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Buflomedil hydro­chloride {systematic name 1-[4-oxo-4-(2,4,6-trimethoxy­phenyl)but-1-yl]pyrrolidinium hydro­chloride}, C17H26NO4+·Cl, is a rheological agent largely used as a vasodilator drug. The N atom of the pyrrolidine ring is protonated and is involved in a hydrogen bond with the Cl anion. In the crystal packing, C—H...O inter­actions form a hydrogen-bonded network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806040025/bt2197sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806040025/bt2197Isup2.hkl
Contains datablock I

CCDC reference: 627338

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.045
  • wR factor = 0.123
  • Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for C13
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.22 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 Cl
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
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.

1-[4-oxo-4-(2,4,6-trimethoxy­phenyl)but-1-yl]pyrrolidinium hydrochloride top
Crystal data top
C17H26NO4+·ClF(000) = 736
Mr = 343.84Dx = 1.246 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7411 reflections
a = 7.0333 (5) Åθ = 2.4–27.0°
b = 29.534 (2) ŵ = 0.23 mm1
c = 9.1257 (6) ÅT = 293 K
β = 104.757 (1)°Block, colourless
V = 1833.1 (2) Å30.19 × 0.15 × 0.07 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2870 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.022
Graphite monochromatorθmax = 25.0°, θmin = 2.4°
ω scansh = 88
17547 measured reflectionsk = 3535
3227 independent reflectionsl = 1010
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0595P)2 + 0.7031P]
where P = (Fo2 + 2Fc2)/3
3227 reflections(Δ/σ)max < 0.001
215 parametersΔρmax = 0.29 e Å3
1 restraintΔρmin = 0.30 e Å3
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.8088 (3)0.11352 (6)0.1744 (2)0.0453 (4)
C20.9975 (3)0.12903 (6)0.2399 (2)0.0472 (4)
H21.09040.11000.30060.057*
C31.0452 (3)0.17314 (6)0.2137 (2)0.0426 (4)
C40.9054 (3)0.20215 (6)0.1242 (2)0.0398 (4)
C50.7182 (3)0.18528 (6)0.0602 (2)0.0413 (4)
C60.6670 (3)0.14093 (6)0.0838 (2)0.0442 (4)
H60.54130.13000.04010.053*
C70.9565 (3)0.25063 (6)0.0998 (2)0.0413 (4)
C80.8696 (3)0.28603 (6)0.1809 (2)0.0450 (4)
H8A0.92060.28180.28920.054*
H8B0.72830.28180.15710.054*
C90.9124 (3)0.33417 (6)0.1407 (2)0.0443 (4)
H9A1.05120.33720.14550.053*
H9B0.83850.34090.03790.053*
C100.8575 (3)0.36738 (6)0.2480 (2)0.0471 (4)
H10A0.71690.36580.23750.057*
H10B0.92340.35900.35120.057*
C110.8917 (4)0.44654 (8)0.3425 (3)0.0672 (6)
H11A0.77980.43830.38090.081*
H11B1.00930.44590.42580.081*
C120.8639 (5)0.49122 (9)0.2738 (3)0.0953 (10)
H12A0.77090.50850.31340.114*
H12B0.98770.50750.29530.114*
C130.7872 (7)0.48433 (10)0.1078 (3)0.1281 (15)
H13A0.86550.50140.05350.154*
H13B0.65220.49480.07500.154*
C140.7976 (4)0.43562 (7)0.0760 (3)0.0615 (6)
H14A0.66670.42270.04500.074*
H14B0.86340.43070.00400.074*
C150.3995 (3)0.20071 (8)0.1026 (3)0.0684 (7)
H15A0.40510.17420.16240.103*
H15B0.33150.22440.16680.103*
H15C0.33100.19370.02690.103*
C160.5848 (4)0.05126 (8)0.1520 (3)0.0709 (7)
H16A0.49650.06780.19700.106*
H16B0.58470.01990.17990.106*
H16C0.54260.05400.04380.106*
C171.3644 (3)0.16844 (9)0.3847 (3)0.0719 (7)
H17A1.30810.16220.46790.108*
H17B1.47980.18680.41930.108*
H17C1.39930.14050.34450.108*
N10.9114 (3)0.41467 (5)0.22003 (18)0.0433 (4)
H1N1.031 (4)0.4146 (8)0.217 (3)0.057 (6)*
O11.0675 (3)0.26025 (5)0.02418 (19)0.0657 (4)
O20.59415 (19)0.21519 (5)0.03062 (17)0.0564 (4)
O30.7778 (2)0.06913 (5)0.20452 (18)0.0606 (4)
O41.22546 (19)0.19188 (5)0.26991 (16)0.0557 (4)
Cl11.34092 (8)0.421344 (19)0.21907 (8)0.0681 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0562 (11)0.0362 (10)0.0459 (10)0.0004 (8)0.0174 (9)0.0024 (8)
C20.0500 (11)0.0409 (10)0.0476 (10)0.0091 (8)0.0067 (8)0.0016 (8)
C30.0411 (9)0.0428 (10)0.0423 (10)0.0014 (8)0.0074 (8)0.0062 (8)
C40.0412 (9)0.0367 (9)0.0407 (9)0.0012 (7)0.0088 (7)0.0049 (7)
C50.0403 (9)0.0383 (9)0.0437 (10)0.0030 (7)0.0080 (7)0.0026 (8)
C60.0416 (10)0.0421 (10)0.0488 (10)0.0042 (8)0.0115 (8)0.0045 (8)
C70.0400 (9)0.0415 (10)0.0394 (9)0.0021 (7)0.0046 (8)0.0028 (7)
C80.0484 (10)0.0370 (10)0.0512 (11)0.0008 (8)0.0158 (8)0.0004 (8)
C90.0465 (10)0.0388 (10)0.0479 (10)0.0016 (8)0.0127 (8)0.0008 (8)
C100.0533 (11)0.0378 (10)0.0537 (11)0.0020 (8)0.0200 (9)0.0027 (8)
C110.0811 (16)0.0566 (13)0.0677 (14)0.0002 (12)0.0259 (12)0.0166 (11)
C120.106 (2)0.0444 (14)0.141 (3)0.0002 (14)0.042 (2)0.0175 (16)
C130.209 (5)0.0523 (16)0.115 (3)0.028 (2)0.027 (3)0.0263 (18)
C140.0662 (14)0.0536 (12)0.0608 (13)0.0037 (10)0.0090 (11)0.0118 (10)
C150.0419 (11)0.0576 (13)0.0922 (17)0.0053 (10)0.0079 (11)0.0000 (12)
C160.0802 (16)0.0466 (12)0.0884 (17)0.0174 (11)0.0262 (13)0.0022 (12)
C170.0507 (13)0.0765 (16)0.0746 (16)0.0085 (11)0.0097 (11)0.0024 (13)
N10.0418 (9)0.0361 (8)0.0536 (9)0.0007 (7)0.0149 (7)0.0013 (7)
O10.0813 (11)0.0507 (9)0.0793 (10)0.0074 (7)0.0464 (9)0.0078 (7)
O20.0444 (7)0.0436 (8)0.0696 (9)0.0003 (6)0.0064 (7)0.0060 (7)
O30.0712 (10)0.0376 (7)0.0711 (10)0.0058 (7)0.0143 (8)0.0061 (7)
O40.0415 (7)0.0540 (8)0.0624 (9)0.0009 (6)0.0037 (6)0.0003 (7)
Cl10.0423 (3)0.0584 (3)0.1032 (5)0.0021 (2)0.0175 (3)0.0090 (3)
Geometric parameters (Å, º) top
C1—O31.369 (2)C11—H11A0.9700
C1—C61.383 (3)C11—H11B0.9700
C1—C21.387 (3)C12—C131.487 (4)
C2—C31.381 (3)C12—H12A0.9700
C2—H20.9300C12—H12B0.9700
C3—O41.359 (2)C13—C141.473 (4)
C3—C41.399 (3)C13—H13A0.9700
C4—C51.389 (2)C13—H13B0.9700
C4—C71.506 (2)C14—N11.488 (3)
C5—O21.364 (2)C14—H14A0.9700
C5—C61.390 (3)C14—H14B0.9700
C6—H60.9300C15—O21.425 (2)
C7—O11.201 (2)C15—H15A0.9600
C7—C81.498 (3)C15—H15B0.9600
C8—C91.518 (2)C15—H15C0.9600
C8—H8A0.9700C16—O31.421 (3)
C8—H8B0.9700C16—H16A0.9600
C9—C101.504 (3)C16—H16B0.9600
C9—H9A0.9700C16—H16C0.9600
C9—H9B0.9700C17—O41.418 (3)
C10—N11.486 (2)C17—H17A0.9600
C10—H10A0.9700C17—H17B0.9600
C10—H10B0.9700C17—H17C0.9600
C11—C121.453 (4)N1—H1N0.85 (2)
C11—N11.495 (3)
O3—C1—C6123.56 (18)C13—C12—C11106.8 (2)
O3—C1—C2114.46 (17)C13—C12—H12A110.4
C6—C1—C2121.96 (17)C11—C12—H12A110.4
C3—C2—C1119.00 (17)C13—C12—H12B110.4
C3—C2—H2120.5C11—C12—H12B110.4
C1—C2—H2120.5H12A—C12—H12B108.6
O4—C3—C2124.29 (17)C12—C13—C14108.1 (2)
O4—C3—C4114.85 (16)C12—C13—H13A110.1
C2—C3—C4120.86 (17)C14—C13—H13A110.1
C5—C4—C3118.38 (17)C12—C13—H13B110.1
C5—C4—C7120.98 (16)C14—C13—H13B110.1
C3—C4—C7120.64 (15)H13A—C13—H13B108.4
O2—C5—C4114.47 (16)N1—C14—C13105.9 (2)
O2—C5—C6123.60 (16)N1—C14—H14A110.5
C4—C5—C6121.89 (17)C13—C14—H14A110.5
C1—C6—C5117.91 (17)N1—C14—H14B110.5
C1—C6—H6121.0C13—C14—H14B110.5
C5—C6—H6121.0H14A—C14—H14B108.7
O1—C7—C8121.72 (17)O2—C15—H15A109.5
O1—C7—C4121.61 (17)O2—C15—H15B109.5
C8—C7—C4116.61 (15)H15A—C15—H15B109.5
C7—C8—C9113.81 (16)O2—C15—H15C109.5
C7—C8—H8A108.8H15A—C15—H15C109.5
C9—C8—H8A108.8H15B—C15—H15C109.5
C7—C8—H8B108.8O3—C16—H16A109.5
C9—C8—H8B108.8O3—C16—H16B109.5
H8A—C8—H8B107.7H16A—C16—H16B109.5
C10—C9—C8110.74 (15)O3—C16—H16C109.5
C10—C9—H9A109.5H16A—C16—H16C109.5
C8—C9—H9A109.5H16B—C16—H16C109.5
C10—C9—H9B109.5O4—C17—H17A109.5
C8—C9—H9B109.5O4—C17—H17B109.5
H9A—C9—H9B108.1H17A—C17—H17B109.5
N1—C10—C9112.46 (15)O4—C17—H17C109.5
N1—C10—H10A109.1H17A—C17—H17C109.5
C9—C10—H10A109.1H17B—C17—H17C109.5
N1—C10—H10B109.1C10—N1—C14116.06 (16)
C9—C10—H10B109.1C10—N1—C11112.77 (16)
H10A—C10—H10B107.8C14—N1—C11105.51 (17)
C12—C11—N1106.1 (2)C10—N1—H1N107.5 (16)
C12—C11—H11A110.5C14—N1—H1N106.7 (16)
N1—C11—H11A110.5C11—N1—H1N107.8 (16)
C12—C11—H11B110.5C5—O2—C15118.46 (16)
N1—C11—H11B110.5C1—O3—C16118.41 (17)
H11A—C11—H11B108.7C3—O4—C17118.76 (17)
O3—C1—C2—C3178.63 (17)O1—C7—C8—C98.0 (3)
C6—C1—C2—C30.1 (3)C4—C7—C8—C9174.97 (15)
C1—C2—C3—O4179.05 (17)C7—C8—C9—C10168.45 (16)
C1—C2—C3—C40.8 (3)C8—C9—C10—N1175.58 (16)
O4—C3—C4—C5178.87 (16)N1—C11—C12—C1322.5 (4)
C2—C3—C4—C51.0 (3)C11—C12—C13—C148.3 (5)
O4—C3—C4—C71.9 (2)C12—C13—C14—N19.2 (4)
C2—C3—C4—C7178.16 (17)C9—C10—N1—C1468.6 (2)
C3—C4—C5—O2177.22 (16)C9—C10—N1—C11169.46 (18)
C7—C4—C5—O23.6 (2)C13—C14—N1—C10148.4 (3)
C3—C4—C5—C60.5 (3)C13—C14—N1—C1122.7 (3)
C7—C4—C5—C6178.69 (17)C12—C11—N1—C10155.8 (2)
O3—C1—C6—C5179.03 (17)C12—C11—N1—C1428.2 (3)
C2—C1—C6—C50.4 (3)C4—C5—O2—C15179.32 (19)
O2—C5—C6—C1177.71 (17)C6—C5—O2—C151.6 (3)
C4—C5—C6—C10.2 (3)C6—C1—O3—C166.1 (3)
C5—C4—C7—O1110.8 (2)C2—C1—O3—C16175.16 (19)
C3—C4—C7—O170.1 (2)C2—C3—O4—C1712.3 (3)
C5—C4—C7—C872.2 (2)C4—C3—O4—C17167.80 (19)
C3—C4—C7—C8106.99 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···Cl10.85 (2)2.19 (3)3.0298 (19)174 (2)
C8—H8A···O1i0.972.473.376 (3)156
C12—H12B···O3ii0.972.463.381 (3)159
C14—H14B···O3iii0.972.573.360 (3)138
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x+2, y+1/2, z+1/2; (iii) x, y+1/2, z1/2.
 

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