N,N-Bis(2-pyridinio­methyl)­glycine diperchlorate

In the crystal structure of the title compound, C₁₄H₁₇N₃O₂²⁺·2ClO₄⁻, at 180 K, O—H...O hydrogen-bonded di­mers are formed across inversion centres.

Key indicators

• Single-crystal X-ray study
• T = 180 K
• Mean [sigma](C-C) = 0.009 Å
• Disorder in solvent or counterion
• R factor = 0.053
• wR factor = 0.143
• Data-to-parameter ratio = 7.5

checkCIF/PLATON results

No syntax errors found



Alert level A
THETM01_ALERT_3_A  The value of sine(theta_max)/wavelength is less than 0.550
            Calculated sin(theta_max)/wavelength =    0.5264
PLAT023_ALERT_3_A Resolution (too) Low [sin(th)/Lambda < 0.6].....      21.97 Deg.
PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............      21.97 Deg.

Alert level B
ABSTM02_ALERT_3_B  The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
            Tmin and Tmax reported:      0.665     0.996
            Tmin' and Tmax expected:      0.950     0.996
            RR' =      0.700
            Please check that your absorption correction is appropriate.
REFNR01_ALERT_3_B  Ratio of reflections to parameters is < 8 for a
            centrosymmetric structure
            sine(theta)/lambda                0.5264
            Proportion of unique data used    1.0000
            Ratio reflections to parameters   7.5000
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large .............       0.70
PLAT088_ALERT_3_B Poor Data / Parameter Ratio ....................       7.50
PLAT430_ALERT_2_B Short Inter D...A Contact  O22A   ..  O22A    ..       2.69 Ang.

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        Cl2
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      23.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9
PLAT432_ALERT_2_C Short Inter X...Y Contact  O12    ..  C15     ..       2.95 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  C1     ..  O22     ..       2.99 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  C2     ..  O23     ..       2.97 Ang.

   3 ALERT level A = In general: serious problem
   5 ALERT level B = Potentially serious problem
   7 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
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   8 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: APEX2 (Bruker–Nonius, 2004); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

N,N-bis(2-pyridiniomethyl)glycine diperchlorate

Crystal data

C14H17N3O2^2+·2ClO4^−	F(000) = 944
Mr = 458.21	Dx = 1.678 Mg m^−3
Monoclinic, P2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yc	Cell parameters from 2492 reflections
a = 14.1367 (12) Å	θ = 2.5–21.2°
b = 7.9021 (8) Å	µ = 0.42 mm^−1
c = 16.8034 (16) Å	T = 180 K
β = 104.907 (3)°	Plate, colourless
V = 1813.9 (3) Å^3	0.12 × 0.08 × 0.01 mm
Z = 4

Data collection

Bruker–Nonius X8APEX-II CCD diffractometer	2175 independent reflections
Radiation source: fine-focus sealed tube	1542 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.068
thin–slice ω and φ scans	θmax = 22.0°, θmin = 3.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −14→14
Tmin = 0.665, Tmax = 0.996	k = −8→8
15019 measured reflections	l = −17→17

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.143	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0784P)^2 + 1.4336P] where P = (Fo^2 + 2Fc^2)/3
2175 reflections	(Δ/σ)max < 0.001
290 parameters	Δρmax = 0.49 e Å^−3
71 restraints	Δρmin = −0.40 e Å^−3

Special details

Experimental. Crystal was best available from the batch, but a little on the small side. As a result, diffraction was weak. The data are truncated to 0.95 Å resolution and the structure is therefore of relatively low precision.

H atoms bound to N evident in Fourier maps but placed in calculated positions (on account of the relatively low resolution and the associated low data:parameter ratio). H atom of carboxyl group located in difference Fourier then moved along the O2—H2 bond vector to give O—H = 0.85 Å. Subsequently allowed to ride on O2 with U_iso(H) = 1.5 x U_eq(O).?

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	Occ. (<1)
O1	0.5944 (3)	0.0907 (5)	0.4784 (2)	0.0362 (11)
O2	0.4933 (3)	0.2109 (5)	0.5458 (2)	0.0363 (11)
H2	0.4685	0.1128	0.5353	0.054*
N1	0.8369 (4)	0.4331 (6)	0.6800 (3)	0.0392 (14)
H1B	0.8159	0.5130	0.6432	0.047*
N2	0.7261 (3)	0.3670 (6)	0.5196 (3)	0.0311 (12)
N3	0.7346 (4)	0.6732 (6)	0.4385 (3)	0.0366 (13)
H3B	0.7716	0.6523	0.4883	0.044*
C1	0.8751 (5)	0.4798 (9)	0.7586 (4)	0.0448 (17)
H1A	0.8809	0.5961	0.7734	0.054*
C2	0.9051 (5)	0.3580 (9)	0.8164 (4)	0.0421 (17)
H2A	0.9318	0.3890	0.8724	0.050*
C3	0.8973 (5)	0.1905 (9)	0.7946 (4)	0.0470 (18)
H3A	0.9186	0.1053	0.8352	0.056*
C4	0.8578 (5)	0.1459 (8)	0.7120 (4)	0.0429 (17)
H4A	0.8511	0.0300	0.6965	0.051*
C5	0.8288 (4)	0.2690 (7)	0.6538 (4)	0.0311 (15)
C6	0.7922 (4)	0.2373 (7)	0.5630 (3)	0.0332 (15)
H6A	0.8490	0.2296	0.5389	0.040*
H6B	0.7580	0.1268	0.5545	0.040*
C7	0.7171 (5)	0.3680 (7)	0.4306 (4)	0.0379 (16)
H7A	0.6650	0.2878	0.4032	0.045*
H7B	0.7794	0.3289	0.4202	0.045*
C8	0.6931 (5)	0.5409 (8)	0.3938 (4)	0.0374 (16)
C9	0.6363 (5)	0.5720 (8)	0.3158 (4)	0.0404 (17)
H9A	0.6044	0.4814	0.2823	0.048*
C10	0.6257 (5)	0.7361 (9)	0.2863 (4)	0.0469 (18)
H10A	0.5878	0.7572	0.2318	0.056*
C11	0.6695 (6)	0.8703 (9)	0.3351 (4)	0.0506 (19)
H11A	0.6621	0.9832	0.3150	0.061*
C12	0.7247 (5)	0.8346 (8)	0.4145 (4)	0.0426 (17)
H12A	0.7547	0.9228	0.4507	0.051*
C14	0.6303 (4)	0.3679 (7)	0.5376 (4)	0.0336 (15)
H14A	0.5916	0.4626	0.5069	0.040*
H14B	0.6401	0.3917	0.5970	0.040*
C15	0.5709 (4)	0.2102 (8)	0.5176 (3)	0.0296 (14)
Cl1	0.65778 (11)	0.78596 (19)	0.66566 (9)	0.0377 (5)
O11	0.7148 (3)	0.7652 (5)	0.7485 (2)	0.0442 (11)
O12	0.6259 (3)	0.9598 (5)	0.6522 (2)	0.0518 (13)
O13	0.7175 (3)	0.7461 (5)	0.6106 (2)	0.0495 (12)
O14	0.5746 (3)	0.6771 (6)	0.6497 (3)	0.0537 (13)
Cl2	0.97009 (12)	0.7695 (2)	0.57606 (11)	0.0487 (6)
O21	0.9149 (3)	0.6172 (5)	0.5635 (3)	0.0687 (15)
O22	1.0681 (6)	0.7609 (17)	0.6188 (7)	0.058 (5)	0.40
O23	0.9772 (9)	0.7831 (14)	0.4847 (5)	0.071 (4)	0.40
O24	0.9222 (10)	0.9166 (12)	0.5853 (8)	0.063 (5)	0.40
O22A	0.9714 (6)	0.7917 (10)	0.6673 (4)	0.076 (3)	0.60
O23A	1.0654 (5)	0.7552 (13)	0.5742 (6)	0.070 (3)	0.60
O24A	0.9175 (6)	0.9087 (10)	0.5367 (6)	0.065 (3)	0.60

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.033 (3)	0.038 (3)	0.043 (3)	−0.0029 (19)	0.019 (2)	−0.002 (2)
O2	0.031 (3)	0.042 (3)	0.043 (3)	−0.0045 (19)	0.022 (2)	−0.0077 (19)
N1	0.035 (3)	0.041 (4)	0.042 (4)	−0.004 (2)	0.009 (3)	−0.001 (3)
N2	0.032 (3)	0.033 (3)	0.033 (3)	0.001 (2)	0.017 (2)	−0.003 (2)
N3	0.048 (4)	0.030 (3)	0.038 (3)	−0.004 (3)	0.022 (3)	−0.006 (3)
C1	0.037 (4)	0.048 (5)	0.048 (5)	−0.005 (3)	0.009 (3)	−0.010 (4)
C2	0.033 (4)	0.048 (5)	0.046 (4)	0.003 (3)	0.010 (3)	0.004 (4)
C3	0.035 (4)	0.060 (6)	0.049 (5)	0.008 (3)	0.016 (3)	0.011 (4)
C4	0.038 (4)	0.033 (4)	0.063 (5)	0.004 (3)	0.023 (4)	0.003 (4)
C5	0.026 (4)	0.027 (4)	0.044 (4)	−0.003 (3)	0.016 (3)	−0.004 (3)
C6	0.027 (4)	0.034 (4)	0.040 (4)	0.001 (3)	0.012 (3)	−0.003 (3)
C7	0.043 (4)	0.034 (4)	0.045 (4)	−0.001 (3)	0.026 (3)	−0.003 (3)
C8	0.046 (4)	0.034 (4)	0.043 (4)	−0.003 (3)	0.030 (4)	−0.004 (3)
C9	0.044 (4)	0.043 (5)	0.038 (4)	0.005 (3)	0.017 (3)	−0.003 (3)
C10	0.052 (5)	0.060 (5)	0.037 (4)	0.012 (4)	0.026 (3)	0.006 (4)
C11	0.076 (5)	0.040 (5)	0.050 (5)	−0.001 (4)	0.042 (4)	−0.001 (4)
C12	0.064 (5)	0.028 (4)	0.048 (5)	0.000 (3)	0.035 (4)	−0.002 (3)
C14	0.037 (4)	0.028 (4)	0.044 (4)	0.000 (3)	0.025 (3)	−0.005 (3)
C15	0.027 (4)	0.042 (4)	0.025 (3)	0.003 (3)	0.016 (3)	0.001 (3)
Cl1	0.0446 (11)	0.0415 (11)	0.0301 (10)	0.0044 (7)	0.0153 (7)	−0.0009 (7)
O11	0.051 (3)	0.050 (3)	0.028 (3)	0.005 (2)	0.005 (2)	0.003 (2)
O12	0.072 (3)	0.039 (3)	0.046 (3)	0.019 (2)	0.018 (2)	0.006 (2)
O13	0.056 (3)	0.058 (3)	0.045 (3)	0.007 (2)	0.032 (2)	−0.005 (2)
O14	0.051 (3)	0.059 (3)	0.052 (3)	−0.013 (2)	0.016 (2)	−0.002 (2)
Cl2	0.0344 (11)	0.0378 (11)	0.0711 (13)	0.0015 (8)	0.0083 (9)	0.0024 (9)
O21	0.057 (3)	0.046 (3)	0.109 (4)	−0.006 (2)	0.032 (3)	0.014 (3)
O22	0.036 (7)	0.080 (8)	0.058 (8)	−0.002 (6)	0.011 (6)	0.029 (7)
O23	0.095 (9)	0.095 (8)	0.031 (6)	−0.036 (7)	0.033 (6)	−0.005 (6)
O24	0.062 (8)	0.050 (8)	0.088 (10)	0.017 (6)	0.040 (8)	−0.016 (7)
O22A	0.075 (6)	0.074 (6)	0.077 (6)	0.004 (5)	0.017 (4)	−0.023 (5)
O23A	0.045 (6)	0.083 (6)	0.099 (8)	0.012 (4)	0.051 (5)	0.049 (6)
O24A	0.052 (6)	0.051 (6)	0.096 (7)	0.012 (4)	0.026 (6)	0.035 (5)

Geometric parameters (Å, º)

O1—C15	1.244 (6)	C7—C8	1.502 (8)
O2—C15	1.303 (6)	C7—H7A	0.990
O2—H2	0.850	C7—H7B	0.990
N1—C1	1.344 (8)	C8—C9	1.371 (8)
N1—C5	1.364 (7)	C9—C10	1.382 (9)
N1—H1B	0.880	C9—H9A	0.950
N2—C6	1.451 (7)	C10—C11	1.386 (9)
N2—C14	1.462 (7)	C10—H10A	0.950
N2—C7	1.469 (7)	C11—C12	1.390 (9)
N3—C8	1.332 (7)	C11—H11A	0.950
N3—C12	1.334 (8)	C12—H12A	0.950
N3—H3B	0.880	C14—C15	1.491 (8)
C1—C2	1.356 (9)	C14—H14A	0.990
C1—H1A	0.950	C14—H14B	0.990
C2—C3	1.371 (9)	Cl1—O14	1.426 (4)
C2—H2A	0.950	Cl1—O11	1.428 (4)
C3—C4	1.401 (9)	Cl1—O13	1.439 (4)
C3—H3A	0.950	Cl1—O12	1.445 (4)
C4—C5	1.366 (8)	Cl2—O24	1.374 (8)
C4—H4A	0.950	Cl2—O22	1.389 (8)
C5—C6	1.500 (8)	Cl2—O21	1.420 (4)
C6—H6A	0.990	Cl2—O23	1.568 (7)
C6—H6B	0.990
C15—O2—H2	105.2	N3—C8—C9	117.6 (6)
C1—N1—C5	123.9 (5)	N3—C8—C7	117.5 (6)
C1—N1—H1B	118.1	C9—C8—C7	124.8 (6)
C5—N1—H1B	118.1	C8—C9—C10	119.6 (6)
C6—N2—C14	114.2 (4)	C8—C9—H9A	120.2
C6—N2—C7	113.1 (4)	C10—C9—H9A	120.2
C14—N2—C7	111.6 (4)	C9—C10—C11	121.0 (6)
C8—N3—C12	125.6 (6)	C9—C10—H10A	119.5
C8—N3—H3B	117.2	C11—C10—H10A	119.5
C12—N3—H3B	117.2	C10—C11—C12	117.9 (6)
N1—C1—C2	118.8 (6)	C10—C11—H11A	121.1
N1—C1—H1A	120.6	C12—C11—H11A	121.1
C2—C1—H1A	120.6	N3—C12—C11	118.3 (6)
C1—C2—C3	120.3 (6)	N3—C12—H12A	120.9
C1—C2—H2A	119.8	C11—C12—H12A	120.9
C3—C2—H2A	119.8	N2—C14—C15	116.6 (5)
C2—C3—C4	119.5 (6)	N2—C14—H14A	108.2
C2—C3—H3A	120.3	C15—C14—H14A	108.2
C4—C3—H3A	120.3	N2—C14—H14B	108.2
C5—C4—C3	120.0 (6)	C15—C14—H14B	108.2
C5—C4—H4A	120.0	H14A—C14—H14B	107.3
C3—C4—H4A	120.0	O1—C15—O2	124.1 (5)
N1—C5—C4	117.5 (6)	O1—C15—C14	122.8 (5)
N1—C5—C6	117.7 (5)	O2—C15—C14	113.1 (5)
C4—C5—C6	124.8 (5)	O14—Cl1—O11	110.3 (3)
N2—C6—C5	113.7 (5)	O14—Cl1—O13	109.8 (3)
N2—C6—H6A	108.8	O11—Cl1—O13	109.0 (3)
C5—C6—H6A	108.8	O14—Cl1—O12	109.6 (3)
N2—C6—H6B	108.8	O11—Cl1—O12	109.7 (2)
C5—C6—H6B	108.8	O13—Cl1—O12	108.6 (2)
H6A—C6—H6B	107.7	O24—Cl2—O22	116.0 (7)
N2—C7—C8	112.0 (5)	O24—Cl2—O21	117.7 (6)
N2—C7—H7A	109.2	O22—Cl2—O21	118.2 (6)
C8—C7—H7A	109.2	O24—Cl2—O23	102.2 (6)
N2—C7—H7B	109.2	O22—Cl2—O23	101.7 (6)
C8—C7—H7B	109.2	O21—Cl2—O23	94.8 (4)
H7A—C7—H7B	107.9
C5—N1—C1—C2	−1.9 (9)	C12—N3—C8—C9	0.9 (8)
N1—C1—C2—C3	0.6 (9)	C12—N3—C8—C7	177.2 (5)
C1—C2—C3—C4	−0.1 (9)	N2—C7—C8—N3	37.3 (7)
C2—C3—C4—C5	1.0 (9)	N2—C7—C8—C9	−146.7 (6)
C1—N1—C5—C4	2.8 (8)	N3—C8—C9—C10	1.2 (8)
C1—N1—C5—C6	−175.1 (5)	C7—C8—C9—C10	−174.8 (5)
C3—C4—C5—N1	−2.2 (8)	C8—C9—C10—C11	−1.7 (9)
C3—C4—C5—C6	175.4 (5)	C9—C10—C11—C12	0.3 (9)
C14—N2—C6—C5	−70.4 (6)	C8—N3—C12—C11	−2.3 (8)
C7—N2—C6—C5	160.5 (5)	C10—C11—C12—N3	1.7 (9)
N1—C5—C6—N2	−29.4 (7)	C6—N2—C14—C15	−59.9 (6)
C4—C5—C6—N2	153.0 (5)	C7—N2—C14—C15	69.9 (6)
C6—N2—C7—C8	−151.7 (5)	N2—C14—C15—O1	−8.8 (8)
C14—N2—C7—C8	77.9 (6)	N2—C14—C15—O2	170.8 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1^i	0.85	1.82	2.669 (5)	173
N1—H1B···O13	0.88	2.29	3.052 (7)	145
N1—H1B···O21	0.88	2.32	2.877 (7)	121
N3—H3B···O13	0.88	2.48	3.017 (6)	120
N3—H3B···O21	0.88	2.11	2.889 (7)	147

Symmetry code: (i) −x+1, −y, −z+1.