3-[4-(2-Chloro­phenyl)­piperazino­methyl]-5-methyl-1-benzoxazolin-2(3H)-one

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.

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

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Computing details

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

Crystal data

C19H20ClN3O2	Z = 2
Mr = 357.84	F(000) = 376
Triclinic, P1	Dx = 1.370 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.2122 (7) Å	Cell parameters from 8369 reflections
b = 10.8899 (12) Å	θ = 29.5–0.0°
c = 13.0580 (14) Å	µ = 0.24 mm^−1
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) Å^3

Data collection

Stoe IPDS-2 diffractometer	3201 independent reflections
Radiation source: fine-focus sealed tube	2762 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
Detector resolution: 6.67 pixels mm^-1	θmax = 26.0°, θmin = 1.6°
rotation method scans	h = −7→7
Absorption correction: spherical (X-RED; Stoe & Cie, 2002)	k = −13→13
Tmin = 1.000, Tmax = 1.000	l = −16→16
6303 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.128	w = 1/[σ^2(Fo^2) + (0.067P)^2 + 0.1P] where P = (Fo^2 + 2Fc^2)/3
S = 1.13	(Δ/σ)max = 0.001
3201 reflections	Δρmax = 0.35 e Å^−3
227 parameters	Δρmin = −0.36 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.010 (3)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.23743 (7)	0.29576 (5)	0.78785 (3)	0.05798 (19)
N2	−0.1430 (2)	0.15072 (12)	1.14123 (9)	0.0379 (3)
N1	−0.1458 (2)	0.29223 (13)	0.94544 (10)	0.0390 (3)
C10	−0.0068 (3)	0.31683 (16)	1.02279 (12)	0.0421 (4)
H10A	−0.0833	0.3798	1.0651	0.050*
H10B	0.1244	0.3478	0.9886	0.050*
N3	0.0516 (2)	0.04494 (13)	1.28028 (10)	0.0424 (3)
C9	0.0534 (3)	0.19866 (16)	1.09021 (12)	0.0408 (4)
H9A	0.1355	0.1369	1.0482	0.049*
H9B	0.1448	0.2152	1.1418	0.049*
O2	0.34422 (19)	0.01274 (13)	1.36719 (11)	0.0564 (4)
C14	0.0028 (3)	0.11307 (15)	1.36625 (12)	0.0398 (4)
C8	−0.2865 (3)	0.13047 (16)	1.06409 (12)	0.0414 (4)
H8A	−0.4188	0.1016	1.0990	0.050*
H8B	−0.2144	0.0663	1.0217	0.050*
C11	−0.0915 (3)	0.03279 (16)	1.20236 (12)	0.0442 (4)
H11A	−0.2253	0.0042	1.2355	0.053*
H11B	−0.0220	−0.0289	1.1571	0.053*
C2	0.0033 (3)	0.40234 (17)	0.78823 (13)	0.0466 (4)
C1	−0.1697 (3)	0.38809 (15)	0.86390 (12)	0.0411 (4)
C7	−0.3449 (3)	0.24784 (17)	0.99580 (13)	0.0428 (4)
H7A	−0.4363	0.2313	0.9441	0.051*
H7B	−0.4256	0.3108	1.0370	0.051*
C13	0.1867 (3)	0.09049 (17)	1.41970 (13)	0.0465 (4)
C6	−0.3589 (3)	0.46950 (18)	0.85420 (14)	0.0528 (4)
H6	−0.4780	0.4615	0.9027	0.063*
C15	−0.1782 (3)	0.18912 (16)	1.40078 (13)	0.0440 (4)
H15	−0.3015	0.2041	1.3645	0.053*
C3	−0.0110 (4)	0.4976 (2)	0.70939 (15)	0.0597 (5)
H3	0.1078	0.5072	0.6609	0.072*
C12	0.2585 (3)	−0.01567 (18)	1.28047 (14)	0.0509 (4)
O1	0.3596 (2)	−0.08099 (15)	1.21970 (13)	0.0715 (4)
C17	0.0161 (4)	0.21698 (19)	1.54526 (14)	0.0587 (5)
H17	0.0187	0.2528	1.6067	0.070*
C18	0.1981 (3)	0.13978 (19)	1.51016 (15)	0.0572 (5)
H18	0.3212	0.1226	1.5465	0.069*
C4	−0.1998 (4)	0.5779 (2)	0.70249 (16)	0.0672 (6)
H4	−0.2089	0.6422	0.6498	0.081*
C16	−0.1699 (3)	0.24320 (18)	1.49267 (14)	0.0509 (4)
C5	−0.3742 (4)	0.5628 (2)	0.77344 (17)	0.0648 (6)
H5	−0.5038	0.6153	0.7676	0.078*
C19	−0.3598 (4)	0.3295 (2)	1.53403 (19)	0.0728 (6)
H19A	−0.3259	0.3591	1.5965	0.109*
H19B	−0.4858	0.2858	1.5485	0.109*
H19C	−0.3894	0.3987	1.4836	0.109*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0533 (3)	0.0736 (4)	0.0462 (3)	−0.0093 (2)	−0.00174 (19)	−0.0025 (2)
N2	0.0448 (7)	0.0384 (8)	0.0307 (6)	−0.0051 (5)	−0.0049 (5)	−0.0020 (5)
N1	0.0441 (7)	0.0414 (8)	0.0325 (6)	−0.0091 (6)	−0.0076 (5)	0.0002 (6)
C10	0.0525 (9)	0.0410 (9)	0.0355 (7)	−0.0118 (7)	−0.0116 (7)	−0.0016 (7)
N3	0.0438 (7)	0.0454 (8)	0.0350 (7)	0.0000 (6)	−0.0035 (5)	0.0031 (6)
C9	0.0437 (8)	0.0427 (9)	0.0370 (8)	−0.0081 (7)	−0.0089 (6)	−0.0002 (7)
O2	0.0446 (6)	0.0581 (9)	0.0633 (8)	0.0003 (6)	−0.0125 (6)	0.0092 (6)
C14	0.0466 (8)	0.0385 (9)	0.0333 (7)	−0.0081 (7)	−0.0059 (6)	0.0069 (6)
C8	0.0419 (8)	0.0450 (10)	0.0386 (8)	−0.0105 (7)	−0.0045 (6)	−0.0028 (7)
C11	0.0527 (9)	0.0432 (10)	0.0362 (8)	−0.0067 (7)	−0.0045 (7)	0.0007 (7)
C2	0.0589 (10)	0.0471 (10)	0.0371 (8)	−0.0156 (8)	−0.0098 (7)	−0.0027 (7)
C1	0.0559 (9)	0.0359 (9)	0.0339 (7)	−0.0091 (7)	−0.0124 (7)	−0.0018 (6)
C7	0.0400 (8)	0.0487 (10)	0.0397 (8)	−0.0053 (7)	−0.0068 (6)	−0.0007 (7)
C13	0.0508 (9)	0.0420 (10)	0.0459 (9)	−0.0087 (7)	−0.0125 (7)	0.0113 (7)
C6	0.0648 (11)	0.0465 (11)	0.0460 (9)	−0.0009 (8)	−0.0112 (8)	−0.0002 (8)
C15	0.0472 (8)	0.0449 (10)	0.0398 (8)	−0.0060 (7)	−0.0065 (7)	0.0002 (7)
C3	0.0821 (13)	0.0570 (12)	0.0424 (9)	−0.0252 (10)	−0.0071 (9)	0.0063 (8)
C12	0.0484 (9)	0.0487 (11)	0.0510 (10)	−0.0011 (8)	−0.0023 (8)	0.0082 (8)
O1	0.0610 (8)	0.0720 (11)	0.0741 (9)	0.0122 (7)	0.0077 (7)	−0.0114 (8)
C17	0.0870 (14)	0.0531 (12)	0.0415 (9)	−0.0240 (10)	−0.0163 (9)	−0.0005 (8)
C18	0.0673 (11)	0.0548 (12)	0.0529 (10)	−0.0163 (9)	−0.0272 (9)	0.0115 (9)
C4	0.1063 (17)	0.0481 (12)	0.0493 (10)	−0.0174 (11)	−0.0215 (11)	0.0105 (9)
C16	0.0655 (11)	0.0453 (11)	0.0431 (9)	−0.0151 (8)	−0.0009 (8)	−0.0029 (8)
C5	0.0862 (14)	0.0461 (12)	0.0611 (12)	0.0026 (10)	−0.0243 (11)	0.0040 (9)
C19	0.0814 (15)	0.0680 (15)	0.0706 (14)	−0.0094 (11)	0.0067 (12)	−0.0263 (12)

Geometric parameters (Å, º)

Cl1—C2	1.7384 (19)	C2—C3	1.385 (3)
N2—C11	1.457 (2)	C2—C1	1.395 (3)
N2—C9	1.459 (2)	C1—C6	1.386 (2)
N2—C8	1.4639 (19)	C7—H7A	0.9700
N1—C1	1.417 (2)	C7—H7B	0.9700
N1—C7	1.455 (2)	C13—C18	1.359 (3)
N1—C10	1.4616 (19)	C6—C5	1.388 (3)
C10—C9	1.510 (2)	C6—H6	0.9300
C10—H10A	0.9700	C15—C16	1.399 (2)
C10—H10B	0.9700	C15—H15	0.9300
N3—C12	1.367 (2)	C3—C4	1.374 (3)
N3—C14	1.395 (2)	C3—H3	0.9300
N3—C11	1.445 (2)	C12—O1	1.194 (2)
C9—H9A	0.9700	C17—C18	1.385 (3)
C9—H9B	0.9700	C17—C16	1.388 (3)
O2—C12	1.379 (2)	C17—H17	0.9300
O2—C13	1.382 (2)	C18—H18	0.9300
C14—C15	1.372 (2)	C4—C5	1.365 (4)
C14—C13	1.382 (2)	C4—H4	0.9300
C8—C7	1.507 (2)	C16—C19	1.500 (3)
C8—H8A	0.9700	C5—H5	0.9300
C8—H8B	0.9700	C19—H19A	0.9600
C11—H11A	0.9700	C19—H19B	0.9600
C11—H11B	0.9700	C19—H19C	0.9600
C11—N2—C9	111.63 (13)	N1—C7—C8	109.11 (13)
C11—N2—C8	107.96 (13)	N1—C7—H7A	109.9
C9—N2—C8	110.08 (12)	C8—C7—H7A	109.9
C1—N1—C7	116.80 (13)	N1—C7—H7B	109.9
C1—N1—C10	114.01 (12)	C8—C7—H7B	109.9
C7—N1—C10	110.21 (12)	H7A—C7—H7B	108.3
N1—C10—C9	109.69 (13)	C18—C13—O2	128.21 (16)
N1—C10—H10A	109.7	C18—C13—C14	122.35 (17)
C9—C10—H10A	109.7	O2—C13—C14	109.44 (15)
N1—C10—H10B	109.7	C1—C6—C5	121.3 (2)
C9—C10—H10B	109.7	C1—C6—H6	119.4
H10A—C10—H10B	108.2	C5—C6—H6	119.4
C12—N3—C14	110.01 (14)	C14—C15—C16	117.41 (16)
C12—N3—C11	122.80 (14)	C14—C15—H15	121.3
C14—N3—C11	127.15 (13)	C16—C15—H15	121.3
N2—C9—C10	110.16 (13)	C4—C3—C2	120.2 (2)
N2—C9—H9A	109.6	C4—C3—H3	119.9
C10—C9—H9A	109.6	C2—C3—H3	119.9
N2—C9—H9B	109.6	O1—C12—N3	130.00 (19)
C10—C9—H9B	109.6	O1—C12—O2	122.61 (17)
H9A—C9—H9B	108.1	N3—C12—O2	107.38 (15)
C12—O2—C13	107.76 (13)	C18—C17—C16	122.81 (17)
C15—C14—C13	121.59 (16)	C18—C17—H17	118.6
C15—C14—N3	133.01 (15)	C16—C17—H17	118.6
C13—C14—N3	105.40 (14)	C13—C18—C17	116.32 (16)
N2—C8—C7	111.51 (13)	C13—C18—H18	121.8
N2—C8—H8A	109.3	C17—C18—H18	121.8
C7—C8—H8A	109.3	C5—C4—C3	119.7 (2)
N2—C8—H8B	109.3	C5—C4—H4	120.2
C7—C8—H8B	109.3	C3—C4—H4	120.2
H8A—C8—H8B	108.0	C17—C16—C15	119.50 (18)
N3—C11—N2	111.34 (14)	C17—C16—C19	120.08 (18)
N3—C11—H11A	109.4	C15—C16—C19	120.42 (18)
N2—C11—H11A	109.4	C4—C5—C6	120.3 (2)
N3—C11—H11B	109.4	C4—C5—H5	119.8
N2—C11—H11B	109.4	C6—C5—H5	119.8
H11A—C11—H11B	108.0	C16—C19—H19A	109.5
C3—C2—C1	121.12 (18)	C16—C19—H19B	109.5
C3—C2—Cl1	118.52 (15)	H19A—C19—H19B	109.5
C1—C2—Cl1	120.30 (14)	C16—C19—H19C	109.5
C6—C1—C2	117.29 (17)	H19A—C19—H19C	109.5
C6—C1—N1	123.30 (16)	H19B—C19—H19C	109.5
C2—C1—N1	119.41 (15)
C1—N1—C10—C9	−165.98 (13)	C12—O2—C13—C14	−0.83 (19)
C7—N1—C10—C9	60.39 (17)	C15—C14—C13—C18	1.4 (3)
C11—N2—C9—C10	176.73 (12)	N3—C14—C13—C18	−178.54 (17)
C8—N2—C9—C10	56.85 (16)	C15—C14—C13—O2	−179.12 (15)
N1—C10—C9—N2	−58.87 (17)	N3—C14—C13—O2	0.97 (18)
C12—N3—C14—C15	179.34 (18)	C2—C1—C6—C5	−1.1 (3)
C11—N3—C14—C15	−3.0 (3)	N1—C1—C6—C5	179.42 (17)
C12—N3—C14—C13	−0.77 (19)	C13—C14—C15—C16	−0.1 (2)
C11—N3—C14—C13	176.94 (15)	N3—C14—C15—C16	179.79 (17)
C11—N2—C8—C7	−178.95 (13)	C1—C2—C3—C4	−2.1 (3)
C9—N2—C8—C7	−56.88 (17)	Cl1—C2—C3—C4	174.95 (15)
C12—N3—C11—N2	−115.75 (17)	C14—N3—C12—O1	−178.7 (2)
C14—N3—C11—N2	66.8 (2)	C11—N3—C12—O1	3.4 (3)
C9—N2—C11—N3	58.53 (16)	C14—N3—C12—O2	0.28 (19)
C8—N2—C11—N3	179.65 (12)	C11—N3—C12—O2	−177.55 (14)
C3—C2—C1—C6	2.8 (3)	C13—O2—C12—O1	179.42 (19)
Cl1—C2—C1—C6	−174.18 (12)	C13—O2—C12—N3	0.33 (19)
C3—C2—C1—N1	−177.71 (15)	O2—C13—C18—C17	179.09 (18)
Cl1—C2—C1—N1	5.3 (2)	C14—C13—C18—C17	−1.5 (3)
C7—N1—C1—C6	23.9 (2)	C16—C17—C18—C13	0.4 (3)
C10—N1—C1—C6	−106.54 (18)	C2—C3—C4—C5	−0.4 (3)
C7—N1—C1—C2	−155.55 (15)	C18—C17—C16—C15	0.8 (3)
C10—N1—C1—C2	74.02 (19)	C18—C17—C16—C19	−178.9 (2)
C1—N1—C7—C8	168.53 (13)	C14—C15—C16—C17	−0.9 (3)
C10—N1—C7—C8	−59.27 (16)	C14—C15—C16—C19	178.74 (18)
N2—C8—C7—N1	57.76 (17)	C3—C4—C5—C6	2.1 (3)
C12—O2—C13—C18	178.65 (18)	C1—C6—C5—C4	−1.3 (3)