Design of two series of 1:1 cocrystals involving 4-amino-5-chloro-2,6-di­methyl­pyrimidine and carb­oxy­lic acids

Two series of a total of ten cocrystals involving 4-amino-5-chloro-2,6-di­methyl­pyrimidine with various carb­oxy­lic acids have been prepared and characterized by single-crystal X-ray diffraction. The pyrimidine unit used for the cocrystals offers two ring N atoms (positions N1 and N3) as proton-accepting sites. Depending upon the site of protonation, two types of cations are possible [Rajam et al. (2017). Acta Cryst. C73, 862–868]. In a parallel arrangement, two series of cocrystals are possible depending upon the hydrogen bonding of the carboxyl group with position N1 or N3. In one series of cocrystals, i.e. 4-amino-5-chloro-2,6-di­methyl­pyrimidine–3-bromo­thio­phene-2-carb­oxy­lic acid (1/1), 1, 4-amino-5-chloro-2,6-di­methyl­pyrimidine–5-chloro­thio­phene-2-carb­oxy­lic acid (1/1), 2, 4-amino-5-chloro-2,6-di­methyl­pyrimidine–2,4-di­chloro­benzoic acid (1/1), 3, and 4-amino-5-chloro-2,6-di­methyl­pyrimidine–2-amino­benzoic acid (1/1), 4, the carboxyl hy­droxy group (–OH) is hydrogen bonded to position N1 (O—H...N1) of the corresponding pyrimidine unit (single point supra­molecular synthon). The inversion-related stacked pyrimidines are doubly bridged by the carboxyl groups via N—H...O and O—H...N hydrogen bonds to form a large cage-like tetra­meric unit with an R₄²(20) graph-set ring motif. These tetra­meric units are further connected via base pairing through a pair of N—H...N hydrogen bonds, generating R₂²(8) motifs (supra­molecular homosynthon). In the other series of cocrystals, i.e. 4-amino-5-chloro-2,6-di­methyl­pyrimidine–5-methyl­thio­phene-2-carb­oxy­lic acid (1/1), 5, 4-amino-5-chloro-2,6-di­methyl­pyrimidine–benzoic acid (1/1), 6, 4-amino-5-chloro-2,6-di­methyl­py­rimi­dine–2-methyl­benzoic acid (1/1), 7, 4-amino-5-chloro-2,6-di­methyl­pyrimidine–3-methyl­benzoic acid (1/1), 8, 4-amino-5-chloro-2,6-di­methyl­pyrimidine–4-methyl­benzoic acid (1/1), 9, and 4-amino-5-chloro-2,6-di­methyl­pyrimidine–4-amino­benzoic acid (1/1), 10, the carboxyl group inter­acts with position N3 and the adjacent 4-amino group of the corresponding pyrimidine ring via O—H...N and N—H...O hydrogen bonds to generate the robust R₂²(8) supra­molecular heterosynthon. These heterosynthons are further connected by N—H...N hydrogen-bond inter­actions in a linear fashion to form a chain-like arrangement. In cocrystal 1, a Br...Br halogen bond is present, in cocrystals 2 and 3, Cl...Cl halogen bonds are present, and in cocrystals 5, 6 and 7, Cl...O halogen bonds are present. In all of the ten cocrystals, π–π stacking inter­actions are observed.

Computing details

Data collection: APEX2 (Bruker, 2014) for COCRYSTAL-1, COCRYSTAL-2, COCRYSTAL-5; CrysAlis PRO (Agilent, 2014) for COCRYSTAL-3, COCRYSTAL-6, COCRYSTAL-7, COCRYSTAL-8, COCRYSTAL-9, COCRYSTAL-10; CrysAlis PRO (Oxford Diffraction, 2011) for COCRYSTAL-4. Cell refinement: SAINT (Bruker, 2014) for COCRYSTAL-1, COCRYSTAL-2; CrysAlis PRO (Agilent, 2014) for COCRYSTAL-3, COCRYSTAL-6, COCRYSTAL-7, COCRYSTAL-8, COCRYSTAL-9, COCRYSTAL-10; CrysAlis PRO (Oxford Diffraction, 2011) for COCRYSTAL-4; SAINT (Bruker, 2013) for COCRYSTAL-5. Data reduction: SAINT (Bruker, 2014) for COCRYSTAL-1, COCRYSTAL-2; CrysAlis PRO (Agilent, 2014) for COCRYSTAL-3, COCRYSTAL-6, COCRYSTAL-7, COCRYSTAL-8, COCRYSTAL-9, COCRYSTAL-10; CrysAlis PRO (Oxford Diffraction, 2011) for COCRYSTAL-4; SAINT (Bruker, 2013) for COCRYSTAL-5. Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for COCRYSTAL-1, COCRYSTAL-2, COCRYSTAL-5; SHELXT (Sheldrick, 2015a) for COCRYSTAL-3, COCRYSTAL-4, COCRYSTAL-6, COCRYSTAL-7, COCRYSTAL-8, COCRYSTAL-9, COCRYSTAL-10. Program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b) for COCRYSTAL-1, COCRYSTAL-2; SHELXL2014 (Sheldrick, 2015b) for COCRYSTAL-3, COCRYSTAL-4, COCRYSTAL-6, COCRYSTAL-7, COCRYSTAL-8, COCRYSTAL-9, COCRYSTAL-10; SHELXL2014 (Sheldrick, 2015b) and shelXle (Hübschle et al., 2011) for COCRYSTAL-5. Molecular graphics: SHELXTL (Sheldrick, 2008) for COCRYSTAL-1, COCRYSTAL-2, COCRYSTAL-3, COCRYSTAL-4, COCRYSTAL-7, COCRYSTAL-8, COCRYSTAL-9, COCRYSTAL-10; SHELXT (Sheldrick, 2008) for COCRYSTAL-6. Software used to prepare material for publication: SHELXTL (Sheldrick, 2008) for COCRYSTAL-1, COCRYSTAL-2, COCRYSTAL-3, COCRYSTAL-4, COCRYSTAL-7, COCRYSTAL-8, COCRYSTAL-9, COCRYSTAL-10; SHELXT (Sheldrick, 2008) for COCRYSTAL-6.

4-Amino-5-chloro-2,6-dimethylpyrimidine–3-bromothiophene-2-carboxylic acid (1/1) (COCRYSTAL-1)

Crystal data

C5H3BrO2S·C6H8ClN3	Z = 2
Mr = 364.65	F(000) = 364
Triclinic, P1	Dx = 1.799 Mg m^−3
a = 7.5237 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.5739 (4) Å	Cell parameters from 9311 reflections
c = 12.5089 (7) Å	θ = 2.8–33.2°
α = 79.629 (2)°	µ = 3.41 mm^−1
β = 79.596 (2)°	T = 100 K
γ = 75.895 (2)°	Block, colourless
V = 673.00 (6) Å^3	0.31 × 0.27 × 0.21 mm

Data collection

Bruker D8 Quest CMOS diffractometer	4471 reflections with I > 2σ(I)
Radiation source: I-mu-S microsource X-ray tube	Rint = 0.032
ω and phi scans	θmax = 33.2°, θmin = 2.8°
Absorption correction: multi-scan (APEX2; Bruker, 2014)	h = −11→10
Tmin = 0.539, Tmax = 0.747	k = −11→11
13063 measured reflections	l = −19→19
5103 independent reflections

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)] = 0.034	Hydrogen site location: mixed
wR(F^2) = 0.070	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.010P)^2 + 0.8813P] where P = (Fo^2 + 2Fc^2)/3
5103 reflections	(Δ/σ)max < 0.001
187 parameters	Δρmax = 0.67 e Å^−3
0 restraints	Δρmin = −0.52 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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Br1	0.17359 (2)	−0.20786 (2)	0.99807 (2)	0.01468 (5)
S1	0.71218 (6)	−0.09607 (6)	0.83962 (4)	0.01414 (9)
O1B	0.4649 (2)	0.1721 (2)	0.71276 (12)	0.0203 (3)
H1A	0.396 (5)	0.264 (5)	0.673 (3)	0.050 (10)*
O2B	0.1948 (2)	0.1035 (2)	0.79633 (13)	0.0221 (3)
C1B	0.3626 (3)	0.0767 (2)	0.78633 (15)	0.0134 (3)
C2B	0.4747 (2)	−0.0686 (2)	0.85783 (14)	0.0113 (3)
C3B	0.4191 (2)	−0.1903 (2)	0.94601 (15)	0.0108 (3)
C4B	0.5662 (2)	−0.3038 (2)	0.99870 (15)	0.0131 (3)
H4AA	0.550993	−0.393948	1.061103	0.016*
C5B	0.7327 (3)	−0.2678 (2)	0.94879 (16)	0.0156 (3)
H5AA	0.847630	−0.331186	0.972153	0.019*
Cl1	0.20623 (6)	0.53889 (6)	0.26918 (4)	0.01714 (9)
N1A	0.2875 (2)	0.4395 (2)	0.58151 (13)	0.0135 (3)
C1A	0.2123 (2)	0.6060 (2)	0.61071 (15)	0.0128 (3)
N3A	0.1304 (2)	0.7519 (2)	0.54593 (13)	0.0127 (3)
N4A	0.0334 (2)	0.8728 (2)	0.37794 (14)	0.0146 (3)
H4B1	−0.013 (4)	0.970 (4)	0.401 (2)	0.027 (7)*
H4B2	0.012 (4)	0.856 (4)	0.318 (2)	0.027 (7)*
C4A	0.1219 (2)	0.7307 (2)	0.44175 (14)	0.0111 (3)
C5A	0.2057 (2)	0.5596 (2)	0.40456 (14)	0.0117 (3)
C6A	0.2853 (2)	0.4153 (2)	0.47652 (15)	0.0129 (3)
C7A	0.2190 (3)	0.6288 (3)	0.72665 (16)	0.0184 (4)
H7BA	0.346202	0.583683	0.742949	0.028*
H7BB	0.137498	0.558307	0.777376	0.028*
H7BC	0.177617	0.759176	0.735254	0.028*
C8A	0.3708 (3)	0.2269 (3)	0.44675 (17)	0.0193 (4)
H8B1	0.413316	0.144726	0.511493	0.029*	0.50 (3)
H8B2	0.476348	0.233326	0.388531	0.029*	0.50 (3)
H8B3	0.278688	0.179407	0.420768	0.029*	0.50 (3)
H8B4	0.376237	0.229615	0.367619	0.029*	0.50 (3)
H8B5	0.295740	0.140367	0.486933	0.029*	0.50 (3)
H8B6	0.496375	0.187476	0.466240	0.029*	0.50 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.01179 (8)	0.01544 (8)	0.01657 (9)	−0.00349 (6)	−0.00291 (6)	−0.00006 (6)
S1	0.01211 (18)	0.01347 (19)	0.0168 (2)	−0.00285 (14)	−0.00211 (15)	−0.00203 (15)
O1B	0.0187 (6)	0.0178 (6)	0.0202 (7)	−0.0021 (5)	−0.0034 (5)	0.0064 (5)
O2B	0.0174 (6)	0.0246 (7)	0.0219 (8)	−0.0032 (5)	−0.0092 (6)	0.0072 (6)
C1B	0.0168 (8)	0.0131 (7)	0.0107 (8)	−0.0022 (6)	−0.0044 (6)	−0.0018 (6)
C2B	0.0122 (7)	0.0107 (7)	0.0115 (8)	−0.0014 (6)	−0.0042 (6)	−0.0018 (6)
C3B	0.0104 (7)	0.0098 (7)	0.0131 (8)	−0.0016 (5)	−0.0033 (6)	−0.0034 (6)
C4B	0.0161 (7)	0.0106 (7)	0.0139 (8)	−0.0024 (6)	−0.0075 (6)	−0.0002 (6)
C5B	0.0147 (7)	0.0130 (8)	0.0196 (9)	−0.0008 (6)	−0.0076 (7)	−0.0019 (6)
Cl1	0.0222 (2)	0.0184 (2)	0.01073 (19)	−0.00160 (16)	−0.00411 (16)	−0.00395 (15)
N1A	0.0160 (7)	0.0110 (6)	0.0125 (7)	−0.0013 (5)	−0.0039 (5)	0.0004 (5)
C1A	0.0138 (7)	0.0125 (7)	0.0118 (8)	−0.0030 (6)	−0.0034 (6)	0.0006 (6)
N3A	0.0156 (7)	0.0112 (6)	0.0111 (7)	−0.0026 (5)	−0.0035 (5)	−0.0004 (5)
N4A	0.0205 (7)	0.0100 (7)	0.0123 (7)	0.0002 (6)	−0.0063 (6)	−0.0002 (5)
C4A	0.0112 (7)	0.0110 (7)	0.0111 (7)	−0.0030 (5)	−0.0019 (6)	−0.0005 (6)
C5A	0.0146 (7)	0.0115 (7)	0.0090 (7)	−0.0025 (6)	−0.0023 (6)	−0.0012 (5)
C6A	0.0131 (7)	0.0118 (7)	0.0130 (8)	−0.0029 (6)	−0.0012 (6)	−0.0001 (6)
C7A	0.0242 (9)	0.0207 (9)	0.0106 (8)	−0.0035 (7)	−0.0062 (7)	−0.0012 (6)
C8A	0.0225 (9)	0.0122 (8)	0.0203 (9)	0.0017 (7)	−0.0032 (7)	−0.0023 (7)

Geometric parameters (Å, º)

Br1—C3B	1.8729 (17)	C1A—N3A	1.335 (2)
Br1—Br1^i	3.5693 (4)	C1A—C7A	1.502 (3)
Br1—Cl1^ii	3.6014 (5)	N3A—C4A	1.356 (2)
Br1—S1^iii	3.6656 (5)	N4A—C4A	1.331 (2)
S1—C5B	1.7083 (19)	N4A—H4B1	0.81 (3)
S1—C2B	1.7253 (17)	N4A—H4B2	0.83 (3)
O1B—C1B	1.318 (2)	C4A—C5A	1.416 (2)
O1B—H1A	0.89 (3)	C5A—C6A	1.373 (2)
O2B—C1B	1.216 (2)	C6A—C8A	1.499 (3)
C1B—C2B	1.479 (2)	C7A—H7BA	0.9800
C2B—C3B	1.377 (2)	C7A—H7BB	0.9800
C3B—C4B	1.412 (2)	C7A—H7BC	0.9800
C4B—C5B	1.362 (3)	C8A—H8B1	0.9800
C4B—H4AA	0.9500	C8A—H8B2	0.9800
C5B—H5AA	0.9500	C8A—H8B3	0.9800
Cl1—C5A	1.7276 (18)	C8A—H8B4	0.9800
N1A—C1A	1.337 (2)	C8A—H8B5	0.9800
N1A—C6A	1.362 (2)	C8A—H8B6	0.9800
C3B—Br1—Br1^i	118.11 (5)	C4A—N4A—H4B2	118.9 (19)
C3B—Br1—Cl1^ii	102.47 (5)	H4B1—N4A—H4B2	120 (3)
Br1^i—Br1—Cl1^ii	111.923 (11)	N4A—C4A—N3A	118.32 (16)
C3B—Br1—S1^iii	73.14 (5)	N4A—C4A—C5A	122.24 (16)
Br1^i—Br1—S1^iii	69.809 (10)	N3A—C4A—C5A	119.44 (15)
Cl1^ii—Br1—S1^iii	73.552 (12)	C6A—C5A—C4A	119.30 (16)
C5B—S1—C2B	91.90 (9)	C6A—C5A—Cl1	121.77 (14)
C1B—O1B—H1A	112 (2)	C4A—C5A—Cl1	118.93 (13)
O2B—C1B—O1B	124.83 (17)	N1A—C6A—C5A	119.82 (16)
O2B—C1B—C2B	122.74 (17)	N1A—C6A—C8A	116.65 (16)
O1B—C1B—C2B	112.43 (15)	C5A—C6A—C8A	123.52 (17)
C3B—C2B—C1B	129.82 (16)	C1A—C7A—H7BA	109.5
C3B—C2B—S1	110.12 (12)	C1A—C7A—H7BB	109.5
C1B—C2B—S1	119.99 (13)	H7BA—C7A—H7BB	109.5
C2B—C3B—C4B	113.85 (15)	C1A—C7A—H7BC	109.5
C2B—C3B—Br1	125.30 (13)	H7BA—C7A—H7BC	109.5
C4B—C3B—Br1	120.84 (13)	H7BB—C7A—H7BC	109.5
C5B—C4B—C3B	111.48 (16)	C6A—C8A—H8B1	109.5
C5B—C4B—H4AA	124.3	C6A—C8A—H8B2	109.5
C3B—C4B—H4AA	124.3	H8B1—C8A—H8B2	109.5
C4B—C5B—S1	112.65 (13)	C6A—C8A—H8B3	109.5
C4B—C5B—H5AA	123.7	H8B1—C8A—H8B3	109.5
S1—C5B—H5AA	123.7	H8B2—C8A—H8B3	109.5
C1A—N1A—C6A	118.14 (15)	C6A—C8A—H8B4	109.5
N3A—C1A—N1A	125.43 (17)	C6A—C8A—H8B5	109.5
N3A—C1A—C7A	117.73 (16)	H8B4—C8A—H8B5	109.5
N1A—C1A—C7A	116.83 (15)	C6A—C8A—H8B6	109.5
C1A—N3A—C4A	117.78 (15)	H8B4—C8A—H8B6	109.5
C4A—N4A—H4B1	121 (2)	H8B5—C8A—H8B6	109.5
O2B—C1B—C2B—C3B	−2.5 (3)	C3B—C4B—C5B—S1	0.7 (2)
O1B—C1B—C2B—C3B	177.09 (18)	C2B—S1—C5B—C4B	−0.41 (15)
O2B—C1B—C2B—S1	−179.15 (15)	C6A—N1A—C1A—N3A	1.6 (3)
O1B—C1B—C2B—S1	0.4 (2)	C6A—N1A—C1A—C7A	−179.29 (16)
C5B—S1—C2B—C3B	0.04 (14)	N1A—C1A—N3A—C4A	0.1 (3)
C5B—S1—C2B—C1B	177.34 (15)	C7A—C1A—N3A—C4A	−179.07 (16)
C1B—C2B—C3B—C4B	−176.64 (17)	C1A—N3A—C4A—N4A	177.07 (16)
S1—C2B—C3B—C4B	0.32 (19)	C1A—N3A—C4A—C5A	−2.6 (2)
C1B—C2B—C3B—Br1	2.0 (3)	N4A—C4A—C5A—C6A	−176.19 (17)
S1—C2B—C3B—Br1	178.93 (9)	N3A—C4A—C5A—C6A	3.4 (3)
Br1^i—Br1—C3B—C2B	−39.37 (17)	N4A—C4A—C5A—Cl1	4.3 (2)
Cl1^ii—Br1—C3B—C2B	−162.85 (14)	N3A—C4A—C5A—Cl1	−176.06 (13)
S1^iii—Br1—C3B—C2B	−94.57 (15)	C1A—N1A—C6A—C5A	−0.6 (3)
Br1^i—Br1—C3B—C4B	139.14 (12)	C1A—N1A—C6A—C8A	−179.97 (16)
Cl1^ii—Br1—C3B—C4B	15.66 (15)	C4A—C5A—C6A—N1A	−1.8 (3)
S1^iii—Br1—C3B—C4B	83.94 (14)	Cl1—C5A—C6A—N1A	177.67 (13)
C2B—C3B—C4B—C5B	−0.6 (2)	C4A—C5A—C6A—C8A	177.52 (17)
Br1—C3B—C4B—C5B	−179.30 (13)	Cl1—C5A—C6A—C8A	−3.0 (3)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1B—H1A···N1A	0.89 (3)	1.73 (4)	2.618 (2)	172 (3)
C5B—H5AA···Br1^iv	0.95	2.92	3.6281 (18)	133
N4A—H4B1···N3A^v	0.81 (3)	2.25 (3)	3.058 (2)	176 (3)
N4A—H4B2···O2B^vi	0.83 (3)	2.23 (3)	2.965 (2)	148 (3)
C8A—H8B4···Cl1	0.98	2.59	3.119 (2)	114

Symmetry codes: (iv) x+1, y, z; (v) −x, −y+2, −z+1; (vi) −x, −y+1, −z+1.

4-Amino-5-chloro-2,6-dimethylpyrimidine–5-chlorothiophene-2-carboxylic acid (1/1) (COCRYSTAL-2)

Crystal data

C6H8ClN3·C5H3ClO2S	Z = 2
Mr = 320.19	F(000) = 328
Triclinic, P1	Dx = 1.612 Mg m^−3
a = 7.2182 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.6364 (3) Å	Cell parameters from 5911 reflections
c = 12.7516 (6) Å	θ = 2.8–29.6°
α = 90.707 (2)°	µ = 0.65 mm^−1
β = 102.629 (2)°	T = 100 K
γ = 105.338 (2)°	Rod, colourless
V = 659.61 (5) Å^3	0.37 × 0.19 × 0.11 mm

Data collection

Bruker D8 Quest CMOS diffractometer	2947 reflections with I > 2σ(I)
Radiation source: I-mu-S microsource X-ray tube	Rint = 0.051
ω and phi scans	θmax = 29.6°, θmin = 2.8°
Absorption correction: multi-scan (APEX2; Bruker, 2014)	h = −10→9
Tmin = 0.477, Tmax = 0.746	k = −10→10
8796 measured reflections	l = −17→17
3636 independent reflections

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)] = 0.051	Hydrogen site location: mixed
wR(F^2) = 0.138	H atoms treated by a mixture of independent and constrained refinement
S = 1.15	w = 1/[σ^2(Fo^2) + (0.0554P)^2 + 0.5883P] where P = (Fo^2 + 2Fc^2)/3
3636 reflections	(Δ/σ)max < 0.001
187 parameters	Δρmax = 0.76 e Å^−3
0 restraints	Δρmin = −0.56 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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1B	−0.28477 (8)	−0.34293 (8)	0.00245 (5)	0.01882 (16)
S1B	0.04024 (8)	−0.07368 (8)	0.15616 (5)	0.01421 (15)
O1B	0.3910 (3)	0.1819 (2)	0.29123 (14)	0.0189 (4)
H1A	0.498 (6)	0.281 (6)	0.332 (4)	0.059 (13)*
O2B	0.6159 (2)	0.1262 (3)	0.20660 (15)	0.0212 (4)
C1B	0.4469 (3)	0.0974 (3)	0.21763 (19)	0.0155 (5)
C2B	0.2832 (3)	−0.0399 (3)	0.14660 (18)	0.0133 (4)
C3B	0.2971 (3)	−0.1483 (3)	0.06501 (19)	0.0153 (4)
H3AA	0.418792	−0.147819	0.047805	0.018*
C4B	0.1128 (3)	−0.2620 (3)	0.00817 (19)	0.0161 (5)
H4AA	0.096144	−0.346000	−0.050993	0.019*
C5B	−0.0382 (3)	−0.2356 (3)	0.04925 (18)	0.0142 (4)
Cl1A	0.94838 (8)	0.51403 (8)	0.72886 (4)	0.01724 (15)
N1A	0.6580 (3)	0.4397 (3)	0.42204 (16)	0.0134 (4)
C2A	0.7088 (3)	0.6114 (3)	0.39334 (18)	0.0128 (4)
N3A	0.8311 (3)	0.7539 (3)	0.45660 (15)	0.0133 (4)
N4A	1.0414 (3)	0.8636 (3)	0.62157 (16)	0.0144 (4)
H4B1	1.076 (5)	0.974 (5)	0.602 (3)	0.035 (9)*
H4B2	1.119 (4)	0.855 (4)	0.683 (3)	0.021 (8)*
C4A	0.9120 (3)	0.7244 (3)	0.55926 (18)	0.0117 (4)
C5A	0.8567 (3)	0.5476 (3)	0.59597 (17)	0.0119 (4)
C6A	0.7326 (3)	0.4068 (3)	0.52538 (18)	0.0135 (4)
C7A	0.6204 (4)	0.6424 (4)	0.27936 (19)	0.0177 (5)
H7BA	0.652565	0.773352	0.270051	0.027*
H7BB	0.476747	0.591891	0.264024	0.027*
H7BC	0.674362	0.582116	0.229662	0.027*
C8A	0.6708 (4)	0.2145 (3)	0.5550 (2)	0.0171 (5)
H8B1	0.610279	0.133235	0.489367	0.026*	0.50 (4)
H8B2	0.574907	0.204034	0.600045	0.026*	0.50 (4)
H8B3	0.786587	0.180211	0.595054	0.026*	0.50 (4)
H8B4	0.718728	0.209791	0.632726	0.026*	0.50 (4)
H8B5	0.726639	0.137893	0.515809	0.026*	0.50 (4)
H8B6	0.526406	0.169796	0.535931	0.026*	0.50 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1B	0.0139 (3)	0.0185 (3)	0.0179 (3)	−0.0015 (2)	−0.0017 (2)	−0.0007 (2)
S1B	0.0142 (3)	0.0142 (3)	0.0121 (3)	0.0010 (2)	0.0022 (2)	−0.0021 (2)
O1B	0.0167 (8)	0.0180 (9)	0.0170 (9)	−0.0026 (7)	0.0025 (7)	−0.0078 (7)
O2B	0.0129 (8)	0.0256 (10)	0.0209 (9)	0.0020 (7)	−0.0009 (7)	−0.0037 (7)
C1B	0.0169 (11)	0.0118 (11)	0.0139 (11)	0.0007 (9)	−0.0007 (8)	0.0001 (9)
C2B	0.0114 (10)	0.0147 (11)	0.0116 (10)	0.0018 (8)	−0.0002 (8)	0.0022 (8)
C3B	0.0141 (10)	0.0150 (11)	0.0158 (11)	0.0036 (9)	0.0022 (8)	0.0009 (9)
C4B	0.0195 (11)	0.0152 (11)	0.0099 (10)	0.0023 (9)	−0.0013 (8)	−0.0041 (9)
C5B	0.0143 (10)	0.0127 (11)	0.0118 (10)	0.0007 (8)	−0.0015 (8)	0.0001 (8)
Cl1A	0.0200 (3)	0.0183 (3)	0.0099 (3)	0.0019 (2)	0.0002 (2)	0.0015 (2)
N1A	0.0117 (9)	0.0128 (9)	0.0131 (9)	−0.0008 (7)	0.0028 (7)	−0.0024 (7)
C2A	0.0107 (10)	0.0156 (11)	0.0106 (10)	0.0022 (8)	0.0014 (8)	−0.0028 (8)
N3A	0.0122 (9)	0.0143 (9)	0.0120 (9)	0.0018 (7)	0.0022 (7)	0.0001 (7)
N4A	0.0167 (9)	0.0121 (10)	0.0101 (9)	−0.0005 (8)	−0.0002 (7)	−0.0025 (8)
C4A	0.0105 (10)	0.0125 (10)	0.0120 (10)	0.0036 (8)	0.0018 (8)	−0.0009 (8)
C5A	0.0127 (10)	0.0145 (11)	0.0071 (9)	0.0025 (8)	0.0010 (7)	−0.0001 (8)
C6A	0.0142 (10)	0.0142 (11)	0.0122 (10)	0.0026 (9)	0.0046 (8)	−0.0008 (8)
C7A	0.0178 (11)	0.0220 (12)	0.0118 (11)	0.0045 (10)	0.0013 (8)	0.0029 (9)
C8A	0.0193 (11)	0.0103 (11)	0.0171 (11)	−0.0026 (9)	0.0031 (9)	0.0006 (9)

Geometric parameters (Å, º)

Cl1B—C5B	1.717 (2)	N3A—C4A	1.360 (3)
S1B—C5B	1.720 (2)	N4A—C4A	1.328 (3)
S1B—C2B	1.735 (2)	N4A—H4B1	0.87 (4)
O1B—C1B	1.322 (3)	N4A—H4B2	0.87 (3)
O1B—H1A	0.97 (5)	C4A—C5A	1.419 (3)
O2B—C1B	1.221 (3)	C5A—C6A	1.372 (3)
C1B—C2B	1.473 (3)	C6A—C8A	1.497 (3)
C2B—C3B	1.359 (3)	C7A—H7BA	0.9800
C3B—C4B	1.414 (3)	C7A—H7BB	0.9800
C3B—H3AA	0.9500	C7A—H7BC	0.9800
C4B—C5B	1.366 (3)	C8A—H8B1	0.9800
C4B—H4AA	0.9500	C8A—H8B2	0.9800
Cl1A—C5A	1.728 (2)	C8A—H8B3	0.9800
N1A—C2A	1.343 (3)	C8A—H8B4	0.9800
N1A—C6A	1.364 (3)	C8A—H8B5	0.9800
C2A—N3A	1.332 (3)	C8A—H8B6	0.9800
C2A—C7A	1.503 (3)
C5B—S1B—C2B	90.45 (11)	N4A—C4A—C5A	122.4 (2)
C1B—O1B—H1A	113 (3)	N3A—C4A—C5A	119.4 (2)
O2B—C1B—O1B	125.2 (2)	C6A—C5A—C4A	119.5 (2)
O2B—C1B—C2B	121.2 (2)	C6A—C5A—Cl1A	121.36 (18)
O1B—C1B—C2B	113.6 (2)	C4A—C5A—Cl1A	119.13 (17)
C3B—C2B—C1B	126.5 (2)	N1A—C6A—C5A	119.7 (2)
C3B—C2B—S1B	111.65 (18)	N1A—C6A—C8A	116.7 (2)
C1B—C2B—S1B	121.84 (18)	C5A—C6A—C8A	123.7 (2)
C2B—C3B—C4B	113.5 (2)	C2A—C7A—H7BA	109.5
C2B—C3B—H3AA	123.3	C2A—C7A—H7BB	109.5
C4B—C3B—H3AA	123.3	H7BA—C7A—H7BB	109.5
C5B—C4B—C3B	111.3 (2)	C2A—C7A—H7BC	109.5
C5B—C4B—H4AA	124.3	H7BA—C7A—H7BC	109.5
C3B—C4B—H4AA	124.3	H7BB—C7A—H7BC	109.5
C4B—C5B—Cl1B	126.31 (19)	C6A—C8A—H8B1	109.5
C4B—C5B—S1B	113.09 (18)	C6A—C8A—H8B2	109.5
Cl1B—C5B—S1B	120.59 (14)	H8B1—C8A—H8B2	109.5
C2A—N1A—C6A	118.1 (2)	C6A—C8A—H8B3	109.5
N3A—C2A—N1A	125.6 (2)	H8B1—C8A—H8B3	109.5
N3A—C2A—C7A	118.0 (2)	H8B2—C8A—H8B3	109.5
N1A—C2A—C7A	116.4 (2)	C6A—C8A—H8B4	109.5
C2A—N3A—C4A	117.65 (19)	C6A—C8A—H8B5	109.5
C4A—N4A—H4B1	124 (2)	H8B4—C8A—H8B5	109.5
C4A—N4A—H4B2	125 (2)	C6A—C8A—H8B6	109.5
H4B1—N4A—H4B2	110 (3)	H8B4—C8A—H8B6	109.5
N4A—C4A—N3A	118.2 (2)	H8B5—C8A—H8B6	109.5
O2B—C1B—C2B—C3B	0.8 (4)	N1A—C2A—N3A—C4A	−0.1 (3)
O1B—C1B—C2B—C3B	−179.3 (2)	C7A—C2A—N3A—C4A	−179.31 (19)
O2B—C1B—C2B—S1B	−176.30 (18)	C2A—N3A—C4A—N4A	176.8 (2)
O1B—C1B—C2B—S1B	3.6 (3)	C2A—N3A—C4A—C5A	−2.9 (3)
C5B—S1B—C2B—C3B	0.25 (18)	N4A—C4A—C5A—C6A	−175.5 (2)
C5B—S1B—C2B—C1B	177.78 (19)	N3A—C4A—C5A—C6A	4.3 (3)
C1B—C2B—C3B—C4B	−177.6 (2)	N4A—C4A—C5A—Cl1A	4.2 (3)
S1B—C2B—C3B—C4B	−0.2 (3)	N3A—C4A—C5A—Cl1A	−176.07 (16)
C2B—C3B—C4B—C5B	0.0 (3)	C2A—N1A—C6A—C5A	−0.4 (3)
C3B—C4B—C5B—Cl1B	178.81 (17)	C2A—N1A—C6A—C8A	179.17 (19)
C3B—C4B—C5B—S1B	0.1 (3)	C4A—C5A—C6A—N1A	−2.5 (3)
C2B—S1B—C5B—C4B	−0.22 (19)	Cl1A—C5A—C6A—N1A	177.80 (16)
C2B—S1B—C5B—Cl1B	−178.97 (15)	C4A—C5A—C6A—C8A	177.9 (2)
C6A—N1A—C2A—N3A	1.8 (3)	Cl1A—C5A—C6A—C8A	−1.7 (3)
C6A—N1A—C2A—C7A	−178.94 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1B—H1A···N1A	0.97 (5)	1.66 (5)	2.623 (3)	169 (4)
C4B—H4AA···Cl1A^i	0.95	2.86	3.734 (2)	154
N4A—H4B1···N3A^ii	0.87 (4)	2.20 (4)	3.070 (3)	176 (3)
N4A—H4B2···O2B^iii	0.87 (3)	2.08 (3)	2.907 (3)	157 (3)
C7A—H7BB···Cl1A^iv	0.98	2.98	3.938 (2)	166
C7A—H7BC···Cl1A^iii	0.98	2.94	3.638 (2)	129
C8A—H8B4···Cl1A	0.98	2.58	3.110 (3)	114
C8A—H8B5···N4A^iii	0.98	2.68	3.523 (3)	145

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

4-Amino-5-chloro-2,6-dimethylpyrimidine—2,4-dichlorobenzoic acid (1/1) (COCRYSTAL-3)

Crystal data

C6H8ClN3·C7H4Cl2O2	Z = 2
Mr = 348.61	F(000) = 356
Triclinic, P1	Dx = 1.568 Mg m^−3
a = 7.3015 (4) Å	Cu Kα radiation, λ = 1.54184 Å
b = 7.5060 (6) Å	Cell parameters from 2184 reflections
c = 14.9665 (8) Å	θ = 3.0–75.8°
α = 92.539 (5)°	µ = 5.70 mm^−1
β = 98.522 (5)°	T = 120 K
γ = 113.657 (7)°	Plate, colorless
V = 738.12 (9) Å^3	0.51 × 0.35 × 0.08 mm

Data collection

Agilent SuperNova Dual Source diffractometer with an Atlas detector	3050 independent reflections
Radiation source: sealed X-ray tube	2546 reflections with I > 2σ(I)
Detector resolution: 10.6501 pixels mm^-1	Rint = 0.038
ω scans	θmax = 76.9°, θmin = 3.0°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	h = −4→9
Tmin = 0.538, Tmax = 1.000	k = −9→8
5965 measured reflections	l = −18→17

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.135	w = 1/[σ^2(Fo^2) + (0.0781P)^2 + 0.423P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
3050 reflections	Δρmax = 0.39 e Å^−3
204 parameters	Δρmin = −0.51 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.

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

	x	y	z	Uiso*/Ueq
Cl1	0.92360 (9)	0.67568 (9)	1.08079 (4)	0.02879 (18)
N1A	0.5642 (3)	0.4615 (3)	0.84009 (15)	0.0255 (5)
C2A	0.4796 (4)	0.2733 (4)	0.85176 (17)	0.0249 (5)
N3A	0.5203 (3)	0.1957 (3)	0.92717 (15)	0.0239 (4)
N4A	0.6923 (4)	0.2415 (4)	1.07384 (16)	0.0278 (5)
H41	0.624 (5)	0.118 (5)	1.077 (2)	0.024 (8)*
H42	0.760 (6)	0.318 (6)	1.124 (3)	0.047 (11)*
C4A	0.6537 (4)	0.3192 (4)	0.99820 (17)	0.0232 (5)
C5A	0.7488 (4)	0.5206 (4)	0.98982 (18)	0.0246 (5)
C6A	0.7034 (4)	0.5891 (4)	0.90944 (18)	0.0251 (5)
C7A	0.3234 (4)	0.1328 (4)	0.77562 (18)	0.0295 (6)
H7AA	0.2789	0.2062	0.7313	0.044*
H7AB	0.2064	0.0450	0.8001	0.044*
H7AC	0.3828	0.0556	0.7458	0.044*
C8A	0.8001 (5)	0.7990 (4)	0.8943 (2)	0.0349 (6)
H8AA	0.7555	0.8135	0.8310	0.052*
H8AB	0.9483	0.8446	0.9068	0.052*
H8AC	0.7600	0.8771	0.9351	0.052*
Cl2	−0.04948 (10)	0.74463 (11)	0.61458 (4)	0.03186 (19)
Cl3	0.20778 (12)	0.87604 (12)	0.29833 (4)	0.0372 (2)
O1B	0.4692 (4)	0.5681 (4)	0.68251 (15)	0.0382 (5)
H1B	0.503 (7)	0.540 (8)	0.739 (4)	0.080 (16)*
O2B	0.2353 (4)	0.6429 (4)	0.73334 (14)	0.0446 (6)
C1B	0.2906 (4)	0.6968 (4)	0.58101 (17)	0.0243 (5)
C2B	0.1298 (4)	0.7480 (4)	0.54990 (18)	0.0253 (5)
C3B	0.1030 (4)	0.8021 (4)	0.46282 (18)	0.0275 (5)
H3BA	−0.0074	0.8352	0.4420	0.033*
C4B	0.2400 (4)	0.8069 (4)	0.40696 (17)	0.0269 (5)
C5B	0.4022 (4)	0.7595 (4)	0.43580 (19)	0.0297 (6)
H5BA	0.4956	0.7643	0.3970	0.036*
C6B	0.4252 (4)	0.7051 (4)	0.52212 (19)	0.0280 (6)
H6BA	0.5361	0.6721	0.5423	0.034*
C7B	0.3271 (4)	0.6335 (4)	0.67360 (18)	0.0262 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0287 (3)	0.0286 (3)	0.0280 (3)	0.0116 (3)	0.0029 (2)	0.0030 (2)
N1A	0.0263 (11)	0.0300 (11)	0.0245 (10)	0.0148 (9)	0.0056 (9)	0.0107 (9)
C2A	0.0243 (12)	0.0306 (13)	0.0246 (12)	0.0154 (10)	0.0056 (10)	0.0079 (10)
N3A	0.0246 (10)	0.0270 (11)	0.0236 (10)	0.0131 (9)	0.0054 (8)	0.0093 (8)
N4A	0.0312 (12)	0.0272 (12)	0.0237 (11)	0.0110 (10)	0.0021 (9)	0.0100 (9)
C4A	0.0220 (11)	0.0282 (13)	0.0240 (12)	0.0137 (10)	0.0064 (9)	0.0075 (10)
C5A	0.0250 (12)	0.0271 (13)	0.0245 (12)	0.0131 (10)	0.0053 (10)	0.0056 (10)
C6A	0.0239 (12)	0.0281 (13)	0.0291 (13)	0.0150 (10)	0.0077 (10)	0.0098 (10)
C7A	0.0320 (13)	0.0322 (14)	0.0245 (12)	0.0140 (11)	0.0029 (11)	0.0076 (10)
C8A	0.0362 (15)	0.0311 (15)	0.0389 (16)	0.0147 (12)	0.0059 (12)	0.0141 (12)
Cl2	0.0287 (3)	0.0419 (4)	0.0303 (3)	0.0192 (3)	0.0063 (3)	0.0086 (3)
Cl3	0.0436 (4)	0.0511 (4)	0.0232 (3)	0.0265 (3)	0.0023 (3)	0.0115 (3)
O1B	0.0455 (12)	0.0577 (14)	0.0298 (11)	0.0366 (11)	0.0114 (9)	0.0233 (10)
O2B	0.0569 (14)	0.0731 (17)	0.0245 (10)	0.0463 (13)	0.0097 (10)	0.0133 (10)
C1B	0.0267 (12)	0.0211 (12)	0.0228 (12)	0.0092 (10)	−0.0004 (9)	0.0021 (9)
C2B	0.0262 (12)	0.0239 (12)	0.0258 (12)	0.0109 (10)	0.0030 (10)	0.0042 (9)
C3B	0.0274 (12)	0.0268 (13)	0.0269 (13)	0.0123 (11)	−0.0025 (10)	0.0034 (10)
C4B	0.0342 (14)	0.0271 (13)	0.0190 (11)	0.0133 (11)	0.0007 (10)	0.0053 (9)
C5B	0.0317 (14)	0.0338 (14)	0.0263 (13)	0.0163 (12)	0.0048 (11)	0.0062 (11)
C6B	0.0290 (13)	0.0320 (14)	0.0270 (13)	0.0176 (11)	0.0016 (10)	0.0066 (10)
C7B	0.0301 (13)	0.0243 (12)	0.0250 (12)	0.0127 (11)	0.0026 (10)	0.0037 (10)

Geometric parameters (Å, º)

Cl1—C5A	1.729 (3)	C8A—H8AC	0.9800
N1A—C2A	1.327 (4)	Cl2—C2B	1.733 (3)
N1A—C6A	1.359 (4)	Cl3—C4B	1.740 (3)
C2A—N3A	1.341 (3)	O1B—C7B	1.307 (3)
C2A—C7A	1.502 (4)	O1B—H1B	0.90 (5)
N3A—C4A	1.349 (3)	O2B—C7B	1.210 (4)
N4A—C4A	1.340 (3)	C1B—C6B	1.399 (4)
N4A—H41	0.87 (4)	C1B—C2B	1.400 (4)
N4A—H42	0.87 (4)	C1B—C7B	1.506 (3)
C4A—C5A	1.408 (4)	C2B—C3B	1.392 (4)
C5A—C6A	1.377 (4)	C3B—C4B	1.387 (4)
C6A—C8A	1.489 (4)	C3B—H3BA	0.9500
C7A—H7AA	0.9800	C4B—C5B	1.384 (4)
C7A—H7AB	0.9800	C5B—C6B	1.379 (4)
C7A—H7AC	0.9800	C5B—H5BA	0.9500
C8A—H8AA	0.9800	C6B—H6BA	0.9500
C8A—H8AB	0.9800
C2A—N1A—C6A	118.5 (2)	C6A—C8A—H8AC	109.5
N1A—C2A—N3A	125.4 (2)	H8AA—C8A—H8AC	109.5
N1A—C2A—C7A	118.4 (2)	H8AB—C8A—H8AC	109.5
N3A—C2A—C7A	116.2 (2)	C7B—O1B—H1B	115 (3)
C2A—N3A—C4A	117.6 (2)	C6B—C1B—C2B	117.7 (2)
C4A—N4A—H41	119 (2)	C6B—C1B—C7B	118.3 (2)
C4A—N4A—H42	119 (3)	C2B—C1B—C7B	124.0 (2)
H41—N4A—H42	119 (3)	C3B—C2B—C1B	121.0 (2)
N4A—C4A—N3A	117.5 (2)	C3B—C2B—Cl2	115.8 (2)
N4A—C4A—C5A	122.9 (2)	C1B—C2B—Cl2	123.2 (2)
N3A—C4A—C5A	119.6 (2)	C4B—C3B—C2B	118.9 (2)
C6A—C5A—C4A	119.6 (2)	C4B—C3B—H3BA	120.5
C6A—C5A—Cl1	121.5 (2)	C2B—C3B—H3BA	120.5
C4A—C5A—Cl1	118.9 (2)	C5B—C4B—C3B	121.6 (2)
N1A—C6A—C5A	119.3 (2)	C5B—C4B—Cl3	119.4 (2)
N1A—C6A—C8A	117.7 (2)	C3B—C4B—Cl3	119.0 (2)
C5A—C6A—C8A	123.0 (3)	C6B—C5B—C4B	118.5 (3)
C2A—C7A—H7AA	109.5	C6B—C5B—H5BA	120.8
C2A—C7A—H7AB	109.5	C4B—C5B—H5BA	120.8
H7AA—C7A—H7AB	109.5	C5B—C6B—C1B	122.2 (3)
C2A—C7A—H7AC	109.5	C5B—C6B—H6BA	118.9
H7AA—C7A—H7AC	109.5	C1B—C6B—H6BA	118.9
H7AB—C7A—H7AC	109.5	O2B—C7B—O1B	123.7 (2)
C6A—C8A—H8AA	109.5	O2B—C7B—C1B	123.7 (2)
C6A—C8A—H8AB	109.5	O1B—C7B—C1B	112.7 (2)
H8AA—C8A—H8AB	109.5
C6A—N1A—C2A—N3A	−0.2 (4)	C7B—C1B—C2B—C3B	−178.9 (2)
C6A—N1A—C2A—C7A	179.1 (2)	C6B—C1B—C2B—Cl2	179.8 (2)
N1A—C2A—N3A—C4A	2.0 (4)	C7B—C1B—C2B—Cl2	−0.1 (4)
C7A—C2A—N3A—C4A	−177.3 (2)	C1B—C2B—C3B—C4B	−0.7 (4)
C2A—N3A—C4A—N4A	179.3 (2)	Cl2—C2B—C3B—C4B	−179.6 (2)
C2A—N3A—C4A—C5A	−2.0 (4)	C2B—C3B—C4B—C5B	−0.1 (4)
N4A—C4A—C5A—C6A	179.1 (2)	C2B—C3B—C4B—Cl3	−179.6 (2)
N3A—C4A—C5A—C6A	0.4 (4)	C3B—C4B—C5B—C6B	0.5 (4)
N4A—C4A—C5A—Cl1	0.1 (4)	Cl3—C4B—C5B—C6B	180.0 (2)
N3A—C4A—C5A—Cl1	−178.59 (19)	C4B—C5B—C6B—C1B	−0.1 (4)
C2A—N1A—C6A—C5A	−1.5 (4)	C2B—C1B—C6B—C5B	−0.6 (4)
C2A—N1A—C6A—C8A	178.6 (2)	C7B—C1B—C6B—C5B	179.3 (3)
C4A—C5A—C6A—N1A	1.4 (4)	C6B—C1B—C7B—O2B	171.1 (3)
Cl1—C5A—C6A—N1A	−179.66 (19)	C2B—C1B—C7B—O2B	−8.9 (4)
C4A—C5A—C6A—C8A	−178.8 (2)	C6B—C1B—C7B—O1B	−8.7 (4)
Cl1—C5A—C6A—C8A	0.2 (4)	C2B—C1B—C7B—O1B	171.3 (3)
C6B—C1B—C2B—C3B	1.1 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4A—H41···N3A^i	0.87 (4)	2.15 (4)	3.014 (3)	172 (3)
N4A—H42···O2B^ii	0.87 (4)	2.14 (4)	2.884 (3)	143 (4)
O1B—H1B···N1A	0.90 (5)	1.71 (5)	2.610 (3)	174 (5)

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

4-Amino-5-chloro-2,6-dimethylpyrimidine–2-aminobenzoic acid (1/1) (COCRYSTAL-4)

Crystal data

C6H8ClN3·C7H7NO2	F(000) = 616
Mr = 294.74	Dx = 1.387 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
a = 8.0965 (2) Å	Cell parameters from 3296 reflections
b = 7.2427 (3) Å	θ = 3.7–76.5°
c = 24.0738 (9) Å	µ = 2.47 mm^−1
β = 90.831 (3)°	T = 120 K
V = 1411.55 (9) Å^3	The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments., pale yellow-orange
Z = 4	0.46 × 0.22 × 0.06 mm

Data collection

Agilent SuperNova Dual Source diffractometer with an Atlas detector	2927 independent reflections
Radiation source: sealed X-ray tube	2481 reflections with I > 2σ(I)
Detector resolution: 10.6501 pixels mm^-1	Rint = 0.028
ω scans	θmax = 76.7°, θmin = 3.7°
Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2011), based on expressions derived by Clark & Reid (1995)]	h = −10→6
Tmin = 0.547, Tmax = 0.877	k = −8→9
6899 measured reflections	l = −30→28

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.110	w = 1/[σ^2(Fo^2) + (0.0615P)^2 + 0.465P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
2927 reflections	Δρmax = 0.23 e Å^−3
203 parameters	Δρmin = −0.46 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.

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

	x	y	z	Uiso*/Ueq
Cl1	0.11199 (5)	0.49692 (6)	0.38012 (2)	0.02408 (14)
N1A	0.27995 (17)	0.51697 (19)	0.53553 (6)	0.0192 (3)
C2A	0.22132 (19)	0.6818 (2)	0.55060 (7)	0.0198 (3)
N3A	0.12834 (16)	0.79300 (19)	0.51880 (6)	0.0189 (3)
N4A	−0.00933 (18)	0.8419 (2)	0.43543 (6)	0.0213 (3)
H4A1	−0.048 (3)	0.946 (4)	0.4501 (10)	0.034 (6)*
H4A2	−0.050 (3)	0.800 (4)	0.4043 (11)	0.042 (7)*
C4A	0.08865 (19)	0.7343 (2)	0.46684 (7)	0.0179 (3)
C5A	0.15295 (19)	0.5643 (2)	0.44778 (7)	0.0187 (3)
C6A	0.24751 (19)	0.4579 (2)	0.48289 (7)	0.0194 (3)
C7A	0.2642 (2)	0.7482 (3)	0.60803 (7)	0.0259 (4)
H7AA	0.1778	0.8320	0.6209	0.039*
H7AB	0.3701	0.8137	0.6075	0.039*
H7AC	0.2728	0.6423	0.6333	0.039*
C8A	0.3162 (2)	0.2746 (3)	0.46605 (7)	0.0246 (4)
H8AA	0.3960	0.2322	0.4943	0.037*
H8AB	0.3715	0.2869	0.4303	0.037*
H8AC	0.2262	0.1847	0.4625	0.037*
O1B	0.46209 (15)	0.30141 (19)	0.59902 (5)	0.0268 (3)
H1B	0.379 (4)	0.383 (5)	0.5759 (14)	0.083 (11)*
O2B	0.25284 (14)	0.25583 (18)	0.65694 (5)	0.0242 (3)
N1B	0.2989 (2)	0.0084 (2)	0.74083 (7)	0.0299 (4)
H1B1	0.225 (3)	0.086 (4)	0.7235 (10)	0.038 (6)*
H1B2	0.275 (3)	−0.052 (4)	0.7695 (11)	0.042 (7)*
C1B	0.50618 (19)	0.0925 (2)	0.67226 (7)	0.0188 (3)
C2B	0.4524 (2)	−0.0091 (2)	0.71897 (7)	0.0200 (3)
C3B	0.5643 (2)	−0.1364 (2)	0.74338 (7)	0.0244 (4)
H3BA	0.5304	−0.2075	0.7744	0.029*
C4B	0.7206 (2)	−0.1595 (3)	0.72327 (8)	0.0265 (4)
H4BA	0.7931	−0.2459	0.7406	0.032*
C5B	0.7748 (2)	−0.0575 (3)	0.67756 (8)	0.0250 (4)
H5BA	0.8837	−0.0726	0.6641	0.030*
C6B	0.6672 (2)	0.0649 (2)	0.65261 (7)	0.0208 (3)
H6BA	0.7026	0.1329	0.6212	0.025*
C7B	0.3958 (2)	0.2228 (2)	0.64266 (7)	0.0197 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0307 (2)	0.0245 (2)	0.0170 (2)	0.00267 (15)	−0.00203 (16)	−0.00299 (15)
N1A	0.0199 (6)	0.0193 (7)	0.0182 (7)	0.0009 (5)	−0.0010 (5)	0.0013 (5)
C2A	0.0193 (7)	0.0194 (8)	0.0207 (8)	−0.0019 (6)	−0.0001 (6)	0.0002 (6)
N3A	0.0204 (6)	0.0183 (7)	0.0180 (7)	0.0001 (5)	−0.0005 (5)	0.0011 (5)
N4A	0.0240 (7)	0.0209 (7)	0.0189 (7)	0.0035 (6)	−0.0033 (6)	0.0008 (6)
C4A	0.0179 (7)	0.0177 (8)	0.0182 (7)	−0.0020 (6)	0.0013 (6)	0.0017 (6)
C5A	0.0210 (7)	0.0185 (8)	0.0165 (7)	−0.0010 (6)	0.0010 (6)	−0.0003 (6)
C6A	0.0189 (7)	0.0196 (8)	0.0197 (8)	−0.0011 (6)	0.0021 (6)	0.0005 (6)
C7A	0.0307 (9)	0.0244 (9)	0.0225 (8)	0.0027 (7)	−0.0060 (7)	−0.0031 (7)
C8A	0.0263 (8)	0.0227 (9)	0.0248 (8)	0.0045 (7)	0.0006 (7)	−0.0014 (7)
O1B	0.0246 (6)	0.0320 (7)	0.0239 (6)	0.0051 (5)	0.0017 (5)	0.0103 (5)
O2B	0.0229 (6)	0.0283 (7)	0.0213 (6)	0.0043 (5)	0.0006 (5)	0.0003 (5)
N1B	0.0282 (8)	0.0341 (9)	0.0275 (8)	0.0037 (7)	0.0068 (7)	0.0111 (7)
C1B	0.0214 (7)	0.0181 (8)	0.0170 (7)	−0.0003 (6)	−0.0025 (6)	−0.0017 (6)
C2B	0.0231 (8)	0.0195 (8)	0.0175 (8)	−0.0015 (6)	−0.0024 (6)	−0.0015 (6)
C3B	0.0324 (9)	0.0213 (9)	0.0194 (8)	−0.0008 (7)	−0.0027 (7)	0.0021 (7)
C4B	0.0318 (9)	0.0222 (9)	0.0252 (9)	0.0050 (7)	−0.0077 (7)	0.0016 (7)
C5B	0.0232 (8)	0.0263 (9)	0.0256 (9)	0.0053 (7)	−0.0010 (7)	−0.0006 (7)
C6B	0.0234 (8)	0.0202 (8)	0.0186 (8)	−0.0009 (6)	−0.0001 (6)	−0.0008 (7)
C7B	0.0218 (7)	0.0209 (8)	0.0164 (7)	−0.0010 (6)	−0.0020 (6)	−0.0014 (6)

Geometric parameters (Å, º)

Cl1—C5A	1.7279 (16)	O1B—C7B	1.316 (2)
N1A—C2A	1.337 (2)	O1B—H1B	1.05 (4)
N1A—C6A	1.360 (2)	O2B—C7B	1.235 (2)
C2A—N3A	1.336 (2)	N1B—C2B	1.363 (2)
C2A—C7A	1.500 (2)	N1B—H1B1	0.91 (3)
N3A—C4A	1.355 (2)	N1B—H1B2	0.84 (3)
N4A—C4A	1.338 (2)	C1B—C6B	1.408 (2)
N4A—H4A1	0.89 (3)	C1B—C2B	1.417 (2)
N4A—H4A2	0.87 (3)	C1B—C7B	1.476 (2)
C4A—C5A	1.416 (2)	C2B—C3B	1.415 (2)
C5A—C6A	1.369 (2)	C3B—C4B	1.372 (3)
C6A—C8A	1.497 (2)	C3B—H3BA	0.9500
C7A—H7AA	0.9800	C4B—C5B	1.401 (3)
C7A—H7AB	0.9800	C4B—H4BA	0.9500
C7A—H7AC	0.9800	C5B—C6B	1.375 (2)
C8A—H8AA	0.9800	C5B—H5BA	0.9500
C8A—H8AB	0.9800	C6B—H6BA	0.9500
C8A—H8AC	0.9800
C2A—N1A—C6A	118.00 (15)	H8AA—C8A—H8AC	109.5
N3A—C2A—N1A	125.62 (16)	H8AB—C8A—H8AC	109.5
N3A—C2A—C7A	117.11 (15)	C7B—O1B—H1B	113.6 (18)
N1A—C2A—C7A	117.28 (15)	C2B—N1B—H1B1	118.2 (15)
C2A—N3A—C4A	117.63 (15)	C2B—N1B—H1B2	119.2 (18)
C4A—N4A—H4A1	118.4 (16)	H1B1—N1B—H1B2	123 (2)
C4A—N4A—H4A2	119.7 (17)	C6B—C1B—C2B	119.32 (15)
H4A1—N4A—H4A2	121 (2)	C6B—C1B—C7B	119.05 (15)
N4A—C4A—N3A	118.01 (15)	C2B—C1B—C7B	121.61 (14)
N4A—C4A—C5A	122.76 (15)	N1B—C2B—C3B	118.84 (16)
N3A—C4A—C5A	119.23 (15)	N1B—C2B—C1B	123.39 (16)
C6A—C5A—C4A	119.62 (15)	C3B—C2B—C1B	117.77 (15)
C6A—C5A—Cl1	121.40 (13)	C4B—C3B—C2B	121.41 (16)
C4A—C5A—Cl1	118.98 (13)	C4B—C3B—H3BA	119.3
N1A—C6A—C5A	119.79 (16)	C2B—C3B—H3BA	119.3
N1A—C6A—C8A	117.64 (15)	C3B—C4B—C5B	120.93 (17)
C5A—C6A—C8A	122.56 (15)	C3B—C4B—H4BA	119.5
C2A—C7A—H7AA	109.5	C5B—C4B—H4BA	119.5
C2A—C7A—H7AB	109.5	C6B—C5B—C4B	118.65 (16)
H7AA—C7A—H7AB	109.5	C6B—C5B—H5BA	120.7
C2A—C7A—H7AC	109.5	C4B—C5B—H5BA	120.7
H7AA—C7A—H7AC	109.5	C5B—C6B—C1B	121.90 (16)
H7AB—C7A—H7AC	109.5	C5B—C6B—H6BA	119.0
C6A—C8A—H8AA	109.5	C1B—C6B—H6BA	119.0
C6A—C8A—H8AB	109.5	O2B—C7B—O1B	122.20 (16)
H8AA—C8A—H8AB	109.5	O2B—C7B—C1B	123.54 (15)
C6A—C8A—H8AC	109.5	O1B—C7B—C1B	114.25 (14)
C6A—N1A—C2A—N3A	2.1 (2)	C6B—C1B—C2B—N1B	−179.98 (17)
C6A—N1A—C2A—C7A	−177.53 (14)	C7B—C1B—C2B—N1B	−1.7 (3)
N1A—C2A—N3A—C4A	0.4 (2)	C6B—C1B—C2B—C3B	−0.8 (2)
C7A—C2A—N3A—C4A	−179.93 (14)	C7B—C1B—C2B—C3B	177.48 (15)
C2A—N3A—C4A—N4A	177.65 (14)	N1B—C2B—C3B—C4B	−179.78 (17)
C2A—N3A—C4A—C5A	−3.0 (2)	C1B—C2B—C3B—C4B	1.0 (3)
N4A—C4A—C5A—C6A	−177.58 (15)	C2B—C3B—C4B—C5B	−0.1 (3)
N3A—C4A—C5A—C6A	3.1 (2)	C3B—C4B—C5B—C6B	−0.9 (3)
N4A—C4A—C5A—Cl1	3.2 (2)	C4B—C5B—C6B—C1B	1.1 (3)
N3A—C4A—C5A—Cl1	−176.17 (12)	C2B—C1B—C6B—C5B	−0.3 (3)
C2A—N1A—C6A—C5A	−2.0 (2)	C7B—C1B—C6B—C5B	−178.55 (16)
C2A—N1A—C6A—C8A	178.93 (14)	C6B—C1B—C7B—O2B	−179.88 (16)
C4A—C5A—C6A—N1A	−0.5 (2)	C2B—C1B—C7B—O2B	1.9 (3)
Cl1—C5A—C6A—N1A	178.68 (12)	C6B—C1B—C7B—O1B	0.5 (2)
C4A—C5A—C6A—C8A	178.53 (14)	C2B—C1B—C7B—O1B	−177.71 (15)
Cl1—C5A—C6A—C8A	−2.3 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4A—H4A1···N3A^i	0.89 (3)	2.14 (3)	3.027 (2)	176 (2)
N4A—H4A2···O2B^ii	0.87 (3)	2.23 (3)	3.034 (2)	154 (2)
C8A—H8AA···O1B	0.98	2.62	3.402 (2)	137
O1B—H1B···N1A	1.05 (4)	1.58 (4)	2.6235 (19)	170 (3)
N1B—H1B1···O2B	0.91 (3)	2.04 (3)	2.722 (2)	131 (2)
N1B—H1B2···O2B^iii	0.84 (3)	2.27 (3)	3.100 (2)	171 (2)

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

4-Amino-5-chloro-2,6-dimethylpyrimidine–5-methylthiophene-2-carboxylic acid (1/1) (COCRYSTAL-5)

Crystal data

C6H8ClN3·C6H6O2S	F(000) = 624
Mr = 299.77	Dx = 1.452 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.273 (3) Å	Cell parameters from 5891 reflections
b = 12.746 (4) Å	θ = 2.2–31.4°
c = 13.320 (4) Å	µ = 0.43 mm^−1
β = 102.390 (5)°	T = 100 K
V = 1371.8 (8) Å^3	Plate, colourless
Z = 4	0.55 × 0.50 × 0.30 mm

Data collection

Bruker APEXII CCD diffractometer	4109 independent reflections
Radiation source: fine focus sealed tube	3735 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
ω and phi scans	θmax = 31.4°, θmin = 2.2°
Absorption correction: multi-scan (APEX2; Bruker, 2014)	h = −11→12
Tmin = 0.608, Tmax = 0.746	k = −17→17
8807 measured reflections	l = −11→18

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)] = 0.034	Hydrogen site location: mixed
wR(F^2) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0473P)^2 + 0.5783P] where P = (Fo^2 + 2Fc^2)/3
4109 reflections	(Δ/σ)max = 0.001
189 parameters	Δρmax = 0.55 e Å^−3
0 restraints	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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	0.38618 (3)	0.84503 (2)	0.35758 (2)	0.01547 (8)
N1A	0.54569 (12)	0.74068 (7)	0.64354 (7)	0.01340 (18)
C2A	0.62308 (14)	0.65402 (8)	0.62325 (8)	0.0128 (2)
N3A	0.63936 (12)	0.62204 (7)	0.52992 (7)	0.01266 (18)
N4A	0.59228 (14)	0.65222 (8)	0.35501 (8)	0.0163 (2)
H41	0.560 (2)	0.6922 (15)	0.3027 (15)	0.032 (5)*
H42	0.647 (2)	0.5971 (15)	0.3525 (14)	0.026 (4)*
C4A	0.57179 (13)	0.68167 (8)	0.44758 (8)	0.01177 (19)
C5A	0.48186 (13)	0.77260 (8)	0.46351 (8)	0.01156 (19)
C6A	0.47182 (13)	0.80027 (8)	0.56179 (8)	0.01207 (19)
C7A	0.69907 (16)	0.58473 (10)	0.71194 (9)	0.0190 (2)
H7A1	0.7278	0.5169	0.6859	0.028*	0.282 (19)
H7A2	0.6198	0.5740	0.7561	0.028*	0.282 (19)
H7A3	0.7992	0.6181	0.7518	0.028*	0.282 (19)
H7A4	0.7034	0.6224	0.7766	0.028*	0.718 (19)
H7A5	0.8115	0.5653	0.7064	0.028*	0.718 (19)
H7A6	0.6320	0.5212	0.7107	0.028*	0.718 (19)
C8A	0.38111 (15)	0.89640 (9)	0.58452 (9)	0.0167 (2)
H8A1	0.3804	0.8984	0.6580	0.025*	0.717 (18)
H8A2	0.2670	0.8944	0.5444	0.025*	0.717 (18)
H8A3	0.4367	0.9591	0.5660	0.025*	0.717 (18)
H8A4	0.3424	0.9362	0.5210	0.025*	0.283 (18)
H8A5	0.4557	0.9403	0.6345	0.025*	0.283 (18)
H8A6	0.2860	0.8755	0.6129	0.025*	0.283 (18)
S1	0.94879 (4)	0.25627 (2)	0.33202 (2)	0.01614 (8)
O1B	0.81492 (12)	0.44704 (7)	0.53060 (7)	0.02158 (19)
H1B	0.752 (3)	0.5071 (18)	0.5248 (16)	0.044 (6)*
O2B	0.76792 (12)	0.45470 (7)	0.35803 (7)	0.02004 (18)
C1B	0.82798 (14)	0.41179 (9)	0.43965 (9)	0.0150 (2)
C2B	0.92271 (14)	0.31337 (9)	0.44446 (9)	0.0145 (2)
C3B	0.99609 (16)	0.25478 (9)	0.52815 (10)	0.0185 (2)
H3BA	0.9950	0.2734	0.5971	0.022*
C4B	1.07400 (16)	0.16312 (10)	0.50029 (10)	0.0200 (2)
H4BA	1.1305	0.1137	0.5488	0.024*
C5B	1.05905 (15)	0.15343 (9)	0.39617 (10)	0.0162 (2)
C6B	1.12401 (17)	0.06825 (10)	0.33793 (11)	0.0232 (3)
H6BA	1.1161	0.0007	0.3716	0.035*
H6BB	1.2400	0.0826	0.3368	0.035*
H6BC	1.0584	0.0658	0.2673	0.035*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.01899 (14)	0.01426 (13)	0.01211 (13)	0.00442 (9)	0.00102 (10)	0.00099 (8)
N1A	0.0154 (4)	0.0144 (4)	0.0109 (4)	−0.0005 (3)	0.0039 (3)	−0.0008 (3)
C2A	0.0143 (5)	0.0139 (5)	0.0105 (5)	−0.0008 (4)	0.0032 (4)	0.0004 (3)
N3A	0.0151 (4)	0.0126 (4)	0.0104 (4)	0.0015 (3)	0.0029 (3)	0.0003 (3)
N4A	0.0248 (5)	0.0146 (4)	0.0096 (4)	0.0071 (4)	0.0039 (4)	0.0000 (3)
C4A	0.0134 (5)	0.0116 (4)	0.0103 (5)	−0.0005 (4)	0.0026 (4)	−0.0011 (4)
C5A	0.0124 (5)	0.0113 (4)	0.0105 (4)	0.0007 (3)	0.0014 (4)	0.0003 (3)
C6A	0.0120 (5)	0.0120 (4)	0.0126 (5)	−0.0014 (4)	0.0034 (4)	−0.0020 (4)
C7A	0.0246 (6)	0.0203 (5)	0.0121 (5)	0.0044 (4)	0.0040 (4)	0.0040 (4)
C8A	0.0189 (5)	0.0149 (5)	0.0173 (5)	0.0025 (4)	0.0062 (4)	−0.0032 (4)
S1	0.01864 (15)	0.01600 (14)	0.01424 (14)	0.00445 (9)	0.00458 (11)	0.00057 (9)
O1B	0.0302 (5)	0.0194 (4)	0.0160 (4)	0.0103 (4)	0.0069 (4)	−0.0002 (3)
O2B	0.0276 (5)	0.0161 (4)	0.0166 (4)	0.0066 (3)	0.0050 (3)	0.0004 (3)
C1B	0.0156 (5)	0.0128 (4)	0.0175 (5)	0.0005 (4)	0.0053 (4)	−0.0010 (4)
C2B	0.0149 (5)	0.0140 (5)	0.0154 (5)	0.0015 (4)	0.0045 (4)	−0.0008 (4)
C3B	0.0204 (6)	0.0197 (5)	0.0149 (5)	0.0038 (4)	0.0027 (4)	0.0001 (4)
C4B	0.0203 (6)	0.0186 (5)	0.0197 (6)	0.0067 (4)	0.0014 (4)	0.0033 (4)
C5B	0.0136 (5)	0.0144 (5)	0.0205 (5)	0.0028 (4)	0.0034 (4)	0.0001 (4)
C6B	0.0210 (6)	0.0191 (5)	0.0305 (7)	0.0051 (5)	0.0078 (5)	−0.0050 (5)

Geometric parameters (Å, º)

Cl1—C5A	1.7293 (11)	C8A—H8A3	0.9800
N1A—C2A	1.3331 (14)	C8A—H8A4	0.9800
N1A—C6A	1.3603 (15)	C8A—H8A5	0.9800
C2A—N3A	1.3421 (14)	C8A—H8A6	0.9800
C2A—C7A	1.5007 (16)	S1—C5B	1.7163 (12)
N3A—C4A	1.3528 (14)	S1—C2B	1.7199 (12)
N4A—C4A	1.3340 (14)	O1B—C1B	1.3180 (15)
N4A—H41	0.86 (2)	O1B—H1B	0.92 (2)
N4A—H42	0.842 (19)	O2B—C1B	1.2232 (15)
C4A—C5A	1.4175 (15)	C1B—C2B	1.4732 (16)
C5A—C6A	1.3753 (15)	C2B—C3B	1.3706 (16)
C6A—C8A	1.5013 (15)	C3B—C4B	1.4215 (17)
C7A—H7A1	0.9800	C3B—H3BA	0.9500
C7A—H7A2	0.9800	C4B—C5B	1.3712 (18)
C7A—H7A3	0.9800	C4B—H4BA	0.9500
C7A—H7A4	0.9800	C5B—C6B	1.4994 (17)
C7A—H7A5	0.9800	C6B—H6BA	0.9800
C7A—H7A6	0.9800	C6B—H6BB	0.9800
C8A—H8A1	0.9800	C6B—H6BC	0.9800
C8A—H8A2	0.9800
C2A—N1A—C6A	116.94 (10)	C6A—C8A—H8A3	109.5
N1A—C2A—N3A	125.97 (10)	H8A1—C8A—H8A3	109.5
N1A—C2A—C7A	117.79 (10)	H8A2—C8A—H8A3	109.5
N3A—C2A—C7A	116.23 (10)	C6A—C8A—H8A4	109.5
C2A—N3A—C4A	118.30 (9)	H8A1—C8A—H8A4	141.1
C4A—N4A—H41	120.2 (13)	H8A2—C8A—H8A4	56.3
C4A—N4A—H42	116.7 (12)	H8A3—C8A—H8A4	56.3
H41—N4A—H42	122.8 (18)	C6A—C8A—H8A5	109.5
N4A—C4A—N3A	118.61 (10)	H8A1—C8A—H8A5	56.3
N4A—C4A—C5A	122.91 (10)	H8A2—C8A—H8A5	141.1
N3A—C4A—C5A	118.48 (10)	H8A3—C8A—H8A5	56.3
C6A—C5A—C4A	119.53 (10)	H8A4—C8A—H8A5	109.5
C6A—C5A—Cl1	121.95 (9)	C6A—C8A—H8A6	109.5
C4A—C5A—Cl1	118.52 (8)	H8A1—C8A—H8A6	56.3
N1A—C6A—C5A	120.68 (10)	H8A2—C8A—H8A6	56.3
N1A—C6A—C8A	116.90 (10)	H8A3—C8A—H8A6	141.1
C5A—C6A—C8A	122.42 (10)	H8A4—C8A—H8A6	109.5
C2A—C7A—H7A1	109.5	H8A5—C8A—H8A6	109.5
C2A—C7A—H7A2	109.5	C5B—S1—C2B	92.42 (6)
H7A1—C7A—H7A2	109.5	C1B—O1B—H1B	111.3 (13)
C2A—C7A—H7A3	109.5	O2B—C1B—O1B	124.53 (11)
H7A1—C7A—H7A3	109.5	O2B—C1B—C2B	122.02 (11)
H7A2—C7A—H7A3	109.5	O1B—C1B—C2B	113.46 (10)
C2A—C7A—H7A4	109.5	C3B—C2B—C1B	129.64 (11)
H7A1—C7A—H7A4	141.1	C3B—C2B—S1	111.17 (9)
H7A2—C7A—H7A4	56.3	C1B—C2B—S1	119.18 (9)
H7A3—C7A—H7A4	56.3	C2B—C3B—C4B	112.46 (11)
C2A—C7A—H7A5	109.5	C2B—C3B—H3BA	123.8
H7A1—C7A—H7A5	56.3	C4B—C3B—H3BA	123.8
H7A2—C7A—H7A5	141.1	C5B—C4B—C3B	112.98 (11)
H7A3—C7A—H7A5	56.3	C5B—C4B—H4BA	123.5
H7A4—C7A—H7A5	109.5	C3B—C4B—H4BA	123.5
C2A—C7A—H7A6	109.5	C4B—C5B—C6B	128.60 (11)
H7A1—C7A—H7A6	56.3	C4B—C5B—S1	110.96 (9)
H7A2—C7A—H7A6	56.3	C6B—C5B—S1	120.44 (10)
H7A3—C7A—H7A6	141.1	C5B—C6B—H6BA	109.5
H7A4—C7A—H7A6	109.5	C5B—C6B—H6BB	109.5
H7A5—C7A—H7A6	109.5	H6BA—C6B—H6BB	109.5
C6A—C8A—H8A1	109.5	C5B—C6B—H6BC	109.5
C6A—C8A—H8A2	109.5	H6BA—C6B—H6BC	109.5
H8A1—C8A—H8A2	109.5	H6BB—C6B—H6BC	109.5
C6A—N1A—C2A—N3A	2.31 (17)	Cl1—C5A—C6A—C8A	−1.57 (15)
C6A—N1A—C2A—C7A	−177.41 (10)	O2B—C1B—C2B—C3B	−179.21 (12)
N1A—C2A—N3A—C4A	−0.18 (17)	O1B—C1B—C2B—C3B	0.46 (18)
C7A—C2A—N3A—C4A	179.55 (10)	O2B—C1B—C2B—S1	−0.45 (16)
C2A—N3A—C4A—N4A	177.78 (10)	O1B—C1B—C2B—S1	179.21 (9)
C2A—N3A—C4A—C5A	−2.41 (15)	C5B—S1—C2B—C3B	−0.20 (10)
N4A—C4A—C5A—C6A	−177.34 (11)	C5B—S1—C2B—C1B	−179.17 (10)
N3A—C4A—C5A—C6A	2.85 (16)	C1B—C2B—C3B—C4B	178.92 (12)
N4A—C4A—C5A—Cl1	3.19 (15)	S1—C2B—C3B—C4B	0.09 (14)
N3A—C4A—C5A—Cl1	−176.62 (8)	C2B—C3B—C4B—C5B	0.11 (17)
C2A—N1A—C6A—C5A	−1.75 (16)	C3B—C4B—C5B—C6B	−179.99 (12)
C2A—N1A—C6A—C8A	178.53 (10)	C3B—C4B—C5B—S1	−0.25 (15)
C4A—C5A—C6A—N1A	−0.72 (16)	C2B—S1—C5B—C4B	0.26 (10)
Cl1—C5A—C6A—N1A	178.72 (8)	C2B—S1—C5B—C6B	−179.98 (10)
C4A—C5A—C6A—C8A	178.98 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4A—H41···N1A^i	0.86 (2)	2.27 (2)	3.0790 (16)	158.0 (18)
N4A—H42···O2B	0.842 (19)	2.065 (19)	2.9028 (15)	173.6 (18)
O1B—H1B···N3A	0.92 (2)	1.74 (2)	2.6607 (14)	173 (2)

Symmetry code: (i) x, −y+3/2, z−1/2.

4-Amino-5-chloro-2,6-dimethylpyrimidine–benzoic acid (1/1) (COCRYSTAL-6)

Crystal data

C6H8ClN3·C7H6O2	F(000) = 584
Mr = 279.72	Dx = 1.391 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 10.1421 (5) Å	Cell parameters from 2966 reflections
b = 10.4218 (5) Å	θ = 4.2–76.3°
c = 13.2681 (6) Å	µ = 2.56 mm^−1
β = 107.804 (5)°	T = 120 K
V = 1335.26 (12) Å^3	Chunk, colorless
Z = 4	0.52 × 0.38 × 0.24 mm

Data collection

Agilent SuperNova Dual Source diffractometer with an Atlas detector	2760 independent reflections
Radiation source: sealed X-ray tube	2560 reflections with I > 2σ(I)
Detector resolution: 10.6501 pixels mm^-1	Rint = 0.029
ω scans	θmax = 76.6°, θmin = 4.6°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	h = −12→12
Tmin = 0.763, Tmax = 1.000	k = −9→12
6087 measured reflections	l = −16→16

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.041	w = 1/[σ^2(Fo^2) + (0.0793P)^2 + 0.3948P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.118	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.33 e Å^−3
2760 reflections	Δρmin = −0.44 e Å^−3
187 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0032 (7)

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.

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

	x	y	z	Uiso*/Ueq
Cl1	0.39577 (4)	0.14749 (3)	0.34668 (3)	0.02536 (16)
N1A	0.54933 (13)	0.30904 (13)	0.63034 (9)	0.0215 (3)
C2A	0.63967 (14)	0.38934 (15)	0.60876 (11)	0.0204 (3)
N3A	0.66375 (12)	0.40143 (12)	0.51529 (9)	0.0201 (3)
N4A	0.61835 (15)	0.33300 (14)	0.34212 (10)	0.0241 (3)
H41	0.682 (2)	0.386 (2)	0.3405 (16)	0.028 (5)*
H42	0.583 (2)	0.273 (2)	0.2896 (17)	0.030 (5)*
C4A	0.59268 (15)	0.32453 (14)	0.43453 (11)	0.0196 (3)
C5A	0.49274 (15)	0.23975 (14)	0.45181 (11)	0.0208 (3)
C6A	0.47284 (15)	0.23477 (15)	0.54949 (12)	0.0214 (3)
C7A	0.72207 (17)	0.47425 (16)	0.69690 (12)	0.0266 (3)
H7AA	0.6936	0.4592	0.7601	0.040*
H7AB	0.7056	0.5643	0.6754	0.040*
H7AC	0.8208	0.4547	0.7127	0.040*
C8A	0.36724 (17)	0.14862 (16)	0.57215 (13)	0.0277 (4)
H8AA	0.3599	0.1683	0.6425	0.042*
H8AB	0.3955	0.0590	0.5701	0.042*
H8AC	0.2772	0.1622	0.5187	0.042*
O1B	0.81428 (11)	0.52642 (10)	0.33828 (8)	0.0236 (3)
O2B	0.84927 (12)	0.58025 (11)	0.50792 (8)	0.0261 (3)
H2B	0.787 (3)	0.521 (2)	0.5057 (18)	0.040 (6)*
C1B	0.96195 (14)	0.70251 (14)	0.40863 (12)	0.0207 (3)
C2B	1.03036 (16)	0.77548 (16)	0.49703 (12)	0.0271 (3)
H2BA	1.0184	0.7568	0.5638	0.032*
C3B	1.11636 (19)	0.87588 (18)	0.48757 (14)	0.0322 (4)
H3BA	1.1636	0.9253	0.5480	0.039*
C4B	1.13303 (18)	0.90380 (17)	0.38984 (14)	0.0307 (4)
H4BA	1.1919	0.9722	0.3835	0.037*
C5B	1.06404 (19)	0.83225 (18)	0.30168 (14)	0.0317 (4)
H5BA	1.0750	0.8521	0.2348	0.038*
C6B	0.97869 (17)	0.73133 (16)	0.31075 (12)	0.0272 (3)
H6BA	0.9318	0.6820	0.2502	0.033*
C7B	0.86845 (14)	0.59440 (14)	0.41483 (11)	0.0200 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0262 (2)	0.0295 (2)	0.0204 (2)	−0.00904 (13)	0.00707 (15)	−0.00331 (12)
N1A	0.0225 (6)	0.0257 (7)	0.0168 (6)	−0.0013 (5)	0.0069 (5)	0.0004 (5)
C2A	0.0209 (7)	0.0233 (7)	0.0180 (6)	0.0017 (6)	0.0073 (5)	0.0011 (6)
N3A	0.0205 (6)	0.0230 (6)	0.0175 (6)	−0.0014 (5)	0.0069 (5)	−0.0008 (5)
N4A	0.0270 (7)	0.0298 (7)	0.0175 (6)	−0.0099 (6)	0.0097 (5)	−0.0038 (5)
C4A	0.0186 (6)	0.0226 (7)	0.0179 (7)	0.0007 (5)	0.0061 (5)	0.0003 (5)
C5A	0.0201 (7)	0.0233 (7)	0.0190 (7)	−0.0022 (5)	0.0058 (5)	0.0001 (5)
C6A	0.0199 (7)	0.0237 (7)	0.0214 (7)	0.0003 (5)	0.0073 (5)	0.0026 (6)
C7A	0.0300 (8)	0.0303 (8)	0.0196 (7)	−0.0042 (6)	0.0079 (6)	−0.0038 (6)
C8A	0.0271 (8)	0.0331 (9)	0.0255 (8)	−0.0078 (6)	0.0119 (7)	0.0017 (6)
O1B	0.0252 (5)	0.0249 (6)	0.0220 (5)	−0.0050 (4)	0.0092 (4)	−0.0015 (4)
O2B	0.0303 (6)	0.0296 (6)	0.0204 (5)	−0.0098 (5)	0.0109 (4)	−0.0009 (4)
C1B	0.0188 (6)	0.0213 (7)	0.0226 (7)	−0.0003 (5)	0.0073 (5)	0.0020 (6)
C2B	0.0296 (8)	0.0302 (8)	0.0210 (7)	−0.0069 (6)	0.0070 (6)	−0.0004 (6)
C3B	0.0346 (9)	0.0332 (9)	0.0270 (8)	−0.0126 (7)	0.0068 (7)	−0.0021 (7)
C4B	0.0312 (8)	0.0290 (8)	0.0330 (8)	−0.0094 (7)	0.0111 (7)	0.0014 (7)
C5B	0.0375 (9)	0.0347 (9)	0.0263 (8)	−0.0102 (7)	0.0148 (7)	0.0010 (7)
C6B	0.0306 (8)	0.0303 (8)	0.0228 (7)	−0.0073 (7)	0.0113 (6)	−0.0019 (6)
C7B	0.0180 (6)	0.0224 (7)	0.0203 (7)	0.0018 (5)	0.0070 (5)	0.0020 (5)

Geometric parameters (Å, º)

Cl1—C5A	1.7316 (15)	C8A—H8AC	0.9800
N1A—C2A	1.335 (2)	O1B—C7B	1.2224 (18)
N1A—C6A	1.357 (2)	O2B—C7B	1.3160 (18)
C2A—N3A	1.3411 (18)	O2B—H2B	0.87 (3)
C2A—C7A	1.500 (2)	C1B—C2B	1.392 (2)
N3A—C4A	1.3557 (19)	C1B—C6B	1.393 (2)
N4A—C4A	1.3320 (19)	C1B—C7B	1.491 (2)
N4A—H41	0.86 (2)	C2B—C3B	1.392 (2)
N4A—H42	0.92 (2)	C2B—H2BA	0.9500
C4A—C5A	1.415 (2)	C3B—C4B	1.389 (2)
C5A—C6A	1.372 (2)	C3B—H3BA	0.9500
C6A—C8A	1.497 (2)	C4B—C5B	1.383 (2)
C7A—H7AA	0.9800	C4B—H4BA	0.9500
C7A—H7AB	0.9800	C5B—C6B	1.391 (2)
C7A—H7AC	0.9800	C5B—H5BA	0.9500
C8A—H8AA	0.9800	C6B—H6BA	0.9500
C8A—H8AB	0.9800
C2A—N1A—C6A	116.86 (12)	C6A—C8A—H8AC	109.5
N1A—C2A—N3A	126.03 (14)	H8AA—C8A—H8AC	109.5
N1A—C2A—C7A	117.24 (12)	H8AB—C8A—H8AC	109.5
N3A—C2A—C7A	116.73 (13)	C7B—O2B—H2B	111.1 (15)
C2A—N3A—C4A	118.18 (12)	C2B—C1B—C6B	119.75 (14)
C4A—N4A—H41	115.3 (14)	C2B—C1B—C7B	121.87 (13)
C4A—N4A—H42	120.6 (13)	C6B—C1B—C7B	118.37 (13)
H41—N4A—H42	122.8 (19)	C1B—C2B—C3B	119.95 (15)
N4A—C4A—N3A	118.82 (13)	C1B—C2B—H2BA	120.0
N4A—C4A—C5A	122.81 (14)	C3B—C2B—H2BA	120.0
N3A—C4A—C5A	118.36 (13)	C4B—C3B—C2B	120.00 (16)
C6A—C5A—C4A	119.74 (13)	C4B—C3B—H3BA	120.0
C6A—C5A—Cl1	121.90 (11)	C2B—C3B—H3BA	120.0
C4A—C5A—Cl1	118.34 (11)	C5B—C4B—C3B	120.14 (15)
N1A—C6A—C5A	120.74 (13)	C5B—C4B—H4BA	119.9
N1A—C6A—C8A	117.03 (13)	C3B—C4B—H4BA	119.9
C5A—C6A—C8A	122.23 (14)	C4B—C5B—C6B	120.12 (15)
C2A—C7A—H7AA	109.5	C4B—C5B—H5BA	119.9
C2A—C7A—H7AB	109.5	C6B—C5B—H5BA	119.9
H7AA—C7A—H7AB	109.5	C5B—C6B—C1B	120.02 (15)
C2A—C7A—H7AC	109.5	C5B—C6B—H6BA	120.0
H7AA—C7A—H7AC	109.5	C1B—C6B—H6BA	120.0
H7AB—C7A—H7AC	109.5	O1B—C7B—O2B	123.85 (13)
C6A—C8A—H8AA	109.5	O1B—C7B—C1B	121.60 (13)
C6A—C8A—H8AB	109.5	O2B—C7B—C1B	114.54 (13)
H8AA—C8A—H8AB	109.5
C6A—N1A—C2A—N3A	−1.5 (2)	C4A—C5A—C6A—C8A	179.03 (14)
C6A—N1A—C2A—C7A	178.46 (13)	Cl1—C5A—C6A—C8A	0.6 (2)
N1A—C2A—N3A—C4A	−1.2 (2)	C6B—C1B—C2B—C3B	−0.7 (2)
C7A—C2A—N3A—C4A	178.89 (13)	C7B—C1B—C2B—C3B	−179.78 (15)
C2A—N3A—C4A—N4A	−178.15 (14)	C1B—C2B—C3B—C4B	0.5 (3)
C2A—N3A—C4A—C5A	2.7 (2)	C2B—C3B—C4B—C5B	0.2 (3)
N4A—C4A—C5A—C6A	179.16 (14)	C3B—C4B—C5B—C6B	−0.6 (3)
N3A—C4A—C5A—C6A	−1.7 (2)	C4B—C5B—C6B—C1B	0.3 (3)
N4A—C4A—C5A—Cl1	−2.3 (2)	C2B—C1B—C6B—C5B	0.3 (2)
N3A—C4A—C5A—Cl1	176.75 (11)	C7B—C1B—C6B—C5B	179.40 (15)
C2A—N1A—C6A—C5A	2.5 (2)	C2B—C1B—C7B—O1B	−176.15 (14)
C2A—N1A—C6A—C8A	−177.49 (13)	C6B—C1B—C7B—O1B	4.8 (2)
C4A—C5A—C6A—N1A	−0.9 (2)	C2B—C1B—C7B—O2B	4.4 (2)
Cl1—C5A—C6A—N1A	−179.35 (11)	C6B—C1B—C7B—O2B	−174.61 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4A—H41···O1B	0.86 (2)	1.99 (2)	2.8419 (17)	173 (2)
N4A—H42···N1A^i	0.92 (2)	2.21 (2)	3.0617 (18)	153.5 (18)
C8A—H8AB···Cl1^ii	0.98	2.98	3.8571 (18)	149
O2B—H2B···N3A	0.87 (3)	1.80 (3)	2.6712 (17)	174 (2)

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

4-Amino-5-chloro-2,6-dimethylpyrimidine–2-methylbenzoic acid (1/1) (COCRYSTAL-7)

Crystal data

C6H8ClN3·C8H8O2	Dx = 1.397 Mg m^−3
Mr = 293.75	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P212121	Cell parameters from 3914 reflections
a = 7.3992 (2) Å	θ = 3.6–76.5°
b = 13.9842 (4) Å	µ = 2.47 mm^−1
c = 26.9897 (8) Å	T = 120 K
V = 2792.68 (14) Å^3	Needle, colorless
Z = 8	0.49 × 0.11 × 0.08 mm
F(000) = 1232

Data collection

Agilent SuperNova Dual Source diffractometer with an Atlas detector	4966 independent reflections
Radiation source: sealed X-ray tube	4617 reflections with I > 2σ(I)
Detector resolution: 10.6501 pixels mm^-1	Rint = 0.030
ω scans	θmax = 76.8°, θmin = 3.3°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	h = −7→9
Tmin = 0.740, Tmax = 1.000	k = −17→14
8897 measured reflections	l = −22→34

Refinement

Refinement on F^2	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0488P)^2 + 0.3891P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.034	(Δ/σ)max = 0.002
wR(F^2) = 0.091	Δρmax = 0.24 e Å^−3
S = 1.04	Δρmin = −0.24 e Å^−3
4966 reflections	Extinction correction: SHELXL2014 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
376 parameters	Extinction coefficient: 0.00039 (10)
0 restraints	Absolute structure: Flack x determined using 1451 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Hydrogen site location: mixed	Absolute structure parameter: −0.001 (10)

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.

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

	x	y	z	Uiso*/Ueq
Cl1	0.91235 (8)	0.87398 (4)	0.43040 (2)	0.02206 (15)
N1A	0.7729 (3)	1.10678 (15)	0.50704 (8)	0.0201 (4)
C2A	0.7196 (4)	1.06463 (18)	0.54874 (9)	0.0192 (5)
N3A	0.7172 (3)	0.97006 (15)	0.55756 (8)	0.0191 (4)
N4A	0.7653 (4)	0.81632 (16)	0.53005 (8)	0.0234 (5)
H4AA	0.7255	0.7950	0.5587	0.028*
H4AB	0.8004	0.7757	0.5071	0.028*
C4A	0.7723 (4)	0.91023 (18)	0.52138 (9)	0.0183 (5)
C5A	0.8346 (4)	0.95017 (19)	0.47634 (9)	0.0185 (5)
C6A	0.8313 (4)	1.0482 (2)	0.47023 (10)	0.0204 (5)
C7A	0.6540 (4)	1.12797 (19)	0.58987 (9)	0.0231 (5)
H7AA	0.7146	1.1902	0.5878	0.035*
H7AB	0.6814	1.0982	0.6219	0.035*
H7AC	0.5231	1.1370	0.5868	0.035*
C8A	0.8890 (4)	1.0961 (2)	0.42303 (10)	0.0258 (6)
H8AA	0.9284	1.1616	0.4302	0.039*
H8AB	0.7871	1.0978	0.3999	0.039*
H8AC	0.9892	1.0603	0.4082	0.039*
Cl2	0.88558 (8)	0.36846 (4)	0.56903 (2)	0.02260 (15)
N1B	0.7984 (3)	0.60749 (15)	0.49210 (8)	0.0203 (4)
C2B	0.7345 (4)	0.56860 (18)	0.45060 (9)	0.0186 (5)
N3B	0.7075 (3)	0.47481 (15)	0.44219 (8)	0.0190 (4)
N4B	0.7245 (4)	0.31988 (16)	0.46998 (8)	0.0231 (5)
H4BA	0.6796	0.3010	0.4414	0.028*
H4BB	0.7517	0.2775	0.4929	0.028*
C4B	0.7514 (4)	0.41261 (18)	0.47854 (9)	0.0190 (5)
C5B	0.8238 (4)	0.44877 (19)	0.52313 (9)	0.0186 (5)
C6B	0.8434 (3)	0.54633 (19)	0.52929 (9)	0.0190 (5)
C7B	0.6863 (4)	0.63491 (19)	0.40878 (10)	0.0250 (5)
H7BA	0.6899	0.7012	0.4205	0.037*
H7BB	0.5645	0.6200	0.3968	0.037*
H7BC	0.7732	0.6268	0.3817	0.037*
C8B	0.9118 (4)	0.59057 (19)	0.57601 (10)	0.0238 (5)
H8BA	0.9847	0.6470	0.5680	0.036*
H8BB	0.9864	0.5441	0.5939	0.036*
H8BC	0.8094	0.6096	0.5968	0.036*
O1C	0.6542 (4)	0.92635 (14)	0.65200 (7)	0.0346 (6)
H1C	0.675 (7)	0.938 (4)	0.6173 (19)	0.071 (16)*
O2C	0.6384 (3)	0.77291 (14)	0.63071 (7)	0.0288 (5)
C1C	0.5787 (4)	0.81731 (18)	0.71489 (9)	0.0191 (5)
C2C	0.5895 (4)	0.72517 (18)	0.73568 (9)	0.0195 (5)
C3C	0.5330 (4)	0.71465 (18)	0.78504 (9)	0.0217 (5)
H3CA	0.5403	0.6535	0.8002	0.026*
C4C	0.4672 (4)	0.7903 (2)	0.81212 (9)	0.0245 (5)
H4CA	0.4281	0.7805	0.8453	0.029*
C5C	0.4574 (4)	0.88148 (19)	0.79126 (10)	0.0239 (5)
H5CA	0.4119	0.9339	0.8098	0.029*
C6C	0.5155 (4)	0.89400 (17)	0.74291 (9)	0.0213 (5)
H6CA	0.5121	0.9560	0.7286	0.026*
C7C	0.6283 (4)	0.83490 (18)	0.66198 (10)	0.0205 (5)
C8C	0.6594 (4)	0.63891 (18)	0.70853 (10)	0.0228 (5)
H8CA	0.7754	0.6544	0.6930	0.034*
H8CB	0.5723	0.6200	0.6830	0.034*
H8CC	0.6759	0.5861	0.7320	0.034*
O1D	0.5864 (3)	0.43696 (13)	0.35050 (7)	0.0299 (5)
H1D	0.633 (6)	0.443 (3)	0.3830 (16)	0.049 (12)*
O2D	0.5744 (3)	0.28307 (13)	0.37102 (7)	0.0258 (4)
C1D	0.4706 (4)	0.33139 (18)	0.29067 (9)	0.0187 (5)
C2D	0.4639 (4)	0.23980 (18)	0.26889 (9)	0.0206 (5)
C3D	0.3967 (4)	0.23334 (19)	0.22030 (10)	0.0224 (5)
H3DA	0.3961	0.1729	0.2042	0.027*
C4D	0.3317 (4)	0.3120 (2)	0.19525 (10)	0.0246 (5)
H4DA	0.2858	0.3050	0.1626	0.029*
C5D	0.3330 (4)	0.40158 (19)	0.21763 (10)	0.0242 (5)
H5DA	0.2869	0.4558	0.2006	0.029*
C6D	0.4023 (4)	0.41093 (18)	0.26514 (10)	0.0209 (5)
H6DA	0.4036	0.4720	0.2806	0.025*
C7D	0.5482 (4)	0.34623 (18)	0.34092 (9)	0.0198 (5)
C8D	0.5261 (4)	0.14993 (18)	0.29421 (10)	0.0250 (6)
H8DA	0.5127	0.0956	0.2715	0.037*
H8DB	0.4529	0.1390	0.3239	0.037*
H8DC	0.6534	0.1566	0.3037	0.037*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0255 (3)	0.0205 (3)	0.0201 (3)	0.0010 (2)	0.0027 (2)	−0.0043 (2)
N1A	0.0225 (11)	0.0162 (10)	0.0217 (9)	−0.0022 (9)	0.0007 (9)	0.0010 (8)
C2A	0.0203 (12)	0.0162 (12)	0.0211 (11)	−0.0015 (10)	−0.0003 (10)	−0.0003 (9)
N3A	0.0231 (10)	0.0153 (10)	0.0190 (9)	−0.0012 (9)	0.0020 (8)	−0.0005 (8)
N4A	0.0345 (13)	0.0151 (10)	0.0207 (9)	−0.0004 (10)	0.0053 (10)	−0.0011 (8)
C4A	0.0196 (12)	0.0148 (11)	0.0206 (11)	0.0015 (10)	−0.0021 (10)	−0.0010 (9)
C5A	0.0200 (12)	0.0188 (12)	0.0168 (10)	0.0004 (10)	0.0008 (10)	−0.0023 (10)
C6A	0.0197 (12)	0.0209 (12)	0.0204 (11)	0.0014 (11)	0.0004 (10)	0.0002 (10)
C7A	0.0301 (13)	0.0165 (11)	0.0227 (11)	0.0000 (11)	0.0038 (11)	−0.0013 (10)
C8A	0.0303 (13)	0.0241 (12)	0.0231 (12)	0.0008 (12)	0.0052 (12)	0.0042 (11)
Cl2	0.0268 (3)	0.0200 (3)	0.0210 (3)	0.0018 (2)	−0.0034 (2)	0.0040 (2)
N1B	0.0237 (11)	0.0161 (9)	0.0212 (9)	0.0016 (9)	−0.0007 (9)	−0.0019 (8)
C2B	0.0215 (12)	0.0141 (11)	0.0202 (11)	0.0021 (10)	0.0012 (10)	−0.0005 (9)
N3B	0.0242 (10)	0.0153 (10)	0.0175 (9)	0.0003 (9)	0.0006 (8)	−0.0007 (8)
N4B	0.0333 (12)	0.0149 (9)	0.0211 (9)	−0.0012 (10)	−0.0050 (10)	0.0009 (8)
C4B	0.0205 (12)	0.0161 (11)	0.0204 (11)	0.0008 (10)	0.0035 (10)	0.0000 (9)
C5B	0.0204 (12)	0.0165 (11)	0.0188 (11)	0.0041 (10)	0.0001 (10)	0.0006 (10)
C6B	0.0178 (12)	0.0194 (12)	0.0199 (11)	0.0023 (10)	0.0002 (10)	−0.0015 (10)
C7B	0.0348 (14)	0.0166 (11)	0.0235 (11)	−0.0006 (12)	−0.0045 (11)	0.0028 (10)
C8B	0.0255 (13)	0.0215 (12)	0.0244 (12)	0.0018 (11)	−0.0060 (11)	−0.0050 (10)
O1C	0.0660 (17)	0.0175 (9)	0.0202 (9)	−0.0079 (10)	0.0104 (10)	−0.0017 (7)
O2C	0.0468 (13)	0.0190 (9)	0.0206 (8)	−0.0022 (9)	0.0030 (9)	−0.0005 (7)
C1C	0.0196 (12)	0.0166 (11)	0.0211 (11)	−0.0019 (10)	−0.0006 (10)	−0.0001 (9)
C2C	0.0200 (12)	0.0173 (11)	0.0211 (11)	−0.0024 (11)	−0.0010 (10)	0.0004 (9)
C3C	0.0257 (13)	0.0173 (11)	0.0221 (11)	−0.0039 (11)	−0.0018 (11)	0.0037 (9)
C4C	0.0281 (13)	0.0269 (13)	0.0186 (11)	−0.0054 (12)	0.0015 (11)	0.0003 (10)
C5C	0.0284 (13)	0.0211 (12)	0.0222 (11)	−0.0011 (11)	0.0030 (11)	−0.0029 (10)
C6C	0.0257 (13)	0.0156 (10)	0.0227 (11)	−0.0017 (10)	−0.0008 (11)	0.0019 (10)
C7C	0.0227 (12)	0.0168 (11)	0.0218 (11)	−0.0034 (10)	−0.0005 (10)	0.0014 (9)
C8C	0.0276 (13)	0.0149 (11)	0.0260 (12)	−0.0016 (11)	0.0011 (11)	0.0013 (10)
O1D	0.0491 (13)	0.0156 (8)	0.0250 (9)	−0.0055 (9)	−0.0112 (10)	−0.0004 (7)
O2D	0.0385 (11)	0.0180 (8)	0.0208 (8)	−0.0034 (9)	−0.0039 (9)	0.0012 (7)
C1D	0.0198 (12)	0.0175 (11)	0.0186 (10)	−0.0012 (10)	0.0005 (10)	−0.0001 (9)
C2D	0.0218 (13)	0.0184 (11)	0.0215 (11)	−0.0002 (10)	0.0015 (10)	−0.0004 (9)
C3D	0.0236 (13)	0.0213 (12)	0.0222 (12)	−0.0030 (11)	0.0010 (10)	−0.0057 (10)
C4D	0.0235 (13)	0.0287 (13)	0.0215 (11)	−0.0035 (11)	−0.0031 (11)	0.0001 (10)
C5D	0.0249 (13)	0.0210 (12)	0.0266 (12)	−0.0006 (11)	−0.0034 (11)	0.0046 (10)
C6D	0.0228 (12)	0.0153 (10)	0.0246 (12)	−0.0016 (11)	0.0013 (11)	−0.0010 (9)
C7D	0.0219 (11)	0.0173 (11)	0.0203 (11)	−0.0019 (10)	0.0021 (10)	−0.0026 (9)
C8D	0.0320 (14)	0.0170 (11)	0.0258 (12)	0.0019 (11)	−0.0012 (11)	−0.0024 (10)

Geometric parameters (Å, º)

Cl1—C5A	1.733 (3)	O1C—C7C	1.321 (3)
N1A—C2A	1.330 (3)	O1C—H1C	0.96 (5)
N1A—C6A	1.359 (3)	O2C—C7C	1.212 (3)
C2A—N3A	1.344 (3)	C1C—C6C	1.393 (4)
C2A—C7A	1.501 (4)	C1C—C2C	1.408 (3)
N3A—C4A	1.349 (3)	C1C—C7C	1.495 (3)
N4A—C4A	1.335 (3)	C2C—C3C	1.404 (3)
N4A—H4AA	0.8800	C2C—C8C	1.503 (4)
N4A—H4AB	0.8800	C3C—C4C	1.375 (4)
C4A—C5A	1.415 (4)	C3C—H3CA	0.9500
C5A—C6A	1.380 (4)	C4C—C5C	1.395 (4)
C6A—C8A	1.502 (4)	C4C—H4CA	0.9500
C7A—H7AA	0.9800	C5C—C6C	1.385 (4)
C7A—H7AB	0.9800	C5C—H5CA	0.9500
C7A—H7AC	0.9800	C6C—H6CA	0.9500
C8A—H8AA	0.9800	C8C—H8CA	0.9800
C8A—H8AB	0.9800	C8C—H8CB	0.9800
C8A—H8AC	0.9800	C8C—H8CC	0.9800
Cl2—C5B	1.734 (3)	O1D—C7D	1.325 (3)
N1B—C2B	1.332 (3)	O1D—H1D	0.95 (4)
N1B—C6B	1.360 (3)	O2D—C7D	1.216 (3)
C2B—N3B	1.346 (3)	C1D—C6D	1.402 (4)
C2B—C7B	1.504 (3)	C1D—C2D	1.410 (4)
N3B—C4B	1.351 (3)	C1D—C7D	1.487 (3)
N4B—C4B	1.332 (3)	C2D—C3D	1.406 (4)
N4B—H4BA	0.8800	C2D—C8D	1.503 (4)
N4B—H4BB	0.8800	C3D—C4D	1.378 (4)
C4B—C5B	1.411 (4)	C3D—H3DA	0.9500
C5B—C6B	1.382 (4)	C4D—C5D	1.391 (4)
C6B—C8B	1.493 (3)	C4D—H4DA	0.9500
C7B—H7BA	0.9800	C5D—C6D	1.387 (4)
C7B—H7BB	0.9800	C5D—H5DA	0.9500
C7B—H7BC	0.9800	C6D—H6DA	0.9500
C8B—H8BA	0.9800	C8D—H8DA	0.9800
C8B—H8BB	0.9800	C8D—H8DB	0.9800
C8B—H8BC	0.9800	C8D—H8DC	0.9800
C2A—N1A—C6A	116.5 (2)	H8BB—C8B—H8BC	109.5
N1A—C2A—N3A	126.1 (2)	C7C—O1C—H1C	112 (3)
N1A—C2A—C7A	117.4 (2)	C6C—C1C—C2C	120.5 (2)
N3A—C2A—C7A	116.5 (2)	C6C—C1C—C7C	118.3 (2)
C2A—N3A—C4A	118.6 (2)	C2C—C1C—C7C	121.2 (2)
C4A—N4A—H4AA	120.0	C3C—C2C—C1C	117.2 (2)
C4A—N4A—H4AB	120.0	C3C—C2C—C8C	118.7 (2)
H4AA—N4A—H4AB	120.0	C1C—C2C—C8C	124.1 (2)
N4A—C4A—N3A	118.1 (2)	C4C—C3C—C2C	121.9 (2)
N4A—C4A—C5A	123.5 (2)	C4C—C3C—H3CA	119.0
N3A—C4A—C5A	118.4 (2)	C2C—C3C—H3CA	119.0
C6A—C5A—C4A	119.3 (2)	C3C—C4C—C5C	120.5 (2)
C6A—C5A—Cl1	122.06 (19)	C3C—C4C—H4CA	119.8
C4A—C5A—Cl1	118.7 (2)	C5C—C4C—H4CA	119.8
N1A—C6A—C5A	121.2 (2)	C6C—C5C—C4C	118.7 (3)
N1A—C6A—C8A	116.2 (2)	C6C—C5C—H5CA	120.7
C5A—C6A—C8A	122.7 (2)	C4C—C5C—H5CA	120.7
C2A—C7A—H7AA	109.5	C5C—C6C—C1C	121.2 (2)
C2A—C7A—H7AB	109.5	C5C—C6C—H6CA	119.4
H7AA—C7A—H7AB	109.5	C1C—C6C—H6CA	119.4
C2A—C7A—H7AC	109.5	O2C—C7C—O1C	122.8 (2)
H7AA—C7A—H7AC	109.5	O2C—C7C—C1C	124.2 (2)
H7AB—C7A—H7AC	109.5	O1C—C7C—C1C	112.9 (2)
C6A—C8A—H8AA	109.5	C2C—C8C—H8CA	109.5
C6A—C8A—H8AB	109.5	C2C—C8C—H8CB	109.5
H8AA—C8A—H8AB	109.5	H8CA—C8C—H8CB	109.5
C6A—C8A—H8AC	109.5	C2C—C8C—H8CC	109.5
H8AA—C8A—H8AC	109.5	H8CA—C8C—H8CC	109.5
H8AB—C8A—H8AC	109.5	H8CB—C8C—H8CC	109.5
C2B—N1B—C6B	116.8 (2)	C7D—O1D—H1D	110 (3)
N1B—C2B—N3B	126.3 (2)	C6D—C1D—C2D	120.2 (2)
N1B—C2B—C7B	117.6 (2)	C6D—C1D—C7D	118.4 (2)
N3B—C2B—C7B	116.1 (2)	C2D—C1D—C7D	121.3 (2)
C2B—N3B—C4B	118.0 (2)	C3D—C2D—C1D	117.4 (2)
C4B—N4B—H4BA	120.0	C3D—C2D—C8D	118.6 (2)
C4B—N4B—H4BB	120.0	C1D—C2D—C8D	124.0 (2)
H4BA—N4B—H4BB	120.0	C4D—C3D—C2D	122.0 (2)
N4B—C4B—N3B	117.7 (2)	C4D—C3D—H3DA	119.0
N4B—C4B—C5B	123.6 (2)	C2D—C3D—H3DA	119.0
N3B—C4B—C5B	118.7 (2)	C3D—C4D—C5D	120.2 (2)
C6B—C5B—C4B	119.7 (2)	C3D—C4D—H4DA	119.9
C6B—C5B—Cl2	121.73 (19)	C5D—C4D—H4DA	119.9
C4B—C5B—Cl2	118.5 (2)	C6D—C5D—C4D	119.3 (3)
N1B—C6B—C5B	120.4 (2)	C6D—C5D—H5DA	120.4
N1B—C6B—C8B	116.5 (2)	C4D—C5D—H5DA	120.4
C5B—C6B—C8B	123.1 (2)	C5D—C6D—C1D	120.8 (2)
C2B—C7B—H7BA	109.5	C5D—C6D—H6DA	119.6
C2B—C7B—H7BB	109.5	C1D—C6D—H6DA	119.6
H7BA—C7B—H7BB	109.5	O2D—C7D—O1D	122.1 (2)
C2B—C7B—H7BC	109.5	O2D—C7D—C1D	124.7 (2)
H7BA—C7B—H7BC	109.5	O1D—C7D—C1D	113.2 (2)
H7BB—C7B—H7BC	109.5	C2D—C8D—H8DA	109.5
C6B—C8B—H8BA	109.5	C2D—C8D—H8DB	109.5
C6B—C8B—H8BB	109.5	H8DA—C8D—H8DB	109.5
H8BA—C8B—H8BB	109.5	C2D—C8D—H8DC	109.5
C6B—C8B—H8BC	109.5	H8DA—C8D—H8DC	109.5
H8BA—C8B—H8BC	109.5	H8DB—C8D—H8DC	109.5
C6A—N1A—C2A—N3A	−0.4 (4)	Cl2—C5B—C6B—C8B	−2.3 (4)
C6A—N1A—C2A—C7A	−179.8 (2)	C6C—C1C—C2C—C3C	0.5 (4)
N1A—C2A—N3A—C4A	−0.4 (4)	C7C—C1C—C2C—C3C	−177.4 (2)
C7A—C2A—N3A—C4A	179.0 (2)	C6C—C1C—C2C—C8C	−178.8 (3)
C2A—N3A—C4A—N4A	−178.4 (3)	C7C—C1C—C2C—C8C	3.4 (4)
C2A—N3A—C4A—C5A	1.7 (4)	C1C—C2C—C3C—C4C	0.9 (4)
N4A—C4A—C5A—C6A	177.9 (3)	C8C—C2C—C3C—C4C	−179.8 (3)
N3A—C4A—C5A—C6A	−2.2 (4)	C2C—C3C—C4C—C5C	−1.1 (4)
N4A—C4A—C5A—Cl1	−1.9 (4)	C3C—C4C—C5C—C6C	−0.1 (4)
N3A—C4A—C5A—Cl1	178.0 (2)	C4C—C5C—C6C—C1C	1.5 (4)
C2A—N1A—C6A—C5A	−0.1 (4)	C2C—C1C—C6C—C5C	−1.7 (4)
C2A—N1A—C6A—C8A	179.2 (2)	C7C—C1C—C6C—C5C	176.2 (3)
C4A—C5A—C6A—N1A	1.4 (4)	C6C—C1C—C7C—O2C	−159.6 (3)
Cl1—C5A—C6A—N1A	−178.8 (2)	C2C—C1C—C7C—O2C	18.3 (4)
C4A—C5A—C6A—C8A	−177.9 (2)	C6C—C1C—C7C—O1C	18.1 (4)
Cl1—C5A—C6A—C8A	1.9 (4)	C2C—C1C—C7C—O1C	−164.0 (3)
C6B—N1B—C2B—N3B	1.1 (4)	C6D—C1D—C2D—C3D	3.6 (4)
C6B—N1B—C2B—C7B	−179.2 (2)	C7D—C1D—C2D—C3D	−176.8 (2)
N1B—C2B—N3B—C4B	−1.2 (4)	C6D—C1D—C2D—C8D	−177.2 (3)
C7B—C2B—N3B—C4B	179.1 (2)	C7D—C1D—C2D—C8D	2.4 (4)
C2B—N3B—C4B—N4B	−180.0 (3)	C1D—C2D—C3D—C4D	−2.9 (4)
C2B—N3B—C4B—C5B	−0.3 (4)	C8D—C2D—C3D—C4D	177.8 (3)
N4B—C4B—C5B—C6B	−178.5 (3)	C2D—C3D—C4D—C5D	0.8 (4)
N3B—C4B—C5B—C6B	1.9 (4)	C3D—C4D—C5D—C6D	0.8 (4)
N4B—C4B—C5B—Cl2	1.3 (4)	C4D—C5D—C6D—C1D	−0.1 (4)
N3B—C4B—C5B—Cl2	−178.3 (2)	C2D—C1D—C6D—C5D	−2.2 (4)
C2B—N1B—C6B—C5B	0.5 (4)	C7D—C1D—C6D—C5D	178.2 (2)
C2B—N1B—C6B—C8B	−179.0 (2)	C6D—C1D—C7D—O2D	162.9 (3)
C4B—C5B—C6B—N1B	−2.0 (4)	C2D—C1D—C7D—O2D	−16.7 (4)
Cl2—C5B—C6B—N1B	178.2 (2)	C6D—C1D—C7D—O1D	−16.7 (4)
C4B—C5B—C6B—C8B	177.5 (2)	C2D—C1D—C7D—O1D	163.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4A—H4AA···O2C	0.88	2.07	2.938 (3)	169
N4A—H4AB···N1B	0.88	2.39	3.104 (3)	139
C7A—H7AA···Cl2^i	0.98	2.84	3.816 (3)	173
C7A—H7AB···O1C	0.98	2.54	3.281 (3)	132
N4B—H4BA···O2D	0.88	2.07	2.938 (3)	170
N4B—H4BB···N1A^ii	0.88	2.42	3.164 (3)	142
C7B—H7BA···Cl1	0.98	2.94	3.783 (3)	145
O1C—H1C···N3A	0.96 (5)	1.70 (5)	2.662 (3)	174 (5)
O1D—H1D···N3B	0.95 (4)	1.75 (4)	2.685 (3)	170 (4)

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

4-Amino-5-chloro-2,6-dimethylpyrimidine–3-methylbenzoic acid (1/1) (COCRYSTAL-8)

Crystal data

C6H8ClN3·C8H8O2	Dx = 1.365 Mg m^−3
Mr = 293.75	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, Pbcn	Cell parameters from 15282 reflections
a = 8.4524 (1) Å	θ = 3.6–76.6°
b = 13.5387 (2) Å	µ = 2.42 mm^−1
c = 24.9813 (3) Å	T = 120 K
V = 2858.72 (6) Å^3	Prism, colorless
Z = 8	0.42 × 0.24 × 0.19 mm
F(000) = 1232

Data collection

Agilent SuperNova Dual Source diffractometer with an Atlas detector	3006 independent reflections
Radiation source: sealed X-ray tube	2904 reflections with I > 2σ(I)
Detector resolution: 10.6501 pixels mm^-1	Rint = 0.033
ω scans	θmax = 76.8°, θmin = 3.5°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	h = −7→10
Tmin = 0.680, Tmax = 1.000	k = −15→16
26401 measured reflections	l = −30→31

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.103	w = 1/[σ^2(Fo^2) + (0.0616P)^2 + 1.3483P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
3006 reflections	Δρmax = 0.30 e Å^−3
196 parameters	Δρmin = −0.31 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.

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

	x	y	z	Uiso*/Ueq
Cl1	0.15056 (4)	0.43229 (2)	0.19457 (2)	0.02742 (13)
N1A	0.27927 (13)	0.68415 (8)	0.26427 (4)	0.0221 (2)
C2A	0.35774 (15)	0.64739 (10)	0.30611 (5)	0.0203 (3)
N3A	0.38017 (13)	0.55115 (8)	0.31659 (4)	0.0201 (2)
N4A	0.33933 (14)	0.38852 (9)	0.29368 (5)	0.0238 (3)
H41	0.391 (2)	0.3742 (13)	0.3208 (7)	0.024 (4)*
H42	0.297 (2)	0.3408 (15)	0.2732 (8)	0.041 (5)*
C4A	0.31709 (15)	0.48386 (9)	0.28280 (5)	0.0196 (3)
C5A	0.23205 (15)	0.51817 (9)	0.23781 (5)	0.0208 (3)
C6A	0.21632 (15)	0.61794 (10)	0.22941 (5)	0.0218 (3)
C7A	0.42722 (17)	0.71901 (9)	0.34549 (5)	0.0272 (3)
H7AA	0.4024	0.7867	0.3343	0.041*
H7AB	0.5423	0.7104	0.3468	0.041*
H7AC	0.3824	0.7068	0.3810	0.041*
C8A	0.13053 (17)	0.65888 (11)	0.18186 (6)	0.0292 (3)
H8AA	0.1421	0.7309	0.1812	0.044*
H8AB	0.0181	0.6418	0.1843	0.044*
H8AC	0.1752	0.6308	0.1490	0.044*
O1B	0.56542 (12)	0.51547 (7)	0.40098 (4)	0.0260 (2)
H1B	0.502 (3)	0.5220 (17)	0.3730 (9)	0.056 (6)*
O2B	0.51805 (11)	0.35371 (7)	0.39001 (4)	0.0259 (2)
C1B	0.68785 (15)	0.40432 (10)	0.46069 (5)	0.0218 (3)
C2B	0.73386 (15)	0.48174 (10)	0.49402 (5)	0.0231 (3)
H2BA	0.6996	0.5470	0.4863	0.028*
C3B	0.82943 (16)	0.46448 (11)	0.53845 (5)	0.0254 (3)
C4B	0.87966 (17)	0.36796 (11)	0.54822 (6)	0.0296 (3)
H4BA	0.9452	0.3549	0.5783	0.035*
C5B	0.83573 (18)	0.29079 (11)	0.51486 (6)	0.0324 (3)
H5BA	0.8722	0.2257	0.5220	0.039*
C6B	0.73882 (17)	0.30830 (10)	0.47111 (6)	0.0277 (3)
H6BA	0.7075	0.2554	0.4485	0.033*
C7B	0.58274 (15)	0.42178 (9)	0.41389 (5)	0.0213 (3)
C8B	0.87751 (18)	0.54831 (12)	0.57482 (6)	0.0312 (3)
H8BA	0.9427	0.5226	0.6041	0.047*
H8BB	0.7827	0.5798	0.5896	0.047*
H8BC	0.9384	0.5970	0.5544	0.047*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0331 (2)	0.0262 (2)	0.02299 (19)	−0.00227 (12)	−0.00619 (12)	−0.00403 (11)
N1A	0.0231 (5)	0.0199 (5)	0.0233 (5)	0.0012 (4)	0.0003 (4)	0.0013 (4)
C2A	0.0201 (6)	0.0183 (6)	0.0225 (6)	−0.0007 (4)	0.0018 (4)	0.0009 (4)
N3A	0.0214 (5)	0.0187 (5)	0.0203 (5)	−0.0009 (4)	−0.0010 (4)	0.0003 (4)
N4A	0.0306 (6)	0.0184 (6)	0.0225 (6)	−0.0004 (4)	−0.0057 (5)	0.0001 (4)
C4A	0.0195 (5)	0.0194 (6)	0.0200 (6)	−0.0012 (5)	0.0031 (5)	−0.0003 (4)
C5A	0.0205 (6)	0.0227 (6)	0.0193 (6)	−0.0011 (5)	0.0001 (5)	−0.0018 (4)
C6A	0.0197 (6)	0.0252 (6)	0.0206 (6)	0.0016 (5)	0.0012 (5)	0.0012 (5)
C7A	0.0323 (7)	0.0204 (6)	0.0290 (7)	−0.0019 (5)	−0.0043 (5)	−0.0012 (5)
C8A	0.0313 (7)	0.0290 (7)	0.0271 (7)	0.0044 (6)	−0.0052 (6)	0.0044 (6)
O1B	0.0317 (5)	0.0204 (5)	0.0260 (5)	0.0007 (4)	−0.0091 (4)	0.0009 (4)
O2B	0.0292 (5)	0.0226 (5)	0.0259 (5)	−0.0029 (4)	−0.0062 (4)	0.0006 (3)
C1B	0.0189 (6)	0.0249 (6)	0.0217 (6)	−0.0010 (5)	−0.0001 (5)	0.0023 (5)
C2B	0.0208 (6)	0.0257 (7)	0.0229 (6)	0.0008 (5)	0.0005 (5)	−0.0003 (5)
C3B	0.0206 (6)	0.0336 (7)	0.0222 (6)	−0.0019 (5)	0.0005 (5)	−0.0006 (5)
C4B	0.0250 (6)	0.0359 (8)	0.0278 (7)	−0.0007 (6)	−0.0064 (5)	0.0060 (6)
C5B	0.0320 (7)	0.0262 (7)	0.0390 (8)	0.0002 (6)	−0.0101 (6)	0.0074 (6)
C6B	0.0265 (7)	0.0244 (7)	0.0323 (7)	−0.0022 (5)	−0.0059 (5)	0.0023 (5)
C7B	0.0198 (6)	0.0227 (6)	0.0214 (6)	0.0005 (5)	0.0013 (5)	0.0009 (5)
C8B	0.0287 (7)	0.0394 (8)	0.0254 (7)	−0.0002 (6)	−0.0042 (5)	−0.0063 (6)

Geometric parameters (Å, º)

Cl1—C5A	1.7301 (13)	O1B—C7B	1.3169 (16)
N1A—C2A	1.3342 (17)	O1B—H1B	0.88 (2)
N1A—C6A	1.3584 (17)	O2B—C7B	1.2264 (16)
C2A—N3A	1.3424 (17)	C1B—C6B	1.3940 (18)
C2A—C7A	1.5011 (18)	C1B—C2B	1.3940 (18)
N3A—C4A	1.3516 (16)	C1B—C7B	1.4874 (18)
N4A—C4A	1.3325 (17)	C2B—C3B	1.3924 (18)
N4A—H41	0.829 (18)	C2B—H2BA	0.9500
N4A—H42	0.90 (2)	C3B—C4B	1.396 (2)
C4A—C5A	1.4125 (18)	C3B—C8B	1.510 (2)
C5A—C6A	1.3735 (19)	C4B—C5B	1.387 (2)
C6A—C8A	1.4979 (18)	C4B—H4BA	0.9500
C7A—H7AA	0.9800	C5B—C6B	1.386 (2)
C7A—H7AB	0.9800	C5B—H5BA	0.9500
C7A—H7AC	0.9800	C6B—H6BA	0.9500
C8A—H8AA	0.9800	C8B—H8BA	0.9800
C8A—H8AB	0.9800	C8B—H8BB	0.9800
C8A—H8AC	0.9800	C8B—H8BC	0.9800
C2A—N1A—C6A	116.79 (11)	C7B—O1B—H1B	110.9 (15)
N1A—C2A—N3A	125.81 (12)	C6B—C1B—C2B	120.23 (12)
N1A—C2A—C7A	117.83 (12)	C6B—C1B—C7B	118.66 (12)
N3A—C2A—C7A	116.35 (11)	C2B—C1B—C7B	121.11 (12)
C2A—N3A—C4A	118.47 (11)	C3B—C2B—C1B	120.78 (13)
C4A—N4A—H41	117.9 (12)	C3B—C2B—H2BA	119.6
C4A—N4A—H42	121.6 (13)	C1B—C2B—H2BA	119.6
H41—N4A—H42	120.5 (18)	C2B—C3B—C4B	118.23 (13)
N4A—C4A—N3A	118.03 (12)	C2B—C3B—C8B	120.65 (14)
N4A—C4A—C5A	123.55 (12)	C4B—C3B—C8B	121.12 (13)
N3A—C4A—C5A	118.42 (11)	C5B—C4B—C3B	121.25 (13)
C6A—C5A—C4A	119.62 (11)	C5B—C4B—H4BA	119.4
C6A—C5A—Cl1	121.80 (10)	C3B—C4B—H4BA	119.4
C4A—C5A—Cl1	118.58 (10)	C6B—C5B—C4B	120.20 (14)
N1A—C6A—C5A	120.87 (11)	C6B—C5B—H5BA	119.9
N1A—C6A—C8A	116.99 (12)	C4B—C5B—H5BA	119.9
C5A—C6A—C8A	122.14 (12)	C5B—C6B—C1B	119.30 (13)
C2A—C7A—H7AA	109.5	C5B—C6B—H6BA	120.3
C2A—C7A—H7AB	109.5	C1B—C6B—H6BA	120.3
H7AA—C7A—H7AB	109.5	O2B—C7B—O1B	123.72 (12)
C2A—C7A—H7AC	109.5	O2B—C7B—C1B	121.95 (12)
H7AA—C7A—H7AC	109.5	O1B—C7B—C1B	114.33 (11)
H7AB—C7A—H7AC	109.5	C3B—C8B—H8BA	109.5
C6A—C8A—H8AA	109.5	C3B—C8B—H8BB	109.5
C6A—C8A—H8AB	109.5	H8BA—C8B—H8BB	109.5
H8AA—C8A—H8AB	109.5	C3B—C8B—H8BC	109.5
C6A—C8A—H8AC	109.5	H8BA—C8B—H8BC	109.5
H8AA—C8A—H8AC	109.5	H8BB—C8B—H8BC	109.5
H8AB—C8A—H8AC	109.5
C6A—N1A—C2A—N3A	0.22 (19)	Cl1—C5A—C6A—C8A	−1.18 (18)
C6A—N1A—C2A—C7A	−179.47 (11)	C6B—C1B—C2B—C3B	−0.8 (2)
N1A—C2A—N3A—C4A	−0.97 (19)	C7B—C1B—C2B—C3B	178.57 (12)
C7A—C2A—N3A—C4A	178.73 (11)	C1B—C2B—C3B—C4B	0.9 (2)
C2A—N3A—C4A—N4A	−179.68 (12)	C1B—C2B—C3B—C8B	−179.30 (13)
C2A—N3A—C4A—C5A	0.64 (18)	C2B—C3B—C4B—C5B	−0.2 (2)
N4A—C4A—C5A—C6A	−179.33 (12)	C8B—C3B—C4B—C5B	−179.97 (14)
N3A—C4A—C5A—C6A	0.33 (18)	C3B—C4B—C5B—C6B	−0.7 (2)
N4A—C4A—C5A—Cl1	0.54 (18)	C4B—C5B—C6B—C1B	0.8 (2)
N3A—C4A—C5A—Cl1	−179.80 (9)	C2B—C1B—C6B—C5B	−0.1 (2)
C2A—N1A—C6A—C5A	0.82 (18)	C7B—C1B—C6B—C5B	−179.46 (13)
C2A—N1A—C6A—C8A	−178.96 (11)	C6B—C1B—C7B—O2B	12.8 (2)
C4A—C5A—C6A—N1A	−1.09 (19)	C2B—C1B—C7B—O2B	−166.53 (12)
Cl1—C5A—C6A—N1A	179.04 (10)	C6B—C1B—C7B—O1B	−167.53 (12)
C4A—C5A—C6A—C8A	178.68 (12)	C2B—C1B—C7B—O1B	13.12 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4A—H41···O2B	0.829 (18)	2.055 (19)	2.8802 (15)	174.2 (17)
N4A—H42···N1A^i	0.90 (2)	2.23 (2)	3.0332 (16)	149.0 (17)
C7A—H7AA···Cl1^ii	0.98	2.97	3.5919 (14)	123
C7A—H7AA···N4A^iii	0.98	2.67	3.4667 (18)	139
C8A—H8AA···O2B^iv	0.98	2.65	3.3295 (17)	127
O1B—H1B···N3A	0.88 (2)	1.79 (2)	2.6701 (15)	173 (2)

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

4-Amino-5-chloro-2,6-dimethylpyrimidine–4-methylbenzoic acid (1/1) (COCRYSTAL-9)

Crystal data

C6H8ClN3·C8H8O2	F(000) = 616
Mr = 293.75	Dx = 1.360 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 8.0223 (5) Å	Cell parameters from 2368 reflections
b = 13.6901 (10) Å	θ = 4.7–76.5°
c = 13.3346 (10) Å	µ = 2.41 mm^−1
β = 101.557 (7)°	T = 120 K
V = 1434.80 (18) Å^3	Plate, colorless
Z = 4	0.51 × 0.17 × 0.08 mm

Data collection

Agilent SuperNova Dual Source diffractometer with an Atlas detector	2966 independent reflections
Radiation source: sealed X-ray tube	2422 reflections with I > 2σ(I)
Detector resolution: 10.6501 pixels mm^-1	Rint = 0.040
ω scans	θmax = 76.7°, θmin = 4.7°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	h = −8→10
Tmin = 0.582, Tmax = 1.000	k = −17→17
6765 measured reflections	l = −16→15

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.047	w = 1/[σ^2(Fo^2) + (0.0813P)^2 + 0.4428P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.140	(Δ/σ)max = 0.001
S = 1.04	Δρmax = 0.28 e Å^−3
2966 reflections	Δρmin = −0.41 e Å^−3
197 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0014 (4)

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.

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

	x	y	z	Uiso*/Ueq
Cl1	1.08463 (7)	0.85968 (4)	0.61237 (4)	0.03229 (19)
N1A	0.9592 (2)	0.72109 (13)	0.34491 (13)	0.0271 (4)
C2A	0.8839 (3)	0.64300 (15)	0.37583 (16)	0.0264 (4)
N3A	0.8637 (2)	0.62518 (13)	0.47148 (13)	0.0262 (4)
N4A	0.8970 (2)	0.67557 (14)	0.63951 (14)	0.0297 (4)
H41	0.852 (3)	0.625 (2)	0.647 (2)	0.030 (7)*
H42	0.934 (3)	0.719 (2)	0.691 (2)	0.042 (7)*
C4A	0.9222 (2)	0.69202 (15)	0.54527 (15)	0.0253 (4)
C5A	1.0068 (2)	0.77534 (15)	0.51821 (15)	0.0265 (4)
C6A	1.0238 (2)	0.78780 (15)	0.41779 (15)	0.0259 (4)
C7A	0.8182 (3)	0.56630 (16)	0.29745 (16)	0.0323 (5)
H7AA	0.8067	0.5941	0.2287	0.048*
H7AB	0.7069	0.5434	0.3073	0.048*
H7AC	0.8980	0.5113	0.3051	0.048*
C8A	1.1093 (3)	0.87516 (16)	0.38284 (17)	0.0308 (4)
H8AA	1.1603	0.8570	0.3246	0.046*
H8AB	1.1984	0.8986	0.4390	0.046*
H8AC	1.0252	0.9270	0.3621	0.046*
O1B	0.7077 (2)	0.45998 (12)	0.49384 (12)	0.0375 (4)
H1B	0.757 (5)	0.519 (3)	0.492 (3)	0.089 (13)*
O2B	0.7255 (2)	0.48776 (12)	0.66154 (12)	0.0373 (4)
C1B	0.5926 (3)	0.34164 (16)	0.58705 (17)	0.0288 (4)
C2B	0.5582 (3)	0.30639 (17)	0.67918 (17)	0.0310 (5)
H2BA	0.5902	0.3436	0.7401	0.037*
C3B	0.4773 (3)	0.21712 (17)	0.68174 (17)	0.0321 (5)
H3BA	0.4540	0.1940	0.7447	0.038*
C4B	0.4296 (3)	0.16065 (16)	0.59342 (17)	0.0304 (5)
C5B	0.4629 (3)	0.19749 (17)	0.50191 (17)	0.0328 (5)
H5BA	0.4295	0.1608	0.4407	0.039*
C6B	0.5437 (3)	0.28656 (16)	0.49835 (16)	0.0304 (5)
H6BA	0.5658	0.3100	0.4352	0.037*
C7B	0.6814 (3)	0.43686 (16)	0.58525 (16)	0.0298 (4)
C8B	0.3480 (3)	0.06233 (18)	0.59702 (19)	0.0384 (5)
H8BA	0.2421	0.0597	0.5456	0.058*
H8BB	0.3230	0.0518	0.6652	0.058*
H8BC	0.4258	0.0114	0.5826	0.058*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0424 (3)	0.0267 (3)	0.0290 (3)	−0.00801 (19)	0.0100 (2)	−0.00421 (18)
N1A	0.0310 (8)	0.0251 (9)	0.0267 (8)	−0.0005 (7)	0.0094 (6)	−0.0003 (7)
C2A	0.0289 (9)	0.0233 (10)	0.0279 (10)	0.0017 (7)	0.0083 (8)	−0.0017 (8)
N3A	0.0303 (8)	0.0220 (8)	0.0274 (8)	−0.0006 (7)	0.0080 (6)	0.0003 (7)
N4A	0.0422 (10)	0.0216 (9)	0.0263 (9)	−0.0077 (8)	0.0096 (7)	−0.0003 (7)
C4A	0.0281 (9)	0.0222 (9)	0.0262 (9)	0.0017 (7)	0.0068 (7)	0.0010 (8)
C5A	0.0282 (9)	0.0226 (10)	0.0298 (10)	0.0008 (8)	0.0081 (8)	−0.0012 (8)
C6A	0.0257 (9)	0.0225 (10)	0.0307 (10)	0.0021 (7)	0.0086 (7)	0.0019 (8)
C7A	0.0425 (11)	0.0280 (11)	0.0286 (10)	−0.0036 (9)	0.0124 (8)	−0.0041 (9)
C8A	0.0351 (10)	0.0279 (10)	0.0312 (10)	−0.0025 (9)	0.0112 (8)	0.0020 (8)
O1B	0.0513 (10)	0.0307 (8)	0.0339 (8)	−0.0130 (7)	0.0165 (7)	−0.0017 (7)
O2B	0.0485 (9)	0.0316 (8)	0.0331 (8)	−0.0099 (7)	0.0113 (7)	−0.0036 (7)
C1B	0.0282 (10)	0.0251 (10)	0.0340 (10)	−0.0005 (8)	0.0088 (8)	0.0000 (8)
C2B	0.0321 (10)	0.0306 (11)	0.0309 (10)	−0.0025 (9)	0.0076 (8)	−0.0012 (9)
C3B	0.0330 (10)	0.0334 (12)	0.0315 (10)	−0.0023 (9)	0.0105 (8)	0.0042 (9)
C4B	0.0272 (10)	0.0266 (10)	0.0383 (11)	0.0003 (8)	0.0091 (8)	0.0008 (9)
C5B	0.0359 (11)	0.0276 (11)	0.0352 (11)	−0.0023 (9)	0.0081 (9)	−0.0044 (9)
C6B	0.0341 (10)	0.0287 (11)	0.0295 (10)	−0.0016 (8)	0.0087 (8)	0.0009 (8)
C7B	0.0305 (10)	0.0274 (10)	0.0329 (10)	0.0000 (8)	0.0092 (8)	0.0005 (9)
C8B	0.0407 (12)	0.0297 (12)	0.0470 (13)	−0.0035 (9)	0.0138 (10)	0.0027 (10)

Geometric parameters (Å, º)

Cl1—C5A	1.728 (2)	O1B—C7B	1.317 (3)
N1A—C2A	1.333 (3)	O1B—H1B	0.90 (4)
N1A—C6A	1.358 (3)	O2B—C7B	1.225 (3)
C2A—N3A	1.340 (3)	C1B—C6B	1.391 (3)
C2A—C7A	1.501 (3)	C1B—C2B	1.398 (3)
N3A—C4A	1.357 (3)	C1B—C7B	1.488 (3)
N4A—C4A	1.331 (3)	C2B—C3B	1.387 (3)
N4A—H41	0.79 (3)	C2B—H2BA	0.9500
N4A—H42	0.91 (3)	C3B—C4B	1.397 (3)
C4A—C5A	1.410 (3)	C3B—H3BA	0.9500
C5A—C6A	1.383 (3)	C4B—C5B	1.395 (3)
C6A—C8A	1.499 (3)	C4B—C8B	1.502 (3)
C7A—H7AA	0.9800	C5B—C6B	1.386 (3)
C7A—H7AB	0.9800	C5B—H5BA	0.9500
C7A—H7AC	0.9800	C6B—H6BA	0.9500
C8A—H8AA	0.9800	C8B—H8BA	0.9800
C8A—H8AB	0.9800	C8B—H8BB	0.9800
C8A—H8AC	0.9800	C8B—H8BC	0.9800
C2A—N1A—C6A	116.70 (17)	C7B—O1B—H1B	113 (3)
N1A—C2A—N3A	126.09 (19)	C6B—C1B—C2B	119.2 (2)
N1A—C2A—C7A	117.61 (18)	C6B—C1B—C7B	121.0 (2)
N3A—C2A—C7A	116.28 (18)	C2B—C1B—C7B	119.7 (2)
C2A—N3A—C4A	118.50 (18)	C3B—C2B—C1B	120.1 (2)
C4A—N4A—H41	114.9 (19)	C3B—C2B—H2BA	120.0
C4A—N4A—H42	121.2 (18)	C1B—C2B—H2BA	120.0
H41—N4A—H42	124 (3)	C2B—C3B—C4B	121.2 (2)
N4A—C4A—N3A	118.32 (19)	C2B—C3B—H3BA	119.4
N4A—C4A—C5A	123.37 (19)	C4B—C3B—H3BA	119.4
N3A—C4A—C5A	118.31 (18)	C5B—C4B—C3B	118.0 (2)
C6A—C5A—C4A	119.55 (19)	C5B—C4B—C8B	120.9 (2)
C6A—C5A—Cl1	121.97 (16)	C3B—C4B—C8B	121.1 (2)
C4A—C5A—Cl1	118.48 (15)	C6B—C5B—C4B	121.4 (2)
N1A—C6A—C5A	120.80 (18)	C6B—C5B—H5BA	119.3
N1A—C6A—C8A	116.54 (18)	C4B—C5B—H5BA	119.3
C5A—C6A—C8A	122.64 (19)	C5B—C6B—C1B	120.1 (2)
C2A—C7A—H7AA	109.5	C5B—C6B—H6BA	119.9
C2A—C7A—H7AB	109.5	C1B—C6B—H6BA	119.9
H7AA—C7A—H7AB	109.5	O2B—C7B—O1B	124.0 (2)
C2A—C7A—H7AC	109.5	O2B—C7B—C1B	123.0 (2)
H7AA—C7A—H7AC	109.5	O1B—C7B—C1B	113.06 (19)
H7AB—C7A—H7AC	109.5	C4B—C8B—H8BA	109.5
C6A—C8A—H8AA	109.5	C4B—C8B—H8BB	109.5
C6A—C8A—H8AB	109.5	H8BA—C8B—H8BB	109.5
H8AA—C8A—H8AB	109.5	C4B—C8B—H8BC	109.5
C6A—C8A—H8AC	109.5	H8BA—C8B—H8BC	109.5
H8AA—C8A—H8AC	109.5	H8BB—C8B—H8BC	109.5
H8AB—C8A—H8AC	109.5
C6A—N1A—C2A—N3A	1.2 (3)	Cl1—C5A—C6A—C8A	−0.5 (3)
C6A—N1A—C2A—C7A	−177.48 (18)	C6B—C1B—C2B—C3B	0.5 (3)
N1A—C2A—N3A—C4A	0.8 (3)	C7B—C1B—C2B—C3B	−179.18 (19)
C7A—C2A—N3A—C4A	179.52 (18)	C1B—C2B—C3B—C4B	0.3 (3)
C2A—N3A—C4A—N4A	177.86 (18)	C2B—C3B—C4B—C5B	−1.1 (3)
C2A—N3A—C4A—C5A	−2.2 (3)	C2B—C3B—C4B—C8B	177.7 (2)
N4A—C4A—C5A—C6A	−178.43 (19)	C3B—C4B—C5B—C6B	1.2 (3)
N3A—C4A—C5A—C6A	1.6 (3)	C8B—C4B—C5B—C6B	−177.6 (2)
N4A—C4A—C5A—Cl1	1.0 (3)	C4B—C5B—C6B—C1B	−0.4 (3)
N3A—C4A—C5A—Cl1	−178.94 (14)	C2B—C1B—C6B—C5B	−0.4 (3)
C2A—N1A—C6A—C5A	−1.8 (3)	C7B—C1B—C6B—C5B	179.21 (19)
C2A—N1A—C6A—C8A	179.60 (17)	C6B—C1B—C7B—O2B	179.5 (2)
C4A—C5A—C6A—N1A	0.4 (3)	C2B—C1B—C7B—O2B	−0.8 (3)
Cl1—C5A—C6A—N1A	−179.01 (15)	C6B—C1B—C7B—O1B	−0.7 (3)
C4A—C5A—C6A—C8A	178.96 (18)	C2B—C1B—C7B—O1B	178.94 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4A—H41···O2B	0.79 (3)	2.17 (3)	2.958 (2)	178 (3)
N4A—H42···N1A^i	0.91 (3)	2.18 (3)	3.034 (2)	156 (2)
O1B—H1B···N3A	0.90 (4)	1.74 (4)	2.630 (2)	171 (4)

Symmetry code: (i) x, −y+3/2, z+1/2.

4-Amino-5-chloro-2,6-dimethylpyrimidine–4-aminobenzoic acid (1/1) (COCRYSTAL-10)

Crystal data

C6H8ClN3·C7H7NO2	F(000) = 616
Mr = 294.74	Dx = 1.435 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 7.8899 (2) Å	Cell parameters from 4256 reflections
b = 13.2361 (3) Å	θ = 3.3–76.1°
c = 13.3212 (3) Å	µ = 2.56 mm^−1
β = 101.254 (2)°	T = 120 K
V = 1364.40 (6) Å^3	Chunk, colorless
Z = 4	0.41 × 0.35 × 0.24 mm

Data collection

Agilent SuperNova Dual Source diffractometer with an Atlas detector	2823 independent reflections
Radiation source: sealed X-ray tube	2749 reflections with I > 2σ(I)
Detector resolution: 10.6501 pixels mm^-1	Rint = 0.017
ω scans	θmax = 76.7°, θmin = 4.8°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	h = −9→9
Tmin = 0.828, Tmax = 1.000	k = −16→15
6214 measured reflections	l = −14→16

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.097	w = 1/[σ^2(Fo^2) + (0.0596P)^2 + 0.5634P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.002
2823 reflections	Δρmax = 0.27 e Å^−3
203 parameters	Δρmin = −0.38 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.

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

	x	y	z	Uiso*/Ueq
Cl1	1.05069 (4)	0.86469 (2)	0.60646 (2)	0.02693 (12)
N1A	0.93400 (14)	0.71297 (8)	0.34395 (8)	0.0197 (2)
C2A	0.86103 (17)	0.63206 (10)	0.37710 (10)	0.0193 (3)
N3A	0.84090 (14)	0.61587 (8)	0.47345 (8)	0.0185 (2)
N4A	0.86802 (16)	0.67391 (9)	0.63872 (9)	0.0230 (3)
H4A1	0.817 (2)	0.6176 (15)	0.6497 (14)	0.028 (4)*
H4A2	0.897 (3)	0.7162 (16)	0.6858 (16)	0.037 (5)*
C4A	0.89549 (16)	0.68774 (10)	0.54425 (10)	0.0184 (3)
C5A	0.97806 (16)	0.77421 (9)	0.51419 (10)	0.0187 (3)
C6A	0.99586 (16)	0.78486 (10)	0.41444 (10)	0.0184 (3)
C7A	0.7941 (2)	0.55104 (11)	0.30121 (11)	0.0265 (3)
H7AA	0.8015	0.5740	0.2322	0.040*
H7AB	0.6734	0.5364	0.3040	0.040*
H7AC	0.8637	0.4898	0.3177	0.040*
C8A	1.07803 (18)	0.87473 (10)	0.37573 (11)	0.0226 (3)
H8AA	1.1481	0.8527	0.3266	0.034*
H8AB	1.1519	0.9092	0.4332	0.034*
H8AC	0.9880	0.9212	0.3420	0.034*
O1B	0.70377 (14)	0.43906 (8)	0.50497 (8)	0.0281 (2)
H1B	0.748 (3)	0.501 (2)	0.5011 (19)	0.052 (6)*
O2B	0.71164 (14)	0.47720 (7)	0.66954 (8)	0.0260 (2)
N1B	0.37076 (18)	0.03549 (10)	0.62891 (11)	0.0289 (3)
H1B1	0.352 (3)	0.0138 (16)	0.6885 (17)	0.035 (5)*
H1B2	0.329 (3)	0.0044 (17)	0.5724 (18)	0.041 (5)*
C1B	0.59620 (17)	0.31826 (10)	0.60438 (10)	0.0201 (3)
C2B	0.57168 (17)	0.28210 (10)	0.69932 (10)	0.0222 (3)
H2BA	0.6064	0.3224	0.7588	0.027*
C3B	0.49760 (18)	0.18860 (11)	0.70760 (10)	0.0232 (3)
H3BA	0.4834	0.1649	0.7728	0.028*
C4B	0.44307 (17)	0.12835 (10)	0.62039 (11)	0.0208 (3)
C5B	0.46641 (18)	0.16502 (10)	0.52511 (10)	0.0224 (3)
H5BA	0.4293	0.1257	0.4652	0.027*
C6B	0.54303 (17)	0.25799 (11)	0.51799 (10)	0.0225 (3)
H6BA	0.5598	0.2813	0.4532	0.027*
C7B	0.67560 (17)	0.41846 (10)	0.59684 (10)	0.0211 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0366 (2)	0.02105 (19)	0.02460 (19)	−0.01009 (12)	0.00947 (14)	−0.00687 (11)
N1A	0.0223 (5)	0.0179 (5)	0.0195 (5)	−0.0010 (4)	0.0059 (4)	−0.0004 (4)
C2A	0.0207 (6)	0.0180 (6)	0.0198 (6)	0.0001 (5)	0.0055 (5)	−0.0016 (5)
N3A	0.0217 (5)	0.0154 (5)	0.0191 (5)	−0.0017 (4)	0.0055 (4)	−0.0010 (4)
N4A	0.0335 (6)	0.0181 (6)	0.0181 (6)	−0.0068 (5)	0.0070 (5)	−0.0015 (4)
C4A	0.0194 (6)	0.0160 (6)	0.0197 (6)	0.0016 (4)	0.0037 (5)	−0.0001 (5)
C5A	0.0201 (6)	0.0154 (6)	0.0207 (6)	−0.0007 (5)	0.0046 (5)	−0.0015 (5)
C6A	0.0165 (5)	0.0163 (6)	0.0225 (6)	0.0015 (4)	0.0042 (5)	0.0010 (5)
C7A	0.0356 (7)	0.0226 (7)	0.0228 (7)	−0.0065 (6)	0.0095 (5)	−0.0056 (5)
C8A	0.0256 (6)	0.0189 (6)	0.0243 (7)	−0.0025 (5)	0.0074 (5)	0.0023 (5)
O1B	0.0412 (6)	0.0209 (5)	0.0248 (5)	−0.0089 (4)	0.0130 (4)	−0.0005 (4)
O2B	0.0358 (5)	0.0186 (5)	0.0255 (5)	−0.0047 (4)	0.0104 (4)	−0.0020 (4)
N1B	0.0371 (7)	0.0233 (6)	0.0274 (7)	−0.0114 (5)	0.0093 (5)	−0.0017 (5)
C1B	0.0200 (6)	0.0171 (6)	0.0241 (6)	−0.0002 (5)	0.0064 (5)	0.0006 (5)
C2B	0.0248 (6)	0.0205 (6)	0.0221 (6)	−0.0012 (5)	0.0064 (5)	−0.0015 (5)
C3B	0.0265 (7)	0.0225 (6)	0.0221 (6)	−0.0024 (5)	0.0088 (5)	0.0006 (5)
C4B	0.0177 (6)	0.0191 (6)	0.0263 (7)	−0.0008 (5)	0.0062 (5)	0.0006 (5)
C5B	0.0242 (6)	0.0211 (6)	0.0215 (6)	−0.0023 (5)	0.0034 (5)	−0.0028 (5)
C6B	0.0250 (6)	0.0222 (6)	0.0210 (6)	−0.0002 (5)	0.0062 (5)	0.0020 (5)
C7B	0.0225 (6)	0.0185 (6)	0.0234 (6)	0.0012 (5)	0.0069 (5)	0.0014 (5)

Geometric parameters (Å, º)

Cl1—C5A	1.7316 (13)	O1B—C7B	1.3145 (17)
N1A—C2A	1.3314 (17)	O1B—H1B	0.90 (3)
N1A—C6A	1.3589 (17)	O2B—C7B	1.2311 (17)
C2A—N3A	1.3410 (17)	N1B—C4B	1.3691 (17)
C2A—C7A	1.4975 (18)	N1B—H1B1	0.89 (2)
N3A—C4A	1.3497 (17)	N1B—H1B2	0.86 (2)
N4A—C4A	1.3307 (17)	C1B—C6B	1.3958 (19)
N4A—H4A1	0.87 (2)	C1B—C2B	1.4005 (19)
N4A—H4A2	0.84 (2)	C1B—C7B	1.4785 (18)
C4A—C5A	1.4129 (18)	C2B—C3B	1.3823 (19)
C5A—C6A	1.3704 (18)	C2B—H2BA	0.9500
C6A—C8A	1.4939 (17)	C3B—C4B	1.4056 (19)
C7A—H7AA	0.9800	C3B—H3BA	0.9500
C7A—H7AB	0.9800	C4B—C5B	1.4041 (19)
C7A—H7AC	0.9800	C5B—C6B	1.3824 (19)
C8A—H8AA	0.9800	C5B—H5BA	0.9500
C8A—H8AB	0.9800	C6B—H6BA	0.9500
C8A—H8AC	0.9800
C2A—N1A—C6A	117.02 (11)	H8AA—C8A—H8AC	109.5
N1A—C2A—N3A	125.85 (12)	H8AB—C8A—H8AC	109.5
N1A—C2A—C7A	118.06 (12)	C7B—O1B—H1B	112.3 (16)
N3A—C2A—C7A	116.08 (11)	C4B—N1B—H1B1	120.9 (13)
C2A—N3A—C4A	118.35 (11)	C4B—N1B—H1B2	116.6 (14)
C4A—N4A—H4A1	116.2 (13)	H1B1—N1B—H1B2	122 (2)
C4A—N4A—H4A2	123.1 (14)	C6B—C1B—C2B	118.49 (12)
H4A1—N4A—H4A2	120.7 (19)	C6B—C1B—C7B	121.32 (12)
N4A—C4A—N3A	118.37 (12)	C2B—C1B—C7B	120.19 (12)
N4A—C4A—C5A	123.28 (12)	C3B—C2B—C1B	120.87 (13)
N3A—C4A—C5A	118.35 (11)	C3B—C2B—H2BA	119.6
C6A—C5A—C4A	119.89 (12)	C1B—C2B—H2BA	119.6
C6A—C5A—Cl1	122.33 (10)	C2B—C3B—C4B	120.53 (13)
C4A—C5A—Cl1	117.77 (10)	C2B—C3B—H3BA	119.7
N1A—C6A—C5A	120.47 (12)	C4B—C3B—H3BA	119.7
N1A—C6A—C8A	116.14 (11)	N1B—C4B—C5B	121.03 (13)
C5A—C6A—C8A	123.37 (12)	N1B—C4B—C3B	120.40 (13)
C2A—C7A—H7AA	109.5	C5B—C4B—C3B	118.56 (12)
C2A—C7A—H7AB	109.5	C6B—C5B—C4B	120.40 (12)
H7AA—C7A—H7AB	109.5	C6B—C5B—H5BA	119.8
C2A—C7A—H7AC	109.5	C4B—C5B—H5BA	119.8
H7AA—C7A—H7AC	109.5	C5B—C6B—C1B	121.15 (12)
H7AB—C7A—H7AC	109.5	C5B—C6B—H6BA	119.4
C6A—C8A—H8AA	109.5	C1B—C6B—H6BA	119.4
C6A—C8A—H8AB	109.5	O2B—C7B—O1B	123.12 (12)
H8AA—C8A—H8AB	109.5	O2B—C7B—C1B	123.29 (12)
C6A—C8A—H8AC	109.5	O1B—C7B—C1B	113.59 (12)
C6A—N1A—C2A—N3A	1.0 (2)	Cl1—C5A—C6A—C8A	−0.28 (18)
C6A—N1A—C2A—C7A	−179.14 (12)	C6B—C1B—C2B—C3B	0.4 (2)
N1A—C2A—N3A—C4A	1.3 (2)	C7B—C1B—C2B—C3B	179.99 (12)
C7A—C2A—N3A—C4A	−178.49 (12)	C1B—C2B—C3B—C4B	−0.9 (2)
C2A—N3A—C4A—N4A	176.81 (12)	C2B—C3B—C4B—N1B	179.58 (13)
C2A—N3A—C4A—C5A	−2.83 (18)	C2B—C3B—C4B—C5B	0.3 (2)
N4A—C4A—C5A—C6A	−177.52 (12)	N1B—C4B—C5B—C6B	−178.59 (13)
N3A—C4A—C5A—C6A	2.10 (19)	C3B—C4B—C5B—C6B	0.6 (2)
N4A—C4A—C5A—Cl1	1.49 (18)	C4B—C5B—C6B—C1B	−1.1 (2)
N3A—C4A—C5A—Cl1	−178.90 (9)	C2B—C1B—C6B—C5B	0.6 (2)
C2A—N1A—C6A—C5A	−1.78 (18)	C7B—C1B—C6B—C5B	−178.99 (12)
C2A—N1A—C6A—C8A	179.69 (11)	C6B—C1B—C7B—O2B	174.06 (13)
C4A—C5A—C6A—N1A	0.26 (19)	C2B—C1B—C7B—O2B	−5.5 (2)
Cl1—C5A—C6A—N1A	−178.69 (9)	C6B—C1B—C7B—O1B	−5.78 (19)
C4A—C5A—C6A—C8A	178.68 (12)	C2B—C1B—C7B—O1B	174.67 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4A—H4A1···O2B	0.87 (2)	2.07 (2)	2.9441 (15)	174.7 (18)
N4A—H4A2···N1A^i	0.84 (2)	2.27 (2)	3.0710 (16)	159.5 (19)
C7A—H7AA···Cl1^ii	0.98	2.94	3.7580 (15)	142
C8A—H8AC···Cl1^iii	0.98	2.95	3.6163 (14)	127
O1B—H1B···N3A	0.90 (3)	1.76 (3)	2.6459 (15)	170 (2)
N1B—H1B1···O2B^iv	0.89 (2)	2.10 (2)	2.9847 (17)	173.4 (19)

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