(2R)-4-[(9H-Fluoren-9-ylmeth-oxy)carbon-yl]-2-methyl-piperazin-1-ium chloride.

The synthesis of the title salt, C(20)H(23)N(2)O(2) (+)·Cl(-), was carried out with a precursor of known absolute configuration (R) and the X-ray analysis confirmed that the product retained the absolute configuration. In the crystal, the dominant packing motif is a chain running along [010] generated by N-H⋯Cl hydrogen bonding. C-H⋯O and C-H⋯Cl inter-actions are also observed.

Related literature

For the use of piperazine and substituted piperazines as good linkers to pharmacophores in attempts to obtain compounds with desired pharmacokinetic and pharmacological properties, see: Cho et al. (2010 ▶); Wang et al. (2009 ▶). For packing coefficients, see: Kitaigorodskij (1973 ▶).

Experimental

Crystal data

C20H23N2O2 +·Cl−

M = 358.85

Monoclinic,

a = 8.3492 (3) Å

b = 7.4954 (2) Å

c = 14.9246 (3) Å

β = 90.6740 (18)°

V = 933.93 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.22 mm−1

T = 293 K

0.28 × 0.20 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer

4227 measured reflections

4221 independent reflections

3684 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.086

S = 1.03

4221 reflections

227 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.15 e Å−3

Absolute structure: Flack (1983 ▶), 1922 Friedel pairs

Flack parameter: −0.04 (5)

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: initial refinement: maXus (MacKay et al., 2000 ▶); final refinement: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: PLATON and ACD/Labs (ACD, 2011 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811048306/kp2361sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811048306/kp2361Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811048306/kp2361Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C20H23N2O2+·Cl−	F(000) = 380
Mr = 358.85	Dx = 1.276 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2263 reflections
a = 8.3492 (3) Å	θ = 1.0–27.5°
b = 7.4954 (2) Å	µ = 0.22 mm−1
c = 14.9246 (3) Å	T = 293 K
β = 90.6740 (18)°	Block, colourless
V = 933.93 (5) Å3	0.28 × 0.20 × 0.08 mm
Z = 2

Nonius KappaCCD diffractometer	3684 reflections with I > 2σ(I)
Radiation source: fine-focus	Rint = 0.022
graphite	θmax = 27.5°, θmin = 3.0°
φ and ω scans with κ offsets	h = −10→10
4227 measured reflections	k = −9→9
4221 independent reflections	l = −19→19

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.036	w = 1/[σ2(Fo2) + (0.037P)2 + 0.176P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.086	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.16 e Å−3
4221 reflections	Δρmin = −0.15 e Å−3
227 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4
1 restraint	Extinction coefficient: 0.075 (4)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1922 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: −0.04 (5)

Experimental. Crystals were crystallized from methanol/heptane by vapour diffusion.Number of collected frames: 212 Number of repeats: 1 Crystal-Detector distance (mm): 30 Exposure time (sec) per frame: 5 Phi-rotation (°) step: 2

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
O8	0.44893 (17)	0.0878 (2)	0.65110 (9)	0.0556 (5)
O9	0.61979 (15)	0.06962 (17)	0.76938 (8)	0.0404 (4)
N1	0.86676 (19)	−0.2463 (2)	0.55195 (9)	0.0431 (5)
N4	0.61615 (18)	−0.1517 (3)	0.66869 (10)	0.0468 (5)
C2	0.7114 (2)	−0.1768 (3)	0.51533 (12)	0.0512 (6)
C3	0.5787 (2)	−0.2213 (3)	0.57921 (13)	0.0540 (7)
C5	0.7678 (2)	−0.2172 (3)	0.70499 (11)	0.0438 (6)
C6	0.9062 (2)	−0.1750 (3)	0.64313 (11)	0.0397 (5)
C7	1.0634 (2)	−0.2547 (3)	0.67673 (14)	0.0532 (7)
C8	0.5532 (2)	0.0098 (3)	0.69198 (11)	0.0398 (5)
C10	0.5939 (2)	0.2555 (2)	0.78753 (11)	0.0380 (5)
C11	0.70593 (19)	0.3087 (2)	0.86403 (10)	0.0336 (5)
C12	0.6628 (2)	0.2475 (2)	0.95797 (11)	0.0358 (5)
C13	0.5230 (2)	0.2774 (3)	1.00485 (13)	0.0446 (6)
C14	0.5175 (3)	0.2224 (3)	1.09407 (13)	0.0529 (7)
C15	0.6472 (3)	0.1385 (3)	1.13435 (13)	0.0571 (7)
C16	0.7860 (3)	0.1070 (3)	1.08760 (13)	0.0514 (7)
C17	0.7936 (2)	0.1632 (2)	0.99900 (11)	0.0389 (5)
C18	0.9257 (2)	0.1579 (2)	0.93493 (11)	0.0370 (5)
C19	1.0795 (2)	0.0892 (3)	0.94323 (15)	0.0504 (7)
C20	1.1808 (2)	0.0990 (3)	0.87068 (16)	0.0555 (7)
C21	1.1300 (2)	0.1765 (3)	0.79113 (15)	0.0528 (7)
C22	0.9768 (2)	0.2495 (3)	0.78302 (12)	0.0429 (5)
C23	0.87605 (19)	0.2402 (2)	0.85559 (11)	0.0349 (5)
Cl1	0.82783 (6)	0.33785 (7)	0.55846 (3)	0.0512 (2)
H1A	0.95740	−0.20530	0.50700	0.0520*
H1B	0.86370	−0.36370	0.54900	0.0520*
H2A	0.71940	−0.04950	0.50940	0.0620*
H2B	0.68890	−0.22870	0.45770	0.0620*
H3A	0.56490	−0.34840	0.58130	0.0650*
H3B	0.48160	−0.16670	0.55770	0.0650*
H5A	0.78820	−0.16100	0.76180	0.0520*
H5B	0.76240	−0.34420	0.71300	0.0520*
H6	0.91990	−0.04800	0.63970	0.0480*
H7A	1.08780	−0.20780	0.73520	0.0640*
H7B	1.14880	−0.22650	0.63670	0.0640*
H7C	1.05130	−0.38190	0.68040	0.0640*
H10A	0.61530	0.32520	0.73510	0.0460*
H10B	0.48460	0.27250	0.80490	0.0460*
H11	0.71090	0.45300	0.85770	0.0400*
H13	0.43480	0.33540	0.97510	0.0540*
H14	0.42200	0.24030	1.12820	0.0640*
H15	0.64190	0.10180	1.19590	0.0690*
H16	0.87520	0.04880	1.11640	0.0620*
H19	1.11280	0.03880	0.99960	0.0610*
H20	1.28690	0.04980	0.87390	0.0670*
H21	1.20490	0.17560	0.74120	0.0630*
H22	0.94320	0.30910	0.72900	0.0510*

	U11	U22	U33	U12	U13	U23
O8	0.0442 (8)	0.0714 (10)	0.0508 (7)	0.0151 (7)	−0.0161 (6)	−0.0121 (7)
O9	0.0444 (7)	0.0403 (7)	0.0363 (6)	0.0044 (6)	−0.0068 (5)	−0.0027 (5)
N1	0.0498 (9)	0.0414 (8)	0.0382 (8)	−0.0015 (7)	0.0020 (6)	−0.0056 (7)
N4	0.0417 (8)	0.0550 (9)	0.0435 (8)	0.0051 (8)	−0.0024 (6)	−0.0121 (8)
C2	0.0568 (12)	0.0583 (12)	0.0383 (8)	0.0044 (10)	−0.0124 (8)	−0.0084 (9)
C3	0.0476 (11)	0.0600 (13)	0.0542 (11)	0.0000 (9)	−0.0064 (9)	−0.0203 (10)
C5	0.0476 (10)	0.0462 (12)	0.0375 (9)	0.0095 (8)	0.0009 (7)	−0.0003 (7)
C6	0.0433 (9)	0.0379 (9)	0.0378 (8)	0.0011 (8)	−0.0045 (7)	−0.0016 (8)
C7	0.0459 (11)	0.0595 (12)	0.0541 (11)	0.0070 (10)	−0.0048 (9)	0.0006 (10)
C8	0.0344 (9)	0.0496 (11)	0.0355 (8)	−0.0001 (8)	0.0007 (7)	−0.0041 (8)
C10	0.0345 (9)	0.0386 (9)	0.0407 (9)	0.0062 (7)	−0.0036 (7)	−0.0001 (8)
C11	0.0320 (8)	0.0346 (10)	0.0340 (8)	0.0027 (7)	−0.0021 (6)	−0.0003 (6)
C12	0.0392 (9)	0.0299 (8)	0.0384 (8)	−0.0017 (7)	0.0004 (7)	−0.0035 (7)
C13	0.0439 (10)	0.0404 (10)	0.0497 (10)	−0.0027 (8)	0.0080 (8)	−0.0064 (8)
C14	0.0638 (13)	0.0478 (12)	0.0476 (11)	−0.0169 (10)	0.0196 (9)	−0.0120 (9)
C15	0.0811 (16)	0.0547 (13)	0.0357 (9)	−0.0228 (12)	0.0046 (10)	0.0017 (9)
C16	0.0641 (13)	0.0472 (12)	0.0425 (10)	−0.0114 (10)	−0.0101 (9)	0.0081 (8)
C17	0.0441 (10)	0.0325 (8)	0.0399 (9)	−0.0059 (7)	−0.0046 (7)	0.0014 (7)
C18	0.0365 (9)	0.0302 (8)	0.0440 (9)	0.0007 (7)	−0.0061 (7)	−0.0009 (7)
C19	0.0427 (11)	0.0424 (11)	0.0659 (12)	0.0049 (9)	−0.0119 (9)	0.0038 (9)
C20	0.0333 (10)	0.0463 (12)	0.0866 (16)	0.0063 (9)	−0.0055 (10)	−0.0070 (11)
C21	0.0379 (10)	0.0565 (12)	0.0641 (13)	−0.0028 (9)	0.0104 (9)	−0.0160 (10)
C22	0.0392 (9)	0.0469 (10)	0.0425 (9)	−0.0032 (8)	0.0013 (7)	−0.0044 (8)
C23	0.0323 (8)	0.0325 (8)	0.0397 (8)	0.0004 (7)	−0.0030 (6)	−0.0025 (7)
Cl1	0.0585 (3)	0.0495 (3)	0.0457 (2)	0.0006 (2)	0.0055 (2)	−0.0020 (2)

O8—C8	1.208 (2)	C19—C20	1.384 (3)
O9—C8	1.353 (2)	C20—C21	1.384 (3)
O9—C10	1.436 (2)	C21—C22	1.395 (3)
N1—C2	1.495 (2)	C22—C23	1.381 (2)
N1—C6	1.495 (2)	C2—H2A	0.9600
N4—C3	1.464 (3)	C2—H2B	0.9600
N4—C5	1.457 (2)	C3—H3A	0.9600
N4—C8	1.366 (3)	C3—H3B	0.9600
N1—H1A	1.0600	C5—H5A	0.9600
N1—H1B	0.8800	C5—H5B	0.9600
C2—C3	1.508 (3)	C6—H6	0.9600
C5—C6	1.521 (2)	C7—H7A	0.9600
C6—C7	1.522 (3)	C7—H7B	0.9600
C10—C11	1.521 (2)	C7—H7C	0.9600
C11—C23	1.517 (2)	C10—H10A	0.9600
C11—C12	1.522 (2)	C10—H10B	0.9600
C12—C17	1.397 (2)	C11—H11	1.0900
C12—C13	1.386 (2)	C13—H13	0.9600
C13—C14	1.395 (3)	C14—H14	0.9600
C14—C15	1.384 (3)	C15—H15	0.9600
C15—C16	1.380 (3)	C16—H16	0.9600
C16—C17	1.390 (3)	C19—H19	0.9600
C17—C18	1.469 (2)	C20—H20	0.9600
C18—C23	1.394 (2)	C21—H21	0.9800
C18—C19	1.388 (2)	C22—H22	0.9600
Cl1···N1i	3.1353 (16)	H1B···H3A	2.5500
Cl1···C22	3.6222 (19)	H2A···H6	2.5500
Cl1···N1ii	3.1167 (16)	H2A···Cl1	3.1300
Cl1···H2A	3.1300	H2B···O8vii	2.4100
Cl1···H22	2.7200	H3A···H1B	2.5500
Cl1···H1Bi	2.2600	H3A···H5B	2.5500
Cl1···H1Aii	2.0800	H3B···O8	2.3800
Cl1···H7Bii	2.9600	H3B···Cl1vii	3.0900
Cl1···H3Biii	3.0900	H5A···H14x	2.5300
O8···C2iii	3.316 (2)	H5A···H7A	2.5600
O9···C22	3.276 (2)	H5A···O9	2.2300
O8···H10B	2.6900	H5B···H7C	2.4800
O8···H2Biii	2.4100	H5B···H3A	2.5500
O8···H21iv	2.5400	H6···H2A	2.5500
O8···H10A	2.5700	H7A···H5A	2.5600
O8···H3B	2.3800	H7A···C21	3.0200
O9···H5A	2.2300	H7B···H1A	2.5000
N1···N4	2.829 (2)	H7B···Cl1v	2.9600
N1···Cl1v	3.1167 (16)	H7C···H1B	2.5000
N1···Cl1vi	3.1353 (16)	H7C···H5B	2.4800
N4···N1	2.829 (2)	H7C···H22vi	2.5900
C2···O8vii	3.316 (2)	H10A···O8	2.5700
C17···C19viii	3.470 (3)	H10B···O8	2.6900
C19···C17ix	3.470 (3)	H10B···C21iv	3.0500
C22···O9	3.276 (2)	H10B···H20iv	2.5700
C22···Cl1	3.6222 (19)	H10B···C15xii	3.1000
C5···H14x	2.9800	H10B···C13	3.0000
C10···H22	3.0800	H10B···C20iv	3.0200
C11···H19viii	3.0600	H11···C14xii	2.8700
C12···H19viii	2.9400	H11···H14xii	2.4300
C13···H10B	3.0000	H13···C16xii	2.8900
C14···H20viii	2.9800	H13···C15xii	2.8800
C14···H11x	2.8700	H14···H5Axii	2.5300
C15···H13x	2.8800	H14···H11x	2.4300
C15···H10Bx	3.1000	H14···C5xii	2.9800
C16···H13x	2.8900	H16···C22ix	2.9600
C16···H19	3.0800	H19···C11ix	3.0600
C17···H19viii	2.9200	H19···C12ix	2.9400
C18···H19viii	3.0400	H19···C16	3.0800
C20···H10Bxi	3.0200	H19···C18ix	3.0400
C21···H10Bxi	3.0500	H19···C17ix	2.9200
C21···H7A	3.0200	H20···C14ix	2.9800
C22···H16viii	2.9600	H20···H10Bxi	2.5700
H1A···Cl1v	2.0800	H21···O8xi	2.5400
H1A···H7B	2.5000	H22···H7Ci	2.5900
H1B···H7C	2.5000	H22···Cl1	2.7200
H1B···Cl1vi	2.2600	H22···C10	3.0800
C8—O9—C10	114.92 (14)	C3—C2—H2B	110.00
C2—N1—C6	112.89 (14)	H2A—C2—H2B	109.00
C3—N4—C5	113.24 (16)	N4—C3—H3A	110.00
C3—N4—C8	117.98 (16)	N4—C3—H3B	109.00
C5—N4—C8	122.64 (17)	C2—C3—H3A	109.00
C2—N1—H1B	108.00	C2—C3—H3B	109.00
C6—N1—H1A	109.00	H3A—C3—H3B	109.00
C2—N1—H1A	107.00	N4—C5—H5A	109.00
H1A—N1—H1B	106.00	N4—C5—H5B	110.00
C6—N1—H1B	114.00	C6—C5—H5A	108.00
N1—C2—C3	109.43 (15)	C6—C5—H5B	109.00
N4—C3—C2	110.33 (15)	H5A—C5—H5B	109.00
N4—C5—C6	111.56 (15)	N1—C6—H6	109.00
C5—C6—C7	112.14 (15)	C5—C6—H6	109.00
N1—C6—C5	108.51 (14)	C7—C6—H6	108.00
N1—C6—C7	109.85 (16)	C6—C7—H7A	109.00
O9—C8—N4	110.82 (15)	C6—C7—H7B	111.00
O8—C8—O9	123.88 (19)	C6—C7—H7C	109.00
O8—C8—N4	125.26 (17)	H7A—C7—H7B	110.00
O9—C10—C11	107.66 (13)	H7A—C7—H7C	109.00
C10—C11—C12	117.54 (13)	H7B—C7—H7C	109.00
C12—C11—C23	101.91 (12)	O9—C10—H10A	110.00
C10—C11—C23	114.66 (13)	O9—C10—H10B	109.00
C11—C12—C13	128.75 (15)	C11—C10—H10A	111.00
C13—C12—C17	120.70 (16)	C11—C10—H10B	110.00
C11—C12—C17	110.36 (14)	H10A—C10—H10B	110.00
C12—C13—C14	118.12 (18)	C10—C11—H11	103.00
C13—C14—C15	121.0 (2)	C12—C11—H11	113.00
C14—C15—C16	121.04 (19)	C23—C11—H11	107.00
C15—C16—C17	118.5 (2)	C12—C13—H13	119.00
C12—C17—C16	120.66 (17)	C14—C13—H13	123.00
C16—C17—C18	130.86 (17)	C13—C14—H14	120.00
C12—C17—C18	108.42 (14)	C15—C14—H14	119.00
C17—C18—C23	108.85 (14)	C14—C15—H15	120.00
C19—C18—C23	120.38 (16)	C16—C15—H15	119.00
C17—C18—C19	130.77 (16)	C15—C16—H16	120.00
C18—C19—C20	118.94 (19)	C17—C16—H16	121.00
C19—C20—C21	120.64 (17)	C18—C19—H19	119.00
C20—C21—C22	120.70 (18)	C20—C19—H19	122.00
C21—C22—C23	118.58 (17)	C19—C20—H20	121.00
C11—C23—C22	128.88 (15)	C21—C20—H20	119.00
C18—C23—C22	120.72 (15)	C20—C21—H21	117.00
C11—C23—C18	110.40 (14)	C22—C21—H21	122.00
N1—C2—H2A	109.00	C21—C22—H22	121.00
N1—C2—H2B	110.00	C23—C22—H22	120.00
C3—C2—H2A	109.00
C10—O9—C8—O8	−17.4 (2)	C11—C12—C13—C14	−173.75 (18)
C10—O9—C8—N4	164.52 (14)	C17—C12—C13—C14	0.6 (3)
C8—O9—C10—C11	−167.41 (13)	C11—C12—C17—C16	175.50 (16)
C6—N1—C2—C3	−57.2 (2)	C11—C12—C17—C18	−2.04 (17)
C2—N1—C6—C5	55.8 (2)	C13—C12—C17—C16	0.2 (3)
C2—N1—C6—C7	178.70 (16)	C13—C12—C17—C18	−177.31 (16)
C5—N4—C3—C2	−57.0 (2)	C12—C13—C14—C15	−0.7 (3)
C8—N4—C3—C2	96.2 (2)	C13—C14—C15—C16	0.1 (3)
C3—N4—C5—C6	56.7 (2)	C14—C15—C16—C17	0.7 (3)
C8—N4—C5—C6	−95.1 (2)	C15—C16—C17—C12	−0.8 (3)
C3—N4—C8—O8	12.5 (3)	C15—C16—C17—C18	176.07 (18)
C3—N4—C8—O9	−169.49 (15)	C12—C17—C18—C19	179.93 (18)
C5—N4—C8—O8	163.05 (18)	C12—C17—C18—C23	0.59 (18)
C5—N4—C8—O9	−19.0 (2)	C16—C17—C18—C19	2.7 (3)
N1—C2—C3—N4	55.6 (2)	C16—C17—C18—C23	−176.61 (18)
N4—C5—C6—N1	−54.2 (2)	C17—C18—C19—C20	178.81 (18)
N4—C5—C6—C7	−175.72 (18)	C23—C18—C19—C20	−1.9 (3)
O9—C10—C11—C12	−74.83 (17)	C17—C18—C23—C11	1.10 (18)
O9—C10—C11—C23	44.87 (17)	C17—C18—C23—C22	−178.39 (16)
C10—C11—C12—C13	−56.5 (2)	C19—C18—C23—C11	−178.32 (16)
C10—C11—C12—C17	128.77 (15)	C19—C18—C23—C22	2.2 (3)
C23—C11—C12—C13	177.33 (17)	C18—C19—C20—C21	0.2 (3)
C23—C11—C12—C17	2.55 (16)	C19—C20—C21—C22	1.3 (3)
C10—C11—C23—C18	−130.26 (14)	C20—C21—C22—C23	−1.0 (3)
C10—C11—C23—C22	49.2 (2)	C21—C22—C23—C11	179.91 (18)
C12—C11—C23—C18	−2.18 (16)	C21—C22—C23—C18	−0.7 (3)
C12—C11—C23—C22	177.26 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1v	1.06	2.08	3.117 (2)	165.
N1—H1B···Cl1vi	0.88	2.26	3.135 (2)	171.
C2—H2B···O8vii	0.96	2.41	3.316 (2)	157.
C3—H3B···O8	0.96	2.38	2.778 (3)	104.
C5—H5A···O9	0.96	2.23	2.665 (2)	106.
C21—H21···O8xi	0.98	2.54	3.469 (2)	158.
C22—H22···Cl1	0.96	2.72	3.622 (2)	157.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cl1i	1.06	2.08	3.117 (2)	165
N1—H1B⋯Cl1ii	0.88	2.26	3.135 (2)	171
C2—H2B⋯O8iii	0.96	2.41	3.316 (2)	157
C21—H21⋯O8iv	0.98	2.54	3.469 (2)	158
C22—H22⋯Cl1	0.96	2.72	3.622 (2)	157

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .