
O10.0551 (14)0.0748 (15)0.0847 (16)0.0046 (12)0.0280 (12)0.0170 (12)
O40.0647 (15)0.0530 (12)0.0869 (16)0.0094 (11)0.0140 (12)0.0155 (12)
N30.0592 (18)0.0472 (14)0.0467 (15)0.0145 (13)0.0012 (13)0.0014 (12)
C60.0439 (17)0.0407 (15)0.0441 (17)0.0025 (14)0.0006 (13)0.0030 (13)
C110.0461 (19)0.062 (2)0.0464 (19)0.0042 (15)0.0020 (14)0.0052 (15)
C220.0470 (19)0.0467 (17)0.0524 (19)0.0010 (15)0.0015 (15)0.0027 (14)
C200.0443 (18)0.0499 (17)0.0563 (19)0.0037 (14)0.0176 (14)0.0023 (14)
C100.0475 (19)0.0474 (16)0.0536 (18)0.0049 (14)0.0061 (14)0.0001 (14)
C260.0456 (19)0.0514 (17)0.0443 (18)0.0040 (14)0.0091 (14)0.0056 (13)
C180.056 (2)0.072 (2)0.059 (2)0.0019 (17)0.0093 (16)0.0008 (16)
C230.0484 (19)0.0570 (19)0.0555 (19)0.0168 (15)0.0139 (15)0.0053 (15)
C50.0512 (19)0.0421 (16)0.0514 (18)0.0026 (14)0.0078 (14)0.0025 (13)
C250.0377 (16)0.0492 (16)0.0398 (16)0.0025 (13)0.0050 (13)0.0011 (13)
C10.054 (2)0.0441 (17)0.069 (2)0.0031 (15)0.0117 (16)0.0111 (15)
N20.0551 (17)0.0638 (17)0.0552 (16)0.0059 (14)0.0051 (13)0.0098 (14)
C140.055 (2)0.0559 (19)0.052 (2)0.0095 (15)0.0081 (15)0.0048 (15)
C40.058 (2)0.0401 (15)0.0506 (18)0.0059 (15)0.0082 (15)0.0033 (13)
C130.0356 (16)0.0451 (16)0.0486 (18)0.0033 (13)0.0093 (13)0.0038 (14)
C280.0470 (18)0.0471 (16)0.0385 (16)0.0028 (14)0.0041 (13)0.0030 (13)
C210.0473 (19)0.0535 (18)0.0576 (19)0.0047 (15)0.0176 (15)0.0075 (15)
N40.093 (2)0.0568 (16)0.0565 (18)0.0188 (17)0.0036 (17)0.0117 (13)
C320.067 (2)0.0425 (16)0.0447 (18)0.0194 (16)0.0062 (16)0.0063 (14)
C90.0510 (19)0.0432 (15)0.0437 (17)0.0011 (14)0.0067 (14)0.0024 (13)
C240.0443 (19)0.069 (2)0.0486 (18)0.0007 (16)0.0157 (14)0.0067 (15)
C120.0402 (18)0.0482 (18)0.059 (2)0.0062 (13)0.0105 (15)0.0053 (15)
C170.052 (2)0.054 (2)0.089 (3)0.0063 (16)0.0194 (19)0.0116 (18)
C20.055 (2)0.0499 (18)0.080 (2)0.0143 (16)0.0147 (17)0.0096 (16)
C330.069 (3)0.061 (2)0.062 (2)0.0053 (19)0.0019 (19)0.0013 (17)
C300.080 (3)0.0473 (17)0.061 (2)0.0081 (18)0.0121 (19)0.0066 (16)
C270.058 (2)0.0592 (18)0.0424 (17)0.0102 (16)0.0096 (15)0.0020 (14)
C80.059 (2)0.0398 (16)0.070 (2)0.0016 (15)0.0057 (17)0.0015 (14)
C290.060 (2)0.0574 (18)0.0435 (17)0.0101 (16)0.0060 (15)0.0000 (14)
C30.0467 (19)0.0559 (19)0.0478 (18)0.0010 (15)0.0069 (14)0.0065 (14)
C150.053 (2)0.067 (2)0.075 (2)0.0106 (17)0.0108 (17)0.0244 (19)
C370.054 (2)0.0583 (19)0.080 (2)0.0057 (16)0.0011 (18)0.0133 (17)
C310.076 (3)0.0487 (18)0.054 (2)0.0194 (18)0.0079 (19)0.0075 (16)
C160.059 (2)0.0464 (19)0.108 (3)0.0020 (17)0.020 (2)0.017 (2)
C360.103 (3)0.078 (3)0.070 (3)0.028 (3)0.028 (2)0.003 (2)
C190.071 (3)0.088 (3)0.106 (3)0.013 (2)0.036 (2)0.022 (2)
C340.077 (3)0.090 (3)0.093 (3)0.007 (2)0.012 (2)0.004 (2)
C380.093 (3)0.062 (2)0.098 (3)0.006 (2)0.021 (2)0.025 (2)
C350.076 (3)0.109 (3)0.111 (4)0.018 (3)0.033 (3)0.017 (3)
Geometric parameters (Å, º) top
Br1—C181.950 (3)C14—C131.385 (4)
Br2—C371.949 (3)C14—H14A0.9300
O3—C71.416 (3)C4—C31.385 (4)
O3—C91.427 (3)C4—H4A0.9300
O6—C261.421 (3)C13—C121.397 (4)
O6—C281.437 (3)C28—C291.506 (4)
O5—C261.407 (3)C28—C271.514 (4)
O5—C271.428 (3)C28—H28A0.9800
N1—C111.356 (3)C21—H21A0.9300
N1—C131.383 (3)N4—C301.311 (4)
N1—C101.454 (3)N4—C311.385 (4)
C7—O21.418 (3)C32—C331.394 (4)
C7—C61.510 (4)C32—C311.395 (4)
C7—C181.519 (4)C9—C81.518 (4)
O2—C81.422 (3)C9—H9A0.9800
O1—C31.360 (4)C24—H24A0.9300
O1—C191.414 (4)C12—C171.388 (4)
O4—C221.367 (3)C17—C161.374 (5)
O4—C381.422 (4)C17—H17A0.9300
N3—C301.361 (4)C2—C31.371 (4)
N3—C321.385 (4)C2—H2B0.9300
N3—C291.449 (4)C33—C341.368 (5)
C6—C51.378 (4)C33—H33A0.9300
C6—C11.382 (4)C30—H30A0.9300
C11—N21.301 (4)C27—H27A0.9700
C11—H11A0.9300C27—H27B0.9700
C22—C211.366 (4)C8—H8A0.9700
C22—C231.382 (4)C8—H8B0.9700
C20—C251.373 (4)C29—H29A0.9700
C20—C211.391 (4)C29—H29B0.9700
C20—H20A0.9300C15—C161.390 (5)
C10—C91.512 (4)C15—H15A0.9300
C10—H10A0.9700C37—H37A0.9700
C10—H10B0.9700C37—H37B0.9700
C26—C371.515 (4)C31—C361.392 (5)
C26—C251.528 (4)C16—H16A0.9300
C18—H18A0.9700C36—C351.365 (5)
C18—H18B0.9700C36—H36A0.9300
C23—C241.375 (4)C19—H19A0.9600
C23—H23A0.9300C19—H19B0.9600
C5—C41.382 (4)C19—H19C0.9600
C5—H5A0.9300C34—C351.406 (6)
C25—C241.394 (4)C34—H34A0.9300
C1—C21.376 (4)C38—H38A0.9600
C1—H1A0.9300C38—H38B0.9600
N2—C121.395 (4)C38—H38C0.9600
C14—C151.364 (4)C35—H35A0.9300
C7—O3—C9108.34 (19)C33—C32—C31123.1 (3)
C26—O6—C28108.4 (2)O3—C9—C10108.4 (2)
C26—O5—C27105.1 (2)O3—C9—C8102.4 (2)
C11—N1—C13106.2 (2)C10—C9—C8112.6 (2)
C11—N1—C10126.9 (2)O3—C9—H9A111.1
C13—N1—C10126.9 (2)C10—C9—H9A111.1
O3—C7—O2106.6 (2)C8—C9—H9A111.1
O3—C7—C6112.0 (2)C23—C24—C25121.6 (3)
O2—C7—C6110.4 (2)C23—C24—H24A119.2
O3—C7—C18108.9 (2)C25—C24—H24A119.2
O2—C7—C18110.6 (2)C17—C12—N2130.2 (3)
C6—C7—C18108.4 (2)C17—C12—C13119.6 (3)
C7—O2—C8109.38 (19)N2—C12—C13110.1 (2)
C3—O1—C19118.2 (2)C16—C17—C12117.5 (3)
C22—O4—C38117.4 (2)C16—C17—H17A121.2
C30—N3—C32106.0 (3)C12—C17—H17A121.2
C30—N3—C29126.6 (3)C3—C2—C1120.5 (3)
C32—N3—C29127.0 (3)C3—C2—H2B119.8
C5—C6—C1118.0 (3)C1—C2—H2B119.8
C5—C6—C7119.9 (2)C34—C33—C32116.0 (3)
C1—C6—C7122.1 (2)C34—C33—H33A122.0
N2—C11—N1114.6 (3)C32—C33—H33A122.0
N2—C11—H11A122.7N4—C30—N3114.0 (3)
N1—C11—H11A122.7N4—C30—H30A123.0
C21—C22—O4124.7 (3)N3—C30—H30A123.0
C21—C22—C23120.4 (3)O5—C27—C28103.5 (2)
O4—C22—C23114.9 (3)O5—C27—H27A111.1
C25—C20—C21121.5 (3)C28—C27—H27A111.1
C25—C20—H20A119.2O5—C27—H27B111.1
C21—C20—H20A119.2C28—C27—H27B111.1
N1—C10—C9114.0 (2)H27A—C27—H27B109.0
N1—C10—H10A108.7O2—C8—C9104.5 (2)
C9—C10—H10A108.7O2—C8—H8A110.8
N1—C10—H10B108.7C9—C8—H8A110.8
C9—C10—H10B108.7O2—C8—H8B110.8
H10A—C10—H10B107.6C9—C8—H8B110.8
O5—C26—O6105.9 (2)H8A—C8—H8B108.9
O5—C26—C37109.9 (2)N3—C29—C28111.6 (2)
O6—C26—C37109.8 (2)N3—C29—H29A109.3
O5—C26—C25111.4 (2)C28—C29—H29A109.3
O6—C26—C25110.7 (2)N3—C29—H29B109.3
C37—C26—C25109.1 (2)C28—C29—H29B109.3
C7—C18—Br1112.5 (2)H29A—C29—H29B108.0
C7—C18—H18A109.1O1—C3—C2115.8 (3)
Br1—C18—H18A109.1O1—C3—C4124.7 (3)
C7—C18—H18B109.1C2—C3—C4119.5 (3)
Br1—C18—H18B109.1C14—C15—C16121.6 (3)
H18A—C18—H18B107.8C14—C15—H15A119.2
C24—C23—C22119.3 (3)C16—C15—H15A119.2
C24—C23—H23A120.3C26—C37—Br2114.2 (2)
C22—C23—H23A120.3C26—C37—H37A108.7
C6—C5—C4121.6 (3)Br2—C37—H37A108.7
C6—C5—H5A119.2C26—C37—H37B108.7
C4—C5—H5A119.2Br2—C37—H37B108.7
C20—C25—C24117.6 (3)H37A—C37—H37B107.6
C20—C25—C26122.6 (2)N4—C31—C36130.3 (3)
C24—C25—C26119.8 (3)N4—C31—C32110.3 (3)
C2—C1—C6121.0 (3)C36—C31—C32119.4 (4)
C2—C1—H1A119.5C17—C16—C15121.9 (3)
C6—C1—H1A119.5C17—C16—H16A119.0
C11—N2—C12104.0 (2)C15—C16—H16A119.0
C15—C14—C13116.7 (3)C35—C36—C31118.3 (4)
C15—C14—H14A121.7C35—C36—H36A120.9
C13—C14—H14A121.7C31—C36—H36A120.9
C5—C4—C3119.4 (3)O1—C19—H19A109.5
C5—C4—H4A120.3O1—C19—H19B109.5
C3—C4—H4A120.3H19A—C19—H19B109.5
N1—C13—C14132.3 (3)O1—C19—H19C109.5
N1—C13—C12105.1 (2)H19A—C19—H19C109.5
C14—C13—C12122.6 (3)H19B—C19—H19C109.5
O6—C28—C29108.7 (2)C33—C34—C35121.9 (4)
O6—C28—C27103.8 (2)C33—C34—H34A119.0
C29—C28—C27113.8 (2)C35—C34—H34A119.0
O6—C28—H28A110.1O4—C38—H38A109.5
C29—C28—H28A110.1O4—C38—H38B109.5
C27—C28—H28A110.1H38A—C38—H38B109.5
C22—C21—C20119.6 (3)O4—C38—H38C109.5
C22—C21—H21A120.2H38A—C38—H38C109.5
C20—C21—H21A120.2H38B—C38—H38C109.5
C30—N4—C31104.4 (3)C36—C35—C34121.3 (4)
N3—C32—C33131.6 (3)C36—C35—H35A119.3
N3—C32—C31105.3 (3)C34—C35—H35A119.3
C9—O3—C7—O221.4 (3)C30—N3—C32—C310.4 (3)
C9—O3—C7—C699.3 (2)C29—N3—C32—C31174.4 (2)
C9—O3—C7—C18140.8 (2)C7—O3—C9—C10148.8 (2)
O3—C7—O2—C83.1 (3)C7—O3—C9—C829.7 (3)
C6—C7—O2—C8118.7 (3)N1—C10—C9—O365.3 (3)
C18—C7—O2—C8121.3 (3)N1—C10—C9—C8177.8 (2)
O3—C7—C6—C537.9 (3)C22—C23—C24—C250.7 (4)
O2—C7—C6—C5156.4 (2)C20—C25—C24—C231.9 (4)
C18—C7—C6—C582.3 (3)C26—C25—C24—C23179.0 (3)
O3—C7—C6—C1144.5 (3)C11—N2—C12—C17178.9 (3)
O2—C7—C6—C125.9 (4)C11—N2—C12—C130.2 (3)
C18—C7—C6—C195.4 (3)N1—C13—C12—C17179.0 (3)
C13—N1—C11—N20.1 (3)C14—C13—C12—C171.1 (4)
C10—N1—C11—N2179.3 (3)N1—C13—C12—N20.2 (3)
C38—O4—C22—C215.2 (4)C14—C13—C12—N2179.7 (3)
C38—O4—C22—C23174.8 (3)N2—C12—C17—C16179.2 (3)
C11—N1—C10—C998.5 (3)C13—C12—C17—C160.2 (4)
C13—N1—C10—C980.5 (3)C6—C1—C2—C30.3 (5)
C27—O5—C26—O635.2 (3)N3—C32—C33—C34178.4 (3)
C27—O5—C26—C37153.8 (2)C31—C32—C33—C340.5 (5)
C27—O5—C26—C2585.2 (3)C31—N4—C30—N30.1 (3)
C28—O6—C26—O520.4 (3)C32—N3—C30—N40.4 (3)
C28—O6—C26—C37139.0 (2)C29—N3—C30—N4174.3 (3)
C28—O6—C26—C25100.5 (2)C26—O5—C27—C2835.5 (3)
O3—C7—C18—Br156.3 (3)O6—C28—C27—O522.5 (3)
O2—C7—C18—Br160.5 (3)C29—C28—C27—O595.5 (3)
C6—C7—C18—Br1178.31 (18)C7—O2—C8—C914.9 (3)
C21—C22—C23—C241.1 (4)O3—C9—C8—O226.8 (3)
O4—C22—C23—C24178.8 (3)C10—C9—C8—O2143.0 (2)
C1—C6—C5—C40.5 (4)C30—N3—C29—C2891.2 (3)
C7—C6—C5—C4178.3 (3)C32—N3—C29—C2881.6 (3)
C21—C20—C25—C241.2 (4)O6—C28—C29—N360.3 (3)
C21—C20—C25—C26179.7 (3)C27—C28—C29—N3175.4 (2)
O5—C26—C25—C20129.8 (3)C19—O1—C3—C2178.7 (3)
O6—C26—C25—C2012.2 (4)C19—O1—C3—C42.9 (4)
C37—C26—C25—C20108.7 (3)C1—C2—C3—O1177.6 (3)
O5—C26—C25—C2451.2 (3)C1—C2—C3—C40.9 (5)
O6—C26—C25—C24168.7 (2)C5—C4—C3—O1177.0 (3)
C37—C26—C25—C2470.3 (3)C5—C4—C3—C21.4 (4)
C5—C6—C1—C21.0 (4)C13—C14—C15—C160.3 (5)
C7—C6—C1—C2178.7 (3)O5—C26—C37—Br254.0 (3)
N1—C11—N2—C120.2 (3)O6—C26—C37—Br262.2 (3)
C6—C5—C4—C30.7 (4)C25—C26—C37—Br2176.4 (2)
C11—N1—C13—C14179.8 (3)C30—N4—C31—C36179.2 (3)
C10—N1—C13—C141.0 (5)C30—N4—C31—C320.2 (3)
C11—N1—C13—C120.0 (3)N3—C32—C31—N40.4 (3)
C10—N1—C13—C12179.1 (2)C33—C32—C31—N4179.5 (3)
C15—C14—C13—N1179.3 (3)N3—C32—C31—C36179.0 (3)
C15—C14—C13—C120.8 (4)C33—C32—C31—C360.1 (4)
C26—O6—C28—C29119.8 (2)C12—C17—C16—C150.9 (5)
C26—O6—C28—C271.6 (3)C14—C15—C16—C171.2 (5)
O4—C22—C21—C20178.2 (3)N4—C31—C36—C35179.3 (3)
C23—C22—C21—C201.7 (4)C32—C31—C36—C350.0 (5)
C25—C20—C21—C220.5 (4)C32—C33—C34—C350.9 (5)
C30—N3—C32—C33179.5 (3)C31—C36—C35—C340.3 (6)
C29—N3—C32—C336.6 (5)C33—C34—C35—C360.8 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C37—H37A···Cg0.972.653.515148
C15—H15A···O1i0.932.563.362 (5)144
C20—H20A···O60.932.442.788 (4)102
Symmetry code: (i) x+1, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC19H19BrN2O3
Mr403.26
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)12.683 (4), 10.967 (4), 26.530 (8)
β (°) 99.677 (7)
V3)3638 (2)
Z8
Radiation typeMo Kα
µ (mm1)2.28
Crystal size (mm)0.41 × 0.21 × 0.14
Data collection
DiffractometerSiemens SMART 1000 CCD area-detector
diffractometer
Absorption correctionMulti-scan
SADABS (Sheldrick, 1996)
Tmin, Tmax0.455, 0.741
No. of measured, independent and
observed [I > 2σ(I)] reflections
19950, 7191, 4269
Rint0.036
(sin θ/λ)max1)0.619
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.104, 0.99
No. of reflections7191
No. of parameters451
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C37—H37A···Cg0.972.6533.515148.37
C15—H15A···O1i0.932.5603.362 (5)143.80
C20—H20A···O60.932.4442.788 (4)101.83
Symmetry code: (i) x+1, y+1/2, z+1/2.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds