1-Carboxy­methyl-3-hydroxy­pyridinium chloride–3-hydroxy­pyridinium-1-acetate (1/1)

Zhao, H.; Huo, L.-H.; Gao, S.; Zhang, Z.-Y.; Zhao, J.-G.; Ng, S.W.

doi:10.1107/S1600536804018938

1-Carboxymethyl-3-hydroxypyridinium chloride-3-hydroxypyridinium-1-acetate (1/1)

H. Zhao, L.-H. Huo, S. Gao, Z.-Y. Zhang, J.-G. Zhao and S. W. Ng

In the crystal structure of the title 1:1 co-crystal, C₇H₈NO₃⁺·Cl^-·C₇H₇NO₃, of 1-carboxymethyl-3-hydroxypyridinium chloride with 3-hydroxypyridinium-1-acetate, the cation interacts with the zwitterion to form a ribbon that runs along the c axis of the orthorhombic unit cell. The Cl^- anions lie at the sides of the ribbon.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804018938/ci6421sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536804018938/ci6421Isup2.hkl Contains datablock I

CCDC reference: 251709

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.003 Å
R factor = 0.033
wR factor = 0.090
Data-to-parameter ratio = 15.8

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.709     0.930
            Tmin' and Tmax expected:      0.885     0.929
            RR' =      0.800
            Please check that your absorption correction is appropriate.
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.80
PLAT731_ALERT_1_C Bond    Calc     0.86(3), Rep   0.860(10) ......       3.00 su-Rat
              O5   -H5O     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.86(3), Rep   0.860(10) ......       3.00 su-Rat
              O5   -H5O     1.555   1.555
PLAT736_ALERT_1_C H...A   Calc     1.68(3), Rep   1.680(10) ......       3.00 su-Rat
              H5O  -O2      1.555   1.555
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C7 H7 N O3
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          3
              Cl

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           27.47
           From the CIF: _reflns_number_total               3484
           Count of symmetry unique reflns         1856
           Completeness (_total/calc)            187.72%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1628
           Fraction of Friedel pairs measured     0.877
           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

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

Computing details top

Data collection: RAPID AUTO (Rigaku, 1998); cell refinement: RAPID AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and POV-RAY (Cason, 2002); software used to prepare material for publication: SHELXL97.

1-Carboxymethyl-3-hydroxypyridinium chloride–3-hydroxypyridinium-1-acetate (1/1) top

Crystal data top

C₇H₈NO₃⁺·Cl⁻·C₇H₇NO₃	F(000) = 712
M_r = 342.73	D_x = 1.496 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 13151 reflections
a = 30.983 (6) Å	θ = 3.3–27.4°
b = 4.920 (1) Å	µ = 0.29 mm⁻¹
c = 9.981 (2) Å	T = 295 K
V = 1521.4 (5) Å³	Prism, colourless
Z = 4	0.42 × 0.35 × 0.26 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	3484 independent reflections
Radiation source: fine-focus sealed tube	3315 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
Detector resolution: 0 pixels mm^-1	θ_max = 27.5°, θ_min = 3.3°
ω scans	h = −39→40
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −6→6
T_min = 0.709, T_max = 0.930	l = −12→12
13459 measured reflections

Refinement top

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)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.090	w = 1/[σ²(F_o²) + (0.0626P)² + 0.1351P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
3484 reflections	Δρ_max = 0.23 e Å⁻³
220 parameters	Δρ_min = −0.15 e Å⁻³
4 restraints	Absolute structure: Flack (1983), with 1637 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.01 (5)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.37226 (1)	−0.1836 (1)	0.50000 (5)	0.0564 (1)
O1	0.65944 (4)	−0.1561 (3)	0.6356 (2)	0.0565 (3)
O2	0.59993 (4)	0.0894 (2)	0.5948 (1)	0.0506 (3)
O3	0.45677 (5)	−0.4617 (4)	0.5463 (2)	0.0654 (4)
O4	0.59179 (4)	0.5976 (3)	0.3821 (2)	0.0598 (3)
O5	0.64613 (4)	0.3093 (2)	0.4177 (2)	0.0528 (3)
O6	0.76769 (4)	0.0890 (3)	0.1124 (1)	0.0604 (4)
N1	0.54828 (4)	−0.2479 (3)	0.7357 (1)	0.0375 (3)
N2	0.70282 (4)	0.5893 (3)	0.2725 (1)	0.0409 (3)
C1	0.62013 (5)	−0.1028 (3)	0.6480 (2)	0.0389 (3)
C2	0.59529 (5)	−0.2992 (3)	0.7372 (2)	0.0424 (3)
C3	0.53216 (6)	−0.0579 (4)	0.8176 (2)	0.0487 (4)
C4	0.48880 (6)	0.0068 (4)	0.8115 (2)	0.0526 (4)
C5	0.46225 (5)	−0.1268 (4)	0.7217 (2)	0.0475 (4)
C6	0.47959 (5)	−0.3220 (3)	0.6370 (2)	0.0433 (3)
C7	0.52351 (5)	−0.3802 (3)	0.6468 (2)	0.0412 (3)
C8	0.62813 (5)	0.5205 (3)	0.3636 (2)	0.0416 (3)
C9	0.65731 (6)	0.6774 (3)	0.2688 (2)	0.0491 (4)
C10	0.73044 (7)	0.7059 (4)	0.3593 (2)	0.0535 (4)
C11	0.77237 (7)	0.6171 (4)	0.3666 (2)	0.0586 (5)
C12	0.78655 (5)	0.4083 (4)	0.2867 (2)	0.0487 (4)
C13	0.75780 (5)	0.2910 (3)	0.1965 (2)	0.0419 (3)
C14	0.71562 (5)	0.3856 (3)	0.1922 (2)	0.0390 (3)
H3O	0.4317 (5)	−0.393 (5)	0.540 (3)	0.09 (1)*
H5O	0.6269 (8)	0.250 (7)	0.472 (3)	0.10 (1)*
H6O	0.7932 (5)	0.025 (5)	0.127 (3)	0.08 (1)*
H2A	0.6007	−0.4837	0.7072	0.051*
H2B	0.6058	−0.2833	0.8283	0.051*
H3	0.5501	0.0302	0.8784	0.058*
H4	0.4775	0.1399	0.8676	0.063*
H5	0.4330	−0.0861	0.7181	0.057*
H7	0.5357	−0.5115	0.5915	0.049*
H9A	0.6465	0.6567	0.1782	0.059*
H9B	0.6559	0.8689	0.2914	0.059*
H10	0.7211	0.8466	0.4143	0.064*
H11	0.7914	0.6992	0.4263	0.070*
H12	0.8148	0.3463	0.2927	0.058*
H14	0.6960	0.3071	0.1332	0.047*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0368 (2)	0.0825 (3)	0.0498 (2)	−0.0086 (2)	0.0004 (2)	0.0007 (2)
O1	0.0308 (5)	0.0594 (7)	0.0794 (9)	−0.0044 (5)	0.0013 (6)	0.0030 (7)
O2	0.0477 (6)	0.0413 (5)	0.0626 (7)	0.0039 (5)	0.0145 (6)	0.0119 (5)
O3	0.0456 (7)	0.0756 (9)	0.0750 (9)	−0.0008 (7)	−0.0116 (6)	−0.0244 (7)
O4	0.0416 (6)	0.0647 (7)	0.0731 (8)	0.0133 (6)	0.0067 (6)	0.0035 (7)
O5	0.0488 (7)	0.0457 (6)	0.0638 (8)	0.0078 (5)	0.0174 (6)	0.0113 (5)
O6	0.0418 (6)	0.0759 (8)	0.0635 (8)	0.0194 (6)	−0.0081 (6)	−0.0246 (7)
N1	0.0318 (6)	0.0378 (5)	0.0429 (6)	−0.0016 (5)	0.0016 (5)	0.0061 (5)
N2	0.0454 (7)	0.0379 (6)	0.0393 (6)	−0.0008 (5)	0.0071 (5)	0.0011 (5)
C1	0.0331 (6)	0.0373 (7)	0.0464 (7)	−0.0032 (5)	0.0018 (6)	−0.0038 (6)
C2	0.0328 (7)	0.0393 (7)	0.0552 (9)	0.0021 (5)	−0.0014 (6)	0.0079 (6)
C3	0.0451 (8)	0.0501 (8)	0.0509 (8)	−0.0001 (7)	−0.0040 (7)	−0.0088 (7)
C4	0.0452 (8)	0.0574 (9)	0.0551 (10)	0.0075 (8)	0.0026 (7)	−0.0135 (8)
C5	0.0333 (7)	0.0582 (9)	0.0508 (9)	0.0047 (7)	0.0020 (6)	−0.0011 (7)
C6	0.0384 (7)	0.0467 (7)	0.0448 (8)	−0.0037 (6)	−0.0012 (6)	−0.0001 (6)
C7	0.0389 (7)	0.0403 (7)	0.0445 (7)	−0.0002 (6)	0.0024 (6)	−0.0013 (6)
C8	0.0409 (7)	0.0398 (7)	0.0442 (7)	0.0051 (6)	0.0035 (6)	−0.0058 (6)
C9	0.0527 (9)	0.0412 (7)	0.0534 (9)	0.0126 (7)	0.0114 (8)	0.0063 (7)
C10	0.070 (1)	0.0495 (8)	0.0410 (8)	−0.0113 (8)	0.0065 (8)	−0.0089 (7)
C11	0.066 (1)	0.066 (1)	0.0436 (9)	−0.024 (1)	−0.0093 (8)	−0.0041 (8)
C12	0.0373 (8)	0.065 (1)	0.0442 (8)	−0.0069 (7)	−0.0051 (6)	0.0065 (8)
C13	0.0375 (8)	0.0498 (8)	0.0383 (7)	0.0011 (6)	0.0001 (6)	−0.0009 (6)
C14	0.0366 (7)	0.0424 (7)	0.0381 (7)	0.0014 (6)	−0.0023 (6)	−0.0041 (6)

Geometric parameters (Å, º) top

O1—C1	1.252 (2)	C11—C12	1.373 (3)
O2—C1	1.252 (2)	C12—C13	1.392 (2)
O3—C6	1.339 (2)	C13—C14	1.388 (2)
O4—C8	1.202 (2)	O3—H3O	0.85 (1)
O5—C8	1.297 (2)	O5—H5O	0.86 (1)
O6—C13	1.337 (2)	O6—H6O	0.86 (1)
N1—C2	1.479 (2)	C2—H2A	0.97
N1—C3	1.338 (2)	C2—H2B	0.97
N1—C7	1.341 (2)	C3—H3	0.93
N2—C9	1.476 (2)	C4—H4	0.93
N2—C10	1.346 (2)	C5—H5	0.93
N2—C14	1.343 (2)	C7—H7	0.93
C1—C2	1.522 (2)	C9—H9A	0.97
C3—C4	1.382 (2)	C9—H9B	0.97
C4—C5	1.383 (3)	C10—H10	0.93
C5—C6	1.388 (2)	C11—H11	0.93
C6—C7	1.394 (2)	C12—H12	0.93
C8—C9	1.519 (2)	C14—H14	0.93
C10—C11	1.373 (3)

C2—N1—C3	118.8 (1)	C8—O5—H5O	104 (2)
C2—N1—C7	119.2 (1)	C13—O6—H6O	112 (2)
C3—N1—C7	122.0 (1)	N1—C2—H2A	109.1
C9—N2—C10	119.9 (2)	C1—C2—H2A	109.1
C9—N2—C14	119.1 (1)	N1—C2—H2B	109.1
C10—N2—C14	121.0 (2)	C1—C2—H2B	109.1
O1—C1—O2	127.0 (2)	H2A—C2—H2B	107.8
O1—C1—C2	114.7 (1)	N1—C3—H3	120.1
O2—C1—C2	118.3 (1)	C4—C3—H3	120.1
N1—C2—C1	112.6 (1)	C3—C4—H4	120.1
N1—C3—C4	119.8 (2)	C5—C4—H4	120.1
C3—C4—C5	119.8 (2)	C4—C5—H5	120.2
C4—C5—C6	119.6 (2)	C6—C5—H5	120.2
O3—C6—C5	124.3 (2)	N1—C7—H7	119.8
O3—C6—C7	117.2 (2)	C6—C7—H7	119.8
C5—C6—C7	118.5 (2)	N2—C9—H9A	108.8
N1—C7—C6	120.4 (1)	C8—C9—H9A	108.8
O4—C8—O5	126.3 (2)	N2—C9—H9B	108.8
O4—C8—C9	119.5 (2)	C8—C9—H9B	108.8
O5—C8—C9	114.2 (1)	H9A—C9—H9B	107.7
N2—C9—C8	113.8 (1)	N2—C10—H10	120.0
N2—C10—C11	120.0 (2)	C11—C10—H10	120.0
C10—C11—C12	120.7 (2)	C10—C11—H11	119.7
C11—C12—C13	118.8 (2)	C12—C11—H11	119.7
O6—C13—C12	124.6 (2)	C11—C12—H12	120.6
O6—C13—C14	116.5 (1)	C13—C12—H12	120.6
C12—C13—C14	118.9 (2)	N2—C14—H14	119.7
N2—C14—C13	120.6 (1)	C13—C14—H14	119.7
C6—O3—H3O	109 (2)

C3—N1—C2—C1	−84.2 (2)	C14—N2—C9—C8	88.0 (2)
C7—N1—C2—C1	91.7 (2)	C10—N2—C9—C8	−89.5 (2)
O1—C1—C2—N1	−173.1 (2)	O4—C8—C9—N2	170.3 (2)
O2—C1—C2—N1	6.3 (2)	O5—C8—C9—N2	−9.7 (2)
C7—N1—C3—C4	−0.2 (3)	C14—N2—C10—C11	0.1 (3)
C2—N1—C3—C4	175.6 (2)	C9—N2—C10—C11	177.5 (2)
N1—C3—C4—C5	0.6 (3)	N2—C10—C11—C12	−0.4 (3)
C3—C4—C5—C6	−1.0 (3)	C10—C11—C12—C13	1.0 (3)
C4—C5—C6—O3	−179.6 (2)	C11—C12—C13—O6	179.3 (2)
C4—C5—C6—C7	1.0 (3)	C11—C12—C13—C14	−1.2 (3)
C3—N1—C7—C6	0.2 (2)	C10—N2—C14—C13	−0.3 (2)
C2—N1—C7—C6	−175.6 (1)	C9—N2—C14—C13	−177.7 (2)
O3—C6—C7—N1	−180.0 (2)	O6—C13—C14—N2	−179.6 (2)
C5—C6—C7—N1	−0.5 (2)	C12—C13—C14—N2	0.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···Cl1	0.85 (1)	2.15 (1)	2.990 (2)	171 (3)
O5—H5O···O2	0.86 (1)	1.68 (1)	2.519 (2)	165 (3)
O6—H6O···O1ⁱ	0.86 (1)	1.72 (1)	2.570 (2)	169 (3)

Symmetry code: (i) −x+3/2, y, z−1/2.

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1-Carboxy­methyl-3-hydroxy­pyridinium chloride-3-hydroxy­pyridinium-1-acetate (1/1)

Supporting information

Key indicators

checkCIF/PLATON results

1-Carboxymethyl-3-hydroxypyridinium chloride-3-hydroxypyridinium-1-acetate (1/1)