Cinchonidinium bis­(perchlorate)

In the title crystal structure, C₁₉H₂₄N₂O²⁺·2ClO₄⁻, cations and anions are connected by inter­molecular O—H...O and N—H...O hydrogen bonds, forming one-dimensional chains propagating in the the a-axis direction. These chains are, in turn, linked by weak C—H...O hydrogen bonds, forming a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.043
• wR factor = 0.121
• Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.51 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C16
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        Cl1
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        Cl2
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              Cl O4
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          3
              Cl O4

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.99
           From the CIF: _reflns_number_total               4390
           Count of symmetry unique reflns         2195
           Completeness (_total/calc)            200.00%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2195
           Fraction of Friedel pairs measured     1.000
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

[(S)-quinolinium-4-yl][(2R,4R,8S)-8-vinylquinuclidinium-2-yl]methanol bis(perchlorate)

Crystal data

C19H24N2O^2+·2ClO4^−	Z = 1
Mr = 495.30	F(000) = 258
Triclinic, P1	Dx = 1.467 Mg m^−3
Hall symbol: P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.544 (1) Å	Cell parameters from 29 reflections
b = 7.819 (2) Å	θ = 6.2–19.0°
c = 11.308 (2) Å	µ = 0.34 mm^−1
α = 88.67 (2)°	T = 292 K
β = 77.03 (1)°	Block, colorless
γ = 83.85 (2)°	0.48 × 0.42 × 0.42 mm
V = 560.6 (2) Å^3

Data collection

Siemens P4 diffractometer	3864 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 26.0°, θmin = 1.9°
ω scans	h = −8→8
Absorption correction: ψ scan (North et al., 1968)	k = −9→9
Tmin = 0.850, Tmax = 0.869	l = −13→13
4539 measured reflections	3 standard reflections every 97 reflections
4390 independent reflections	intensity decay: 4.1%

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.043	w = 1/[σ^2(Fo^2) + (0.0806P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.121	(Δ/σ)max = 0.001
S = 1.06	Δρmax = 0.32 e Å^−3
4390 reflections	Δρmin = −0.26 e Å^−3
302 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
6 restraints	Extinction coefficient: 0.059 (7)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 2195 Friedels
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.01 (6)

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	1.43901 (11)	0.05951 (8)	0.26197 (7)	0.0519 (2)
Cl2	1.12107 (12)	1.27761 (10)	−0.14977 (7)	0.0609 (3)
O1	1.0889 (4)	0.4472 (3)	0.2811 (2)	0.0614 (6)
N1	0.9169 (5)	0.9060 (4)	0.0014 (3)	0.0563 (7)
N2	0.6397 (4)	0.3807 (3)	0.4261 (2)	0.0454 (6)
C1	0.7791 (5)	0.7912 (4)	−0.0087 (3)	0.0509 (7)
C2	0.6465 (6)	0.8212 (6)	−0.0888 (3)	0.0697 (11)
H2	0.6496	0.9201	−0.1363	0.084*
C3	0.5118 (7)	0.7025 (8)	−0.0963 (4)	0.0860 (15)
H3	0.4221	0.7214	−0.1495	0.103*
C4	0.5056 (7)	0.5551 (7)	−0.0268 (4)	0.0814 (15)
H4	0.4130	0.4759	−0.0346	0.098*
C5	0.6331 (5)	0.5236 (5)	0.0535 (3)	0.0579 (8)
H5	0.6274	0.4232	0.0993	0.069*
C6	0.7741 (5)	0.6434 (4)	0.0671 (3)	0.0430 (7)
C7	0.9088 (4)	0.6233 (4)	0.1498 (2)	0.0396 (6)
C8	1.0425 (5)	0.7467 (4)	0.1514 (3)	0.0458 (7)
H8	1.1327	0.7352	0.2046	0.055*
C9	1.0454 (5)	0.8859 (4)	0.0763 (3)	0.0544 (8)
H9	1.1386	0.9672	0.0781	0.065*
C10	0.8982 (4)	0.4780 (4)	0.2399 (3)	0.0422 (7)
H10	0.8705	0.3733	0.2027	0.051*
C11	0.7152 (4)	0.5316 (3)	0.3493 (2)	0.0370 (6)
H11	0.5967	0.5834	0.3163	0.044*
C12	0.7617 (5)	0.6643 (4)	0.4341 (3)	0.0462 (7)
H12A	0.7014	0.7779	0.4157	0.055*
H12B	0.9129	0.6661	0.4226	0.055*
C13	0.6668 (5)	0.6179 (4)	0.5657 (3)	0.0508 (7)
H13	0.6788	0.7107	0.6197	0.061*
C14	0.4346 (5)	0.5872 (4)	0.5819 (3)	0.0501 (7)
H14	0.3825	0.5541	0.6665	0.060*
C15	0.4244 (5)	0.4355 (4)	0.5019 (3)	0.0495 (7)
H15A	0.3724	0.3404	0.5523	0.059*
H15B	0.3277	0.4683	0.4496	0.059*
C16	0.7861 (6)	0.4523 (6)	0.5981 (4)	0.0732 (11)
H16A	0.7214	0.4165	0.6794	0.088*
H16B	0.9309	0.4711	0.5964	0.088*
C17	0.7817 (6)	0.3120 (5)	0.5070 (4)	0.0623 (9)
H17A	0.9228	0.2799	0.4591	0.075*
H17B	0.7296	0.2107	0.5495	0.075*
C18	0.2963 (6)	0.7454 (5)	0.5562 (4)	0.0654 (9)
H18	0.3230	0.7897	0.4778	0.078*
C19	0.1464 (8)	0.8213 (7)	0.6347 (6)	0.0929 (14)
H19A	0.1157	0.7802	0.7138	0.111*
H19B	0.0673	0.9181	0.6130	0.111*
O2	1.3649 (7)	0.1540 (5)	0.1689 (4)	0.1150 (13)
O3	1.4516 (5)	−0.1179 (3)	0.2418 (3)	0.0696 (7)
O4	1.6490 (6)	0.1037 (5)	0.2582 (4)	0.1075 (13)
O5	1.3154 (6)	0.1110 (4)	0.3764 (3)	0.1051 (12)
O6	0.9559 (6)	1.1820 (4)	−0.1709 (3)	0.1021 (12)
O7	1.3188 (7)	1.2167 (6)	−0.2160 (5)	0.1427 (19)
O8	1.0772 (6)	1.4547 (4)	−0.1756 (3)	0.0846 (9)
O9	1.1151 (6)	1.2660 (5)	−0.0221 (3)	0.0956 (11)
H1N	0.907 (6)	0.999 (3)	−0.039 (3)	0.054 (10)*
H2N	0.636 (6)	0.296 (3)	0.380 (3)	0.062 (11)*
H1O	1.181 (6)	0.375 (5)	0.245 (4)	0.093 (16)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0604 (5)	0.0353 (3)	0.0633 (5)	0.0032 (3)	−0.0242 (4)	−0.0047 (3)
Cl2	0.0688 (6)	0.0606 (5)	0.0544 (5)	−0.0193 (4)	−0.0115 (4)	0.0155 (4)
O1	0.0483 (13)	0.0549 (14)	0.0733 (16)	0.0115 (10)	−0.0065 (11)	0.0121 (12)
N1	0.0613 (17)	0.0520 (16)	0.0508 (15)	−0.0087 (13)	−0.0023 (13)	0.0116 (13)
N2	0.0532 (15)	0.0400 (13)	0.0420 (13)	−0.0121 (11)	−0.0057 (11)	0.0027 (10)
C1	0.0510 (17)	0.0632 (19)	0.0329 (14)	0.0002 (14)	−0.0003 (12)	−0.0020 (13)
C2	0.069 (2)	0.102 (3)	0.0347 (17)	−0.004 (2)	−0.0067 (16)	0.0073 (18)
C3	0.070 (3)	0.149 (5)	0.0391 (19)	−0.008 (3)	−0.0125 (17)	−0.019 (3)
C4	0.066 (3)	0.125 (4)	0.056 (2)	−0.038 (2)	−0.0036 (19)	−0.026 (3)
C5	0.0550 (19)	0.071 (2)	0.0474 (17)	−0.0187 (16)	−0.0030 (14)	−0.0135 (16)
C6	0.0403 (13)	0.0513 (18)	0.0333 (13)	−0.0061 (12)	0.0015 (10)	−0.0058 (12)
C7	0.0387 (14)	0.0382 (13)	0.0373 (14)	−0.0030 (11)	0.0012 (11)	−0.0064 (11)
C8	0.0446 (16)	0.0470 (16)	0.0456 (16)	−0.0096 (13)	−0.0076 (13)	−0.0002 (13)
C9	0.056 (2)	0.0525 (19)	0.0536 (19)	−0.0184 (15)	−0.0043 (15)	0.0018 (14)
C10	0.0415 (15)	0.0348 (13)	0.0455 (17)	0.0004 (11)	−0.0013 (12)	−0.0016 (12)
C11	0.0393 (14)	0.0328 (13)	0.0375 (14)	−0.0041 (10)	−0.0056 (11)	0.0017 (10)
C12	0.0485 (16)	0.0466 (15)	0.0439 (15)	−0.0146 (12)	−0.0057 (12)	−0.0049 (12)
C13	0.0548 (18)	0.0588 (18)	0.0423 (15)	−0.0168 (14)	−0.0126 (13)	−0.0051 (13)
C14	0.0531 (18)	0.0562 (18)	0.0374 (15)	−0.0078 (13)	−0.0019 (13)	0.0024 (13)
C15	0.0442 (16)	0.0582 (19)	0.0442 (16)	−0.0145 (13)	−0.0020 (12)	0.0056 (14)
C16	0.064 (2)	0.106 (3)	0.057 (2)	−0.016 (2)	−0.0277 (18)	0.022 (2)
C17	0.059 (2)	0.058 (2)	0.067 (2)	0.0007 (16)	−0.0125 (17)	0.0238 (17)
C18	0.062 (2)	0.0528 (19)	0.075 (2)	0.0000 (16)	−0.0032 (18)	0.0054 (17)
C19	0.085 (3)	0.077 (3)	0.105 (4)	0.015 (2)	−0.006 (3)	−0.011 (3)
O2	0.167 (4)	0.084 (2)	0.104 (3)	0.012 (2)	−0.065 (3)	0.014 (2)
O3	0.0799 (17)	0.0414 (13)	0.0887 (19)	−0.0007 (11)	−0.0225 (14)	−0.0125 (12)
O4	0.081 (2)	0.086 (2)	0.163 (4)	−0.0201 (17)	−0.035 (2)	−0.032 (2)
O5	0.134 (3)	0.072 (2)	0.090 (2)	0.008 (2)	0.007 (2)	−0.0141 (18)
O6	0.140 (3)	0.087 (2)	0.103 (2)	−0.053 (2)	−0.062 (2)	0.0304 (19)
O7	0.139 (4)	0.117 (3)	0.136 (4)	0.027 (3)	0.027 (3)	0.006 (3)
O8	0.106 (2)	0.0668 (18)	0.0786 (19)	−0.0251 (15)	−0.0107 (17)	0.0226 (15)
O9	0.133 (3)	0.095 (2)	0.072 (2)	−0.043 (2)	−0.0392 (19)	0.0285 (17)

Geometric parameters (Å, º)

Cl1—O3	1.402 (2)	C7—C10	1.505 (4)
Cl1—O5	1.406 (3)	C8—C9	1.363 (5)
Cl1—O2	1.416 (3)	C8—H8	0.9300
Cl1—O4	1.444 (3)	C9—H9	0.9300
Cl2—O7	1.383 (4)	C10—C11	1.546 (4)
Cl2—O8	1.421 (3)	C10—H10	0.9800
Cl2—O9	1.437 (3)	C11—C12	1.528 (4)
Cl2—O6	1.443 (3)	C11—H11	0.9800
O1—C10	1.422 (4)	C12—C13	1.529 (4)
O1—H1O	0.82 (4)	C12—H12A	0.9700
N1—C9	1.317 (5)	C12—H12B	0.9700
N1—C1	1.362 (4)	C13—C16	1.520 (5)
N1—H1N	0.85 (3)	C13—C14	1.534 (4)
N2—C17	1.497 (4)	C13—H13	0.9800
N2—C15	1.500 (4)	C14—C18	1.514 (5)
N2—C11	1.508 (4)	C14—C15	1.524 (5)
N2—H2N	0.86 (3)	C14—H14	0.9800
C1—C2	1.388 (5)	C15—H15A	0.9700
C1—C6	1.422 (4)	C15—H15B	0.9700
C2—C3	1.363 (7)	C16—C17	1.529 (6)
C2—H2	0.9300	C16—H16A	0.9700
C3—C4	1.379 (7)	C16—H16B	0.9700
C3—H3	0.9300	C17—H17A	0.9700
C4—C5	1.366 (6)	C17—H17B	0.9700
C4—H4	0.9300	C18—C19	1.269 (6)
C5—C6	1.417 (4)	C18—H18	0.9300
C5—H5	0.9300	C19—H19A	0.9300
C6—C7	1.418 (4)	C19—H19B	0.9300
C7—C8	1.373 (4)
O3—Cl1—O5	113.2 (2)	O1—C10—H10	109.8
O3—Cl1—O2	111.0 (2)	C7—C10—H10	109.8
O5—Cl1—O2	110.4 (2)	C11—C10—H10	109.8
O3—Cl1—O4	108.11 (19)	N2—C11—C12	107.3 (2)
O5—Cl1—O4	106.6 (3)	N2—C11—C10	112.8 (2)
O2—Cl1—O4	107.2 (3)	C12—C11—C10	115.2 (2)
O7—Cl2—O8	109.7 (3)	N2—C11—H11	107.0
O7—Cl2—O9	110.3 (3)	C12—C11—H11	107.0
O8—Cl2—O9	106.6 (2)	C10—C11—H11	107.0
O7—Cl2—O6	113.1 (3)	C11—C12—C13	109.4 (2)
O8—Cl2—O6	110.2 (2)	C11—C12—H12A	109.8
O9—Cl2—O6	106.7 (2)	C13—C12—H12A	109.8
C10—O1—H1O	118 (4)	C11—C12—H12B	109.8
C9—N1—C1	123.5 (3)	C13—C12—H12B	109.8
C9—N1—H1N	121 (2)	H12A—C12—H12B	108.2
C1—N1—H1N	116 (2)	C16—C13—C12	108.8 (3)
C17—N2—C15	109.3 (2)	C16—C13—C14	108.0 (3)
C17—N2—C11	114.2 (2)	C12—C13—C14	110.9 (2)
C15—N2—C11	108.2 (2)	C16—C13—H13	109.7
C17—N2—H2N	105 (3)	C12—C13—H13	109.7
C15—N2—H2N	111 (3)	C14—C13—H13	109.7
C11—N2—H2N	110 (3)	C18—C14—C15	112.1 (3)
N1—C1—C2	120.5 (3)	C18—C14—C13	113.2 (3)
N1—C1—C6	117.5 (3)	C15—C14—C13	108.0 (3)
C2—C1—C6	121.9 (3)	C18—C14—H14	107.8
C3—C2—C1	118.5 (4)	C15—C14—H14	107.8
C3—C2—H2	120.8	C13—C14—H14	107.8
C1—C2—H2	120.8	N2—C15—C14	109.8 (2)
C2—C3—C4	121.5 (4)	N2—C15—H15A	109.7
C2—C3—H3	119.2	C14—C15—H15A	109.7
C4—C3—H3	119.2	N2—C15—H15B	109.7
C5—C4—C3	121.0 (4)	C14—C15—H15B	109.7
C5—C4—H4	119.5	H15A—C15—H15B	108.2
C3—C4—H4	119.5	C13—C16—C17	109.4 (3)
C4—C5—C6	120.2 (4)	C13—C16—H16A	109.8
C4—C5—H5	119.9	C17—C16—H16A	109.8
C6—C5—H5	119.9	C13—C16—H16B	109.8
C5—C6—C7	124.1 (3)	C17—C16—H16B	109.8
C5—C6—C1	116.7 (3)	H16A—C16—H16B	108.3
C7—C6—C1	119.1 (3)	N2—C17—C16	108.3 (3)
C8—C7—C6	118.2 (3)	N2—C17—H17A	110.0
C8—C7—C10	120.0 (3)	C16—C17—H17A	110.0
C6—C7—C10	121.8 (3)	N2—C17—H17B	110.0
C9—C8—C7	121.3 (3)	C16—C17—H17B	110.0
C9—C8—H8	119.4	H17A—C17—H17B	108.4
C7—C8—H8	119.4	C19—C18—C14	124.2 (4)
N1—C9—C8	120.3 (3)	C19—C18—H18	117.9
N1—C9—H9	119.8	C14—C18—H18	117.9
C8—C9—H9	119.8	C18—C19—H19A	120.0
O1—C10—C7	111.1 (2)	C18—C19—H19B	120.0
O1—C10—C11	108.9 (2)	H19A—C19—H19B	120.0
C7—C10—C11	107.3 (2)
C9—N1—C1—C2	179.4 (3)	C15—N2—C11—C12	70.5 (3)
C9—N1—C1—C6	0.7 (5)	C17—N2—C11—C10	76.4 (3)
N1—C1—C2—C3	179.8 (3)	C15—N2—C11—C10	−161.6 (2)
C6—C1—C2—C3	−1.6 (5)	O1—C10—C11—N2	−78.6 (3)
C1—C2—C3—C4	−0.1 (6)	C7—C10—C11—N2	161.0 (2)
C2—C3—C4—C5	0.7 (7)	O1—C10—C11—C12	45.1 (3)
C3—C4—C5—C6	0.4 (6)	C7—C10—C11—C12	−75.2 (3)
C4—C5—C6—C7	178.6 (3)	N2—C11—C12—C13	−13.5 (3)
C4—C5—C6—C1	−2.0 (5)	C10—C11—C12—C13	−140.1 (3)
N1—C1—C6—C5	−178.7 (3)	C11—C12—C13—C16	67.7 (3)
C2—C1—C6—C5	2.6 (4)	C11—C12—C13—C14	−50.8 (4)
N1—C1—C6—C7	0.8 (4)	C16—C13—C14—C18	178.1 (3)
C2—C1—C6—C7	−177.9 (3)	C12—C13—C14—C18	−62.8 (4)
C5—C6—C7—C8	178.1 (3)	C16—C13—C14—C15	−57.2 (3)
C1—C6—C7—C8	−1.3 (4)	C12—C13—C14—C15	61.9 (3)
C5—C6—C7—C10	−5.9 (4)	C17—N2—C15—C14	65.6 (3)
C1—C6—C7—C10	174.7 (3)	C11—N2—C15—C14	−59.3 (3)
C6—C7—C8—C9	0.5 (4)	C18—C14—C15—N2	119.6 (3)
C10—C7—C8—C9	−175.6 (3)	C13—C14—C15—N2	−5.8 (3)
C1—N1—C9—C8	−1.6 (5)	C12—C13—C16—C17	−55.4 (4)
C7—C8—C9—N1	0.9 (5)	C14—C13—C16—C17	65.0 (4)
C8—C7—C10—O1	−24.9 (4)	C15—N2—C17—C16	−57.7 (3)
C6—C7—C10—O1	159.1 (3)	C11—N2—C17—C16	63.7 (3)
C8—C7—C10—C11	94.0 (3)	C13—C16—C17—N2	−6.6 (4)
C6—C7—C10—C11	−81.9 (3)	C15—C14—C18—C19	121.0 (5)
C17—N2—C11—C12	−51.5 (3)	C13—C14—C18—C19	−116.6 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O2	0.82 (4)	2.08 (4)	2.889 (5)	167 (4)
N1—H1N···O6	0.85 (3)	2.04 (3)	2.867 (4)	163 (3)
N2—H2N···O4^i	0.86 (3)	2.05 (3)	2.900 (4)	175 (3)
C8—H8···O1	0.93	2.42	2.760 (6)	102
C9—H9···O2^ii	0.93	2.57	3.448 (5)	158
C9—H9···O9	0.93	2.58	3.192 (5)	124
C12—H12B···O1	0.97	2.39	2.856 (4)	109
C14—H14···O8^iii	0.98	2.54	3.402 (3)	147
C17—H17A···O1	0.97	2.48	3.116 (5)	123

Symmetry codes: (i) x−1, y, z; (ii) x, y+1, z; (iii) x−1, y−1, z+1.