Download citation
Download citation
link to html
In the title N,S-substituted compound, C24H26Cl3N3O2S, the butadiene unit assumes a configuration close to cisoid. The piperazine ring adopts a chair conformation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807004023/ww2065sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807004023/ww2065Isup2.hkl
Contains datablock I

CCDC reference: 640521

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.013 Å
  • R factor = 0.099
  • wR factor = 0.173
  • Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ... 13
Alert level C ABSTM02_ALERT_3_C The ratio of Tmax/Tmin expected RT(exp) is > 1.10 Absorption corrections should be applied. Tmin and Tmax expected: 0.803 0.911 RT(exp) = 1.134 SHFSU01_ALERT_2_C The absolute value of parameter shift to su ratio > 0.05 Absolute value of the parameter shift to su ratio given 0.090 Additional refinement cycles may be required. PLAT057_ALERT_3_C Correction for Absorption Required RT(exp) ... 1.14 PLAT080_ALERT_2_C Maximum Shift/Error ............................ 0.09 PLAT230_ALERT_2_C Hirshfeld Test Diff for C7 - C8 .. 6.43 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C8 - C9 .. 5.01 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C8 PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C8 -C13 1.37 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 10
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.05 From the CIF: _reflns_number_total 4516 Count of symmetry unique reflns 2571 Completeness (_total/calc) 175.65% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1945 Fraction of Friedel pairs measured 0.757 Are heavy atom types Z>Si present yes PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 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

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS86 (Sheldrick, 1985); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

3,4,4-Trichloro-1-[4-(diphenylmethyl)piperazin-1-yl]-2-nitro- 1-(propylsulfanyl)buta-1,3-diene top
Crystal data top
C24H26Cl3N3O2SF(000) = 1096
Mr = 526.89Dx = 1.369 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 13171 reflections
a = 9.3870 (2) Åθ = 2.4–25.0°
b = 14.9382 (3) ŵ = 0.47 mm1
c = 18.2241 (4) ÅT = 293 K
V = 2555.47 (9) Å3Prism, yellow
Z = 40.5 × 0.4 × 0.2 mm
Data collection top
Rigaku R-AXIS RAPID-S area-detector
diffractometer
Rint = 0.083
ω scansθmax = 25.1°, θmin = 2.6°
49160 measured reflectionsh = 1011
4516 independent reflectionsk = 1717
4486 reflections with I > 2σ(I)l = 2121
Refinement top
Refinement on F2H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full w = 1/[σ2(Fo2) + 5.2662P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.099(Δ/σ)max = 0.09
wR(F2) = 0.173Δρmax = 0.34 e Å3
S = 1.54Δρmin = 0.29 e Å3
4516 reflectionsAbsolute structure: Flack (1983), with 1945 Friedel pairs
303 parametersAbsolute structure parameter: 0.08 (15)
0 restraints
Special details top

Geometry. Least Squares Planes

————– Plane number 1 —————

Atoms Defining Plane Distance e.s.d. C21 [1;0;0;0] -0.1452 0.0029 C20 [1;0;0;0] 0.2043 0.0040 C19 [1;0;0;0] -0.1770 0.0035 C18 [1;0;0;0] 0.0719 0.0014

Mean deviation from plane is 0.1496 angstrom Chi-squared: 2461.373

————– Plane number 2 —————

Atoms Defining Plane Distance e.s.d. S1 [1;0;0;0] 0.0011 0.0002 C22 [1;0;0;0] -0.0147 0.0029 C23 [1;0;0;0] -0.0249 0.0050 C24 [1;0;0;0] 0.0330 0.0066

Mean deviation from plane is 0.0185 angstrom Chi-squared: 35.489

————– Plane number 3 —————

Atoms Defining Plane Distance e.s.d. C14 [1;0;0;0] -0.0093 0.0038 C15 [1;0;0;0] 0.0082 0.0033 C16 [1;0;0;0] -0.0070 0.0028 C17 [1;0;0;0] 0.0071 0.0029

Additional Atoms Distance e.s.d. N2 (1) 0.6399 0.0081 N1 (1) -0.6919 0.0078

Mean deviation from plane is 0.0079 angstrom Chi-squared: 6.246

————– Plane number 4 —————

Atoms Defining Plane Distance e.s.d. C1 [1;0;0;0] 0.0050 0.0042 C2 [1;0;0;0] -0.0036 0.0047 C3 [1;0;0;0] 0.0015 0.0069 C4 [1;0;0;0] -0.0008 0.0074 C5 [1;0;0;0] 0.0044 0.0066 C6 [1;0;0;0] -0.0066 0.0055

Mean deviation from plane is 0.0037 angstrom Chi-squared: 1.499

————– Plane number 5 —————

Atoms Defining Plane Distance e.s.d. C8 [1;0;0;0] -0.0006 0.0038 C9 [1;0;0;0] -0.0005 0.0063 C10 [1;0;0;0] 0.0057 0.0076 C11 [1;0;0;0] -0.0078 0.0072 C12 [1;0;0;0] 0.0051 0.0068 C13 [1;0;0;0] -0.0006 0.0052

Mean deviation from plane is 0.0034 angstrom Chi-squared: 1.584

Dihedral angles between least-squares planes ——————————————–

plane plane angle e.s.d. 1 2 128.814 0.374 1 3 67.172 0.293 1 4 12.964 0.310 1 5 80.832 0.364 2 3 89.971 0.569 2 4 124.525 0.425 2 5 49.374 0.246 3 4 54.269 0.269 3 5 79.752 0.307 4 5 80.598 0.282

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.8753 (2)0.78769 (14)0.07266 (13)0.0676 (6)
Cl30.7612 (3)0.54162 (16)0.17899 (12)0.0768 (7)
S11.0701 (2)0.58886 (16)0.00832 (12)0.0605 (6)
Cl20.8941 (3)0.7272 (2)0.22162 (13)0.0885 (8)
N10.8916 (6)0.7273 (4)0.2165 (3)0.0486 (15)
N20.8679 (7)0.6201 (4)0.0858 (3)0.0527 (16)
O10.6241 (7)0.5250 (4)0.0414 (3)0.0757 (18)
O20.5428 (6)0.5822 (5)0.0595 (4)0.0824 (19)
N30.6413 (7)0.5672 (4)0.0162 (4)0.0580 (17)
C180.8892 (7)0.5999 (4)0.0151 (4)0.0441 (17)
C140.8041 (8)0.7542 (5)0.1546 (4)0.0490 (19)
H14A0.85980.79230.12250.059*
H14B0.72390.78890.17240.059*
C200.7983 (8)0.6219 (5)0.1118 (4)0.0476 (19)
C190.7803 (7)0.5969 (5)0.0366 (4)0.0450 (17)
C170.9614 (9)0.5934 (6)0.1473 (4)0.061 (2)
H17A1.04260.56030.12860.074*
H17B0.90940.55470.18070.074*
C80.8283 (8)0.8716 (5)0.2784 (4)0.0461 (18)
C70.9442 (9)0.8023 (5)0.2609 (4)0.051 (2)
C210.8463 (9)0.7007 (6)0.1336 (4)0.058 (2)
C61.0184 (8)0.7698 (5)0.3301 (4)0.0507 (19)
C150.7485 (8)0.6748 (5)0.1108 (4)0.0517 (19)
H15A0.68570.63910.14130.062*
H15B0.69450.6960.06890.062*
C161.0120 (9)0.6749 (6)0.1877 (4)0.059 (2)
H16A1.07310.65680.2280.07*
H16B1.06780.7120.15470.07*
C221.0767 (9)0.5031 (5)0.0784 (4)0.062 (2)
H22A1.02890.52530.1220.074*
H22B1.17550.49230.09120.074*
C231.0092 (12)0.4153 (7)0.0565 (6)0.086 (3)
H23A0.91140.42570.04160.103*
H23B1.06020.39050.01490.103*
C10.9776 (10)0.6930 (6)0.3650 (5)0.068 (3)
H0230.90450.65860.34520.082*
C51.1240 (9)0.8213 (6)0.3608 (4)0.062 (2)
H0241.15090.87440.3380.075*
C21.0434 (12)0.6649 (7)0.4301 (5)0.084 (3)
H0251.0160.61220.45320.101*
C110.6206 (13)0.9941 (8)0.3140 (7)0.100 (4)
H0260.5511.03590.32630.12*
C90.7283 (12)0.8529 (7)0.3300 (6)0.087 (3)
H0270.73050.79780.35370.104*
C130.8253 (10)0.9527 (6)0.2432 (5)0.067 (2)
H0280.89270.96650.20750.08*
C120.7202 (11)1.0137 (7)0.2616 (7)0.088 (3)
H0290.71721.06880.2380.106*
C241.0117 (14)0.3483 (6)0.1197 (6)0.096 (4)
H24A0.9490.36840.15790.145*
H24B0.98090.29080.10230.145*
H24C1.10690.34360.13860.145*
C31.1508 (13)0.7182 (8)0.4591 (5)0.090 (4)
H0311.19640.70130.50220.108*
C100.6240 (13)0.9136 (9)0.3479 (6)0.102 (4)
H0320.5560.89940.38310.122*
C41.1896 (10)0.7960 (8)0.4239 (5)0.082 (3)
H0331.26150.83150.44350.098*
H71.003 (5)0.835 (3)0.232 (3)0.000 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0630 (13)0.0523 (11)0.0874 (15)0.0051 (11)0.0071 (12)0.0006 (11)
Cl30.0982 (18)0.0771 (15)0.0552 (12)0.0060 (14)0.0220 (13)0.0172 (12)
S10.0449 (10)0.0799 (15)0.0567 (13)0.0036 (11)0.0026 (10)0.0186 (12)
Cl20.0895 (19)0.118 (2)0.0580 (13)0.0005 (17)0.0111 (13)0.0252 (14)
N10.049 (4)0.054 (4)0.043 (3)0.005 (3)0.002 (3)0.004 (3)
N20.051 (4)0.052 (4)0.055 (4)0.015 (3)0.004 (3)0.006 (3)
O10.088 (5)0.070 (4)0.070 (4)0.031 (4)0.010 (4)0.002 (3)
O20.051 (4)0.105 (5)0.092 (5)0.004 (4)0.015 (4)0.002 (4)
N30.054 (4)0.048 (4)0.072 (5)0.004 (3)0.009 (4)0.014 (4)
C180.050 (4)0.037 (4)0.045 (4)0.003 (3)0.013 (3)0.003 (3)
C140.041 (4)0.062 (5)0.044 (4)0.003 (4)0.011 (3)0.004 (4)
C200.051 (5)0.041 (4)0.051 (5)0.010 (4)0.007 (4)0.006 (4)
C190.043 (4)0.047 (4)0.046 (4)0.007 (4)0.003 (3)0.012 (4)
C170.073 (6)0.063 (5)0.048 (5)0.025 (5)0.012 (4)0.019 (4)
C80.046 (4)0.055 (5)0.037 (4)0.003 (4)0.002 (3)0.019 (4)
C70.067 (5)0.055 (5)0.030 (4)0.026 (4)0.014 (4)0.005 (3)
C210.050 (5)0.080 (6)0.044 (4)0.023 (5)0.001 (4)0.007 (4)
C60.057 (5)0.056 (5)0.038 (4)0.002 (4)0.011 (4)0.006 (4)
C150.047 (4)0.053 (5)0.054 (5)0.002 (4)0.000 (4)0.009 (4)
C160.061 (5)0.073 (6)0.042 (4)0.026 (5)0.003 (4)0.002 (4)
C220.060 (5)0.068 (5)0.057 (5)0.011 (5)0.006 (4)0.019 (4)
C230.098 (7)0.078 (7)0.080 (7)0.014 (6)0.019 (6)0.008 (6)
C10.082 (7)0.068 (6)0.054 (5)0.002 (5)0.002 (5)0.004 (5)
C50.064 (5)0.069 (6)0.055 (5)0.013 (5)0.005 (4)0.004 (4)
C20.110 (9)0.088 (7)0.054 (6)0.010 (7)0.011 (6)0.023 (5)
C110.085 (8)0.089 (8)0.125 (10)0.036 (7)0.031 (8)0.073 (8)
C90.098 (8)0.077 (7)0.086 (7)0.030 (6)0.009 (7)0.008 (6)
C130.074 (6)0.057 (5)0.070 (6)0.004 (5)0.024 (5)0.006 (5)
C120.069 (7)0.065 (7)0.130 (10)0.007 (6)0.037 (7)0.012 (7)
C240.138 (10)0.057 (6)0.094 (8)0.018 (7)0.008 (7)0.018 (6)
C30.113 (9)0.113 (9)0.045 (5)0.042 (8)0.013 (6)0.002 (6)
C100.095 (9)0.119 (10)0.091 (8)0.038 (9)0.015 (7)0.014 (8)
C40.073 (6)0.109 (8)0.064 (6)0.013 (6)0.018 (5)0.018 (6)
Geometric parameters (Å, º) top
Cl1—C211.731 (9)C15—H15B0.97
Cl3—C201.749 (7)C16—H16A0.97
S1—C181.759 (7)C16—H16B0.97
S1—C221.810 (7)C22—C231.510 (9)
Cl2—C211.712 (8)C22—H22A0.97
N1—C141.452 (9)C22—H22B0.97
N1—C71.468 (9)C23—C241.526 (9)
N1—C161.472 (9)C23—H23A0.97
N2—C181.337 (9)C23—H23B0.97
N2—C151.461 (9)C1—C21.401 (9)
N2—C171.480 (9)C1—H0230.93
O1—N31.235 (8)C5—C41.359 (9)
O2—N31.236 (8)C5—H0240.93
N3—C191.427 (9)C2—C31.388 (9)
C18—C191.391 (9)C2—H0250.93
C14—C151.521 (9)C11—C101.353 (9)
C14—H14A0.97C11—C121.368 (9)
C14—H14B0.97C11—H0260.93
C20—C211.321 (9)C9—C101.374 (9)
C20—C191.432 (9)C9—H0270.93
C17—C161.500 (9)C13—C121.384 (9)
C17—H17A0.97C13—H0280.93
C17—H17B0.97C12—H0290.93
C8—C91.357 (9)C24—H24A0.96
C8—C131.371 (9)C24—H24B0.96
C8—C71.536 (9)C24—H24C0.96
C7—C61.519 (9)C3—C41.376 (9)
C7—H70.90 (5)C3—H0310.93
C6—C11.367 (9)C10—H0320.93
C6—C51.374 (9)C4—H0330.93
C15—H15A0.97
C18—S1—C22105.7 (4)N1—C16—H16A109.4
C14—N1—C7114.1 (6)C17—C16—H16A109.4
C14—N1—C16107.7 (6)N1—C16—H16B109.4
C7—N1—C16110.1 (6)C17—C16—H16B109.4
C18—N2—C15122.9 (6)H16A—C16—H16B108
C18—N2—C17125.5 (6)C23—C22—S1114.5 (6)
C15—N2—C17111.6 (6)C23—C22—H22A108.6
O1—N3—O2122.5 (7)S1—C22—H22A108.6
O1—N3—C19119.9 (7)C23—C22—H22B108.6
O2—N3—C19117.5 (7)S1—C22—H22B108.6
N2—C18—C19123.3 (6)H22A—C22—H22B107.6
N2—C18—S1113.6 (6)C22—C23—C24111.3 (8)
C19—C18—S1122.8 (5)C22—C23—H23A109.4
N1—C14—C15112.7 (6)C24—C23—H23A109.4
N1—C14—H14A109.1C22—C23—H23B109.4
C15—C14—H14A109.1C24—C23—H23B109.4
N1—C14—H14B109.1H23A—C23—H23B108
C15—C14—H14B109.1C6—C1—C2121.4 (10)
H14A—C14—H14B107.8C6—C1—H023119.3
C21—C20—C19124.1 (7)C2—C1—H023119.3
C21—C20—Cl3118.0 (6)C4—C5—C6121.0 (9)
C19—C20—Cl3117.9 (6)C4—C5—H024119.5
C18—C19—N3120.4 (7)C6—C5—H024119.5
C18—C19—C20123.6 (7)C3—C2—C1118.1 (10)
N3—C19—C20116.0 (7)C3—C2—H025120.9
N2—C17—C16109.9 (6)C1—C2—H025120.9
N2—C17—H17A109.7C10—C11—C12119.5 (10)
C16—C17—H17A109.7C10—C11—H026120.3
N2—C17—H17B109.7C12—C11—H026120.3
C16—C17—H17B109.7C8—C9—C10121.4 (10)
H17A—C17—H17B108.2C8—C9—H027119.3
C9—C8—C13119.5 (8)C10—C9—H027119.3
C9—C8—C7119.6 (8)C8—C13—C12118.8 (10)
C13—C8—C7120.9 (7)C8—C13—H028120.6
N1—C7—C6111.6 (6)C12—C13—H028120.6
N1—C7—C8112.9 (6)C11—C12—C13121.1 (11)
C6—C7—C8111.7 (6)C11—C12—H029119.4
N1—C7—H7108 (3)C13—C12—H029119.4
C6—C7—H7112 (3)C23—C24—H24A109.5
C8—C7—H7101 (3)C23—C24—H24B109.5
C20—C21—Cl2125.2 (7)H24A—C24—H24B109.5
C20—C21—Cl1122.0 (6)C23—C24—H24C109.5
Cl2—C21—Cl1112.7 (5)H24A—C24—H24C109.5
C1—C6—C5118.9 (8)H24B—C24—H24C109.5
C1—C6—C7121.8 (8)C4—C3—C2119.9 (9)
C5—C6—C7119.3 (7)C4—C3—H031120
N2—C15—C14109.7 (6)C2—C3—H031120
N2—C15—H15A109.7C11—C10—C9119.7 (12)
C14—C15—H15A109.7C11—C10—H032120.2
N2—C15—H15B109.7C9—C10—H032120.2
C14—C15—H15B109.7C5—C4—C3120.6 (10)
H15A—C15—H15B108.2C5—C4—H033119.7
N1—C16—C17111.3 (7)C3—C4—H033119.7
C15—N2—C18—C1925.8 (11)Cl3—C20—C21—Cl27.6 (10)
C17—N2—C18—C19156.2 (8)C19—C20—C21—Cl17.1 (12)
C15—N2—C18—S1147.9 (6)Cl3—C20—C21—Cl1175.6 (4)
C17—N2—C18—S130.1 (10)N1—C7—C6—C131.9 (10)
C22—S1—C18—N2146.5 (6)C8—C7—C6—C195.6 (9)
C22—S1—C18—C1939.8 (7)N1—C7—C6—C5151.9 (7)
C7—N1—C14—C15178.7 (6)C8—C7—C6—C580.7 (9)
C16—N1—C14—C1558.8 (8)C18—N2—C15—C14124.3 (7)
N2—C18—C19—N334.4 (11)C17—N2—C15—C1453.9 (8)
S1—C18—C19—N3152.4 (6)N1—C14—C15—N256.8 (8)
N2—C18—C19—C20146.0 (7)C14—N1—C16—C1759.9 (8)
S1—C18—C19—C2027.1 (10)C7—N1—C16—C17175.2 (6)
O1—N3—C19—C1816.8 (10)N2—C17—C16—N159.0 (9)
O2—N3—C19—C18166.2 (7)C18—S1—C22—C2355.2 (8)
O1—N3—C19—C20162.8 (7)S1—C22—C23—C24176.9 (7)
O2—N3—C19—C2014.2 (10)C5—C6—C1—C21.6 (13)
C21—C20—C19—C1856.0 (11)C7—C6—C1—C2177.9 (8)
Cl3—C20—C19—C18121.3 (7)C1—C6—C5—C41.5 (12)
C21—C20—C19—N3124.5 (8)C7—C6—C5—C4177.9 (8)
Cl3—C20—C19—N358.2 (8)C6—C1—C2—C30.9 (14)
C18—N2—C17—C16122.3 (8)C13—C8—C9—C100.1 (15)
C15—N2—C17—C1655.9 (9)C7—C8—C9—C10179.1 (9)
C14—N1—C7—C6172.6 (6)C9—C8—C13—C120.3 (13)
C16—N1—C7—C666.2 (8)C7—C8—C13—C12178.9 (7)
C14—N1—C7—C845.8 (8)C10—C11—C12—C130.6 (16)
C16—N1—C7—C8167.0 (6)C8—C13—C12—C110.1 (14)
C9—C8—C7—N175.5 (9)C1—C2—C3—C40.0 (15)
C13—C8—C7—N1105.3 (8)C12—C11—C10—C90.8 (17)
C9—C8—C7—C651.2 (10)C8—C9—C10—C110.5 (18)
C13—C8—C7—C6127.9 (8)C6—C5—C4—C30.6 (14)
C19—C20—C21—Cl2169.7 (6)C2—C3—C4—C50.1 (16)
 

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