Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805041127/lh6563sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805041127/lh6563Isup2.hkl |
CCDC reference: 296611
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.007 Å
- R factor = 0.037
- wR factor = 0.091
- Data-to-parameter ratio = 12.2
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C3 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C13 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. O1 .. 3.11 Ang.
Alert level G REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 26.35 From the CIF: _reflns_number_total 3083 Count of symmetry unique reflns 2334 Completeness (_total/calc) 132.09% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 749 Fraction of Friedel pairs measured 0.321 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 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 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
The title compound was prepared by the reaction of 4-bromobenzaldehyde (1 mmol) with dimedone (2 mmol) and ammonium acetate (1 mmol) under microwave irradiation (yield 93%; m.p. >574 K). Single crystals suitable for X-ray diffraction were obtained by slow evaportation of (I) from an ethanol solution.
H atoms bonded to C atoms were placed in geometrically idealized positions (C—H = 0.93–0.98 Å) and allowed to ride on their parent atoms, with Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for other H atoms. The H atom bonded to N1 was refined isotropically.
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL.
Fig. 1. The molecular structure (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme. | |
Fig. 2. View (Spek, 2003) of the hydrogen bonded (dashed lines) chain in (I). |
C23H26BrNO2 | Dx = 1.315 Mg m−3 |
Mr = 428.36 | Melting point > 574 K |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 2822 reflections |
a = 14.1598 (16) Å | θ = 2.8–23.0° |
b = 14.0629 (16) Å | µ = 1.92 mm−1 |
c = 10.8624 (12) Å | T = 294 K |
V = 2163.0 (4) Å3 | Block, yellow |
Z = 4 | 0.26 × 0.20 × 0.16 mm |
F(000) = 888 |
Bruker SMART CCD area-detector diffractometer | 3083 independent reflections |
Radiation source: fine-focus sealed tube | 2016 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.052 |
ϕ and ω scans | θmax = 26.4°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −17→17 |
Tmin = 0.610, Tmax = 0.736 | k = −16→17 |
11747 measured reflections | l = −13→6 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.037 | w = 1/[σ2(Fo2) + (0.0196P)2 + 1.345P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.091 | (Δ/σ)max < 0.001 |
S = 1.00 | Δρmax = 0.42 e Å−3 |
3083 reflections | Δρmin = −0.54 e Å−3 |
252 parameters | Absolute structure: Flack (1983), 750 Friedel pairs |
2 restraints | Absolute structure parameter: 0.003 (13) |
C23H26BrNO2 | V = 2163.0 (4) Å3 |
Mr = 428.36 | Z = 4 |
Orthorhombic, Pna21 | Mo Kα radiation |
a = 14.1598 (16) Å | µ = 1.92 mm−1 |
b = 14.0629 (16) Å | T = 294 K |
c = 10.8624 (12) Å | 0.26 × 0.20 × 0.16 mm |
Bruker SMART CCD area-detector diffractometer | 3083 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2016 reflections with I > 2σ(I) |
Tmin = 0.610, Tmax = 0.736 | Rint = 0.052 |
11747 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.091 | Δρmax = 0.42 e Å−3 |
S = 1.00 | Δρmin = −0.54 e Å−3 |
3083 reflections | Absolute structure: Flack (1983), 750 Friedel pairs |
252 parameters | Absolute structure parameter: 0.003 (13) |
2 restraints |
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 | 0.80581 (4) | 0.86019 (5) | 0.05271 (7) | 0.1019 (3) | |
O1 | 0.6134 (2) | 0.4835 (2) | 0.3398 (3) | 0.0626 (9) | |
O2 | 0.76103 (19) | 0.7332 (2) | 0.6366 (3) | 0.0575 (9) | |
N1 | 0.4359 (2) | 0.7000 (3) | 0.5773 (4) | 0.0493 (11) | |
H1 | 0.3813 (16) | 0.715 (3) | 0.608 (4) | 0.063 (15)* | |
C1 | 0.5363 (3) | 0.5144 (3) | 0.3745 (4) | 0.0477 (12) | |
C2 | 0.4449 (4) | 0.4714 (3) | 0.3287 (5) | 0.0585 (13) | |
H2A | 0.4565 | 0.4061 | 0.3041 | 0.070* | |
H2B | 0.4241 | 0.5062 | 0.2565 | 0.070* | |
C3 | 0.3663 (3) | 0.4728 (3) | 0.4247 (5) | 0.0509 (12) | |
C4 | 0.3925 (4) | 0.4083 (4) | 0.5322 (6) | 0.0735 (16) | |
H4A | 0.4518 | 0.4284 | 0.5663 | 0.110* | |
H4B | 0.3979 | 0.3439 | 0.5037 | 0.110* | |
H4C | 0.3444 | 0.4119 | 0.5943 | 0.110* | |
C5 | 0.2726 (4) | 0.4385 (4) | 0.3676 (6) | 0.0816 (19) | |
H5A | 0.2776 | 0.3723 | 0.3471 | 0.122* | |
H5B | 0.2595 | 0.4745 | 0.2945 | 0.122* | |
H5C | 0.2223 | 0.4474 | 0.4258 | 0.122* | |
C6 | 0.3546 (3) | 0.5742 (3) | 0.4692 (5) | 0.0553 (14) | |
H6A | 0.3221 | 0.6104 | 0.4060 | 0.066* | |
H6B | 0.3148 | 0.5740 | 0.5419 | 0.066* | |
C7 | 0.4451 (3) | 0.6238 (3) | 0.4997 (4) | 0.0423 (11) | |
C8 | 0.5304 (3) | 0.5958 (3) | 0.4564 (4) | 0.0393 (10) | |
C9 | 0.6203 (3) | 0.6481 (3) | 0.4908 (4) | 0.0426 (11) | |
H9 | 0.6655 | 0.6011 | 0.5217 | 0.051* | |
C10 | 0.6010 (3) | 0.7182 (3) | 0.5932 (4) | 0.0396 (10) | |
C11 | 0.5125 (3) | 0.7435 (3) | 0.6280 (4) | 0.0425 (11) | |
C12 | 0.4902 (3) | 0.8153 (3) | 0.7259 (5) | 0.0558 (13) | |
H12A | 0.4788 | 0.7823 | 0.8029 | 0.067* | |
H12B | 0.4326 | 0.8485 | 0.7037 | 0.067* | |
C13 | 0.5690 (3) | 0.8880 (3) | 0.7447 (5) | 0.0536 (12) | |
C14 | 0.5759 (4) | 0.9559 (4) | 0.6370 (6) | 0.0829 (18) | |
H14A | 0.5922 | 0.9212 | 0.5639 | 0.124* | |
H14B | 0.6237 | 1.0026 | 0.6534 | 0.124* | |
H14C | 0.5162 | 0.9871 | 0.6252 | 0.124* | |
C15 | 0.5499 (4) | 0.9446 (4) | 0.8623 (5) | 0.086 (2) | |
H15A | 0.4948 | 0.9833 | 0.8511 | 0.130* | |
H15B | 0.6032 | 0.9844 | 0.8802 | 0.130* | |
H15C | 0.5398 | 0.9014 | 0.9295 | 0.130* | |
C16 | 0.6613 (3) | 0.8308 (4) | 0.7572 (5) | 0.0588 (14) | |
H16A | 0.7138 | 0.8751 | 0.7585 | 0.071* | |
H16B | 0.6605 | 0.7981 | 0.8358 | 0.071* | |
C17 | 0.6787 (3) | 0.7601 (3) | 0.6597 (4) | 0.0474 (11) | |
C18 | 0.6649 (3) | 0.6979 (3) | 0.3818 (4) | 0.0445 (11) | |
C19 | 0.7558 (3) | 0.6763 (4) | 0.3432 (5) | 0.0600 (14) | |
H19 | 0.7896 | 0.6290 | 0.3839 | 0.072* | |
C20 | 0.7974 (3) | 0.7235 (4) | 0.2452 (5) | 0.0687 (16) | |
H20 | 0.8584 | 0.7079 | 0.2209 | 0.082* | |
C21 | 0.7489 (4) | 0.7927 (4) | 0.1847 (5) | 0.0656 (15) | |
C22 | 0.6584 (4) | 0.8155 (4) | 0.2208 (5) | 0.0704 (16) | |
H22 | 0.6253 | 0.8632 | 0.1802 | 0.084* | |
C23 | 0.6172 (3) | 0.7673 (3) | 0.3177 (5) | 0.0551 (13) | |
H23 | 0.5556 | 0.7822 | 0.3402 | 0.066* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.1107 (5) | 0.1424 (6) | 0.0527 (3) | −0.0667 (4) | 0.0017 (5) | 0.0173 (5) |
O1 | 0.069 (2) | 0.058 (2) | 0.060 (2) | 0.0170 (18) | 0.0135 (19) | −0.0044 (19) |
O2 | 0.0302 (16) | 0.073 (2) | 0.070 (2) | −0.0073 (15) | −0.0019 (17) | 0.0091 (19) |
N1 | 0.0268 (18) | 0.049 (2) | 0.072 (3) | 0.0034 (16) | 0.000 (2) | −0.022 (2) |
C1 | 0.059 (3) | 0.044 (3) | 0.039 (3) | 0.008 (2) | 0.008 (2) | 0.007 (2) |
C2 | 0.073 (4) | 0.050 (3) | 0.052 (3) | −0.010 (3) | 0.004 (3) | −0.010 (3) |
C3 | 0.050 (3) | 0.045 (3) | 0.057 (3) | −0.007 (2) | −0.006 (3) | −0.014 (3) |
C4 | 0.085 (3) | 0.065 (3) | 0.071 (4) | −0.017 (2) | 0.004 (4) | 0.003 (4) |
C5 | 0.079 (4) | 0.076 (4) | 0.090 (5) | −0.017 (3) | −0.009 (3) | −0.034 (4) |
C6 | 0.038 (2) | 0.051 (3) | 0.078 (4) | −0.006 (2) | −0.003 (3) | −0.013 (3) |
C7 | 0.035 (2) | 0.038 (2) | 0.054 (3) | −0.0009 (19) | −0.003 (2) | −0.002 (2) |
C8 | 0.040 (2) | 0.037 (2) | 0.041 (2) | 0.0017 (19) | 0.004 (2) | −0.001 (2) |
C9 | 0.031 (2) | 0.044 (3) | 0.053 (3) | 0.0066 (19) | 0.002 (2) | 0.004 (2) |
C10 | 0.032 (2) | 0.044 (3) | 0.043 (3) | −0.0009 (18) | 0.0020 (19) | 0.000 (2) |
C11 | 0.031 (2) | 0.047 (3) | 0.050 (3) | −0.0006 (19) | −0.003 (2) | −0.006 (2) |
C12 | 0.043 (3) | 0.058 (3) | 0.067 (3) | −0.001 (2) | 0.004 (3) | −0.017 (3) |
C13 | 0.051 (3) | 0.054 (3) | 0.057 (3) | −0.010 (2) | −0.006 (3) | −0.008 (3) |
C14 | 0.101 (4) | 0.061 (4) | 0.086 (5) | −0.004 (3) | −0.007 (4) | 0.010 (3) |
C15 | 0.087 (4) | 0.090 (5) | 0.082 (5) | −0.013 (3) | 0.001 (4) | −0.043 (4) |
C16 | 0.052 (3) | 0.066 (3) | 0.059 (3) | −0.018 (2) | −0.013 (3) | −0.002 (3) |
C17 | 0.038 (3) | 0.058 (3) | 0.046 (3) | −0.005 (2) | −0.003 (2) | 0.012 (2) |
C18 | 0.038 (3) | 0.049 (3) | 0.047 (3) | 0.001 (2) | 0.009 (2) | −0.002 (2) |
C19 | 0.051 (3) | 0.064 (3) | 0.065 (3) | 0.006 (3) | 0.012 (3) | 0.005 (3) |
C20 | 0.047 (3) | 0.094 (4) | 0.065 (4) | −0.008 (3) | 0.024 (3) | −0.004 (3) |
C21 | 0.074 (4) | 0.081 (4) | 0.042 (3) | −0.037 (3) | −0.003 (3) | 0.001 (3) |
C22 | 0.074 (4) | 0.077 (4) | 0.060 (4) | −0.007 (3) | −0.012 (3) | 0.020 (3) |
C23 | 0.047 (3) | 0.063 (3) | 0.055 (3) | 0.003 (2) | 0.002 (3) | 0.013 (3) |
Br1—C21 | 1.899 (5) | C10—C11 | 1.357 (5) |
O1—C1 | 1.234 (5) | C10—C17 | 1.442 (6) |
O2—C17 | 1.251 (5) | C11—C12 | 1.499 (6) |
N1—C11 | 1.361 (5) | C12—C13 | 1.528 (6) |
N1—C7 | 1.370 (5) | C12—H12A | 0.9700 |
N1—H1 | 0.87 (3) | C12—H12B | 0.9700 |
C1—C8 | 1.452 (6) | C13—C14 | 1.513 (7) |
C1—C2 | 1.512 (6) | C13—C15 | 1.529 (7) |
C2—C3 | 1.525 (7) | C13—C16 | 1.541 (6) |
C2—H2A | 0.9700 | C14—H14A | 0.9600 |
C2—H2B | 0.9700 | C14—H14B | 0.9600 |
C3—C6 | 1.515 (6) | C14—H14C | 0.9600 |
C3—C4 | 1.525 (7) | C15—H15A | 0.9600 |
C3—C5 | 1.542 (7) | C15—H15B | 0.9600 |
C4—H4A | 0.9600 | C15—H15C | 0.9600 |
C4—H4B | 0.9600 | C16—C17 | 1.473 (7) |
C4—H4C | 0.9600 | C16—H16A | 0.9700 |
C5—H5A | 0.9600 | C16—H16B | 0.9700 |
C5—H5B | 0.9600 | C18—C23 | 1.377 (6) |
C5—H5C | 0.9600 | C18—C19 | 1.388 (6) |
C6—C7 | 1.495 (6) | C19—C20 | 1.385 (7) |
C6—H6A | 0.9700 | C19—H19 | 0.9300 |
C6—H6B | 0.9700 | C20—C21 | 1.361 (7) |
C7—C8 | 1.355 (5) | C20—H20 | 0.9300 |
C8—C9 | 1.517 (6) | C21—C22 | 1.378 (8) |
C9—C10 | 1.511 (6) | C22—C23 | 1.381 (7) |
C9—C18 | 1.513 (6) | C22—H22 | 0.9300 |
C9—H9 | 0.9800 | C23—H23 | 0.9300 |
C11—N1—C7 | 121.7 (3) | N1—C11—C12 | 115.0 (4) |
C11—N1—H1 | 117 (3) | C11—C12—C13 | 113.0 (4) |
C7—N1—H1 | 120 (3) | C11—C12—H12A | 109.0 |
O1—C1—C8 | 121.0 (4) | C13—C12—H12A | 109.0 |
O1—C1—C2 | 121.1 (4) | C11—C12—H12B | 109.0 |
C8—C1—C2 | 117.9 (4) | C13—C12—H12B | 109.0 |
C1—C2—C3 | 113.3 (4) | H12A—C12—H12B | 107.8 |
C1—C2—H2A | 108.9 | C14—C13—C12 | 111.5 (5) |
C3—C2—H2A | 108.9 | C14—C13—C15 | 109.2 (4) |
C1—C2—H2B | 108.9 | C12—C13—C15 | 109.3 (4) |
C3—C2—H2B | 108.9 | C14—C13—C16 | 110.1 (4) |
H2A—C2—H2B | 107.7 | C12—C13—C16 | 106.3 (4) |
C6—C3—C4 | 110.0 (4) | C15—C13—C16 | 110.4 (4) |
C6—C3—C2 | 108.0 (4) | C13—C14—H14A | 109.5 |
C4—C3—C2 | 109.8 (4) | C13—C14—H14B | 109.5 |
C6—C3—C5 | 109.2 (4) | H14A—C14—H14B | 109.5 |
C4—C3—C5 | 109.4 (4) | C13—C14—H14C | 109.5 |
C2—C3—C5 | 110.4 (4) | H14A—C14—H14C | 109.5 |
C3—C4—H4A | 109.5 | H14B—C14—H14C | 109.5 |
C3—C4—H4B | 109.5 | C13—C15—H15A | 109.5 |
H4A—C4—H4B | 109.5 | C13—C15—H15B | 109.5 |
C3—C4—H4C | 109.5 | H15A—C15—H15B | 109.5 |
H4A—C4—H4C | 109.5 | C13—C15—H15C | 109.5 |
H4B—C4—H4C | 109.5 | H15A—C15—H15C | 109.5 |
C3—C5—H5A | 109.5 | H15B—C15—H15C | 109.5 |
C3—C5—H5B | 109.5 | C17—C16—C13 | 115.5 (4) |
H5A—C5—H5B | 109.5 | C17—C16—H16A | 108.4 |
C3—C5—H5C | 109.5 | C13—C16—H16A | 108.4 |
H5A—C5—H5C | 109.5 | C17—C16—H16B | 108.4 |
H5B—C5—H5C | 109.5 | C13—C16—H16B | 108.4 |
C7—C6—C3 | 114.6 (4) | H16A—C16—H16B | 107.5 |
C7—C6—H6A | 108.6 | O2—C17—C10 | 119.1 (4) |
C3—C6—H6A | 108.6 | O2—C17—C16 | 120.3 (4) |
C7—C6—H6B | 108.6 | C10—C17—C16 | 120.5 (4) |
C3—C6—H6B | 108.6 | C23—C18—C19 | 117.2 (5) |
H6A—C6—H6B | 107.6 | C23—C18—C9 | 121.2 (4) |
C8—C7—N1 | 121.7 (4) | C19—C18—C9 | 121.6 (4) |
C8—C7—C6 | 123.5 (4) | C20—C19—C18 | 121.4 (5) |
N1—C7—C6 | 114.8 (4) | C20—C19—H19 | 119.3 |
C7—C8—C1 | 119.5 (4) | C18—C19—H19 | 119.3 |
C7—C8—C9 | 121.5 (4) | C21—C20—C19 | 120.0 (5) |
C1—C8—C9 | 119.0 (4) | C21—C20—H20 | 120.0 |
C10—C9—C18 | 110.5 (3) | C19—C20—H20 | 120.0 |
C10—C9—C8 | 110.3 (3) | C20—C21—C22 | 119.9 (5) |
C18—C9—C8 | 112.5 (4) | C20—C21—Br1 | 120.5 (4) |
C10—C9—H9 | 107.8 | C22—C21—Br1 | 119.6 (5) |
C18—C9—H9 | 107.8 | C21—C22—C23 | 119.7 (5) |
C8—C9—H9 | 107.8 | C21—C22—H22 | 120.2 |
C11—C10—C17 | 117.3 (4) | C23—C22—H22 | 120.2 |
C11—C10—C9 | 122.9 (4) | C18—C23—C22 | 121.8 (5) |
C17—C10—C9 | 119.8 (4) | C18—C23—H23 | 119.1 |
C10—C11—N1 | 120.3 (4) | C22—C23—H23 | 119.1 |
C10—C11—C12 | 124.6 (4) | ||
O1—C1—C2—C3 | 146.4 (5) | C9—C10—C11—C12 | −177.7 (4) |
C8—C1—C2—C3 | −36.2 (6) | C7—N1—C11—C10 | 6.5 (7) |
C1—C2—C3—C6 | 54.3 (5) | C7—N1—C11—C12 | −170.7 (4) |
C1—C2—C3—C4 | −65.7 (5) | C10—C11—C12—C13 | 25.2 (7) |
C1—C2—C3—C5 | 173.6 (4) | N1—C11—C12—C13 | −157.7 (4) |
C4—C3—C6—C7 | 73.4 (5) | C11—C12—C13—C14 | 70.9 (5) |
C2—C3—C6—C7 | −46.4 (6) | C11—C12—C13—C15 | −168.3 (4) |
C5—C3—C6—C7 | −166.5 (5) | C11—C12—C13—C16 | −49.1 (6) |
C11—N1—C7—C8 | −8.9 (7) | C14—C13—C16—C17 | −70.1 (5) |
C11—N1—C7—C6 | 170.1 (4) | C12—C13—C16—C17 | 50.9 (6) |
C3—C6—C7—C8 | 20.4 (7) | C15—C13—C16—C17 | 169.3 (4) |
C3—C6—C7—N1 | −158.6 (4) | C11—C10—C17—O2 | 174.7 (4) |
N1—C7—C8—C1 | 179.8 (4) | C9—C10—C17—O2 | −4.4 (6) |
C6—C7—C8—C1 | 0.9 (7) | C11—C10—C17—C16 | −2.8 (6) |
N1—C7—C8—C9 | −0.6 (7) | C9—C10—C17—C16 | 178.1 (4) |
C6—C7—C8—C9 | −179.5 (4) | C13—C16—C17—O2 | 156.2 (4) |
O1—C1—C8—C7 | −175.4 (4) | C13—C16—C17—C10 | −26.3 (7) |
C2—C1—C8—C7 | 7.3 (6) | C10—C9—C18—C23 | −63.3 (5) |
O1—C1—C8—C9 | 5.1 (7) | C8—C9—C18—C23 | 60.4 (6) |
C2—C1—C8—C9 | −172.3 (4) | C10—C9—C18—C19 | 116.0 (5) |
C7—C8—C9—C10 | 10.6 (6) | C8—C9—C18—C19 | −120.3 (5) |
C1—C8—C9—C10 | −169.8 (4) | C23—C18—C19—C20 | 0.9 (7) |
C7—C8—C9—C18 | −113.2 (5) | C9—C18—C19—C20 | −178.4 (5) |
C1—C8—C9—C18 | 66.4 (5) | C18—C19—C20—C21 | −0.1 (8) |
C18—C9—C10—C11 | 111.9 (5) | C19—C20—C21—C22 | −0.1 (8) |
C8—C9—C10—C11 | −13.1 (5) | C19—C20—C21—Br1 | 178.5 (4) |
C18—C9—C10—C17 | −69.1 (5) | C20—C21—C22—C23 | −0.6 (8) |
C8—C9—C10—C17 | 166.0 (4) | Br1—C21—C22—C23 | −179.2 (4) |
C17—C10—C11—N1 | −173.7 (4) | C19—C18—C23—C22 | −1.6 (8) |
C9—C10—C11—N1 | 5.4 (7) | C9—C18—C23—C22 | 177.7 (5) |
C17—C10—C11—C12 | 3.3 (7) | C21—C22—C23—C18 | 1.5 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.87 (3) | 1.88 (2) | 2.726 (4) | 165 (4) |
Symmetry code: (i) x−1/2, −y+3/2, z. |
Experimental details
Crystal data | |
Chemical formula | C23H26BrNO2 |
Mr | 428.36 |
Crystal system, space group | Orthorhombic, Pna21 |
Temperature (K) | 294 |
a, b, c (Å) | 14.1598 (16), 14.0629 (16), 10.8624 (12) |
V (Å3) | 2163.0 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.92 |
Crystal size (mm) | 0.26 × 0.20 × 0.16 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.610, 0.736 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11747, 3083, 2016 |
Rint | 0.052 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.091, 1.00 |
No. of reflections | 3083 |
No. of parameters | 252 |
No. of restraints | 2 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.42, −0.54 |
Absolute structure | Flack (1983), 750 Friedel pairs |
Absolute structure parameter | 0.003 (13) |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b) and PLATON (Spek, 2003), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.87 (3) | 1.881 (16) | 2.726 (4) | 165 (4) |
Symmetry code: (i) x−1/2, −y+3/2, z. |
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Acridine derivatives with their interesting chemical and physical properties, have immense utility in the pharmaceutical and dyeing industries, and are well known therapeutic agents (Wysocka-Skrzela & Ledochowski, 1976; Nasim & Brychey, 1979; Thull & Testa, 1994). The discovery of acridines as antimalarial and antitumor agents has attracted the attention of organic chemists and thus led to intensive interest in the synthesis of several drugs based on acridine (Khurana et al., 1990; Matsumoto et al., 1983), We report here the crystal structure of the title compound, (I).
The dihydropyridine ring in (I) is in a slight boat conformmation, with atoms N1 and C9 deviating from the C7/C8/C10/C11 mean plane by 0.077 (3) and 0.150 (3) Å, respectively (Fig. 1). Both cyclohexene rings adopt sofa conformations: atom C3 deviaties from the C1/C2/C6/C7/C8 by −0.617 (3) Å and atom C13 deviates from the C10/C11/C12/C16/C17 plane by 0.651 (3) Å. The dihedral angle between the C7/C8/C10/C11 and C7/C8/C10/C11 planes is 2.61 (7)° and that between the C7/C8/C10/C11 and C10/C11/C12/C16/C17 planes is 7.55 (7)°. In the crystal structure, molecules are linked via N—H···O hydrogen bonds, forming one-dimensional chains in the a-axis direction (Table 1 and Fig. 2).