2-Amino-6-chloro­pyridine–glutaric acid (1/1)

In the title 1:1 co-crystal [systematic name: 6-chloro­pyridin-2-amine–penta­nedioic acid (1/1)], C₅H₅ClN₂·C₅H₈O₄, the pyridine ring is essentially planar, with a maximum deviation of 0.003 (1) Å. The base and acid mol­ecules are linked via N—H...O and O—H...N hydrogen bonds, while inversion-related acid mol­ecules are linked via pairs of O—H...O hydrogen bonds. These inter­actions together with a C—H...O hydrogen bond connect the two components, forming (001) sheets.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.033
• wR factor = 0.094
• Data-to-parameter ratio = 23.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          3 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          7 Note
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT063_ALERT_4_G Crystal Size Likely too Large for Beam Size ....       0.80 mm
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          2 Report
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          4 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          4 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          8 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          3 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          8 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  10 ALERT level G = General information/check it is not something unexpected

   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
   3 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS2016 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

6-Chloropyridin-2-amine–pentanedioic acid (1/1)

Crystal data

C5H5ClN2·C5H8O4	F(000) = 544
Mr = 260.67	Dx = 1.489 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.7115 (16) Å	Cell parameters from 3966 reflections
b = 4.9598 (6) Å	θ = 3.1–31.8°
c = 17.3105 (19) Å	µ = 0.33 mm^−1
β = 112.960 (2)°	T = 296 K
V = 1163.0 (2) Å^3	Plate, yellow
Z = 4	0.80 × 0.30 × 0.04 mm

Data collection

Bruker SMART APEXII CCD diffractometer	3264 reflections with I > 2σ(I)
ω and φ scan	Rint = 0.036
Absorption correction: multi-scan (SADABS; Bruker, 2012)	θmax = 31.8°, θmin = 3.1°
Tmin = 0.774, Tmax = 0.987	h = −21→21
14500 measured reflections	k = −7→6
3966 independent reflections	l = −25→25

Refinement

Refinement on F^2	4 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.094	w = 1/[σ^2(Fo^2) + (0.0538P)^2 + 0.4259P] where P = (Fo^2 + 2Fc^2)/3
S = 0.93	(Δ/σ)max < 0.001
3966 reflections	Δρmax = 0.49 e Å^−3
170 parameters	Δρmin = −0.29 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. The C-bound H atoms were positioned geometrically (C—H = 0.93 or 0.97 Å) and were refined using a riding model, with U_iso(H) = 1.2U_eq(C). Other H atoms were located in a difference map and refined with bond length restraints [O—H = 0.83 (1) Å and N—H = 0.88 (1) Å].

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.32219 (7)	0.5358 (2)	0.18568 (6)	0.01383 (18)
C2	0.40778 (8)	0.6161 (2)	0.17751 (7)	0.0171 (2)
H2	0.468418	0.536117	0.208091	0.021*
C3	0.39787 (8)	0.8254 (2)	0.12033 (7)	0.0183 (2)
H3	0.453167	0.888572	0.112474	0.022*
C4	0.30710 (8)	0.9376 (2)	0.07589 (6)	0.0171 (2)
H4	0.300439	1.076883	0.038085	0.021*
C5	0.22388 (8)	0.8382 (2)	0.08852 (6)	0.01566 (19)
C6	0.36785 (8)	−0.0963 (2)	0.42745 (7)	0.0158 (2)
C7	0.26506 (7)	−0.1901 (2)	0.37424 (7)	0.01589 (19)
H7A	0.257736	−0.376398	0.387846	0.019*
H7B	0.255794	−0.182763	0.315646	0.019*
C8	0.18569 (7)	−0.0211 (2)	0.38679 (7)	0.01630 (19)
H8A	0.198131	−0.014805	0.446066	0.020*
H8B	0.188724	0.161843	0.368117	0.020*
C9	0.08316 (8)	−0.1353 (2)	0.33855 (7)	0.0173 (2)
H9A	0.067398	−0.118190	0.278884	0.021*
H9B	0.083179	−0.325822	0.351259	0.021*
C10	0.00447 (7)	0.0044 (2)	0.35926 (6)	0.0161 (2)
N1	0.23222 (6)	0.6371 (2)	0.14376 (5)	0.01474 (17)
N2	0.13245 (7)	0.9357 (2)	0.04534 (7)	0.0232 (2)
H2A	0.0834 (10)	0.882 (4)	0.0580 (11)	0.039 (5)*
H2B	0.1237 (11)	1.074 (2)	0.0120 (9)	0.026 (4)*
O1	0.43745 (6)	−0.2565 (2)	0.42360 (6)	0.0258 (2)
H1A	0.4925 (9)	−0.197 (4)	0.4543 (10)	0.039 (5)*
O2	0.38508 (6)	0.10702 (17)	0.47067 (5)	0.01919 (17)
O3	0.02085 (6)	0.19918 (19)	0.40576 (6)	0.0255 (2)
O4	−0.08387 (6)	−0.10152 (19)	0.32075 (5)	0.02091 (18)
H4A	−0.1240 (12)	−0.019 (4)	0.3347 (12)	0.052 (6)*
Cl1	0.32782 (2)	0.28122 (6)	0.25664 (2)	0.01679 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0167 (4)	0.0121 (5)	0.0126 (4)	−0.0002 (4)	0.0056 (3)	0.0002 (3)
C2	0.0156 (4)	0.0188 (5)	0.0165 (4)	−0.0003 (4)	0.0057 (4)	0.0007 (4)
C3	0.0196 (5)	0.0193 (6)	0.0169 (4)	−0.0036 (4)	0.0082 (4)	−0.0008 (4)
C4	0.0215 (5)	0.0160 (5)	0.0148 (4)	−0.0023 (4)	0.0081 (4)	0.0007 (4)
C5	0.0184 (4)	0.0149 (5)	0.0135 (4)	−0.0001 (4)	0.0061 (4)	0.0012 (4)
C6	0.0168 (4)	0.0154 (5)	0.0167 (4)	−0.0001 (4)	0.0081 (4)	0.0004 (4)
C7	0.0153 (4)	0.0155 (5)	0.0170 (4)	−0.0010 (4)	0.0064 (4)	−0.0019 (4)
C8	0.0158 (4)	0.0149 (5)	0.0181 (4)	−0.0003 (4)	0.0065 (4)	−0.0021 (4)
C9	0.0155 (4)	0.0174 (5)	0.0186 (5)	−0.0002 (4)	0.0061 (4)	−0.0038 (4)
C10	0.0150 (4)	0.0164 (5)	0.0155 (4)	−0.0005 (4)	0.0042 (3)	−0.0005 (4)
N1	0.0153 (4)	0.0147 (4)	0.0139 (4)	0.0001 (3)	0.0054 (3)	0.0017 (3)
N2	0.0187 (4)	0.0256 (6)	0.0246 (5)	0.0033 (4)	0.0075 (4)	0.0126 (4)
O1	0.0141 (4)	0.0260 (5)	0.0345 (5)	0.0004 (3)	0.0063 (3)	−0.0149 (4)
O2	0.0169 (3)	0.0168 (4)	0.0231 (4)	−0.0004 (3)	0.0070 (3)	−0.0051 (3)
O3	0.0173 (4)	0.0266 (5)	0.0316 (5)	−0.0025 (3)	0.0083 (3)	−0.0143 (4)
O4	0.0148 (3)	0.0227 (5)	0.0254 (4)	−0.0033 (3)	0.0081 (3)	−0.0081 (3)
Cl1	0.01809 (12)	0.01660 (13)	0.01572 (12)	0.00172 (9)	0.00664 (9)	0.00420 (9)

Geometric parameters (Å, º)

C1—N1	1.3346 (13)	C7—H7A	0.9700
C1—C2	1.3794 (14)	C7—H7B	0.9700
C1—Cl1	1.7409 (11)	C8—C9	1.5202 (15)
C2—C3	1.4022 (16)	C8—H8A	0.9700
C2—H2	0.9300	C8—H8B	0.9700
C3—C4	1.3724 (16)	C9—C10	1.5076 (15)
C3—H3	0.9300	C9—H9A	0.9700
C4—C5	1.4137 (14)	C9—H9B	0.9700
C4—H4	0.9300	C10—O3	1.2199 (14)
C5—N2	1.3481 (14)	C10—O4	1.3165 (13)
C5—N1	1.3540 (14)	N2—H2A	0.873 (9)
C6—O2	1.2217 (14)	N2—H2B	0.873 (9)
C6—O1	1.3181 (13)	O1—H1A	0.830 (9)
C6—C7	1.5049 (15)	O4—H4A	0.828 (9)
C7—C8	1.5202 (15)
N1—C1—C2	125.94 (10)	H7A—C7—H7B	107.8
N1—C1—Cl1	114.88 (7)	C9—C8—C7	111.65 (9)
C2—C1—Cl1	119.18 (8)	C9—C8—H8A	109.3
C1—C2—C3	116.00 (10)	C7—C8—H8A	109.3
C1—C2—H2	122.0	C9—C8—H8B	109.3
C3—C2—H2	122.0	C7—C8—H8B	109.3
C4—C3—C2	120.43 (10)	H8A—C8—H8B	108.0
C4—C3—H3	119.8	C10—C9—C8	112.80 (9)
C2—C3—H3	119.8	C10—C9—H9A	109.0
C3—C4—C5	118.93 (10)	C8—C9—H9A	109.0
C3—C4—H4	120.5	C10—C9—H9B	109.0
C5—C4—H4	120.5	C8—C9—H9B	109.0
N2—C5—N1	116.87 (9)	H9A—C9—H9B	107.8
N2—C5—C4	121.74 (10)	O3—C10—O4	123.51 (10)
N1—C5—C4	121.39 (10)	O3—C10—C9	123.27 (10)
O2—C6—O1	123.27 (10)	O4—C10—C9	113.20 (9)
O2—C6—C7	123.29 (10)	C1—N1—C5	117.31 (9)
O1—C6—C7	113.43 (9)	C5—N2—H2A	119.6 (13)
C6—C7—C8	112.74 (9)	C5—N2—H2B	120.4 (10)
C6—C7—H7A	109.0	H2A—N2—H2B	119.0 (16)
C8—C7—H7A	109.0	C6—O1—H1A	109.8 (13)
C6—C7—H7B	109.0	C10—O4—H4A	109.2 (14)
C8—C7—H7B	109.0
N1—C1—C2—C3	0.78 (17)	C6—C7—C8—C9	−174.76 (9)
Cl1—C1—C2—C3	−178.87 (8)	C7—C8—C9—C10	171.92 (9)
C1—C2—C3—C4	−0.39 (16)	C8—C9—C10—O3	4.34 (16)
C2—C3—C4—C5	−0.21 (16)	C8—C9—C10—O4	−176.99 (9)
C3—C4—C5—N2	−178.41 (11)	C2—C1—N1—C5	−0.50 (16)
C3—C4—C5—N1	0.52 (16)	Cl1—C1—N1—C5	179.16 (8)
O2—C6—C7—C8	−5.66 (15)	N2—C5—N1—C1	178.80 (10)
O1—C6—C7—C8	173.62 (10)	C4—C5—N1—C1	−0.18 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2^i	0.93	2.55	3.3711 (13)	147
N2—H2A···O3^ii	0.87 (1)	2.08 (1)	2.9443 (13)	171 (2)
N2—H2B···O3^i	0.87 (1)	2.18 (1)	2.9525 (13)	147 (1)
O1—H1A···O2^iii	0.83 (1)	1.82 (1)	2.6433 (12)	173 (2)
O4—H4A···N1^iv	0.83 (1)	1.93 (1)	2.7545 (12)	171 (2)

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) −x, y+1/2, −z+1/2; (iii) −x+1, −y, −z+1; (iv) −x, y−1/2, −z+1/2.