Literature DB >> 22199675

Isopropyl-triphenyl-phospho-nium bromide monohydrate.

Hai Wang¹, Xi-Man Zhang, Ping Li, Hong-Yu Chen.

Abstract

In the title water-solvated salt, C(21)H(22)P(+)·Br(-)·H(2)O, the ionic components are linked by short C-H⋯Br contacts along the a-axis direction. The two half occupied water mol-ecules are connected to each other by strong O-H⋯O hydrogen bonds and they are also linked to the bromide anion by short O-H⋯Br contacts.

Entities: Chemical Disease Species

Year: 2011 PMID： 22199675 PMCID： PMC3238822 DOI： 10.1107/S1600536811044849

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For information on phase-transfer catalysts, see: Asai et al. (1994 ▶). For the crystal structure of tetraphenylphosphoniuum bromide, see: Alcock et al. (1985 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C21H22P+·Br−·H2O M = 403.28 Orthorhombic, a = 9.078 (5) Å b = 13.043 (5) Å c = 17.755 (5) Å V = 2102.3 (15) Å3 Z = 4 Mo Kα radiation μ = 2.04 mm−1 T = 293 K 0.20 × 0.15 × 0.13 mm

Data collection

Brucker APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.668, T max = 0.688 12177 measured reflections 4250 independent reflections 3331 reflections with I > 2σ(I) R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.049 wR(F 2) = 0.140 S = 1.03 4250 reflections 228 parameters 6 restraints H-atom parameters constrained Δρmax = 0.82 e Å−3 Δρmin = −0.28 e Å−3 Absolute structure: Flack (1983 ▶), 1799 Friedel pairs Flack parameter: 0.014 (13) Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811044849/su2327sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811044849/su2327Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811044849/su2327Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₂₁H₂₂P⁺·Br⁻·H₂O	F(000) = 832
M_r = 403.28	D_x = 1.274 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3565 reflections
a = 9.078 (5) Å	θ = 2.5–23.5°
b = 13.043 (5) Å	µ = 2.04 mm⁻¹
c = 17.755 (5) Å	T = 293 K
V = 2102.3 (15) Å³	ROD, colourless
Z = 4	0.20 × 0.15 × 0.13 mm

Brucker APEXII CCD area-detector diffractometer	4250 independent reflections
Radiation source: fine-focus sealed tube	3331 reflections with I > 2σ(I)
graphite	R_int = 0.034
phi and ω scans	θ_max = 26.4°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→11
T_min = 0.668, T_max = 0.688	k = −16→15
12177 measured reflections	l = −21→21

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.049	H-atom parameters constrained
wR(F²) = 0.140	w = 1/[σ²(F_o²) + (0.0853P)²] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
4250 reflections	Δρ_max = 0.82 e Å⁻³
228 parameters	Δρ_min = −0.28 e Å⁻³
6 restraints	Absolute structure: Flack (1983), 1799 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.014 (13)

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.

	x	y	z	U_iso*/U_eq	Occ. (<1)
Br1	0.46181 (8)	0.58731 (5)	0.00805 (3)	0.0720 (2)
C1	0.2804 (4)	0.5002 (3)	0.7564 (2)	0.0320 (8)
C2	0.2503 (5)	0.4645 (3)	0.8289 (3)	0.0468 (11)
H2	0.2722	0.5050	0.8705	0.056*
C3	0.1873 (6)	0.3679 (4)	0.8386 (3)	0.0570 (13)
H3	0.1690	0.3433	0.8868	0.068*
C4	0.1527 (5)	0.3098 (3)	0.7778 (3)	0.0502 (13)
H4	0.1075	0.2466	0.7850	0.060*
C5	0.1833 (5)	0.3426 (3)	0.7054 (3)	0.0463 (12)
H5	0.1607	0.3011	0.6644	0.056*
C6	0.2478 (4)	0.4378 (3)	0.6943 (2)	0.0371 (9)
H6	0.2694	0.4602	0.6458	0.045*
C7	0.3207 (5)	0.6876 (3)	0.6626 (2)	0.0340 (9)
C8	0.4105 (6)	0.7668 (3)	0.6355 (3)	0.0493 (12)
H8	0.5032	0.7770	0.6564	0.059*
C9	0.3631 (8)	0.8296 (4)	0.5783 (3)	0.0737 (18)
H9	0.4228	0.8822	0.5604	0.088*
C10	0.2238 (10)	0.8130 (5)	0.5476 (3)	0.082 (2)
H10	0.1893	0.8561	0.5098	0.098*
C11	0.1386 (7)	0.7354 (6)	0.5719 (3)	0.0754 (18)
H11	0.0478	0.7239	0.5491	0.090*
C12	0.1835 (5)	0.6726 (4)	0.6299 (3)	0.0498 (12)
H12	0.1223	0.6205	0.6471	0.060*
C13	0.5706 (4)	0.5878 (3)	0.7380 (2)	0.0312 (8)
C14	0.6312 (5)	0.5673 (3)	0.6682 (3)	0.0430 (10)
H14	0.5765	0.5766	0.6245	0.052*
C15	0.7767 (5)	0.5321 (3)	0.6648 (3)	0.0538 (14)
H15	0.8199	0.5187	0.6183	0.065*
C16	0.8552 (5)	0.5173 (3)	0.7293 (4)	0.0567 (14)
H16	0.9514	0.4930	0.7264	0.068*
C17	0.7943 (5)	0.5379 (4)	0.7989 (3)	0.0569 (14)
H17	0.8493	0.5277	0.8425	0.068*
C18	0.6508 (4)	0.5737 (3)	0.8037 (3)	0.0446 (11)
H18	0.6089	0.5880	0.8503	0.054*
C19	0.3403 (5)	0.7009 (3)	0.8260 (2)	0.0352 (9)
H19	0.3655	0.6618	0.8713	0.042*
C20	0.4348 (6)	0.7974 (3)	0.8257 (3)	0.0538 (13)
H20A	0.4054	0.8408	0.7847	0.081*
H20B	0.5365	0.7789	0.8198	0.081*
H20C	0.4220	0.8334	0.8724	0.081*
C21	0.1779 (5)	0.7266 (4)	0.8303 (3)	0.0530 (12)
H21A	0.1593	0.7669	0.8745	0.079*
H21B	0.1216	0.6644	0.8327	0.079*
H21C	0.1498	0.7648	0.7864	0.079*
O1	0.4288 (9)	0.4940 (6)	0.5103 (4)	0.0650 (19)	0.50
H1O1	0.3405	0.4745	0.5027	0.097*	0.50
H2O1	0.4722	0.4469	0.4855	0.097*	0.50
O2	0.6608 (8)	0.3426 (5)	0.4736 (4)	0.0566 (18)	0.50
H1O2	0.6370	0.2797	0.4777	0.085*	0.50
H2O2	0.7522	0.3365	0.4835	0.085*	0.50
P1	0.37744 (10)	0.61951 (7)	0.74506 (6)	0.0269 (2)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0904 (5)	0.0823 (4)	0.0433 (3)	0.0170 (3)	−0.0098 (3)	0.0009 (3)
C1	0.0245 (18)	0.0290 (17)	0.042 (2)	0.0013 (15)	0.0014 (18)	0.0014 (17)
C2	0.054 (3)	0.039 (2)	0.047 (3)	−0.008 (2)	0.000 (2)	0.005 (2)
C3	0.062 (3)	0.048 (3)	0.061 (3)	−0.016 (3)	0.000 (3)	0.019 (2)
C4	0.035 (3)	0.032 (2)	0.084 (4)	−0.0057 (18)	−0.004 (2)	0.004 (2)
C5	0.035 (2)	0.035 (2)	0.068 (3)	−0.001 (2)	−0.006 (2)	−0.018 (2)
C6	0.033 (2)	0.037 (2)	0.041 (2)	0.0025 (18)	0.0034 (18)	−0.0061 (18)
C7	0.033 (2)	0.032 (2)	0.036 (2)	0.0060 (17)	0.0020 (18)	0.0009 (17)
C8	0.059 (3)	0.040 (2)	0.049 (3)	0.000 (2)	0.006 (2)	0.006 (2)
C9	0.111 (5)	0.050 (3)	0.061 (4)	0.020 (3)	0.026 (4)	0.021 (3)
C10	0.125 (6)	0.077 (4)	0.042 (3)	0.043 (4)	−0.001 (4)	0.021 (3)
C11	0.071 (4)	0.110 (5)	0.045 (3)	0.026 (4)	−0.017 (3)	0.006 (3)
C12	0.043 (3)	0.064 (3)	0.043 (3)	0.014 (2)	−0.006 (2)	0.005 (2)
C13	0.0247 (17)	0.0274 (17)	0.042 (2)	0.0007 (14)	0.0065 (16)	−0.0011 (17)
C14	0.041 (2)	0.036 (2)	0.053 (3)	0.000 (2)	0.009 (2)	−0.0011 (19)
C15	0.041 (3)	0.042 (3)	0.079 (4)	0.000 (2)	0.028 (3)	−0.007 (3)
C16	0.029 (2)	0.038 (2)	0.104 (5)	0.0034 (19)	0.016 (3)	0.006 (3)
C17	0.035 (3)	0.053 (3)	0.083 (4)	0.003 (2)	−0.007 (3)	0.016 (3)
C18	0.030 (2)	0.049 (3)	0.055 (3)	0.006 (2)	0.0002 (19)	0.004 (2)
C19	0.037 (2)	0.032 (2)	0.036 (2)	0.0005 (17)	0.0023 (18)	−0.0023 (16)
C20	0.053 (3)	0.037 (2)	0.071 (3)	−0.009 (2)	0.008 (3)	−0.010 (2)
C21	0.036 (2)	0.061 (3)	0.061 (3)	0.009 (2)	0.006 (2)	−0.012 (2)
O1	0.072 (5)	0.077 (5)	0.045 (4)	−0.015 (4)	−0.011 (4)	0.001 (3)
O2	0.062 (4)	0.059 (4)	0.049 (4)	−0.009 (3)	0.008 (3)	0.013 (3)
P1	0.0222 (4)	0.0273 (4)	0.0313 (5)	0.0001 (4)	0.0016 (4)	0.0009 (4)

C1—C2	1.395 (6)	C13—C18	1.387 (6)
C1—C6	1.402 (6)	C13—P1	1.806 (4)
C1—P1	1.800 (4)	C14—C15	1.400 (6)
C2—C3	1.394 (6)	C14—H14	0.9300
C2—H2	0.9300	C15—C16	1.363 (8)
C3—C4	1.355 (7)	C15—H15	0.9300
C3—H3	0.9300	C16—C17	1.381 (8)
C4—C5	1.384 (7)	C16—H16	0.9300
C4—H4	0.9300	C17—C18	1.386 (6)
C5—C6	1.387 (6)	C17—H17	0.9300
C5—H5	0.9300	C18—H18	0.9300
C6—H6	0.9300	C19—C21	1.514 (6)
C7—C12	1.388 (6)	C19—C20	1.523 (6)
C7—C8	1.400 (6)	C19—P1	1.818 (4)
C7—P1	1.789 (4)	C19—H19	0.9800
C8—C9	1.374 (7)	C20—H20A	0.9600
C8—H8	0.9300	C20—H20B	0.9600
C9—C10	1.394 (10)	C20—H20C	0.9600
C9—H9	0.9300	C21—H21A	0.9600
C10—C11	1.345 (10)	C21—H21B	0.9600
C10—H10	0.9300	C21—H21C	0.9600
C11—C12	1.377 (7)	O1—H1O1	0.8522
C11—H11	0.9300	O1—H2O1	0.8527
C12—H12	0.9300	O2—H1O2	0.8515
C13—C14	1.382 (6)	O2—H2O2	0.8512

C2—C1—C6	119.4 (4)	C13—C14—H14	120.7
C2—C1—P1	119.2 (3)	C15—C14—H14	120.7
C6—C1—P1	121.1 (3)	C16—C15—C14	120.2 (5)
C3—C2—C1	119.7 (5)	C16—C15—H15	119.9
C3—C2—H2	120.2	C14—C15—H15	119.9
C1—C2—H2	120.2	C15—C16—C17	121.1 (4)
C4—C3—C2	120.2 (5)	C15—C16—H16	119.5
C4—C3—H3	119.9	C17—C16—H16	119.5
C2—C3—H3	119.9	C16—C17—C18	119.7 (5)
C3—C4—C5	121.4 (4)	C16—C17—H17	120.1
C3—C4—H4	119.3	C18—C17—H17	120.1
C5—C4—H4	119.3	C17—C18—C13	119.2 (5)
C4—C5—C6	119.5 (4)	C17—C18—H18	120.4
C4—C5—H5	120.2	C13—C18—H18	120.4
C6—C5—H5	120.2	C21—C19—C20	111.4 (4)
C5—C6—C1	119.8 (4)	C21—C19—P1	110.5 (3)
C5—C6—H6	120.1	C20—C19—P1	112.1 (3)
C1—C6—H6	120.1	C21—C19—H19	107.6
C12—C7—C8	118.9 (4)	C20—C19—H19	107.6
C12—C7—P1	122.0 (3)	P1—C19—H19	107.6
C8—C7—P1	118.7 (3)	C19—C20—H20A	109.5
C9—C8—C7	120.8 (5)	C19—C20—H20B	109.5
C9—C8—H8	119.6	H20A—C20—H20B	109.5
C7—C8—H8	119.6	C19—C20—H20C	109.5
C8—C9—C10	118.7 (6)	H20A—C20—H20C	109.5
C8—C9—H9	120.7	H20B—C20—H20C	109.5
C10—C9—H9	120.7	C19—C21—H21A	109.5
C11—C10—C9	120.9 (5)	C19—C21—H21B	109.5
C11—C10—H10	119.6	H21A—C21—H21B	109.5
C9—C10—H10	119.6	C19—C21—H21C	109.5
C10—C11—C12	121.1 (6)	H21A—C21—H21C	109.5
C10—C11—H11	119.4	H21B—C21—H21C	109.5
C12—C11—H11	119.4	H1O1—O1—H2O1	98.0
C11—C12—C7	119.6 (5)	H1O2—O2—H2O2	98.0
C11—C12—H12	120.2	C7—P1—C1	112.38 (19)
C7—C12—H12	120.2	C7—P1—C13	109.67 (19)
C14—C13—C18	121.2 (4)	C1—P1—C13	106.56 (17)
C14—C13—P1	119.5 (3)	C7—P1—C19	107.68 (18)
C18—C13—P1	118.8 (3)	C1—P1—C19	108.99 (19)
C13—C14—C15	118.6 (5)	C13—P1—C19	111.62 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···Br1ⁱ	0.85	2.86	3.701 (8)	169.
O1—H2O1···O2	0.85	2.20	2.960 (11)	149.
O2—H1O2···Br1ⁱⁱ	0.85	2.68	3.526 (7)	175.
O2—H2O2···Br1ⁱⁱⁱ	0.85	2.81	3.598 (8)	154.
C19—H19···Br1^iv	0.98	2.76	3.723 (4)	169.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯Br1ⁱ	0.85	2.86	3.701 (8)	169
O1—H2O1⋯O2	0.85	2.20	2.960 (11)	149
O2—H1O2⋯Br1ⁱⁱ	0.85	2.68	3.526 (7)	175
O2—H2O2⋯Br1ⁱⁱⁱ	0.85	2.81	3.598 (8)	154
C19—H19⋯Br1^iv	0.98	2.76	3.723 (4)	169

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

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