Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807038494/om2147sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807038494/om2147Isup2.hkl |
CCDC reference: 660232
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.007 Å
- R factor = 0.045
- wR factor = 0.105
- Data-to-parameter ratio = 18.9
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.96
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.72 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 3000 Deg. PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 7
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.717 Tmax scaled 0.231 Tmin scaled 0.113
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 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
For related structures see Yang (2006a,b,c,d,e, 2007); Yang & Guo (2006); Zhao (2005); You & Chi (2006). For related literature, see: Allen et al. (1987); Bernardo et al. (1996); Musie et al. (2001); Paul et al. (2002).
3,5-Dibromosalicylaldehyde (0.1 mmol, 18.0 mg) and cyclopropylamine (0.1 mmol, 5.7 mg) were dissolved in MeOH (10 ml). The mixture was stirred at room temperature to give a clear yellow solution. Crystals of the title compound were formed by gradual evaporation of the solvent over a period of about one week at room temperature.
H atoms were placed in idealized positions and constrained to ride on their parent atoms, with O—H distances of 0.82 Å, C—H distances of 0.93–0.97 Å, and with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(O).
Schiff base compounds have been of great interest for a long time. These compounds play an important role in the development of coordination chemistry (Musie et al., 2001; Bernardo et al., 1996; Paul et al., 2002). Recently, we have reported a few Schiff base compounds (Yang, 2006a,b,c,d,e, 2007; Yang & Guo, 2006). As a further investigation of this work, the crystal structure of the title compound is reported here.
The asymmetric unit of the title compound consists of two molecules (Fig. 1). In both molecules, the benzene ring and the cyclopropyl ring are nearly perpendicular, with the dihedral angles of 85.8 (4) and 75.5 (4)°, respectively. All the bond lengths in the molecules are within normal ranges (Allen et al., 1987), and comparable to those of the similar compounds (Zhao, 2005, You & Chi, 2006). The C7═N1 and C17═N2 bond lengths of 1.272 (5) and 1.276 (5) Å conform to the values for double bonds. In the crystal structure, there are no obviously short contacts among the molecules.
For related structures see Yang (2006a,b,c,d,e, 2007); Yang & Guo (2006); Zhao (2005); You & Chi (2006). For related literature, see: Allen et al. (1987); Bernardo et al. (1996); Musie et al. (2001); Paul et al. (2002).
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); 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); software used to prepare material for publication: SHELXL97.
Fig. 1. The structure of the title compound showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Intramolecular hydrogen bonds are shown as dashed lines. |
C10H9Br2NO | Z = 4 |
Mr = 319.00 | F(000) = 616 |
Triclinic, P1 | Dx = 1.926 Mg m−3 |
a = 9.1840 (18) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.495 (2) Å | Cell parameters from 2313 reflections |
c = 12.265 (3) Å | θ = 2.4–25.1° |
α = 70.85 (3)° | µ = 7.33 mm−1 |
β = 68.62 (3)° | T = 298 K |
γ = 69.69 (3)° | Block, yellow |
V = 1100.2 (4) Å3 | 0.40 × 0.20 × 0.20 mm |
Bruker SMART CCD diffractometer | 4830 independent reflections |
Radiation source: fine-focus sealed tube | 2945 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
ω scans | θmax = 27.5°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→11 |
Tmin = 0.157, Tmax = 0.322 | k = −14→14 |
9324 measured reflections | l = −15→15 |
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.105 | H-atom parameters constrained |
S = 0.95 | w = 1/[σ2(Fo2) + (0.0426P)2] where P = (Fo2 + 2Fc2)/3 |
4830 reflections | (Δ/σ)max < 0.001 |
255 parameters | Δρmax = 0.64 e Å−3 |
0 restraints | Δρmin = −0.69 e Å−3 |
C10H9Br2NO | γ = 69.69 (3)° |
Mr = 319.00 | V = 1100.2 (4) Å3 |
Triclinic, P1 | Z = 4 |
a = 9.1840 (18) Å | Mo Kα radiation |
b = 11.495 (2) Å | µ = 7.33 mm−1 |
c = 12.265 (3) Å | T = 298 K |
α = 70.85 (3)° | 0.40 × 0.20 × 0.20 mm |
β = 68.62 (3)° |
Bruker SMART CCD diffractometer | 4830 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2945 reflections with I > 2σ(I) |
Tmin = 0.157, Tmax = 0.322 | Rint = 0.039 |
9324 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.105 | H-atom parameters constrained |
S = 0.95 | Δρmax = 0.64 e Å−3 |
4830 reflections | Δρmin = −0.69 e Å−3 |
255 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 | −0.11261 (8) | −0.17137 (5) | 0.31199 (6) | 0.0654 (2) | |
Br2 | 0.54050 (7) | −0.29887 (5) | 0.31061 (5) | 0.05466 (18) | |
Br3 | 0.48615 (7) | 0.32486 (6) | 0.37844 (5) | 0.0631 (2) | |
Br4 | 0.67363 (7) | 0.01999 (5) | 0.04642 (5) | 0.05876 (19) | |
O1 | −0.1149 (4) | 0.0760 (3) | 0.3466 (3) | 0.0472 (8) | |
H1 | −0.1128 | 0.1446 | 0.3518 | 0.071* | |
O2 | 0.3037 (4) | 0.5125 (3) | 0.2034 (3) | 0.0462 (8) | |
H2 | 0.2358 | 0.5531 | 0.1669 | 0.069* | |
N1 | 0.0071 (5) | 0.2383 (3) | 0.3665 (3) | 0.0427 (10) | |
N2 | 0.1932 (4) | 0.5883 (3) | 0.0169 (3) | 0.0384 (9) | |
C1 | 0.1612 (6) | 0.0265 (4) | 0.3465 (4) | 0.0363 (11) | |
C2 | 0.0329 (6) | −0.0049 (4) | 0.3375 (4) | 0.0361 (11) | |
C3 | 0.0627 (6) | −0.1257 (4) | 0.3186 (4) | 0.0400 (11) | |
C4 | 0.2121 (6) | −0.2115 (4) | 0.3086 (4) | 0.0418 (12) | |
H4 | 0.2293 | −0.2909 | 0.2950 | 0.050* | |
C5 | 0.3354 (6) | −0.1783 (4) | 0.3188 (4) | 0.0407 (11) | |
C6 | 0.3111 (6) | −0.0607 (4) | 0.3378 (4) | 0.0405 (11) | |
H6 | 0.3958 | −0.0397 | 0.3449 | 0.049* | |
C7 | 0.1393 (6) | 0.1521 (4) | 0.3654 (4) | 0.0411 (11) | |
H7 | 0.2241 | 0.1690 | 0.3767 | 0.049* | |
C8 | −0.0023 (6) | 0.3593 (4) | 0.3822 (5) | 0.0461 (13) | |
H8 | 0.0894 | 0.3654 | 0.4011 | 0.055* | |
C9 | −0.0850 (7) | 0.4753 (5) | 0.3070 (5) | 0.0587 (15) | |
H9A | −0.0430 | 0.5497 | 0.2794 | 0.070* | |
H9B | −0.1274 | 0.4635 | 0.2507 | 0.070* | |
C10 | −0.1668 (7) | 0.4377 (5) | 0.4370 (5) | 0.0597 (15) | |
H10A | −0.2586 | 0.4026 | 0.4600 | 0.072* | |
H10B | −0.1741 | 0.4890 | 0.4887 | 0.072* | |
C11 | 0.3820 (5) | 0.3853 (4) | 0.0594 (4) | 0.0347 (10) | |
C12 | 0.3856 (5) | 0.4019 (4) | 0.1673 (4) | 0.0340 (10) | |
C13 | 0.4791 (5) | 0.3044 (4) | 0.2334 (4) | 0.0372 (11) | |
C14 | 0.5632 (5) | 0.1906 (4) | 0.1997 (4) | 0.0384 (11) | |
H14 | 0.6235 | 0.1251 | 0.2467 | 0.046* | |
C15 | 0.5562 (5) | 0.1755 (4) | 0.0950 (4) | 0.0380 (11) | |
C16 | 0.4685 (5) | 0.2713 (4) | 0.0247 (4) | 0.0401 (12) | |
H16 | 0.4669 | 0.2599 | −0.0465 | 0.048* | |
C17 | 0.2896 (5) | 0.4881 (4) | −0.0175 (4) | 0.0391 (11) | |
H17 | 0.3018 | 0.4798 | −0.0935 | 0.047* | |
C18 | 0.1096 (6) | 0.6847 (4) | −0.0628 (4) | 0.0445 (12) | |
H18 | 0.1489 | 0.6790 | −0.1471 | 0.053* | |
C19 | −0.0688 (6) | 0.7366 (5) | −0.0140 (5) | 0.0579 (15) | |
H19A | −0.1357 | 0.7597 | −0.0673 | 0.069* | |
H19B | −0.1192 | 0.7019 | 0.0698 | 0.069* | |
C20 | 0.0415 (6) | 0.8155 (4) | −0.0400 (5) | 0.0476 (13) | |
H20A | 0.0586 | 0.8294 | 0.0277 | 0.057* | |
H20B | 0.0422 | 0.8872 | −0.1093 | 0.057* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0728 (4) | 0.0560 (4) | 0.0896 (5) | −0.0173 (3) | −0.0424 (4) | −0.0221 (3) |
Br2 | 0.0543 (4) | 0.0474 (3) | 0.0566 (4) | 0.0070 (2) | −0.0191 (3) | −0.0225 (3) |
Br3 | 0.0665 (4) | 0.0767 (4) | 0.0512 (4) | 0.0029 (3) | −0.0293 (3) | −0.0300 (3) |
Br4 | 0.0586 (4) | 0.0438 (3) | 0.0791 (4) | 0.0062 (2) | −0.0294 (3) | −0.0304 (3) |
O1 | 0.050 (2) | 0.0368 (19) | 0.057 (2) | −0.0050 (16) | −0.0227 (18) | −0.0119 (17) |
O2 | 0.048 (2) | 0.043 (2) | 0.051 (2) | −0.0001 (15) | −0.0168 (17) | −0.0238 (17) |
N1 | 0.049 (3) | 0.030 (2) | 0.047 (3) | −0.0089 (19) | −0.013 (2) | −0.0089 (18) |
N2 | 0.035 (2) | 0.036 (2) | 0.043 (2) | −0.0059 (18) | −0.0137 (19) | −0.0076 (18) |
C1 | 0.044 (3) | 0.029 (2) | 0.036 (3) | −0.010 (2) | −0.010 (2) | −0.007 (2) |
C2 | 0.043 (3) | 0.029 (2) | 0.029 (3) | −0.003 (2) | −0.010 (2) | −0.0046 (19) |
C3 | 0.058 (3) | 0.036 (3) | 0.035 (3) | −0.016 (2) | −0.023 (2) | −0.004 (2) |
C4 | 0.055 (3) | 0.031 (3) | 0.040 (3) | −0.001 (2) | −0.021 (2) | −0.012 (2) |
C5 | 0.045 (3) | 0.033 (3) | 0.040 (3) | 0.000 (2) | −0.014 (2) | −0.011 (2) |
C6 | 0.039 (3) | 0.045 (3) | 0.038 (3) | −0.013 (2) | −0.008 (2) | −0.010 (2) |
C7 | 0.041 (3) | 0.033 (3) | 0.044 (3) | −0.008 (2) | −0.008 (2) | −0.009 (2) |
C8 | 0.047 (3) | 0.027 (2) | 0.066 (3) | −0.005 (2) | −0.019 (3) | −0.015 (2) |
C9 | 0.077 (4) | 0.037 (3) | 0.062 (4) | −0.021 (3) | −0.019 (3) | −0.005 (3) |
C10 | 0.062 (4) | 0.040 (3) | 0.066 (4) | −0.003 (3) | −0.008 (3) | −0.019 (3) |
C11 | 0.028 (3) | 0.039 (3) | 0.038 (3) | −0.007 (2) | −0.008 (2) | −0.014 (2) |
C12 | 0.029 (3) | 0.036 (3) | 0.040 (3) | −0.008 (2) | −0.008 (2) | −0.014 (2) |
C13 | 0.034 (3) | 0.048 (3) | 0.034 (3) | −0.014 (2) | −0.008 (2) | −0.013 (2) |
C14 | 0.028 (3) | 0.041 (3) | 0.044 (3) | −0.009 (2) | −0.012 (2) | −0.005 (2) |
C15 | 0.031 (3) | 0.036 (3) | 0.047 (3) | −0.007 (2) | −0.007 (2) | −0.015 (2) |
C16 | 0.037 (3) | 0.041 (3) | 0.047 (3) | −0.004 (2) | −0.015 (2) | −0.019 (2) |
C17 | 0.040 (3) | 0.041 (3) | 0.040 (3) | −0.009 (2) | −0.017 (2) | −0.010 (2) |
C18 | 0.045 (3) | 0.039 (3) | 0.043 (3) | 0.001 (2) | −0.019 (2) | −0.008 (2) |
C19 | 0.038 (3) | 0.060 (4) | 0.072 (4) | −0.007 (3) | −0.025 (3) | −0.006 (3) |
C20 | 0.045 (3) | 0.040 (3) | 0.051 (3) | −0.005 (2) | −0.015 (3) | −0.006 (2) |
Br1—C3 | 1.894 (5) | C8—H8 | 0.9800 |
Br2—C5 | 1.903 (4) | C9—C10 | 1.481 (7) |
Br3—C13 | 1.895 (4) | C9—H9A | 0.9700 |
Br4—C15 | 1.899 (4) | C9—H9B | 0.9700 |
O1—C2 | 1.342 (5) | C10—H10A | 0.9700 |
O1—H1 | 0.8200 | C10—H10B | 0.9700 |
O2—C12 | 1.356 (5) | C11—C16 | 1.389 (6) |
O2—H2 | 0.8200 | C11—C12 | 1.410 (6) |
N1—C7 | 1.272 (5) | C11—C17 | 1.471 (6) |
N1—C8 | 1.436 (5) | C12—C13 | 1.377 (6) |
N2—C17 | 1.276 (5) | C13—C14 | 1.379 (6) |
N2—C18 | 1.421 (5) | C14—C15 | 1.376 (6) |
C1—C6 | 1.384 (6) | C14—H14 | 0.9300 |
C1—C2 | 1.396 (6) | C15—C16 | 1.368 (6) |
C1—C7 | 1.470 (6) | C16—H16 | 0.9300 |
C2—C3 | 1.398 (6) | C17—H17 | 0.9300 |
C3—C4 | 1.375 (6) | C18—C20 | 1.492 (6) |
C4—C5 | 1.371 (6) | C18—C19 | 1.496 (7) |
C4—H4 | 0.9300 | C18—H18 | 0.9800 |
C5—C6 | 1.374 (6) | C19—C20 | 1.470 (7) |
C6—H6 | 0.9300 | C19—H19A | 0.9700 |
C7—H7 | 0.9300 | C19—H19B | 0.9700 |
C8—C9 | 1.485 (6) | C20—H20A | 0.9700 |
C8—C10 | 1.503 (6) | C20—H20B | 0.9700 |
C2—O1—H1 | 109.5 | C8—C10—H10B | 117.8 |
C12—O2—H2 | 109.5 | H10A—C10—H10B | 114.9 |
C7—N1—C8 | 117.8 (4) | C16—C11—C12 | 119.6 (4) |
C17—N2—C18 | 118.9 (4) | C16—C11—C17 | 119.6 (4) |
C6—C1—C2 | 120.1 (4) | C12—C11—C17 | 120.7 (4) |
C6—C1—C7 | 119.2 (4) | O2—C12—C13 | 120.5 (4) |
C2—C1—C7 | 120.7 (4) | O2—C12—C11 | 121.2 (4) |
O1—C2—C1 | 122.3 (4) | C13—C12—C11 | 118.3 (4) |
O1—C2—C3 | 120.1 (4) | C12—C13—C14 | 122.0 (4) |
C1—C2—C3 | 117.6 (4) | C12—C13—Br3 | 119.0 (3) |
C4—C3—C2 | 122.1 (4) | C14—C13—Br3 | 118.9 (3) |
C4—C3—Br1 | 120.0 (3) | C15—C14—C13 | 118.8 (4) |
C2—C3—Br1 | 117.9 (4) | C15—C14—H14 | 120.6 |
C5—C4—C3 | 118.9 (4) | C13—C14—H14 | 120.6 |
C5—C4—H4 | 120.6 | C16—C15—C14 | 121.2 (4) |
C3—C4—H4 | 120.6 | C16—C15—Br4 | 119.6 (3) |
C4—C5—C6 | 120.8 (4) | C14—C15—Br4 | 119.2 (3) |
C4—C5—Br2 | 119.1 (3) | C15—C16—C11 | 120.1 (4) |
C6—C5—Br2 | 120.0 (4) | C15—C16—H16 | 120.0 |
C5—C6—C1 | 120.4 (4) | C11—C16—H16 | 120.0 |
C5—C6—H6 | 119.8 | N2—C17—C11 | 122.0 (4) |
C1—C6—H6 | 119.8 | N2—C17—H17 | 119.0 |
N1—C7—C1 | 121.5 (5) | C11—C17—H17 | 119.0 |
N1—C7—H7 | 119.2 | N2—C18—C20 | 118.0 (4) |
C1—C7—H7 | 119.2 | N2—C18—C19 | 117.6 (4) |
N1—C8—C9 | 117.2 (4) | C20—C18—C19 | 59.0 (3) |
N1—C8—C10 | 117.4 (4) | N2—C18—H18 | 116.6 |
C9—C8—C10 | 59.4 (3) | C20—C18—H18 | 116.6 |
N1—C8—H8 | 116.8 | C19—C18—H18 | 116.6 |
C9—C8—H8 | 116.8 | C20—C19—C18 | 60.4 (3) |
C10—C8—H8 | 116.8 | C20—C19—H19A | 117.7 |
C10—C9—C8 | 60.9 (3) | C18—C19—H19A | 117.7 |
C10—C9—H9A | 117.7 | C20—C19—H19B | 117.7 |
C8—C9—H9A | 117.7 | C18—C19—H19B | 117.7 |
C10—C9—H9B | 117.7 | H19A—C19—H19B | 114.9 |
C8—C9—H9B | 117.7 | C19—C20—C18 | 60.7 (3) |
H9A—C9—H9B | 114.8 | C19—C20—H20A | 117.7 |
C9—C10—C8 | 59.7 (3) | C18—C20—H20A | 117.7 |
C9—C10—H10A | 117.8 | C19—C20—H20B | 117.7 |
C8—C10—H10A | 117.8 | C18—C20—H20B | 117.7 |
C9—C10—H10B | 117.8 | H20A—C20—H20B | 114.8 |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···N2 | 0.82 | 1.90 | 2.607 (5) | 143 |
O1—H1···N1 | 0.82 | 1.87 | 2.597 (5) | 147 |
Experimental details
Crystal data | |
Chemical formula | C10H9Br2NO |
Mr | 319.00 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 9.1840 (18), 11.495 (2), 12.265 (3) |
α, β, γ (°) | 70.85 (3), 68.62 (3), 69.69 (3) |
V (Å3) | 1100.2 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 7.33 |
Crystal size (mm) | 0.40 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.157, 0.322 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9324, 4830, 2945 |
Rint | 0.039 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.105, 0.95 |
No. of reflections | 4830 |
No. of parameters | 255 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.64, −0.69 |
Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SAINT, SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···N2 | 0.82 | 1.90 | 2.607 (5) | 143 |
O1—H1···N1 | 0.82 | 1.87 | 2.597 (5) | 147 |
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Schiff base compounds have been of great interest for a long time. These compounds play an important role in the development of coordination chemistry (Musie et al., 2001; Bernardo et al., 1996; Paul et al., 2002). Recently, we have reported a few Schiff base compounds (Yang, 2006a,b,c,d,e, 2007; Yang & Guo, 2006). As a further investigation of this work, the crystal structure of the title compound is reported here.
The asymmetric unit of the title compound consists of two molecules (Fig. 1). In both molecules, the benzene ring and the cyclopropyl ring are nearly perpendicular, with the dihedral angles of 85.8 (4) and 75.5 (4)°, respectively. All the bond lengths in the molecules are within normal ranges (Allen et al., 1987), and comparable to those of the similar compounds (Zhao, 2005, You & Chi, 2006). The C7═N1 and C17═N2 bond lengths of 1.272 (5) and 1.276 (5) Å conform to the values for double bonds. In the crystal structure, there are no obviously short contacts among the molecules.