Download citation
Download citation
link to html
The title compound, C19H20ClN3O2, is composed of an essentially planar benzoxazolinone ring system, a chloro­phenyl group and a central piperazine ring. The benzoxazolinone ring system is nearly perpendicular to the piperazine ring, which displays an almost perfect chair conformation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803026230/su6057sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803026230/su6057Isup2.hkl
Contains datablock I

CCDC reference: 227901

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.040
  • wR factor = 0.127
  • Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level A ABSTM02_ALERT_3_A Test not performed as the _exptl_absorpt_correction_type has not been identified. See test ABSTY_01. ABSTY01_ALERT_1_A The absorption correction should be one of the following * none * analytical * integration * numerical * gaussian * empirical * psi-scan * multi-scan * refdelf * sphere * cylinder PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.94
Alert level C REFLT03_ALERT_3_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 26.00 From the CIF: _diffrn_reflns_theta_full 0.00 From the CIF: _reflns_number_total 3201 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 3410 Completeness (_total/calc) 93.87% PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.94 PLAT431_ALERT_2_C Short Inter HL..A Contact Cl1 .. O1 = 3.20 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C19 H20 Cl N3 O2
3 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97; molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: WinGX (Farrugia, 1997) and PARST (Nardelli, 1995).

3-[4-(2-Chlorophenyl)piperazinomethyl]-5-methyl-1-benzoxazolin-2(3H)-one top
Crystal data top
C19H20ClN3O2Z = 2
Mr = 357.84F(000) = 376
Triclinic, P1Dx = 1.370 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.2122 (7) ÅCell parameters from 8369 reflections
b = 10.8899 (12) Åθ = 29.5–0.0°
c = 13.0580 (14) ŵ = 0.24 mm1
α = 84.042 (8)°T = 293 K
β = 84.028 (9)°Prismatic, colourless
γ = 82.499 (9)°0.70 × 0.57 × 0.35 mm
V = 867.41 (17) Å3
Data collection top
Stoe IPDS-2
diffractometer
3201 independent reflections
Radiation source: fine-focus sealed tube2762 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 1.6°
rotation method scansh = 77
Absorption correction: spherical
(X-RED; Stoe & Cie, 2002)
k = 1313
Tmin = 1.000, Tmax = 1.000l = 1616
6303 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.128 w = 1/[σ2(Fo2) + (0.067P)2 + 0.1P]
where P = (Fo2 + 2Fc2)/3
S = 1.13(Δ/σ)max = 0.001
3201 reflectionsΔρmax = 0.35 e Å3
227 parametersΔρmin = 0.36 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.010 (3)
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
Cl10.23743 (7)0.29576 (5)0.78785 (3)0.05798 (19)
N20.1430 (2)0.15072 (12)1.14123 (9)0.0379 (3)
N10.1458 (2)0.29223 (13)0.94544 (10)0.0390 (3)
C100.0068 (3)0.31683 (16)1.02279 (12)0.0421 (4)
H10A0.08330.37981.06510.050*
H10B0.12440.34780.98860.050*
N30.0516 (2)0.04494 (13)1.28028 (10)0.0424 (3)
C90.0534 (3)0.19866 (16)1.09021 (12)0.0408 (4)
H9A0.13550.13691.04820.049*
H9B0.14480.21521.14180.049*
O20.34422 (19)0.01274 (13)1.36719 (11)0.0564 (4)
C140.0028 (3)0.11307 (15)1.36625 (12)0.0398 (4)
C80.2865 (3)0.13047 (16)1.06409 (12)0.0414 (4)
H8A0.41880.10161.09900.050*
H8B0.21440.06631.02170.050*
C110.0915 (3)0.03279 (16)1.20236 (12)0.0442 (4)
H11A0.22530.00421.23550.053*
H11B0.02200.02891.15710.053*
C20.0033 (3)0.40234 (17)0.78823 (13)0.0466 (4)
C10.1697 (3)0.38809 (15)0.86390 (12)0.0411 (4)
C70.3449 (3)0.24784 (17)0.99580 (13)0.0428 (4)
H7A0.43630.23130.94410.051*
H7B0.42560.31081.03700.051*
C130.1867 (3)0.09049 (17)1.41970 (13)0.0465 (4)
C60.3589 (3)0.46950 (18)0.85420 (14)0.0528 (4)
H60.47800.46150.90270.063*
C150.1782 (3)0.18912 (16)1.40078 (13)0.0440 (4)
H150.30150.20411.36450.053*
C30.0110 (4)0.4976 (2)0.70939 (15)0.0597 (5)
H30.10780.50720.66090.072*
C120.2585 (3)0.01567 (18)1.28047 (14)0.0509 (4)
O10.3596 (2)0.08099 (15)1.21970 (13)0.0715 (4)
C170.0161 (4)0.21698 (19)1.54526 (14)0.0587 (5)
H170.01870.25281.60670.070*
C180.1981 (3)0.13978 (19)1.51016 (15)0.0572 (5)
H180.32120.12261.54650.069*
C40.1998 (4)0.5779 (2)0.70249 (16)0.0672 (6)
H40.20890.64220.64980.081*
C160.1699 (3)0.24320 (18)1.49267 (14)0.0509 (4)
C50.3742 (4)0.5628 (2)0.77344 (17)0.0648 (6)
H50.50380.61530.76760.078*
C190.3598 (4)0.3295 (2)1.53403 (19)0.0728 (6)
H19A0.32590.35911.59650.109*
H19B0.48580.28581.54850.109*
H19C0.38940.39871.48360.109*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0533 (3)0.0736 (4)0.0462 (3)0.0093 (2)0.00174 (19)0.0025 (2)
N20.0448 (7)0.0384 (8)0.0307 (6)0.0051 (5)0.0049 (5)0.0020 (5)
N10.0441 (7)0.0414 (8)0.0325 (6)0.0091 (6)0.0076 (5)0.0002 (6)
C100.0525 (9)0.0410 (9)0.0355 (7)0.0118 (7)0.0116 (7)0.0016 (7)
N30.0438 (7)0.0454 (8)0.0350 (7)0.0000 (6)0.0035 (5)0.0031 (6)
C90.0437 (8)0.0427 (9)0.0370 (8)0.0081 (7)0.0089 (6)0.0002 (7)
O20.0446 (6)0.0581 (9)0.0633 (8)0.0003 (6)0.0125 (6)0.0092 (6)
C140.0466 (8)0.0385 (9)0.0333 (7)0.0081 (7)0.0059 (6)0.0069 (6)
C80.0419 (8)0.0450 (10)0.0386 (8)0.0105 (7)0.0045 (6)0.0028 (7)
C110.0527 (9)0.0432 (10)0.0362 (8)0.0067 (7)0.0045 (7)0.0007 (7)
C20.0589 (10)0.0471 (10)0.0371 (8)0.0156 (8)0.0098 (7)0.0027 (7)
C10.0559 (9)0.0359 (9)0.0339 (7)0.0091 (7)0.0124 (7)0.0018 (6)
C70.0400 (8)0.0487 (10)0.0397 (8)0.0053 (7)0.0068 (6)0.0007 (7)
C130.0508 (9)0.0420 (10)0.0459 (9)0.0087 (7)0.0125 (7)0.0113 (7)
C60.0648 (11)0.0465 (11)0.0460 (9)0.0009 (8)0.0112 (8)0.0002 (8)
C150.0472 (8)0.0449 (10)0.0398 (8)0.0060 (7)0.0065 (7)0.0002 (7)
C30.0821 (13)0.0570 (12)0.0424 (9)0.0252 (10)0.0071 (9)0.0063 (8)
C120.0484 (9)0.0487 (11)0.0510 (10)0.0011 (8)0.0023 (8)0.0082 (8)
O10.0610 (8)0.0720 (11)0.0741 (9)0.0122 (7)0.0077 (7)0.0114 (8)
C170.0870 (14)0.0531 (12)0.0415 (9)0.0240 (10)0.0163 (9)0.0005 (8)
C180.0673 (11)0.0548 (12)0.0529 (10)0.0163 (9)0.0272 (9)0.0115 (9)
C40.1063 (17)0.0481 (12)0.0493 (10)0.0174 (11)0.0215 (11)0.0105 (9)
C160.0655 (11)0.0453 (11)0.0431 (9)0.0151 (8)0.0009 (8)0.0029 (8)
C50.0862 (14)0.0461 (12)0.0611 (12)0.0026 (10)0.0243 (11)0.0040 (9)
C190.0814 (15)0.0680 (15)0.0706 (14)0.0094 (11)0.0067 (12)0.0263 (12)
Geometric parameters (Å, º) top
Cl1—C21.7384 (19)C2—C31.385 (3)
N2—C111.457 (2)C2—C11.395 (3)
N2—C91.459 (2)C1—C61.386 (2)
N2—C81.4639 (19)C7—H7A0.9700
N1—C11.417 (2)C7—H7B0.9700
N1—C71.455 (2)C13—C181.359 (3)
N1—C101.4616 (19)C6—C51.388 (3)
C10—C91.510 (2)C6—H60.9300
C10—H10A0.9700C15—C161.399 (2)
C10—H10B0.9700C15—H150.9300
N3—C121.367 (2)C3—C41.374 (3)
N3—C141.395 (2)C3—H30.9300
N3—C111.445 (2)C12—O11.194 (2)
C9—H9A0.9700C17—C181.385 (3)
C9—H9B0.9700C17—C161.388 (3)
O2—C121.379 (2)C17—H170.9300
O2—C131.382 (2)C18—H180.9300
C14—C151.372 (2)C4—C51.365 (4)
C14—C131.382 (2)C4—H40.9300
C8—C71.507 (2)C16—C191.500 (3)
C8—H8A0.9700C5—H50.9300
C8—H8B0.9700C19—H19A0.9600
C11—H11A0.9700C19—H19B0.9600
C11—H11B0.9700C19—H19C0.9600
C11—N2—C9111.63 (13)N1—C7—C8109.11 (13)
C11—N2—C8107.96 (13)N1—C7—H7A109.9
C9—N2—C8110.08 (12)C8—C7—H7A109.9
C1—N1—C7116.80 (13)N1—C7—H7B109.9
C1—N1—C10114.01 (12)C8—C7—H7B109.9
C7—N1—C10110.21 (12)H7A—C7—H7B108.3
N1—C10—C9109.69 (13)C18—C13—O2128.21 (16)
N1—C10—H10A109.7C18—C13—C14122.35 (17)
C9—C10—H10A109.7O2—C13—C14109.44 (15)
N1—C10—H10B109.7C1—C6—C5121.3 (2)
C9—C10—H10B109.7C1—C6—H6119.4
H10A—C10—H10B108.2C5—C6—H6119.4
C12—N3—C14110.01 (14)C14—C15—C16117.41 (16)
C12—N3—C11122.80 (14)C14—C15—H15121.3
C14—N3—C11127.15 (13)C16—C15—H15121.3
N2—C9—C10110.16 (13)C4—C3—C2120.2 (2)
N2—C9—H9A109.6C4—C3—H3119.9
C10—C9—H9A109.6C2—C3—H3119.9
N2—C9—H9B109.6O1—C12—N3130.00 (19)
C10—C9—H9B109.6O1—C12—O2122.61 (17)
H9A—C9—H9B108.1N3—C12—O2107.38 (15)
C12—O2—C13107.76 (13)C18—C17—C16122.81 (17)
C15—C14—C13121.59 (16)C18—C17—H17118.6
C15—C14—N3133.01 (15)C16—C17—H17118.6
C13—C14—N3105.40 (14)C13—C18—C17116.32 (16)
N2—C8—C7111.51 (13)C13—C18—H18121.8
N2—C8—H8A109.3C17—C18—H18121.8
C7—C8—H8A109.3C5—C4—C3119.7 (2)
N2—C8—H8B109.3C5—C4—H4120.2
C7—C8—H8B109.3C3—C4—H4120.2
H8A—C8—H8B108.0C17—C16—C15119.50 (18)
N3—C11—N2111.34 (14)C17—C16—C19120.08 (18)
N3—C11—H11A109.4C15—C16—C19120.42 (18)
N2—C11—H11A109.4C4—C5—C6120.3 (2)
N3—C11—H11B109.4C4—C5—H5119.8
N2—C11—H11B109.4C6—C5—H5119.8
H11A—C11—H11B108.0C16—C19—H19A109.5
C3—C2—C1121.12 (18)C16—C19—H19B109.5
C3—C2—Cl1118.52 (15)H19A—C19—H19B109.5
C1—C2—Cl1120.30 (14)C16—C19—H19C109.5
C6—C1—C2117.29 (17)H19A—C19—H19C109.5
C6—C1—N1123.30 (16)H19B—C19—H19C109.5
C2—C1—N1119.41 (15)
C1—N1—C10—C9165.98 (13)C12—O2—C13—C140.83 (19)
C7—N1—C10—C960.39 (17)C15—C14—C13—C181.4 (3)
C11—N2—C9—C10176.73 (12)N3—C14—C13—C18178.54 (17)
C8—N2—C9—C1056.85 (16)C15—C14—C13—O2179.12 (15)
N1—C10—C9—N258.87 (17)N3—C14—C13—O20.97 (18)
C12—N3—C14—C15179.34 (18)C2—C1—C6—C51.1 (3)
C11—N3—C14—C153.0 (3)N1—C1—C6—C5179.42 (17)
C12—N3—C14—C130.77 (19)C13—C14—C15—C160.1 (2)
C11—N3—C14—C13176.94 (15)N3—C14—C15—C16179.79 (17)
C11—N2—C8—C7178.95 (13)C1—C2—C3—C42.1 (3)
C9—N2—C8—C756.88 (17)Cl1—C2—C3—C4174.95 (15)
C12—N3—C11—N2115.75 (17)C14—N3—C12—O1178.7 (2)
C14—N3—C11—N266.8 (2)C11—N3—C12—O13.4 (3)
C9—N2—C11—N358.53 (16)C14—N3—C12—O20.28 (19)
C8—N2—C11—N3179.65 (12)C11—N3—C12—O2177.55 (14)
C3—C2—C1—C62.8 (3)C13—O2—C12—O1179.42 (19)
Cl1—C2—C1—C6174.18 (12)C13—O2—C12—N30.33 (19)
C3—C2—C1—N1177.71 (15)O2—C13—C18—C17179.09 (18)
Cl1—C2—C1—N15.3 (2)C14—C13—C18—C171.5 (3)
C7—N1—C1—C623.9 (2)C16—C17—C18—C130.4 (3)
C10—N1—C1—C6106.54 (18)C2—C3—C4—C50.4 (3)
C7—N1—C1—C2155.55 (15)C18—C17—C16—C150.8 (3)
C10—N1—C1—C274.02 (19)C18—C17—C16—C19178.9 (2)
C1—N1—C7—C8168.53 (13)C14—C15—C16—C170.9 (3)
C10—N1—C7—C859.27 (16)C14—C15—C16—C19178.74 (18)
N2—C8—C7—N157.76 (17)C3—C4—C5—C62.1 (3)
C12—O2—C13—C18178.65 (18)C1—C6—C5—C41.3 (3)
 

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