In the title compound, C
25H
18Cl
2N
2O, the cyclohexene ring has a sofa conformation. All the substituents in the cyclohexene ring, except the cyano group (which is axial) occupy equatorial positions. The crystal structure is stabilized through N—H

O hydrogen bonds, forming a chain extending along the
b axis and through C—H

N and C—H

Cl interactions. It is remarkable that only one of the amino H atoms is involved in hydrogen bonding.
Supporting information
CCDC reference: 697779
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean
(C-C) = 0.004 Å
- R factor = 0.041
- wR factor = 0.127
- Data-to-parameter ratio = 12.1
checkCIF/PLATON results
No syntax errors found
Alert level B
THETM01_ALERT_3_B The value of sine(theta_max)/wavelength is less than 0.575
Calculated sin(theta_max)/wavelength = 0.5655
PLAT023_ALERT_3_B Resolution (too) Low [sin(theta)/Lambda < 0.6].. 23.70 Deg.
PLAT919_ALERT_3_B Reflection(s) # Likely Affected by the Beamstop 1
Alert level C
PLAT420_ALERT_2_C D-H Without Acceptor N2 - H2A ... ?
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.565 15
PLAT480_ALERT_4_C Long H...A H-Bond Reported H33 .. N11 .. 2.72 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H52 .. CL2 .. 2.97 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H54 .. N11 .. 2.72 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1
C25 H18 Cl2 N2 O
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
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 1
C2 -C1 -C11 -N11 121.00 8.00 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 2
C6 -C1 -C11 -N11 -2.00 8.00 1.555 1.555 1.555 1.555
PLAT793_ALERT_4_G The Model has Chirality at C1 (Verify) .... S
PLAT793_ALERT_4_G The Model has Chirality at C5 (Verify) .... R
PLAT793_ALERT_4_G The Model has Chirality at C6 (Verify) .... R
0 ALERT level A = In general: serious problem
3 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
7 ALERT level G = General alerts; check
2 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
4 ALERT type 3 Indicator that the structure quality may be low
9 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
A mixture of 1,3-diphenylacetone 5 (1 mmol),
2-[(2,4-dichlorophenyl)methylene]malononitrile (1 mmol), and sodium ethoxide
(2 mmol) was ground well in a mortar and pestle at ambient temperature for
about 15–30 sec. Then water (50–70 ml) was added to the mixture and the
product was filtered and washed with water, dried in vacuo and
subjected to flash chromatographic purification employing flash silica gel
(230–400 mesh) with petroleum ether-ethyl acetate mixture as eluent. The
products were further recrystallized from ethanol-ethyl acetate mixture (1:2
v/v).
All the H atoms were positioned geometrically and refined using a riding model,
with C—H = 0.93 Å and Uiso(H) = 1.2 Ueq (parent atom).
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL/PC (Sheldrick, 2008); program(s) used to refine structure: SHELXTL/PC (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL/PC (Sheldrick, 2008).
2-Amino-6-(2,4-dichlorophenyl)-4-oxo-3,5-diphenylcyclohex-2-enecarbonitrile
top
Crystal data top
C25H18Cl2N2O | F(000) = 896 |
Mr = 433.31 | Dx = 1.327 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4312 reflections |
a = 10.8650 (9) Å | θ = 2.1–20.1° |
b = 14.0010 (3) Å | µ = 0.32 mm−1 |
c = 14.3021 (6) Å | T = 293 K |
β = 94.697 (10)° | Block, colourless |
V = 2168.3 (2) Å3 | 0.21 × 0.18 × 0.12 mm |
Z = 4 | |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 2457 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.041 |
Graphite monochromator | θmax = 23.7°, θmin = 1.9° |
ω scans | h = −12→12 |
18613 measured reflections | k = −15→15 |
3269 independent reflections | l = −11→16 |
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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.127 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0688P)2 + 0.6095P] where P = (Fo2 + 2Fc2)/3 |
3269 reflections | (Δ/σ)max < 0.001 |
271 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
Crystal data top
C25H18Cl2N2O | V = 2168.3 (2) Å3 |
Mr = 433.31 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.8650 (9) Å | µ = 0.32 mm−1 |
b = 14.0010 (3) Å | T = 293 K |
c = 14.3021 (6) Å | 0.21 × 0.18 × 0.12 mm |
β = 94.697 (10)° | |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 2457 reflections with I > 2σ(I) |
18613 measured reflections | Rint = 0.041 |
3269 independent reflections | θmax = 23.7° |
Refinement top
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.127 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.19 e Å−3 |
3269 reflections | Δρmin = −0.24 e Å−3 |
271 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 F^2^ against ALL reflections. The weighted
R-factor wR and goodness of fit S are based on
F^2^, conventional R-factors R are based on F,
with F set to zero for negative F^2^. The threshold expression
of F^2^ > σ(F^2^) is used only for calculating
R-factors(gt) etc. and is not relevant to the choice of
reflections for refinement. R-factors based on F^2^ 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 | |
C1 | −0.4045 (2) | 0.02803 (16) | 0.72770 (17) | 0.0330 (6) | |
H1 | −0.4171 | 0.0873 | 0.6918 | 0.040* | |
C11 | −0.3249 (3) | 0.04896 (18) | 0.8132 (2) | 0.0431 (7) | |
N11 | −0.2610 (3) | 0.0631 (2) | 0.8783 (2) | 0.0732 (8) | |
C2 | −0.5291 (2) | −0.00720 (16) | 0.75371 (18) | 0.0368 (6) | |
N2 | −0.6097 (2) | 0.06106 (15) | 0.76626 (19) | 0.0593 (7) | |
H2A | −0.6820 | 0.0468 | 0.7825 | 0.071* | |
H2B | −0.5901 | 0.1198 | 0.7582 | 0.071* | |
C3 | −0.5514 (2) | −0.10311 (16) | 0.76488 (18) | 0.0339 (6) | |
C31 | −0.6736 (2) | −0.13559 (16) | 0.79292 (18) | 0.0349 (6) | |
C32 | −0.7174 (3) | −0.1068 (2) | 0.8762 (2) | 0.0499 (7) | |
H32 | −0.6686 | −0.0681 | 0.9170 | 0.060* | |
C33 | −0.8332 (3) | −0.1348 (2) | 0.9000 (2) | 0.0570 (8) | |
H33 | −0.8622 | −0.1139 | 0.9559 | 0.068* | |
C34 | −0.9040 (3) | −0.1925 (2) | 0.8420 (2) | 0.0529 (8) | |
H34 | −0.9823 | −0.2105 | 0.8573 | 0.064* | |
C35 | −0.8600 (3) | −0.2245 (2) | 0.7603 (2) | 0.0553 (8) | |
H35 | −0.9075 | −0.2658 | 0.7214 | 0.066* | |
C36 | −0.7462 (2) | −0.19578 (18) | 0.7358 (2) | 0.0450 (7) | |
H36 | −0.7179 | −0.2173 | 0.6800 | 0.054* | |
C4 | −0.4589 (2) | −0.17242 (16) | 0.74985 (17) | 0.0341 (6) | |
O1 | −0.47452 (17) | −0.25760 (11) | 0.76898 (14) | 0.0518 (5) | |
C5 | −0.3365 (2) | −0.14431 (15) | 0.71259 (17) | 0.0317 (6) | |
H5 | −0.2750 | −0.1411 | 0.7665 | 0.038* | |
C51 | −0.2942 (2) | −0.22077 (16) | 0.64729 (17) | 0.0326 (6) | |
C52 | −0.3644 (3) | −0.2437 (2) | 0.56597 (19) | 0.0503 (7) | |
H52 | −0.4376 | −0.2109 | 0.5501 | 0.060* | |
C53 | −0.3271 (3) | −0.3151 (2) | 0.5073 (2) | 0.0637 (9) | |
H53 | −0.3759 | −0.3305 | 0.4529 | 0.076* | |
C54 | −0.2196 (3) | −0.3629 (2) | 0.5289 (2) | 0.0623 (9) | |
H54 | −0.1945 | −0.4104 | 0.4891 | 0.075* | |
C55 | −0.1493 (3) | −0.3410 (2) | 0.6084 (2) | 0.0587 (8) | |
H55 | −0.0756 | −0.3735 | 0.6233 | 0.070* | |
C56 | −0.1864 (2) | −0.27073 (18) | 0.6676 (2) | 0.0442 (7) | |
H56 | −0.1376 | −0.2569 | 0.7224 | 0.053* | |
C6 | −0.3415 (2) | −0.04533 (15) | 0.66641 (16) | 0.0304 (6) | |
H6 | −0.3942 | −0.0514 | 0.6078 | 0.037* | |
C61 | −0.2188 (2) | −0.00592 (16) | 0.64069 (17) | 0.0331 (6) | |
C62 | −0.1086 (2) | −0.02628 (18) | 0.69160 (19) | 0.0421 (7) | |
H62 | −0.1091 | −0.0689 | 0.7414 | 0.051* | |
C63 | 0.0019 (3) | 0.01363 (19) | 0.6720 (2) | 0.0495 (7) | |
H63 | 0.0744 | −0.0020 | 0.7078 | 0.059* | |
C64 | 0.0039 (2) | 0.07653 (18) | 0.5992 (2) | 0.0447 (7) | |
C65 | −0.1028 (3) | 0.09852 (19) | 0.54492 (19) | 0.0482 (7) | |
H65 | −0.1012 | 0.1407 | 0.4948 | 0.058* | |
C66 | −0.2121 (2) | 0.05682 (18) | 0.56630 (18) | 0.0408 (6) | |
Cl1 | 0.14075 (7) | 0.13127 (6) | 0.57487 (7) | 0.0697 (3) | |
Cl2 | −0.34352 (8) | 0.08729 (7) | 0.49620 (6) | 0.0767 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0406 (14) | 0.0178 (12) | 0.0411 (15) | −0.0015 (10) | 0.0056 (12) | 0.0034 (10) |
C11 | 0.0529 (17) | 0.0276 (14) | 0.0496 (19) | −0.0052 (12) | 0.0085 (15) | −0.0023 (13) |
N11 | 0.091 (2) | 0.0676 (19) | 0.0584 (18) | −0.0100 (16) | −0.0111 (17) | −0.0102 (15) |
C2 | 0.0385 (14) | 0.0216 (13) | 0.0509 (16) | −0.0003 (11) | 0.0069 (12) | −0.0025 (11) |
N2 | 0.0484 (14) | 0.0201 (11) | 0.113 (2) | 0.0014 (10) | 0.0288 (14) | 0.0001 (12) |
C3 | 0.0390 (14) | 0.0188 (12) | 0.0445 (15) | −0.0007 (10) | 0.0072 (11) | −0.0015 (10) |
C31 | 0.0398 (14) | 0.0173 (12) | 0.0481 (16) | −0.0011 (10) | 0.0057 (12) | 0.0014 (11) |
C32 | 0.0500 (17) | 0.0442 (16) | 0.0569 (19) | −0.0121 (13) | 0.0128 (14) | −0.0087 (14) |
C33 | 0.0554 (18) | 0.059 (2) | 0.059 (2) | −0.0105 (16) | 0.0200 (15) | −0.0041 (16) |
C34 | 0.0399 (15) | 0.0469 (17) | 0.073 (2) | −0.0075 (13) | 0.0103 (15) | 0.0120 (15) |
C35 | 0.0475 (17) | 0.0484 (18) | 0.069 (2) | −0.0146 (14) | 0.0020 (16) | −0.0070 (15) |
C36 | 0.0460 (16) | 0.0388 (15) | 0.0505 (17) | −0.0032 (13) | 0.0063 (13) | −0.0033 (13) |
C4 | 0.0414 (14) | 0.0208 (13) | 0.0401 (15) | −0.0012 (11) | 0.0043 (11) | −0.0006 (10) |
O1 | 0.0584 (12) | 0.0189 (10) | 0.0814 (14) | 0.0015 (8) | 0.0262 (10) | 0.0072 (9) |
C5 | 0.0370 (13) | 0.0220 (12) | 0.0352 (14) | 0.0006 (10) | −0.0015 (11) | 0.0004 (10) |
C51 | 0.0376 (14) | 0.0218 (12) | 0.0388 (15) | −0.0035 (10) | 0.0065 (12) | 0.0008 (10) |
C52 | 0.0589 (17) | 0.0416 (16) | 0.0487 (18) | 0.0059 (14) | −0.0059 (14) | −0.0082 (14) |
C53 | 0.091 (3) | 0.057 (2) | 0.0431 (18) | −0.0098 (19) | 0.0013 (17) | −0.0123 (15) |
C54 | 0.083 (2) | 0.0398 (17) | 0.068 (2) | −0.0021 (17) | 0.0296 (19) | −0.0153 (16) |
C55 | 0.0547 (18) | 0.0407 (17) | 0.083 (2) | 0.0088 (14) | 0.0164 (17) | −0.0076 (16) |
C56 | 0.0407 (15) | 0.0344 (15) | 0.0573 (18) | 0.0007 (12) | 0.0024 (13) | −0.0041 (13) |
C6 | 0.0348 (13) | 0.0208 (12) | 0.0354 (14) | −0.0018 (10) | 0.0008 (11) | 0.0017 (10) |
C61 | 0.0396 (14) | 0.0224 (12) | 0.0376 (15) | −0.0010 (10) | 0.0054 (11) | −0.0021 (11) |
C62 | 0.0411 (15) | 0.0352 (14) | 0.0498 (17) | −0.0036 (12) | 0.0021 (13) | 0.0074 (12) |
C63 | 0.0398 (15) | 0.0422 (16) | 0.066 (2) | −0.0031 (13) | 0.0035 (14) | −0.0018 (15) |
C64 | 0.0464 (17) | 0.0334 (15) | 0.0574 (18) | −0.0070 (12) | 0.0222 (14) | −0.0106 (13) |
C65 | 0.063 (2) | 0.0375 (15) | 0.0464 (17) | −0.0061 (14) | 0.0205 (15) | 0.0027 (13) |
C66 | 0.0467 (15) | 0.0349 (14) | 0.0405 (15) | −0.0003 (12) | 0.0026 (12) | 0.0035 (12) |
Cl1 | 0.0587 (5) | 0.0600 (5) | 0.0957 (7) | −0.0188 (4) | 0.0390 (4) | −0.0138 (4) |
Cl2 | 0.0674 (6) | 0.0881 (7) | 0.0720 (6) | −0.0043 (5) | −0.0109 (4) | 0.0438 (5) |
Geometric parameters (Å, º) top
C1—C11 | 1.469 (4) | C5—H5 | 0.9800 |
C1—C2 | 1.516 (3) | C51—C56 | 1.375 (3) |
C1—C6 | 1.546 (3) | C51—C52 | 1.375 (4) |
C1—H1 | 0.9800 | C52—C53 | 1.388 (4) |
C11—N11 | 1.132 (3) | C52—H52 | 0.9300 |
C2—N2 | 1.319 (3) | C53—C54 | 1.358 (5) |
C2—C3 | 1.376 (3) | C53—H53 | 0.9300 |
N2—H2A | 0.8600 | C54—C55 | 1.353 (5) |
N2—H2B | 0.8600 | C54—H54 | 0.9300 |
C3—C4 | 1.426 (3) | C55—C56 | 1.380 (4) |
C3—C31 | 1.489 (3) | C55—H55 | 0.9300 |
C31—C36 | 1.376 (3) | C56—H56 | 0.9300 |
C31—C32 | 1.379 (4) | C6—C61 | 1.516 (3) |
C32—C33 | 1.387 (4) | C6—H6 | 0.9800 |
C32—H32 | 0.9300 | C61—C62 | 1.379 (3) |
C33—C34 | 1.353 (4) | C61—C66 | 1.386 (3) |
C33—H33 | 0.9300 | C62—C63 | 1.374 (4) |
C34—C35 | 1.373 (4) | C62—H62 | 0.9300 |
C34—H34 | 0.9300 | C63—C64 | 1.365 (4) |
C35—C36 | 1.371 (4) | C63—H63 | 0.9300 |
C35—H35 | 0.9300 | C64—C65 | 1.376 (4) |
C36—H36 | 0.9300 | C64—Cl1 | 1.734 (3) |
C4—O1 | 1.238 (3) | C65—C66 | 1.380 (4) |
C4—C5 | 1.524 (3) | C65—H65 | 0.9300 |
C5—C51 | 1.517 (3) | C66—Cl2 | 1.730 (3) |
C5—C6 | 1.534 (3) | | |
| | | |
C11—C1—C2 | 109.7 (2) | C56—C51—C52 | 117.7 (2) |
C11—C1—C6 | 110.3 (2) | C56—C51—C5 | 121.7 (2) |
C2—C1—C6 | 111.65 (18) | C52—C51—C5 | 120.7 (2) |
C11—C1—H1 | 108.4 | C51—C52—C53 | 120.7 (3) |
C2—C1—H1 | 108.4 | C51—C52—H52 | 119.7 |
C6—C1—H1 | 108.4 | C53—C52—H52 | 119.7 |
N11—C11—C1 | 177.9 (3) | C54—C53—C52 | 120.4 (3) |
N2—C2—C3 | 124.5 (2) | C54—C53—H53 | 119.8 |
N2—C2—C1 | 114.5 (2) | C52—C53—H53 | 119.8 |
C3—C2—C1 | 121.0 (2) | C55—C54—C53 | 119.7 (3) |
C2—N2—H2A | 120.0 | C55—C54—H54 | 120.1 |
C2—N2—H2B | 120.0 | C53—C54—H54 | 120.1 |
H2A—N2—H2B | 120.0 | C54—C55—C56 | 120.2 (3) |
C2—C3—C4 | 120.9 (2) | C54—C55—H55 | 119.9 |
C2—C3—C31 | 119.9 (2) | C56—C55—H55 | 119.9 |
C4—C3—C31 | 119.2 (2) | C51—C56—C55 | 121.4 (3) |
C36—C31—C32 | 118.0 (2) | C51—C56—H56 | 119.3 |
C36—C31—C3 | 120.5 (2) | C55—C56—H56 | 119.3 |
C32—C31—C3 | 121.5 (2) | C61—C6—C5 | 115.67 (19) |
C31—C32—C33 | 121.0 (3) | C61—C6—C1 | 109.56 (18) |
C31—C32—H32 | 119.5 | C5—C6—C1 | 110.94 (18) |
C33—C32—H32 | 119.5 | C61—C6—H6 | 106.7 |
C34—C33—C32 | 120.0 (3) | C5—C6—H6 | 106.7 |
C34—C33—H33 | 120.0 | C1—C6—H6 | 106.7 |
C32—C33—H33 | 120.0 | C62—C61—C66 | 116.0 (2) |
C33—C34—C35 | 119.8 (3) | C62—C61—C6 | 122.6 (2) |
C33—C34—H34 | 120.1 | C66—C61—C6 | 121.3 (2) |
C35—C34—H34 | 120.1 | C63—C62—C61 | 122.9 (3) |
C36—C35—C34 | 120.4 (3) | C63—C62—H62 | 118.5 |
C36—C35—H35 | 119.8 | C61—C62—H62 | 118.5 |
C34—C35—H35 | 119.8 | C64—C63—C62 | 119.1 (3) |
C35—C36—C31 | 120.9 (3) | C64—C63—H63 | 120.4 |
C35—C36—H36 | 119.6 | C62—C63—H63 | 120.4 |
C31—C36—H36 | 119.6 | C63—C64—C65 | 120.6 (2) |
O1—C4—C3 | 120.7 (2) | C63—C64—Cl1 | 120.4 (2) |
O1—C4—C5 | 117.7 (2) | C65—C64—Cl1 | 119.0 (2) |
C3—C4—C5 | 121.5 (2) | C64—C65—C66 | 118.7 (3) |
C51—C5—C4 | 110.51 (19) | C64—C65—H65 | 120.6 |
C51—C5—C6 | 111.97 (19) | C66—C65—H65 | 120.6 |
C4—C5—C6 | 112.53 (19) | C65—C66—C61 | 122.6 (2) |
C51—C5—H5 | 107.2 | C65—C66—Cl2 | 116.9 (2) |
C4—C5—H5 | 107.2 | C61—C66—Cl2 | 120.5 (2) |
C6—C5—H5 | 107.2 | | |
| | | |
C2—C1—C11—N11 | 121 (8) | C56—C51—C52—C53 | 0.3 (4) |
C6—C1—C11—N11 | −2 (8) | C5—C51—C52—C53 | −178.5 (2) |
C11—C1—C2—N2 | 87.0 (3) | C51—C52—C53—C54 | −0.8 (5) |
C6—C1—C2—N2 | −150.4 (2) | C52—C53—C54—C55 | 0.5 (5) |
C11—C1—C2—C3 | −91.5 (3) | C53—C54—C55—C56 | 0.1 (5) |
C6—C1—C2—C3 | 31.1 (3) | C52—C51—C56—C55 | 0.4 (4) |
N2—C2—C3—C4 | 180.0 (3) | C5—C51—C56—C55 | 179.2 (2) |
C1—C2—C3—C4 | −1.7 (4) | C54—C55—C56—C51 | −0.6 (4) |
N2—C2—C3—C31 | 0.0 (4) | C51—C5—C6—C61 | −63.6 (3) |
C1—C2—C3—C31 | 178.4 (2) | C4—C5—C6—C61 | 171.2 (2) |
C2—C3—C31—C36 | 120.0 (3) | C51—C5—C6—C1 | 170.83 (19) |
C4—C3—C31—C36 | −59.9 (3) | C4—C5—C6—C1 | 45.6 (3) |
C2—C3—C31—C32 | −60.1 (4) | C11—C1—C6—C61 | −58.9 (2) |
C4—C3—C31—C32 | 120.0 (3) | C2—C1—C6—C61 | 178.81 (19) |
C36—C31—C32—C33 | −2.4 (4) | C11—C1—C6—C5 | 70.0 (2) |
C3—C31—C32—C33 | 177.7 (3) | C2—C1—C6—C5 | −52.3 (3) |
C31—C32—C33—C34 | 1.2 (5) | C5—C6—C61—C62 | −31.7 (3) |
C32—C33—C34—C35 | 1.1 (5) | C1—C6—C61—C62 | 94.5 (3) |
C33—C34—C35—C36 | −2.1 (5) | C5—C6—C61—C66 | 151.3 (2) |
C34—C35—C36—C31 | 0.8 (4) | C1—C6—C61—C66 | −82.4 (3) |
C32—C31—C36—C35 | 1.4 (4) | C66—C61—C62—C63 | 1.0 (4) |
C3—C31—C36—C35 | −178.7 (2) | C6—C61—C62—C63 | −176.1 (2) |
C2—C3—C4—O1 | 172.7 (2) | C61—C62—C63—C64 | 0.2 (4) |
C31—C3—C4—O1 | −7.4 (4) | C62—C63—C64—C65 | −1.3 (4) |
C2—C3—C4—C5 | −5.6 (4) | C62—C63—C64—Cl1 | 177.9 (2) |
C31—C3—C4—C5 | 174.4 (2) | C63—C64—C65—C66 | 1.0 (4) |
O1—C4—C5—C51 | 38.1 (3) | Cl1—C64—C65—C66 | −178.2 (2) |
C3—C4—C5—C51 | −143.6 (2) | C64—C65—C66—C61 | 0.4 (4) |
O1—C4—C5—C6 | 164.1 (2) | C64—C65—C66—Cl2 | 179.7 (2) |
C3—C4—C5—C6 | −17.7 (3) | C62—C61—C66—C65 | −1.4 (4) |
C4—C5—C51—C56 | −117.1 (3) | C6—C61—C66—C65 | 175.8 (2) |
C6—C5—C51—C56 | 116.6 (2) | C62—C61—C66—Cl2 | 179.4 (2) |
C4—C5—C51—C52 | 61.7 (3) | C6—C61—C66—Cl2 | −3.5 (3) |
C6—C5—C51—C52 | −64.6 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2B···O1i | 0.86 | 1.91 | 2.759 (3) | 171 |
C33—H33···N11ii | 0.93 | 2.72 | 3.402 (4) | 131 |
C52—H52···Cl2iii | 0.93 | 2.97 | 3.897 (3) | 174 |
C54—H54···N11iv | 0.93 | 2.72 | 3.541 (4) | 147 |
Symmetry codes: (i) −x−1, y+1/2, −z+3/2; (ii) −x−1, −y, −z+2; (iii) −x−1, −y, −z+1; (iv) x, −y−1/2, z−1/2. |
Experimental details
Crystal data |
Chemical formula | C25H18Cl2N2O |
Mr | 433.31 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 10.8650 (9), 14.0010 (3), 14.3021 (6) |
β (°) | 94.697 (10) |
V (Å3) | 2168.3 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.32 |
Crystal size (mm) | 0.21 × 0.18 × 0.12 |
|
Data collection |
Diffractometer | Bruker SMART APEX CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18613, 3269, 2457 |
Rint | 0.041 |
θmax (°) | 23.7 |
(sin θ/λ)max (Å−1) | 0.566 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.127, 1.07 |
No. of reflections | 3269 |
No. of parameters | 271 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.19, −0.24 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2B···O1i | 0.86 | 1.91 | 2.759 (3) | 171 |
C33—H33···N11ii | 0.93 | 2.72 | 3.402 (4) | 131 |
C52—H52···Cl2iii | 0.93 | 2.97 | 3.897 (3) | 174 |
C54—H54···N11iv | 0.93 | 2.72 | 3.541 (4) | 147 |
Symmetry codes: (i) −x−1, y+1/2, −z+3/2; (ii) −x−1, −y, −z+2; (iii) −x−1, −y, −z+1; (iv) x, −y−1/2, z−1/2. |
Alkenes undergo co-halogenation reactions to afford bifunctional compounds which serve as potential synthons towards the synthesis of various heterocyclic compounds (Rodriguez & Dulcere, 1993). The regio/stereoselectivity of such addition reactions is governed by various factors, one being structural features of the alkene. We were interested in investigating some of the structure features in the title compound, which may alter the regio/stereoselectivity in addition reactions.
The molecular structure of the title compound is shown in Fig. 1. The cyclohexene ring is in a sofa conformation. Two phenyl rings are oriented with a dihedral angle of 54.8 (1)° to each other. Further, the dichlorophenyl rings are making dihedral angles of 66.7 (1)° and 84.3 (1)° with the phenyl rings of C31/C36 and C51/C56 respectively. The crystal structure is stabilized by intermolecular C—H···N, C—H···Cl and classical N—H···O hydrgeon bonds (Tab. 1). The packing diagram of the title compound is shown in Fig. 2.
A chain C(6) motif extending along the b axis of the unit cell is observed through classical N—H···O hydrogen bond (Fig.3). Centrosymmetric ring R22(16) motif is formed around the crystallographic inversion centre through C—H···Cl bond (Fig. 4). Further, another ring R22(18) motif is observed around crystallographic inversion centre through a C—H···N bond (Fig. 5). These ring motifs are connected along c axis of the unit cell through another C—H···N bond [C54—H54···N11(x, -y - 1/2, z - 1/2)].