Crystal structure of 2-amino­pyridinium 6-chloro­nicotinate

. 2015 Aug 12;71(Pt 9):o655–o656. doi: 10.1107/S2056989015014796

Cl1—C1	1.7438 (8)	C10—C11	1.4173 (12)
O1—C6	1.2489 (9)	C7—H7A	0.9500
O2—C6	1.2719 (9)	C8—H8A	0.9500
N2—C11	1.3556 (10)	C9—H9A	0.9500
N2—C7	1.3609 (11)	C10—H10A	0.9500
N3—C11	1.3305 (11)	C1—C2	1.3917 (12)
N2—H1N2	0.923 (17)	C2—C3	1.3863 (12)
N3—H2N3	0.844 (16)	C3—C4	1.3980 (11)
N3—H1N3	0.890 (15)	C4—C5	1.3905 (10)
N1—C5	1.3444 (11)	C4—C6	1.5075 (10)
N1—C1	1.3218 (11)	C2—H2A	0.9500
C7—C8	1.3645 (13)	C3—H3A	0.9500
C8—C9	1.4129 (13)	C5—H5A	0.9500
C9—C10	1.3687 (13)

Cl1···C4ⁱ	3.5893 (8)	C6···N2^v	3.4200 (10)
Cl1···C5ⁱ	3.2804 (8)	C6···O2^v	3.2056 (10)
Cl1···C9	3.6238 (10)	C7···C3	3.5149 (12)
Cl1···H8Aⁱⁱ	3.1000	C7···C2	3.2663 (12)
Cl1···H3Aⁱⁱⁱ	3.1000	C7···N1^vii	3.2808 (11)
Cl1···H9A^iv	3.0200	C9···Cl1	3.6238 (10)
O1···N3^v	2.7830 (10)	C10···O1ⁱⁱⁱ	3.1574 (10)
O1···C2^vi	3.2450 (10)	C11···C1	3.5787 (11)
O1···C10^vii	3.1574 (10)	C11···N1	3.3719 (11)
O2···C6^v	3.2056 (10)	C3···H3A^vi	3.0700
O2···C4^v	3.3415 (10)	C5···H7Aⁱⁱⁱ	2.8500
O2···N3^viii	2.8490 (9)	C6···H1N3^viii	3.049 (15)
O2···N2^v	2.7000 (9)	C6···H1N2^v	2.544 (17)
O1···H3A	2.5000	C6···H2N3^v	2.833 (16)
O1···H1N2^v	2.726 (16)	H1N2···H2N3	2.28 (2)
O1···H10A^vii	2.2500	H1N2···O1^v	2.726 (16)
O1···H2N3^v	1.942 (17)	H1N2···O2^v	1.781 (17)
O2···H5A	2.5200	H1N2···C6^v	2.544 (17)
O2···H1N2^v	1.781 (17)	H2N3···O1^v	1.942 (17)
O2···H1N3^viii	1.962 (15)	H2N3···C6^v	2.833 (16)
N1···C11	3.3719 (11)	H2N3···H1N2	2.28 (2)
N1···C7ⁱⁱⁱ	3.2808 (11)	H1N3···C6^ix	3.049 (15)
N2···O2^v	2.7000 (9)	H1N3···H10A	2.5000
N2···C6^v	3.4200 (10)	H1N3···O2^ix	1.962 (15)
N3···O1^v	2.7830 (10)	H1N3···H5A^ix	2.3700
N3···O2^ix	2.8490 (9)	H3A···O1	2.5000
N1···H7Aⁱⁱⁱ	2.4400	H3A···C3^vi	3.0700
N3···H5A^ix	2.8700	H3A···Cl1^vii	3.1000
C1···C11	3.5787 (11)	H5A···O2	2.5200
C2···C3^vi	3.5309 (12)	H5A···N3^viii	2.8700
C2···C7	3.2663 (12)	H5A···H1N3^viii	2.3700
C2···O1^vi	3.2450 (10)	H5A···H7Aⁱⁱⁱ	2.5100
C3···C3^vi	3.1853 (12)	H7A···H5A^vii	2.5100
C3···C7	3.5149 (12)	H7A···N1^vii	2.4400
C3···C2^vi	3.5309 (12)	H7A···C5^vii	2.8500
C4···Cl1^iv	3.5893 (8)	H8A···Cl1ⁱⁱ	3.1000
C4···O2^v	3.3415 (10)	H9A···Cl1ⁱ	3.0200
C5···Cl1^iv	3.2804 (8)	H10A···O1ⁱⁱⁱ	2.2500
C6···C6^v	3.3366 (10)	H10A···H1N3	2.5000

C7—N2—C11	122.45 (7)	C9—C10—H10A	120.00
C7—N2—H1N2	116.2 (10)	C11—C10—H10A	120.00
C11—N2—H1N2	121.4 (10)	Cl1—C1—N1	116.05 (6)
C11—N3—H2N3	118.0 (11)	Cl1—C1—C2	118.64 (6)
C11—N3—H1N3	121.1 (10)	N1—C1—C2	125.31 (7)
H2N3—N3—H1N3	120.5 (14)	C1—C2—C3	116.97 (7)
C1—N1—C5	116.58 (7)	C2—C3—C4	119.68 (7)
N2—C7—C8	121.16 (8)	C3—C4—C5	117.59 (7)
C7—C8—C9	117.85 (8)	C3—C4—C6	120.56 (6)
C8—C9—C10	120.92 (8)	C5—C4—C6	121.80 (6)
C9—C10—C11	119.58 (8)	N1—C5—C4	123.81 (7)
N3—C11—C10	123.60 (7)	O1—C6—O2	125.14 (7)
N2—C11—N3	118.37 (7)	O1—C6—C4	117.13 (6)
N2—C11—C10	118.04 (7)	O2—C6—C4	117.71 (6)
N2—C7—H7A	119.00	C1—C2—H2A	122.00
C8—C7—H7A	119.00	C3—C2—H2A	121.00
C9—C8—H8A	121.00	C2—C3—H3A	120.00
C7—C8—H8A	121.00	C4—C3—H3A	120.00
C8—C9—H9A	120.00	N1—C5—H5A	118.00
C10—C9—H9A	120.00	C4—C5—H5A	118.00

C11—N2—C7—C8	1.11 (12)	Cl1—C1—C2—C3	−177.22 (6)
C7—N2—C11—N3	179.67 (8)	N1—C1—C2—C3	2.22 (13)
C7—N2—C11—C10	−0.50 (11)	C1—C2—C3—C4	−0.29 (12)
C1—N1—C5—C4	−0.78 (12)	C2—C3—C4—C5	−1.86 (11)
C5—N1—C1—Cl1	177.76 (6)	C2—C3—C4—C6	175.44 (7)
C5—N1—C1—C2	−1.69 (12)	C3—C4—C5—N1	2.51 (12)
N2—C7—C8—C9	−0.90 (13)	C6—C4—C5—N1	−174.75 (7)
C7—C8—C9—C10	0.14 (14)	C3—C4—C6—O1	−2.82 (11)
C8—C9—C10—C11	0.44 (13)	C3—C4—C6—O2	178.64 (7)
C9—C10—C11—N2	−0.26 (12)	C5—C4—C6—O1	174.36 (7)
C9—C10—C11—N3	179.55 (8)	C5—C4—C6—O2	−4.18 (11)