Solvates of selected fenamic acids with substituted pyridines: structure, thermal stability and desolvation

Mefenamic acid (MA) formed solvates with 2-picoline (2PIC), 3-picoline (3PIC), 4-picoline (4PIC) and 3-chloropyridine (3CLPYR). The solvates crystallized in the space group with the carboxylic acid of MA hydrogen-bonded to the nitrogen of the substituted pyridine. Tolfenamic acid (TFA) formed solvates with 2PIC and 3PIC, the crystal structures successfully solved in the space groups P2₁/n and Pbca, respectively. The fenamate conformation varied depending on the acid and the included solvent. Similarities were observed in the structures involving MA. The two solvate structures of TFA had different packing arrangements. Grinding and slurry experiments were also successful for the preparation of all of the compounds except MA·2PIC. Recrystallization, grinding and slurry investigations of MA and 2PIC yielded a polymorph; the structure was successfully solved in P2₁/n. Additionally, the thermal stability of the solvates was determined. Desolvation experiments were also performed and the resultant powders were analysed using powder X-ray diffraction.

Computing details

Data collection: APEX2 (Bruker, 2005) for ma2picformI, ma3pic, ma3clpyr, ma4pic, tfa2pic, tfa3pic; COLLECT (2000) for ma2picformII. Cell refinement: SAINT-Plus (Bruker, 2004) for ma2picformI, ma3pic, ma3clpyr, ma4pic, tfa2pic, tfa3pic; DENZO-SMN (Otwinowski & Minor, 1997) for ma2picformII. Data reduction: SAINT-Plus and XPREP (Bruker 2004) for ma2picformI, ma3pic, ma3clpyr, ma4pic, tfa2pic, tfa3pic; DENZO-SMN (Otwinowski & Minor, 1997) for ma2picformII. For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 1999); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

(ma2picformI) 2-(2,3-dimethylphenyl)aminobenzoic acid 2-methylpyridine solvate form I

Crystal data

C21H22N2O2	Z = 2
Mr = 334.41	F(000) = 356
Triclinic, P1	Dx = 1.250 Mg m^−3
a = 7.6021 (15) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.4538 (17) Å	Cell parameters from 22483 reflections
c = 15.375 (3) Å	θ = 1.3–28.4°
α = 88.99 (3)°	µ = 0.08 mm^−1
β = 84.05 (3)°	T = 173 K
γ = 64.75 (3)°	Block, colourless
V = 888.5 (3) Å^3	0.48 × 0.27 × 0.14 mm

Data collection

Bruker Kappa Duo Apex II diffractometer	4474 independent reflections
Radiation source: fine-focus sealed tube	3761 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
1.2° φ scans and ω scans	θmax = 28.4°, θmin = 1.3°
Absorption correction: multi-scan SADABS	h = −10→10
Tmin = 0.933, Tmax = 0.989	k = −11→11
22483 measured reflections	l = −20→20

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0574P)^2 + 0.2396P] where P = (Fo^2 + 2Fc^2)/3
4474 reflections	(Δ/σ)max = 0.002
234 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3

Special details

Experimental. 'SADABS (Sheldrick, 1996)'

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
O1	0.93288 (15)	0.85226 (13)	0.23162 (6)	0.0416 (2)
N1	0.77690 (16)	0.63686 (14)	0.19267 (7)	0.0338 (2)
C9	0.74740 (15)	0.55465 (15)	0.04623 (7)	0.0273 (2)
O2	0.88541 (16)	0.94907 (14)	0.36922 (6)	0.0462 (3)
H2	0.9614	0.9926	0.3491	0.055*
C2	0.72635 (16)	0.77680 (14)	0.33511 (7)	0.0272 (2)
N2	1.12083 (15)	1.09333 (13)	0.31868 (7)	0.0325 (2)
H7	0.846 (2)	0.698 (2)	0.1775 (11)	0.048 (4)*
C10	0.75967 (15)	0.42546 (16)	−0.01340 (8)	0.0305 (2)
C8	0.78127 (16)	0.50911 (15)	0.13294 (7)	0.0278 (2)
C7	0.68887 (16)	0.66913 (14)	0.27698 (7)	0.0271 (2)
C6	0.54976 (18)	0.60615 (15)	0.30710 (8)	0.0327 (3)
H6	0.5212	0.5347	0.2692	0.039*
C13	0.82653 (17)	0.33916 (16)	0.15942 (8)	0.0327 (3)
H13	0.8506	0.3094	0.2183	0.039*
C1	0.85811 (17)	0.86047 (15)	0.30668 (8)	0.0303 (2)
C3	0.62827 (18)	0.81340 (16)	0.41939 (8)	0.0333 (3)
H3	0.6550	0.8846	0.4583	0.040*
C11	0.80384 (18)	0.25699 (16)	0.01462 (9)	0.0360 (3)
H11	0.8117	0.1701	−0.0259	0.043*
C5	0.45488 (19)	0.64628 (17)	0.39020 (9)	0.0381 (3)
H5	0.3610	0.6028	0.4086	0.046*
C12	0.83660 (18)	0.21329 (16)	0.10028 (9)	0.0366 (3)
H12	0.8659	0.0976	0.1185	0.044*
C14	0.69770 (19)	0.73804 (16)	0.01700 (8)	0.0368 (3)
H14A	0.6753	0.8146	0.0681	0.055*
H14C	0.5791	0.7801	−0.0131	0.055*
H14B	0.8062	0.7390	−0.0230	0.055*
C16	1.11804 (18)	1.22465 (16)	0.36674 (8)	0.0335 (3)
C4	0.4936 (2)	0.74934 (17)	0.44798 (9)	0.0391 (3)
H4	0.4289	0.7750	0.5057	0.047*
C15	0.72063 (19)	0.4705 (2)	−0.10663 (8)	0.0408 (3)
H15B	0.7449	0.3642	−0.1401	0.061*
H15C	0.8074	0.5214	−0.1325	0.061*
H15A	0.5841	0.5552	−0.1081	0.061*
C20	1.2549 (2)	1.02909 (17)	0.24974 (9)	0.0388 (3)
H20	1.2546	0.9368	0.2154	0.047*
C17	1.2552 (2)	1.29112 (19)	0.34653 (10)	0.0471 (3)
H17	1.2531	1.3838	0.3814	0.057*
C19	1.3933 (2)	1.09044 (18)	0.22616 (10)	0.0445 (3)
H19	1.4862	1.0423	0.1765	0.053*
C21	0.9619 (2)	1.2946 (2)	0.44185 (10)	0.0472 (3)
H21C	0.8340	1.3529	0.4196	0.071*
H21A	0.9850	1.3787	0.4765	0.071*
H21B	0.9644	1.1980	0.4787	0.071*
C18	1.3940 (2)	1.2228 (2)	0.27613 (11)	0.0499 (4)
H18	1.4894	1.2666	0.2622	0.060*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0530 (6)	0.0476 (5)	0.0372 (5)	−0.0360 (5)	0.0063 (4)	−0.0081 (4)
N1	0.0444 (6)	0.0409 (6)	0.0277 (5)	−0.0294 (5)	−0.0015 (4)	−0.0040 (4)
C9	0.0230 (5)	0.0309 (5)	0.0276 (5)	−0.0115 (4)	−0.0005 (4)	−0.0023 (4)
O2	0.0628 (6)	0.0614 (6)	0.0374 (5)	−0.0493 (5)	−0.0001 (4)	−0.0086 (4)
C2	0.0287 (5)	0.0265 (5)	0.0296 (5)	−0.0145 (4)	−0.0044 (4)	−0.0006 (4)
N2	0.0345 (5)	0.0309 (5)	0.0373 (5)	−0.0176 (4)	−0.0103 (4)	0.0019 (4)
C10	0.0218 (5)	0.0385 (6)	0.0291 (6)	−0.0113 (4)	0.0005 (4)	−0.0075 (5)
C8	0.0265 (5)	0.0316 (5)	0.0280 (5)	−0.0148 (4)	−0.0029 (4)	−0.0032 (4)
C7	0.0289 (5)	0.0269 (5)	0.0278 (5)	−0.0135 (4)	−0.0059 (4)	0.0003 (4)
C6	0.0358 (6)	0.0322 (6)	0.0366 (6)	−0.0208 (5)	−0.0040 (5)	−0.0037 (5)
C13	0.0306 (6)	0.0339 (6)	0.0330 (6)	−0.0127 (5)	−0.0060 (5)	0.0025 (5)
C1	0.0326 (6)	0.0294 (5)	0.0335 (6)	−0.0173 (5)	−0.0042 (5)	−0.0019 (4)
C3	0.0392 (6)	0.0329 (6)	0.0324 (6)	−0.0200 (5)	−0.0010 (5)	−0.0063 (5)
C11	0.0303 (6)	0.0353 (6)	0.0415 (7)	−0.0138 (5)	0.0025 (5)	−0.0150 (5)
C5	0.0399 (6)	0.0380 (6)	0.0437 (7)	−0.0254 (5)	0.0051 (5)	−0.0050 (5)
C12	0.0324 (6)	0.0270 (5)	0.0476 (7)	−0.0109 (5)	0.0001 (5)	−0.0019 (5)
C14	0.0410 (7)	0.0356 (6)	0.0331 (6)	−0.0162 (5)	−0.0026 (5)	0.0030 (5)
C16	0.0387 (6)	0.0315 (6)	0.0357 (6)	−0.0190 (5)	−0.0090 (5)	0.0015 (5)
C4	0.0454 (7)	0.0416 (7)	0.0347 (6)	−0.0254 (6)	0.0085 (5)	−0.0086 (5)
C15	0.0339 (6)	0.0569 (8)	0.0283 (6)	−0.0167 (6)	0.0000 (5)	−0.0092 (5)
C20	0.0414 (7)	0.0312 (6)	0.0421 (7)	−0.0126 (5)	−0.0091 (5)	−0.0015 (5)
C17	0.0577 (9)	0.0417 (7)	0.0556 (9)	−0.0347 (7)	−0.0031 (7)	−0.0035 (6)
C19	0.0406 (7)	0.0416 (7)	0.0450 (8)	−0.0128 (6)	0.0007 (6)	0.0055 (6)
C21	0.0505 (8)	0.0538 (8)	0.0425 (8)	−0.0282 (7)	0.0007 (6)	−0.0097 (6)
C18	0.0491 (8)	0.0467 (8)	0.0633 (10)	−0.0308 (7)	−0.0009 (7)	0.0096 (7)

Geometric parameters (Å, º)

O1—C1	1.2218 (15)	C11—C12	1.380 (2)
N1—C7	1.3709 (15)	C11—H11	0.9500
N1—C8	1.4174 (15)	C5—C4	1.3910 (18)
N1—H7	0.894 (17)	C5—H5	0.9500
C9—C8	1.4002 (16)	C12—H12	0.9500
C9—C10	1.4045 (16)	C14—H14A	0.9800
C9—C14	1.5031 (17)	C14—H14C	0.9800
O2—C1	1.3145 (14)	C14—H14B	0.9800
O2—H2	0.8400	C16—C17	1.3881 (18)
C2—C3	1.3956 (17)	C16—C21	1.494 (2)
C2—C7	1.4182 (15)	C4—H4	0.9500
C2—C1	1.4825 (15)	C15—H15B	0.9800
N2—C20	1.3347 (18)	C15—H15C	0.9800
N2—C16	1.3358 (15)	C15—H15A	0.9800
C10—C11	1.3882 (18)	C20—C19	1.374 (2)
C10—C15	1.5034 (17)	C20—H20	0.9500
C8—C13	1.3911 (17)	C17—C18	1.373 (2)
C7—C6	1.4094 (16)	C17—H17	0.9500
C6—C5	1.3724 (18)	C19—C18	1.370 (2)
C6—H6	0.9500	C19—H19	0.9500
C13—C12	1.3839 (18)	C21—H21C	0.9800
C13—H13	0.9500	C21—H21A	0.9800
C3—C4	1.3805 (17)	C21—H21B	0.9800
C3—H3	0.9500	C18—H18	0.9500
C7—N1—C8	126.51 (10)	C11—C12—H12	120.2
C7—N1—H7	114.2 (10)	C13—C12—H12	120.2
C8—N1—H7	119.0 (11)	C9—C14—H14A	109.5
C8—C9—C10	118.69 (11)	C9—C14—H14C	109.5
C8—C9—C14	121.06 (11)	H14A—C14—H14C	109.5
C10—C9—C14	120.25 (11)	C9—C14—H14B	109.5
C1—O2—H2	109.5	H14A—C14—H14B	109.5
C3—C2—C7	119.35 (10)	H14C—C14—H14B	109.5
C3—C2—C1	119.07 (10)	N2—C16—C17	120.55 (12)
C7—C2—C1	121.46 (10)	N2—C16—C21	116.94 (11)
C20—N2—C16	119.12 (11)	C17—C16—C21	122.50 (12)
C11—C10—C9	119.69 (11)	C3—C4—C5	118.41 (11)
C11—C10—C15	120.17 (11)	C3—C4—H4	120.8
C9—C10—C15	120.13 (11)	C5—C4—H4	120.8
C13—C8—C9	120.63 (11)	C10—C15—H15B	109.5
C13—C8—N1	120.29 (11)	C10—C15—H15C	109.5
C9—C8—N1	119.03 (10)	H15B—C15—H15C	109.5
N1—C7—C6	121.44 (10)	C10—C15—H15A	109.5
N1—C7—C2	120.64 (10)	H15B—C15—H15A	109.5
C6—C7—C2	117.80 (11)	H15C—C15—H15A	109.5
C5—C6—C7	121.17 (11)	N2—C20—C19	122.92 (12)
C5—C6—H6	119.4	N2—C20—H20	118.5
C7—C6—H6	119.4	C19—C20—H20	118.5
C12—C13—C8	120.18 (11)	C18—C17—C16	119.90 (13)
C12—C13—H13	119.9	C18—C17—H17	120.1
C8—C13—H13	119.9	C16—C17—H17	120.1
O1—C1—O2	122.07 (11)	C18—C19—C20	118.36 (13)
O1—C1—C2	123.79 (10)	C18—C19—H19	120.8
O2—C1—C2	114.13 (10)	C20—C19—H19	120.8
C4—C3—C2	122.01 (11)	C16—C21—H21C	109.5
C4—C3—H3	119.0	C16—C21—H21A	109.5
C2—C3—H3	119.0	H21C—C21—H21A	109.5
C12—C11—C10	121.25 (11)	C16—C21—H21B	109.5
C12—C11—H11	119.4	H21C—C21—H21B	109.5
C10—C11—H11	119.4	H21A—C21—H21B	109.5
C6—C5—C4	121.25 (11)	C19—C18—C17	119.13 (13)
C6—C5—H5	119.4	C19—C18—H18	120.4
C4—C5—H5	119.4	C17—C18—H18	120.4
C11—C12—C13	119.56 (11)
C8—C9—C10—C11	0.29 (16)	C7—C2—C1—O1	4.62 (18)
C14—C9—C10—C11	−179.38 (10)	C3—C2—C1—O2	7.04 (17)
C8—C9—C10—C15	178.90 (10)	C7—C2—C1—O2	−176.82 (11)
C14—C9—C10—C15	−0.77 (16)	C7—C2—C3—C4	−0.68 (19)
C10—C9—C8—C13	0.12 (16)	C1—C2—C3—C4	175.55 (12)
C14—C9—C8—C13	179.78 (10)	C9—C10—C11—C12	−0.15 (17)
C10—C9—C8—N1	177.49 (10)	C15—C10—C11—C12	−178.76 (11)
C14—C9—C8—N1	−2.84 (16)	C7—C6—C5—C4	−0.5 (2)
C7—N1—C8—C13	−46.26 (17)	C10—C11—C12—C13	−0.39 (18)
C7—N1—C8—C9	136.35 (12)	C8—C13—C12—C11	0.80 (18)
C8—N1—C7—C6	−16.14 (18)	C20—N2—C16—C17	−1.39 (19)
C8—N1—C7—C2	167.88 (11)	C20—N2—C16—C21	178.53 (12)
C3—C2—C7—N1	177.29 (11)	C2—C3—C4—C5	−0.4 (2)
C1—C2—C7—N1	1.15 (17)	C6—C5—C4—C3	1.0 (2)
C3—C2—C7—C6	1.16 (16)	C16—N2—C20—C19	0.89 (19)
C1—C2—C7—C6	−174.98 (11)	N2—C16—C17—C18	0.6 (2)
N1—C7—C6—C5	−176.68 (12)	C21—C16—C17—C18	−179.31 (14)
C2—C7—C6—C5	−0.58 (18)	N2—C20—C19—C18	0.4 (2)
C9—C8—C13—C12	−0.67 (17)	C20—C19—C18—C17	−1.2 (2)
N1—C8—C13—C12	−178.01 (11)	C16—C17—C18—C19	0.7 (2)
C3—C2—C1—O1	−171.53 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N2	0.84	1.78	2.6142 (15)	174
N1—H7···O1	0.894 (17)	1.928 (17)	2.6661 (14)	138.7 (14)
C12—H12···O1^i	0.95	2.60	3.480 (2)	155
C15—H15B···O1^ii	0.98	2.62	3.329 (2)	129

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

(ma2picformII) 2-(2,3-dimethylphenyl)aminobenzoic acid 2methylpyridine solvate form II

Crystal data

C21H22N2O2	F(000) = 712
Mr = 334.41	Dx = 1.256 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.7857 (16) Å	Cell parameters from 7473 reflections
b = 8.1859 (16) Å	θ = 2.6–27.1°
c = 27.953 (6) Å	µ = 0.08 mm^−1
β = 96.87 (3)°	T = 173 K
V = 1768.7 (6) Å^3	Block, colourless
Z = 4	0.34 × 0.19 × 0.11 mm

Data collection

Nonius KappaCCD area-detector diffractometer	2906 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.020
Graphite monochromator	θmax = 27.1°, θmin = 3.8°
1° φ scans and ω scans	h = −9→9
7453 measured reflections	k = −10→10
3879 independent reflections	l = −35→35

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0708P)^2 + 0.3517P] where P = (Fo^2 + 2Fc^2)/3
3879 reflections	(Δ/σ)max = 0.009
237 parameters	Δρmax = 0.28 e Å^−3
0 restraints	Δρmin = −0.35 e Å^−3

Special details

Experimental. none

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
O1	0.50682 (12)	0.84893 (14)	0.06316 (4)	0.0420 (3)
O2	0.67821 (14)	0.80923 (15)	0.00585 (4)	0.0433 (3)
N2	0.40271 (15)	0.66874 (15)	−0.03983 (4)	0.0368 (3)
H2	0.569 (3)	0.751 (3)	−0.0100 (8)	0.089 (7)*
H7	0.554 (2)	0.949 (2)	0.1254 (6)	0.041 (4)*
C10	0.45991 (16)	1.05292 (18)	0.25931 (5)	0.0315 (3)
N1	0.63459 (16)	1.00338 (18)	0.14251 (4)	0.0400 (3)
C2	0.80224 (17)	0.93327 (17)	0.07796 (5)	0.0306 (3)
C7	0.79050 (17)	1.00271 (17)	0.12387 (5)	0.0301 (3)
C5	1.09864 (18)	1.05909 (18)	0.13103 (5)	0.0369 (3)
H5	1.1994	1.1017	0.1493	0.044*
C9	0.50040 (16)	0.98256 (17)	0.21616 (5)	0.0297 (3)
C6	0.94329 (17)	1.06320 (18)	0.14995 (5)	0.0333 (3)
H6	0.9391	1.1077	0.1812	0.040*
C13	0.65067 (18)	1.23202 (18)	0.19910 (5)	0.0369 (3)
H13	0.7138	1.2940	0.1784	0.044*
C8	0.59697 (16)	1.07363 (18)	0.18626 (5)	0.0313 (3)
C1	0.64933 (18)	0.86171 (17)	0.04862 (5)	0.0330 (3)
C3	0.96283 (18)	0.93070 (18)	0.05994 (5)	0.0370 (3)
H3	0.9703	0.8843	0.0291	0.044*
C11	0.51849 (18)	1.20889 (19)	0.27175 (5)	0.0377 (3)
H11	0.4939	1.2551	0.3014	0.045*
C16	0.41120 (19)	0.56900 (18)	−0.07752 (5)	0.0365 (3)
C19	0.0992 (2)	0.6203 (2)	−0.04358 (6)	0.0425 (4)
H19	−0.0074	0.6412	−0.0314	0.051*
C14	0.44577 (19)	0.81117 (19)	0.20204 (6)	0.0399 (4)
H14C	0.3969	0.7585	0.2288	0.060*
H14A	0.5465	0.7490	0.1943	0.060*
H14B	0.3584	0.8145	0.1737	0.060*
C12	0.61206 (18)	1.29841 (19)	0.24184 (6)	0.0405 (4)
H12	0.6497	1.4057	0.2508	0.049*
C18	0.1070 (2)	0.5160 (2)	−0.08204 (6)	0.0439 (4)
H18	0.0057	0.4623	−0.0965	0.053*
C15	0.3563 (2)	0.9609 (2)	0.29288 (6)	0.0437 (4)
H15A	0.3317	1.0330	0.3192	0.066*
H15C	0.4228	0.8662	0.3062	0.066*
H15B	0.2473	0.9237	0.2751	0.066*
C20	0.24944 (19)	0.6929 (2)	−0.02345 (5)	0.0409 (4)
H20	0.2448	0.7637	0.0033	0.049*
C17	0.2637 (2)	0.4906 (2)	−0.09922 (6)	0.0418 (4)
H17	0.2708	0.4198	−0.1258	0.050*
C4	1.11037 (18)	0.9937 (2)	0.08569 (6)	0.0413 (4)
H4	1.2176	0.9923	0.0727	0.050*
C21	0.5852 (2)	0.5465 (2)	−0.09444 (6)	0.0490 (4)
H21C	0.6635	0.6329	−0.0809	0.073*
H21A	0.5735	0.5520	−0.1297	0.073*
H21B	0.6323	0.4398	−0.0838	0.073*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0292 (5)	0.0559 (7)	0.0417 (6)	−0.0035 (5)	0.0083 (4)	−0.0117 (5)
O2	0.0381 (6)	0.0591 (7)	0.0337 (6)	−0.0048 (5)	0.0091 (4)	−0.0092 (5)
N2	0.0367 (7)	0.0398 (7)	0.0339 (6)	0.0014 (5)	0.0041 (5)	0.0000 (5)
C10	0.0237 (6)	0.0403 (8)	0.0305 (7)	0.0048 (6)	0.0031 (5)	0.0012 (6)
N1	0.0299 (6)	0.0587 (8)	0.0330 (7)	−0.0122 (6)	0.0097 (5)	−0.0105 (6)
C2	0.0292 (7)	0.0292 (7)	0.0340 (7)	0.0007 (5)	0.0067 (5)	0.0030 (6)
C7	0.0297 (7)	0.0301 (7)	0.0314 (7)	−0.0005 (5)	0.0071 (5)	0.0046 (6)
C5	0.0276 (7)	0.0361 (8)	0.0464 (9)	−0.0010 (6)	0.0023 (6)	0.0022 (6)
C9	0.0223 (6)	0.0346 (7)	0.0321 (7)	0.0002 (5)	0.0030 (5)	−0.0010 (6)
C6	0.0323 (7)	0.0338 (7)	0.0338 (7)	−0.0017 (6)	0.0041 (6)	0.0021 (6)
C13	0.0297 (7)	0.0382 (8)	0.0429 (8)	−0.0036 (6)	0.0048 (6)	0.0035 (7)
C8	0.0241 (6)	0.0398 (8)	0.0301 (7)	−0.0015 (6)	0.0032 (5)	−0.0016 (6)
C1	0.0330 (7)	0.0344 (7)	0.0321 (7)	0.0030 (6)	0.0066 (6)	0.0002 (6)
C3	0.0352 (8)	0.0375 (8)	0.0400 (8)	0.0026 (6)	0.0115 (6)	−0.0026 (6)
C11	0.0301 (7)	0.0470 (9)	0.0356 (8)	0.0035 (6)	0.0022 (6)	−0.0099 (7)
C16	0.0406 (8)	0.0365 (8)	0.0325 (7)	0.0035 (6)	0.0052 (6)	0.0038 (6)
C19	0.0360 (8)	0.0475 (9)	0.0444 (8)	0.0046 (7)	0.0064 (6)	0.0076 (7)
C14	0.0373 (8)	0.0383 (8)	0.0458 (8)	−0.0054 (6)	0.0115 (6)	−0.0048 (7)
C12	0.0297 (7)	0.0358 (8)	0.0553 (9)	−0.0021 (6)	0.0024 (6)	−0.0101 (7)
C18	0.0407 (8)	0.0449 (9)	0.0442 (9)	−0.0061 (7)	−0.0027 (7)	0.0077 (7)
C15	0.0426 (8)	0.0527 (10)	0.0379 (8)	0.0048 (7)	0.0138 (6)	0.0046 (7)
C20	0.0407 (8)	0.0437 (8)	0.0387 (8)	0.0043 (7)	0.0066 (6)	−0.0009 (7)
C17	0.0489 (9)	0.0396 (8)	0.0361 (8)	−0.0022 (7)	0.0023 (7)	−0.0017 (7)
C4	0.0281 (7)	0.0434 (9)	0.0544 (9)	0.0024 (6)	0.0135 (6)	0.0002 (7)
C21	0.0444 (9)	0.0577 (11)	0.0463 (9)	−0.0001 (8)	0.0117 (7)	−0.0066 (8)

Geometric parameters (Å, º)

O1—C1	1.2308 (17)	C5—C6	1.3772 (19)
O2—C1	1.3150 (17)	C5—C4	1.389 (2)
N2—C16	1.3408 (19)	C9—C8	1.4036 (19)
N2—C20	1.3430 (19)	C9—C14	1.505 (2)
C10—C11	1.386 (2)	C13—C12	1.378 (2)
C10—C9	1.4059 (19)	C13—C8	1.396 (2)
C10—C15	1.510 (2)	C3—C4	1.380 (2)
N1—C7	1.3771 (17)	C11—C12	1.383 (2)
N1—C8	1.4134 (18)	C16—C17	1.390 (2)
C2—C3	1.4029 (19)	C16—C21	1.499 (2)
C2—C7	1.4165 (19)	C19—C20	1.372 (2)
C2—C1	1.483 (2)	C19—C18	1.380 (2)
C7—C6	1.409 (2)	C18—C17	1.379 (2)
C16—N2—C20	119.14 (13)	C13—C8—C9	120.36 (13)
C11—C10—C9	119.46 (13)	C13—C8—N1	120.91 (13)
C11—C10—C15	119.19 (13)	C9—C8—N1	118.71 (13)
C9—C10—C15	121.34 (13)	O1—C1—O2	122.10 (13)
C7—N1—C8	127.75 (12)	O1—C1—C2	123.14 (12)
C3—C2—C7	119.22 (13)	O2—C1—C2	114.75 (12)
C3—C2—C1	119.11 (12)	C4—C3—C2	121.93 (14)
C7—C2—C1	121.67 (12)	C12—C11—C10	121.18 (13)
N1—C7—C6	122.07 (13)	N2—C16—C17	120.55 (13)
N1—C7—C2	119.97 (12)	N2—C16—C21	117.02 (13)
C6—C7—C2	117.90 (12)	C17—C16—C21	122.43 (14)
C6—C5—C4	121.09 (13)	C20—C19—C18	118.27 (14)
C8—C9—C10	118.97 (13)	C13—C12—C11	120.04 (14)
C8—C9—C14	119.58 (12)	C17—C18—C19	119.16 (15)
C10—C9—C14	121.44 (12)	N2—C20—C19	123.02 (14)
C5—C6—C7	121.25 (13)	C18—C17—C16	119.85 (15)
C12—C13—C8	119.97 (14)	C3—C4—C5	118.58 (13)
C8—N1—C7—C6	6.1 (2)	C3—C2—C1—O1	174.85 (14)
C8—N1—C7—C2	−176.69 (14)	C7—C2—C1—O1	−4.6 (2)
C3—C2—C7—N1	−178.74 (13)	C3—C2—C1—O2	−3.80 (19)
C1—C2—C7—N1	0.7 (2)	C7—C2—C1—O2	176.79 (12)
C3—C2—C7—C6	−1.4 (2)	C7—C2—C3—C4	0.1 (2)
C1—C2—C7—C6	178.00 (12)	C1—C2—C3—C4	−179.28 (14)
C11—C10—C9—C8	−1.12 (19)	C9—C10—C11—C12	1.8 (2)
C15—C10—C9—C8	179.95 (12)	C15—C10—C11—C12	−179.23 (13)
C11—C10—C9—C14	177.57 (12)	C20—N2—C16—C17	−0.4 (2)
C15—C10—C9—C14	−1.4 (2)	C20—N2—C16—C21	179.87 (14)
C4—C5—C6—C7	−0.6 (2)	C8—C13—C12—C11	−0.7 (2)
N1—C7—C6—C5	178.93 (13)	C10—C11—C12—C13	−0.9 (2)
C2—C7—C6—C5	1.7 (2)	C20—C19—C18—C17	−1.0 (2)
C12—C13—C8—C9	1.4 (2)	C16—N2—C20—C19	−0.1 (2)
C12—C13—C8—N1	179.75 (13)	C18—C19—C20—N2	0.8 (2)
C10—C9—C8—C13	−0.46 (19)	C19—C18—C17—C16	0.5 (2)
C14—C9—C8—C13	−179.17 (12)	N2—C16—C17—C18	0.3 (2)
C10—C9—C8—N1	−178.86 (12)	C21—C16—C17—C18	179.94 (15)
C14—C9—C8—N1	2.43 (19)	C2—C3—C4—C5	0.9 (2)
C7—N1—C8—C13	46.8 (2)	C6—C5—C4—C3	−0.7 (2)
C7—N1—C8—C9	−134.76 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N2	1.03 (2)	1.60 (2)	2.6265 (17)	174 (2)
N1—H7···O1	0.863 (17)	1.919 (17)	2.6421 (17)	140.4 (15)
C4—H4···O1^i	0.95	2.58	3.4341 (19)	150

Symmetry code: (i) x+1, y, z.

(ma3pic) 2-(2,3-dimethylphenyl)aminobenzoic acid 3-methylpyridine solvate

Crystal data

C21H22N2O2	Z = 2
Mr = 334.41	F(000) = 356
Triclinic, P1	Dx = 1.288 Mg m^−3
a = 7.6738 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.7598 (6) Å	Cell parameters from 20017 reflections
c = 16.2725 (12) Å	θ = 2.6–28.4°
α = 78.957 (1)°	µ = 0.08 mm^−1
β = 83.673 (2)°	T = 173 K
γ = 65.094 (1)°	Block, orange
V = 862.12 (11) Å^3	0.36 × 0.30 × 0.29 mm

Data collection

Bruker Kappa Duo Apex II diffractometer	4332 independent reflections
Radiation source: fine-focus sealed tube	3671 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
1.2° φ scans and ω scans	θmax = 28.4°, θmin = 2.6°
Absorption correction: multi-scan SADABS	h = −10→10
Tmin = 0.926, Tmax = 0.976	k = −10→10
20017 measured reflections	l = −21→21

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.059P)^2 + 0.2156P] where P = (Fo^2 + 2Fc^2)/3
4332 reflections	(Δ/σ)max = 0.002
237 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

Special details

Experimental. 'SADABS (Sheldrick, 1996)'

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
O1	0.07469 (13)	0.79435 (12)	0.14251 (5)	0.0330 (2)
O2	0.22929 (13)	0.97608 (13)	0.08350 (5)	0.0327 (2)
C2	0.04471 (14)	1.05798 (14)	0.20703 (6)	0.0201 (2)
N2	0.31639 (13)	0.77296 (13)	−0.03672 (6)	0.0256 (2)
H7	−0.090 (2)	0.811 (2)	0.2390 (11)	0.052 (5)*
H2	0.259 (3)	0.896 (3)	0.0361 (13)	0.076 (6)*
N1	−0.11771 (14)	0.86658 (13)	0.28649 (6)	0.0265 (2)
C7	−0.07473 (15)	1.02547 (14)	0.27549 (6)	0.0206 (2)
C3	0.08860 (16)	1.21816 (15)	0.19842 (7)	0.0241 (2)
H3	0.1695	1.2391	0.1527	0.029*
C9	−0.22886 (15)	0.78590 (14)	0.43067 (7)	0.0220 (2)
C5	−0.10301 (17)	1.31722 (15)	0.32046 (7)	0.0267 (2)
H5	−0.1553	1.4065	0.3586	0.032*
C8	−0.25752 (15)	0.83326 (14)	0.34426 (7)	0.0227 (2)
C1	0.11681 (15)	0.93041 (15)	0.14213 (7)	0.0225 (2)
C6	−0.14809 (16)	1.15946 (15)	0.33131 (7)	0.0241 (2)
H6	−0.2299	1.1412	0.3772	0.029*
C18	0.42441 (16)	0.53182 (17)	−0.15498 (7)	0.0272 (2)
H18	0.4625	0.4491	−0.1958	0.033*
C16	0.26442 (16)	0.62605 (16)	−0.02772 (7)	0.0252 (2)
H16	0.1885	0.6070	0.0204	0.030*
C10	−0.36719 (15)	0.74252 (15)	0.48415 (7)	0.0236 (2)
C13	−0.41997 (17)	0.83661 (16)	0.31176 (7)	0.0268 (2)
H13	−0.4387	0.8702	0.2531	0.032*
C20	0.42201 (17)	0.80132 (16)	−0.10473 (7)	0.0274 (2)
H20	0.4597	0.9053	−0.1115	0.033*
C17	0.31535 (16)	0.49975 (15)	−0.08496 (7)	0.0251 (2)
C11	−0.52731 (16)	0.74461 (16)	0.45027 (7)	0.0277 (2)
H11	−0.6196	0.7136	0.4864	0.033*
C19	0.47803 (17)	0.68418 (17)	−0.16552 (7)	0.0290 (2)
H19	0.5519	0.7079	−0.2136	0.035*
C4	0.01763 (17)	1.34698 (16)	0.25454 (7)	0.0277 (2)
H4	0.0508	1.4539	0.2481	0.033*
C14	−0.05255 (16)	0.77641 (17)	0.46698 (7)	0.0288 (2)
H14B	0.0373	0.7917	0.4215	0.043*
H14C	0.0094	0.6516	0.5028	0.043*
H14A	−0.0894	0.8798	0.5004	0.043*
C15	−0.34218 (18)	0.69274 (18)	0.57753 (7)	0.0310 (3)
H15B	−0.3589	0.8077	0.5998	0.047*
H15A	−0.2131	0.5925	0.5895	0.047*
H15C	−0.4384	0.6457	0.6040	0.047*
C21	0.2557 (2)	0.33491 (19)	−0.06983 (9)	0.0361 (3)
H21B	0.1759	0.3476	−0.1156	0.054*
H21A	0.1820	0.3363	−0.0166	0.054*
H21C	0.3703	0.2133	−0.0674	0.054*
C12	−0.55404 (17)	0.79110 (17)	0.36474 (8)	0.0301 (3)
H12	−0.6638	0.7918	0.3425	0.036*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0433 (5)	0.0337 (4)	0.0328 (5)	−0.0255 (4)	0.0158 (4)	−0.0168 (4)
O2	0.0431 (5)	0.0366 (5)	0.0285 (4)	−0.0265 (4)	0.0162 (4)	−0.0140 (4)
C2	0.0203 (5)	0.0203 (5)	0.0203 (5)	−0.0088 (4)	−0.0005 (4)	−0.0039 (4)
N2	0.0272 (5)	0.0261 (4)	0.0236 (5)	−0.0107 (4)	0.0012 (4)	−0.0059 (4)
N1	0.0345 (5)	0.0256 (5)	0.0252 (5)	−0.0183 (4)	0.0112 (4)	−0.0100 (4)
C7	0.0220 (5)	0.0195 (5)	0.0205 (5)	−0.0089 (4)	−0.0004 (4)	−0.0031 (4)
C3	0.0259 (5)	0.0255 (5)	0.0239 (5)	−0.0141 (4)	−0.0008 (4)	−0.0026 (4)
C9	0.0218 (5)	0.0192 (5)	0.0250 (5)	−0.0084 (4)	0.0022 (4)	−0.0048 (4)
C5	0.0335 (6)	0.0225 (5)	0.0241 (5)	−0.0095 (4)	−0.0041 (4)	−0.0072 (4)
C8	0.0253 (5)	0.0194 (5)	0.0247 (5)	−0.0110 (4)	0.0055 (4)	−0.0055 (4)
C1	0.0236 (5)	0.0242 (5)	0.0213 (5)	−0.0114 (4)	0.0028 (4)	−0.0051 (4)
C6	0.0272 (5)	0.0239 (5)	0.0202 (5)	−0.0096 (4)	0.0022 (4)	−0.0051 (4)
C18	0.0274 (5)	0.0306 (6)	0.0240 (5)	−0.0101 (4)	−0.0021 (4)	−0.0088 (4)
C16	0.0235 (5)	0.0286 (5)	0.0237 (5)	−0.0115 (4)	0.0002 (4)	−0.0033 (4)
C10	0.0241 (5)	0.0201 (5)	0.0246 (5)	−0.0077 (4)	0.0038 (4)	−0.0043 (4)
C13	0.0316 (6)	0.0273 (5)	0.0235 (5)	−0.0143 (5)	−0.0014 (4)	−0.0029 (4)
C20	0.0323 (6)	0.0275 (5)	0.0253 (5)	−0.0156 (5)	−0.0001 (4)	−0.0030 (4)
C17	0.0242 (5)	0.0246 (5)	0.0273 (5)	−0.0101 (4)	−0.0056 (4)	−0.0028 (4)
C11	0.0246 (5)	0.0289 (5)	0.0304 (6)	−0.0136 (4)	0.0056 (4)	−0.0038 (4)
C19	0.0306 (6)	0.0353 (6)	0.0227 (5)	−0.0159 (5)	0.0029 (4)	−0.0046 (4)
C4	0.0355 (6)	0.0237 (5)	0.0294 (6)	−0.0165 (5)	−0.0050 (5)	−0.0041 (4)
C14	0.0260 (5)	0.0312 (6)	0.0310 (6)	−0.0140 (5)	−0.0016 (4)	−0.0033 (4)
C15	0.0333 (6)	0.0336 (6)	0.0238 (5)	−0.0130 (5)	0.0040 (4)	−0.0035 (4)
C21	0.0428 (7)	0.0344 (6)	0.0398 (7)	−0.0235 (6)	−0.0029 (6)	−0.0064 (5)
C12	0.0266 (6)	0.0340 (6)	0.0328 (6)	−0.0159 (5)	−0.0018 (5)	−0.0040 (5)

Geometric parameters (Å, º)

O1—C1	1.2262 (13)	C9—C14	1.5035 (15)
O2—C1	1.3143 (12)	C5—C6	1.3820 (15)
C2—C3	1.3978 (14)	C5—C4	1.3883 (16)
C2—C7	1.4165 (14)	C8—C13	1.3955 (15)
C2—C1	1.4872 (14)	C18—C19	1.3831 (16)
N2—C16	1.3365 (14)	C18—C17	1.3846 (16)
N2—C20	1.3376 (14)	C16—C17	1.3884 (15)
N1—C7	1.3806 (13)	C10—C11	1.3940 (16)
N1—C8	1.4212 (13)	C10—C15	1.5073 (15)
C7—C6	1.4068 (14)	C13—C12	1.3857 (16)
C3—C4	1.3825 (15)	C20—C19	1.3825 (16)
C9—C8	1.4010 (15)	C17—C21	1.5012 (15)
C9—C10	1.4080 (14)	C11—C12	1.3848 (17)
C3—C2—C7	119.22 (9)	O1—C1—C2	123.21 (9)
C3—C2—C1	119.37 (9)	O2—C1—C2	114.41 (9)
C7—C2—C1	121.35 (9)	C5—C6—C7	121.03 (10)
C16—N2—C20	118.48 (9)	C19—C18—C17	120.09 (10)
C7—N1—C8	125.80 (9)	N2—C16—C17	123.54 (10)
N1—C7—C6	121.29 (9)	C11—C10—C9	119.65 (10)
N1—C7—C2	120.53 (9)	C11—C10—C15	120.00 (10)
C6—C7—C2	118.18 (9)	C9—C10—C15	120.35 (10)
C4—C3—C2	121.88 (10)	C12—C13—C8	120.22 (10)
C8—C9—C10	118.85 (10)	N2—C20—C19	122.11 (10)
C8—C9—C14	121.53 (9)	C18—C17—C16	117.06 (10)
C10—C9—C14	119.61 (10)	C18—C17—C21	122.26 (10)
C6—C5—C4	120.89 (10)	C16—C17—C21	120.67 (10)
C13—C8—C9	120.55 (9)	C12—C11—C10	121.05 (10)
C13—C8—N1	117.70 (10)	C20—C19—C18	118.72 (10)
C9—C8—N1	121.61 (10)	C3—C4—C5	118.77 (10)
O1—C1—O2	122.38 (9)	C13—C12—C11	119.68 (10)
C8—N1—C7—C6	10.05 (17)	C20—N2—C16—C17	0.51 (16)
C8—N1—C7—C2	−169.75 (10)	C8—C9—C10—C11	0.98 (15)
C3—C2—C7—N1	−178.81 (10)	C14—C9—C10—C11	−177.73 (10)
C1—C2—C7—N1	4.04 (15)	C8—C9—C10—C15	−179.42 (9)
C3—C2—C7—C6	1.39 (15)	C14—C9—C10—C15	1.87 (15)
C1—C2—C7—C6	−175.76 (9)	C9—C8—C13—C12	−0.64 (16)
C7—C2—C3—C4	−0.47 (16)	N1—C8—C13—C12	175.23 (10)
C1—C2—C3—C4	176.74 (10)	C16—N2—C20—C19	0.15 (17)
C10—C9—C8—C13	−0.26 (15)	C19—C18—C17—C16	0.07 (16)
C14—C9—C8—C13	178.42 (10)	C19—C18—C17—C21	−179.09 (11)
C10—C9—C8—N1	−175.96 (9)	N2—C16—C17—C18	−0.61 (17)
C14—C9—C8—N1	2.72 (15)	N2—C16—C17—C21	178.56 (10)
C7—N1—C8—C13	112.29 (12)	C9—C10—C11—C12	−0.82 (16)
C7—N1—C8—C9	−71.89 (15)	C15—C10—C11—C12	179.58 (10)
C3—C2—C1—O1	−175.36 (10)	N2—C20—C19—C18	−0.65 (18)
C7—C2—C1—O1	1.79 (17)	C17—C18—C19—C20	0.53 (17)
C3—C2—C1—O2	4.24 (15)	C2—C3—C4—C5	−1.02 (17)
C7—C2—C1—O2	−178.62 (9)	C6—C5—C4—C3	1.57 (17)
C4—C5—C6—C7	−0.64 (17)	C8—C13—C12—C11	0.81 (17)
N1—C7—C6—C5	179.34 (10)	C10—C11—C12—C13	−0.08 (17)
C2—C7—C6—C5	−0.86 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H7···O1	0.918 (18)	1.892 (17)	2.6508 (12)	138.6 (15)
O2—H2···N2	1.03 (2)	1.57 (2)	2.6006 (12)	176.7 (18)
C16—H16···O1	0.95	2.54	3.2241 (14)	129

(ma3clpyr) 2-(2,3-dimethylphenyl)aminobenzoic acid 3-chloropyridine solvate

Crystal data

C20H19ClN2O2	Z = 2
Mr = 354.82	F(000) = 372
Triclinic, P1	Dx = 1.379 Mg m^−3
a = 7.6718 (15) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.7441 (15) Å	Cell parameters from 20017 reflections
c = 16.056 (3) Å	θ = 1.3–28.5°
α = 80.06 (3)°	µ = 0.24 mm^−1
β = 84.88 (3)°	T = 173 K
γ = 65.50 (3)°	Block, orange
V = 854.8 (4) Å^3	0.15 × 0.14 × 0.13 mm

Data collection

Bruker Kappa Duo Apex II diffractometer	4290 independent reflections
Radiation source: fine-focus sealed tube	3370 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
1.2° φ scans and ω scans	θmax = 28.5°, θmin = 1.3°
Absorption correction: multi-scan SADABS	h = −10→10
Tmin = 0.891, Tmax = 0.969	k = −10→10
13863 measured reflections	l = −21→21

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0691P)^2 + 0.0888P] where P = (Fo^2 + 2Fc^2)/3
4290 reflections	(Δ/σ)max < 0.001
236 parameters	Δρmax = 0.32 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3

Special details

Experimental. 'SADABS (Sheldrick, 1996)'

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
Cl1	0.23755 (6)	0.32298 (5)	0.42612 (3)	0.03577 (14)
O1	0.07259 (17)	0.80218 (16)	0.63918 (7)	0.0343 (3)
N1	−0.12767 (19)	0.87330 (17)	0.78256 (8)	0.0262 (3)
O2	0.22928 (18)	0.98357 (17)	0.58659 (7)	0.0336 (3)
N2	0.32388 (18)	0.77170 (17)	0.46329 (8)	0.0245 (3)
H7	−0.100 (3)	0.819 (3)	0.7356 (13)	0.048 (6)*
H2	0.265 (4)	0.912 (4)	0.5493 (16)	0.075 (8)*
C2	0.0346 (2)	1.06653 (19)	0.70739 (9)	0.0198 (3)
C7	−0.0851 (2)	1.03223 (18)	0.77437 (9)	0.0204 (3)
C10	−0.3683 (2)	0.74311 (19)	0.98100 (9)	0.0230 (3)
C1	0.1122 (2)	0.9384 (2)	0.64203 (9)	0.0222 (3)
C17	0.3176 (2)	0.5047 (2)	0.41166 (9)	0.0234 (3)
C3	0.0751 (2)	1.2292 (2)	0.70079 (9)	0.0235 (3)
H3	0.1551	1.2522	0.6555	0.028*
C8	−0.2646 (2)	0.83698 (19)	0.84015 (9)	0.0224 (3)
C20	0.4374 (2)	0.7914 (2)	0.39738 (9)	0.0260 (3)
H20	0.4807	0.8913	0.3924	0.031*
C5	−0.1173 (2)	1.3237 (2)	0.82320 (9)	0.0264 (3)
H5	−0.1706	1.4117	0.8626	0.032*
C6	−0.1599 (2)	1.1646 (2)	0.83154 (9)	0.0238 (3)
H6	−0.2412	1.1446	0.8768	0.029*
C16	0.2637 (2)	0.6305 (2)	0.47012 (10)	0.0245 (3)
H16	0.1817	0.6163	0.5163	0.029*
C13	−0.4278 (2)	0.8397 (2)	0.80699 (10)	0.0260 (3)
H13	−0.4488	0.8736	0.7479	0.031*
C18	0.4339 (2)	0.5242 (2)	0.34379 (10)	0.0267 (3)
H18	0.4720	0.4388	0.3032	0.032*
C4	0.0017 (2)	1.3567 (2)	0.75833 (10)	0.0270 (3)
H4	0.0324	1.4650	0.7535	0.032*
C12	−0.5592 (2)	0.7929 (2)	0.85997 (10)	0.0288 (3)
H12	−0.6697	0.7936	0.8373	0.035*
C19	0.4939 (2)	0.6725 (2)	0.33637 (10)	0.0274 (3)
H19	0.5729	0.6918	0.2899	0.033*
C9	−0.2324 (2)	0.78832 (18)	0.92743 (9)	0.0218 (3)
C11	−0.5291 (2)	0.7452 (2)	0.94626 (10)	0.0268 (3)
H11	−0.6199	0.7134	0.9824	0.032*
C14	−0.0550 (2)	0.7795 (2)	0.96435 (10)	0.0284 (3)
H14A	0.0325	0.7964	0.9185	0.043*
H14C	0.0084	0.6546	0.9994	0.043*
H14B	−0.0903	0.8817	0.9991	0.043*
C15	−0.3403 (2)	0.6938 (2)	1.07514 (10)	0.0302 (3)
H15B	−0.3627	0.8101	1.0987	0.045*
H15A	−0.2090	0.5993	1.0869	0.045*
H15C	−0.4310	0.6400	1.1012	0.045*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0409 (3)	0.0307 (2)	0.0437 (3)	−0.02279 (18)	0.00057 (19)	−0.00538 (17)
O1	0.0440 (7)	0.0346 (6)	0.0371 (7)	−0.0272 (5)	0.0196 (5)	−0.0192 (5)
N1	0.0338 (7)	0.0235 (6)	0.0264 (7)	−0.0169 (5)	0.0132 (6)	−0.0100 (5)
O2	0.0448 (7)	0.0364 (6)	0.0312 (6)	−0.0277 (6)	0.0195 (5)	−0.0156 (5)
N2	0.0252 (7)	0.0254 (6)	0.0237 (6)	−0.0111 (5)	0.0012 (5)	−0.0042 (5)
C2	0.0196 (7)	0.0190 (6)	0.0208 (7)	−0.0075 (5)	−0.0005 (5)	−0.0035 (5)
C7	0.0220 (7)	0.0183 (6)	0.0208 (7)	−0.0081 (5)	−0.0007 (6)	−0.0024 (5)
C10	0.0232 (7)	0.0181 (6)	0.0255 (7)	−0.0070 (5)	0.0043 (6)	−0.0044 (5)
C1	0.0224 (7)	0.0235 (6)	0.0218 (7)	−0.0109 (6)	0.0029 (6)	−0.0045 (5)
C17	0.0227 (7)	0.0226 (6)	0.0264 (8)	−0.0110 (6)	−0.0045 (6)	−0.0007 (5)
C3	0.0246 (7)	0.0227 (6)	0.0257 (8)	−0.0124 (6)	−0.0011 (6)	−0.0027 (6)
C8	0.0245 (7)	0.0180 (6)	0.0253 (7)	−0.0096 (5)	0.0064 (6)	−0.0056 (5)
C20	0.0288 (8)	0.0281 (7)	0.0244 (8)	−0.0157 (6)	0.0002 (6)	−0.0021 (6)
C5	0.0322 (8)	0.0208 (7)	0.0248 (8)	−0.0074 (6)	−0.0042 (6)	−0.0074 (6)
C6	0.0251 (8)	0.0235 (7)	0.0210 (7)	−0.0083 (6)	0.0027 (6)	−0.0046 (5)
C16	0.0224 (7)	0.0273 (7)	0.0236 (7)	−0.0107 (6)	0.0003 (6)	−0.0024 (6)
C13	0.0313 (8)	0.0257 (7)	0.0225 (7)	−0.0134 (6)	−0.0003 (6)	−0.0030 (6)
C18	0.0261 (8)	0.0299 (7)	0.0241 (8)	−0.0098 (6)	−0.0002 (6)	−0.0086 (6)
C4	0.0327 (8)	0.0214 (7)	0.0311 (8)	−0.0139 (6)	−0.0053 (7)	−0.0049 (6)
C12	0.0258 (8)	0.0304 (7)	0.0326 (9)	−0.0140 (6)	−0.0013 (6)	−0.0036 (6)
C19	0.0280 (8)	0.0351 (8)	0.0213 (7)	−0.0159 (7)	0.0036 (6)	−0.0036 (6)
C9	0.0208 (7)	0.0172 (6)	0.0267 (8)	−0.0070 (5)	0.0022 (6)	−0.0043 (5)
C11	0.0239 (8)	0.0265 (7)	0.0302 (8)	−0.0116 (6)	0.0058 (6)	−0.0043 (6)
C14	0.0254 (8)	0.0295 (7)	0.0314 (8)	−0.0128 (6)	−0.0025 (6)	−0.0022 (6)
C15	0.0322 (9)	0.0306 (8)	0.0252 (8)	−0.0111 (7)	0.0034 (7)	−0.0039 (6)

Geometric parameters (Å, º)

Cl1—C17	1.7293 (14)	C10—C15	1.506 (2)
O1—C1	1.2215 (17)	C17—C18	1.374 (2)
N1—C7	1.3816 (17)	C17—C16	1.383 (2)
N1—C8	1.4212 (19)	C3—C4	1.381 (2)
O2—C1	1.3159 (18)	C8—C13	1.394 (2)
N2—C16	1.3379 (18)	C8—C9	1.403 (2)
N2—C20	1.339 (2)	C20—C19	1.378 (2)
C2—C3	1.4022 (18)	C5—C6	1.3828 (19)
C2—C7	1.413 (2)	C5—C4	1.384 (2)
C2—C1	1.483 (2)	C13—C12	1.384 (2)
C7—C6	1.402 (2)	C18—C19	1.389 (2)
C10—C11	1.391 (2)	C12—C11	1.385 (2)
C10—C9	1.410 (2)	C9—C14	1.503 (2)
C7—N1—C8	125.61 (12)	C4—C3—C2	121.72 (14)
C16—N2—C20	118.50 (13)	C13—C8—C9	120.55 (13)
C3—C2—C7	119.31 (13)	C13—C8—N1	117.98 (13)
C3—C2—C1	119.23 (13)	C9—C8—N1	121.36 (13)
C7—C2—C1	121.41 (12)	N2—C20—C19	122.62 (13)
N1—C7—C6	121.24 (13)	C6—C5—C4	120.96 (13)
N1—C7—C2	120.68 (12)	C5—C6—C7	121.19 (14)
C6—C7—C2	118.08 (12)	N2—C16—C17	121.67 (14)
C11—C10—C9	119.50 (14)	C12—C13—C8	120.18 (14)
C11—C10—C15	120.20 (13)	C17—C18—C19	117.96 (14)
C9—C10—C15	120.30 (14)	C3—C4—C5	118.73 (13)
O1—C1—O2	122.29 (13)	C11—C12—C13	119.76 (14)
O1—C1—C2	123.64 (13)	C20—C19—C18	119.08 (14)
O2—C1—C2	114.06 (12)	C8—C9—C10	118.83 (13)
C18—C17—C16	120.16 (13)	C8—C9—C14	121.47 (13)
C18—C17—Cl1	120.99 (11)	C10—C9—C14	119.68 (13)
C16—C17—Cl1	118.86 (12)	C12—C11—C10	121.18 (14)
C8—N1—C7—C6	8.2 (2)	C9—C8—C13—C12	−0.4 (2)
C8—N1—C7—C2	−171.39 (14)	N1—C8—C13—C12	175.79 (13)
C3—C2—C7—N1	179.98 (13)	C16—C17—C18—C19	0.0 (2)
C1—C2—C7—N1	2.4 (2)	Cl1—C17—C18—C19	−179.57 (11)
C3—C2—C7—C6	0.4 (2)	C2—C3—C4—C5	−1.1 (2)
C1—C2—C7—C6	−177.16 (13)	C6—C5—C4—C3	1.1 (2)
C3—C2—C1—O1	−174.28 (14)	C8—C13—C12—C11	0.6 (2)
C7—C2—C1—O1	3.3 (2)	N2—C20—C19—C18	−1.0 (2)
C3—C2—C1—O2	5.8 (2)	C17—C18—C19—C20	0.9 (2)
C7—C2—C1—O2	−176.57 (13)	C13—C8—C9—C10	−0.3 (2)
C7—C2—C3—C4	0.3 (2)	N1—C8—C9—C10	−176.40 (12)
C1—C2—C3—C4	177.94 (13)	C13—C8—C9—C14	178.38 (13)
C7—N1—C8—C13	112.88 (17)	N1—C8—C9—C14	2.3 (2)
C7—N1—C8—C9	−70.9 (2)	C11—C10—C9—C8	0.8 (2)
C16—N2—C20—C19	0.2 (2)	C15—C10—C9—C8	−178.86 (12)
C4—C5—C6—C7	−0.4 (2)	C11—C10—C9—C14	−177.87 (12)
N1—C7—C6—C5	−179.91 (13)	C15—C10—C9—C14	2.4 (2)
C2—C7—C6—C5	−0.4 (2)	C13—C12—C11—C10	−0.1 (2)
C20—N2—C16—C17	0.8 (2)	C9—C10—C11—C12	−0.7 (2)
C18—C17—C16—N2	−0.9 (2)	C15—C10—C11—C12	179.04 (14)
Cl1—C17—C16—N2	178.71 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O1	0.95	2.52	3.194 (2)	128
O2—H2···N2	0.84 (3)	1.81 (3)	2.6487 (19)	175 (3)
N1—H7···O1	0.89 (2)	1.93 (2)	2.6586 (19)	137.6 (17)

(ma4pic) 2-(2,3-dimethylphenyl)aminobenzoic acid 4-methylpyridine solvate

Crystal data

C21H22N2O2	Z = 2
Mr = 334.41	F(000) = 356
Triclinic, P1	Dx = 1.271 Mg m^−3
a = 7.5271 (15) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.5702 (15) Å	Cell parameters from 8595 reflections
c = 15.664 (3) Å	θ = 1.3–27.9°
α = 88.11 (3)°	µ = 0.08 mm^−1
β = 78.41 (3)°	T = 173 K
γ = 89.20 (3)°	Block, colorless
V = 873.9 (3) Å^3	0.57 × 0.46 × 0.08 mm

Data collection

Bruker Kappa Duo Apex II diffractometer	4147 independent reflections
Radiation source: fine-focus sealed tube	3128 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
1.2° φ scans and ω scans	θmax = 27.9°, θmin = 1.3°
Absorption correction: multi-scan SADABS	h = −9→9
Tmin = 0.922, Tmax = 0.993	k = −9→9
8595 measured reflections	l = −20→19

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.070P)^2 + 0.1127P] where P = (Fo^2 + 2Fc^2)/3
4147 reflections	(Δ/σ)max = 0.006
237 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Special details

Experimental. 'SADABS (Sheldrick, 1996)'

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
O2	0.45990 (15)	0.67963 (14)	0.40671 (7)	0.0387 (3)
O1	0.66682 (14)	0.47895 (15)	0.35169 (7)	0.0387 (3)
C2	0.39780 (17)	0.50945 (17)	0.29351 (8)	0.0241 (3)
N1	0.61076 (17)	0.29489 (16)	0.21643 (8)	0.0315 (3)
H7	0.674 (3)	0.308 (2)	0.2562 (12)	0.046 (5)*
H2	0.552 (3)	0.707 (3)	0.4441 (14)	0.066 (6)*
C1	0.52078 (18)	0.55275 (18)	0.35244 (9)	0.0268 (3)
C7	0.44662 (18)	0.38226 (17)	0.22829 (8)	0.0258 (3)
C9	0.71015 (18)	0.18245 (18)	0.06917 (9)	0.0280 (3)
C10	0.75189 (18)	0.03796 (18)	0.01443 (9)	0.0280 (3)
C3	0.22802 (19)	0.59221 (18)	0.30341 (9)	0.0289 (3)
H3	0.1958	0.6776	0.3471	0.035*
C8	0.65690 (18)	0.15059 (18)	0.15901 (9)	0.0276 (3)
C5	0.1546 (2)	0.4295 (2)	0.18786 (9)	0.0336 (3)
H5	0.0718	0.4013	0.1520	0.040*
C6	0.32081 (19)	0.34641 (19)	0.17562 (9)	0.0306 (3)
H6	0.3515	0.2632	0.1308	0.037*
C11	0.74201 (19)	−0.13180 (19)	0.05060 (9)	0.0317 (3)
H11	0.7700	−0.2294	0.0135	0.038*
C13	0.64906 (19)	−0.02063 (19)	0.19399 (9)	0.0302 (3)
H13	0.6140	−0.0406	0.2552	0.036*
C12	0.6921 (2)	−0.1622 (2)	0.13999 (10)	0.0338 (3)
H12	0.6875	−0.2794	0.1639	0.041*
C4	0.10550 (19)	0.5539 (2)	0.25182 (9)	0.0336 (3)
H4	−0.0095	0.6113	0.2599	0.040*
C15	0.8059 (2)	0.0672 (2)	−0.08305 (9)	0.0361 (4)
H15B	0.8607	−0.0413	−0.1095	0.054*
H15A	0.8938	0.1635	−0.0962	0.054*
H15C	0.6983	0.0984	−0.1068	0.054*
C14	0.7237 (2)	0.3677 (2)	0.03110 (11)	0.0419 (4)
H14A	0.6908	0.4518	0.0780	0.063*
H14C	0.6410	0.3825	−0.0096	0.063*
H14B	0.8484	0.3898	0.0000	0.063*
N2	0.68427 (16)	0.76449 (15)	0.50589 (7)	0.0299 (3)
C18	0.93135 (19)	0.86481 (18)	0.60673 (9)	0.0286 (3)
C19	0.75445 (19)	0.92713 (18)	0.62262 (9)	0.0289 (3)
H19	0.7142	1.0053	0.6689	0.035*
C20	0.63648 (19)	0.87580 (19)	0.57129 (9)	0.0293 (3)
H20	0.5161	0.9215	0.5829	0.035*
C17	0.9810 (2)	0.75022 (19)	0.53821 (10)	0.0335 (3)
H17	1.1012	0.7045	0.5244	0.040*
C16	0.8550 (2)	0.7033 (2)	0.49045 (10)	0.0342 (3)
H16	0.8910	0.6238	0.4444	0.041*
C21	1.0629 (2)	0.9182 (2)	0.66117 (11)	0.0414 (4)
H21A	1.0249	0.8685	0.7205	0.062*
H21C	1.0656	1.0474	0.6629	0.062*
H21B	1.1841	0.8735	0.6357	0.062*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.0428 (6)	0.0389 (6)	0.0382 (6)	0.0116 (5)	−0.0154 (5)	−0.0192 (5)
O1	0.0301 (5)	0.0477 (7)	0.0415 (6)	0.0073 (5)	−0.0118 (4)	−0.0203 (5)
C2	0.0273 (7)	0.0224 (6)	0.0215 (6)	−0.0013 (5)	−0.0023 (5)	0.0000 (5)
N1	0.0312 (6)	0.0354 (7)	0.0306 (6)	0.0076 (5)	−0.0110 (5)	−0.0142 (5)
C1	0.0288 (7)	0.0258 (7)	0.0246 (6)	−0.0003 (5)	−0.0019 (5)	−0.0045 (5)
C7	0.0277 (7)	0.0249 (7)	0.0242 (6)	0.0003 (5)	−0.0042 (5)	−0.0005 (5)
C9	0.0277 (7)	0.0267 (7)	0.0304 (7)	0.0009 (5)	−0.0073 (5)	−0.0039 (5)
C10	0.0253 (7)	0.0316 (7)	0.0275 (7)	−0.0007 (5)	−0.0055 (5)	−0.0064 (5)
C3	0.0302 (7)	0.0281 (7)	0.0262 (7)	0.0032 (5)	−0.0003 (5)	−0.0019 (5)
C8	0.0256 (7)	0.0291 (7)	0.0290 (7)	0.0031 (5)	−0.0068 (5)	−0.0086 (5)
C5	0.0318 (7)	0.0414 (8)	0.0294 (7)	−0.0019 (6)	−0.0106 (6)	0.0019 (6)
C6	0.0354 (8)	0.0326 (8)	0.0251 (7)	−0.0001 (6)	−0.0083 (6)	−0.0052 (6)
C11	0.0332 (7)	0.0291 (7)	0.0324 (7)	0.0004 (6)	−0.0043 (6)	−0.0095 (6)
C13	0.0299 (7)	0.0351 (8)	0.0251 (7)	0.0012 (6)	−0.0042 (5)	−0.0020 (6)
C12	0.0382 (8)	0.0266 (7)	0.0355 (8)	−0.0013 (6)	−0.0051 (6)	0.0005 (6)
C4	0.0280 (7)	0.0383 (8)	0.0337 (8)	0.0044 (6)	−0.0051 (6)	0.0024 (6)
C15	0.0389 (8)	0.0415 (9)	0.0275 (7)	−0.0028 (6)	−0.0046 (6)	−0.0059 (6)
C14	0.0551 (10)	0.0298 (8)	0.0386 (9)	−0.0002 (7)	−0.0043 (7)	−0.0005 (6)
N2	0.0330 (6)	0.0299 (6)	0.0263 (6)	0.0014 (5)	−0.0052 (5)	−0.0025 (5)
C18	0.0305 (7)	0.0262 (7)	0.0289 (7)	−0.0029 (5)	−0.0067 (5)	0.0074 (5)
C19	0.0318 (7)	0.0278 (7)	0.0264 (7)	0.0006 (5)	−0.0035 (5)	−0.0045 (5)
C20	0.0275 (7)	0.0303 (7)	0.0291 (7)	0.0036 (5)	−0.0027 (5)	−0.0033 (6)
C17	0.0289 (7)	0.0318 (8)	0.0373 (8)	0.0053 (6)	−0.0013 (6)	0.0023 (6)
C16	0.0390 (8)	0.0311 (8)	0.0301 (7)	0.0056 (6)	−0.0007 (6)	−0.0060 (6)
C21	0.0371 (9)	0.0432 (9)	0.0467 (9)	−0.0054 (7)	−0.0160 (7)	0.0052 (7)

Geometric parameters (Å, º)

O2—C1	1.3192 (16)	C3—C4	1.382 (2)
O1—C1	1.2243 (17)	C8—C13	1.388 (2)
C2—C3	1.3979 (19)	C5—C6	1.373 (2)
C2—C7	1.4177 (18)	C5—C4	1.390 (2)
C2—C1	1.4793 (19)	C11—C12	1.387 (2)
N1—C7	1.3754 (18)	C13—C12	1.382 (2)
N1—C8	1.4322 (17)	N2—C20	1.3376 (18)
C7—C6	1.4095 (19)	N2—C16	1.3382 (19)
C9—C8	1.3975 (19)	C18—C19	1.384 (2)
C9—C10	1.4051 (19)	C18—C17	1.391 (2)
C9—C14	1.503 (2)	C18—C21	1.498 (2)
C10—C11	1.384 (2)	C19—C20	1.379 (2)
C10—C15	1.5089 (19)	C17—C16	1.377 (2)
C3—C2—C7	119.08 (12)	C13—C8—C9	120.67 (12)
C3—C2—C1	119.54 (12)	C13—C8—N1	119.04 (12)
C7—C2—C1	121.36 (12)	C9—C8—N1	120.29 (13)
C7—N1—C8	123.49 (12)	C6—C5—C4	121.18 (14)
O1—C1—O2	122.15 (13)	C5—C6—C7	121.24 (13)
O1—C1—C2	123.74 (12)	C10—C11—C12	121.26 (13)
O2—C1—C2	114.11 (12)	C12—C13—C8	120.18 (13)
N1—C7—C6	120.46 (12)	C13—C12—C11	119.48 (14)
N1—C7—C2	121.60 (12)	C3—C4—C5	118.36 (13)
C6—C7—C2	117.94 (12)	C20—N2—C16	117.38 (13)
C8—C9—C10	118.93 (13)	C19—C18—C17	116.99 (13)
C8—C9—C14	120.95 (13)	C19—C18—C21	121.35 (13)
C10—C9—C14	120.12 (13)	C17—C18—C21	121.66 (14)
C11—C10—C9	119.46 (13)	C20—C19—C18	120.03 (13)
C11—C10—C15	120.17 (13)	N2—C20—C19	122.82 (13)
C9—C10—C15	120.37 (13)	C16—C17—C18	119.66 (14)
C4—C3—C2	122.20 (13)	N2—C16—C17	123.10 (13)
C3—C2—C1—O1	175.47 (13)	C7—N1—C8—C9	78.66 (18)
C7—C2—C1—O1	−3.0 (2)	C4—C5—C6—C7	1.0 (2)
C3—C2—C1—O2	−4.67 (18)	N1—C7—C6—C5	178.50 (13)
C7—C2—C1—O2	176.87 (12)	C2—C7—C6—C5	−1.1 (2)
C8—N1—C7—C6	−7.6 (2)	C9—C10—C11—C12	−0.2 (2)
C8—N1—C7—C2	172.05 (13)	C15—C10—C11—C12	−179.78 (13)
C3—C2—C7—N1	−179.07 (12)	C9—C8—C13—C12	−0.7 (2)
C1—C2—C7—N1	−0.61 (19)	N1—C8—C13—C12	179.71 (13)
C3—C2—C7—C6	0.56 (19)	C8—C13—C12—C11	−0.4 (2)
C1—C2—C7—C6	179.03 (12)	C10—C11—C12—C13	0.9 (2)
C8—C9—C10—C11	−0.9 (2)	C2—C3—C4—C5	−0.4 (2)
C14—C9—C10—C11	178.80 (13)	C6—C5—C4—C3	−0.2 (2)
C8—C9—C10—C15	178.66 (13)	C17—C18—C19—C20	−0.27 (19)
C14—C9—C10—C15	−1.6 (2)	C21—C18—C19—C20	179.92 (13)
C7—C2—C3—C4	0.2 (2)	C16—N2—C20—C19	−0.6 (2)
C1—C2—C3—C4	−178.33 (12)	C18—C19—C20—N2	0.8 (2)
C10—C9—C8—C13	1.4 (2)	C19—C18—C17—C16	−0.5 (2)
C14—C9—C8—C13	−178.35 (13)	C21—C18—C17—C16	179.33 (13)
C10—C9—C8—N1	−179.04 (12)	C20—N2—C16—C17	−0.2 (2)
C14—C9—C8—N1	1.2 (2)	C18—C17—C16—N2	0.8 (2)
C7—N1—C8—C13	−101.76 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H7···O1	0.868 (19)	2.000 (19)	2.6793 (17)	134.4 (16)
O2—H2···N2	1.02 (2)	1.60 (2)	2.6132 (18)	175.0 (19)

(tfa2pic) 2-[(3-chloro-2-methylphenyl)amino]benzoic acid) 2-methylpyridine solvate

Crystal data

C20H19ClN2O2	F(000) = 744
Mr = 354.82	Dx = 1.353 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.7585 (16) Å	Cell parameters from 24570 reflections
b = 8.0699 (16) Å	θ = 2.6–28.4°
c = 28.056 (6) Å	µ = 0.24 mm^−1
β = 97.29 (3)°	T = 173 K
V = 1742.4 (6) Å^3	Block, colorless
Z = 4	0.24 × 0.23 × 0.22 mm

Data collection

Bruker Kappa Duo Apex II diffractometer	4345 independent reflections
Radiation source: fine-focus sealed tube	3478 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
1.2° φ scans and ω scans	θmax = 28.4°, θmin = 2.6°
Absorption correction: multi-scan SADABS	h = −10→10
Tmin = 0.897, Tmax = 0.950	k = −10→10
24570 measured reflections	l = −37→37

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0509P)^2 + 0.5161P] where P = (Fo^2 + 2Fc^2)/3
4345 reflections	(Δ/σ)max = 0.002
236 parameters	Δρmax = 0.30 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

Special details

Experimental. 'SADABS (Sheldrick, 1996)'

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
Cl1	0.66000 (5)	0.93524 (5)	0.205423 (13)	0.03861 (12)
O1	0.49311 (12)	0.84441 (14)	0.43656 (4)	0.0345 (2)
O2	0.32335 (14)	0.80501 (15)	0.49381 (4)	0.0359 (3)
C2	0.19649 (17)	0.93174 (16)	0.42215 (5)	0.0247 (3)
N2	0.59942 (15)	0.66601 (15)	0.53974 (4)	0.0301 (3)
H7	0.442 (2)	0.946 (2)	0.3738 (6)	0.031 (4)*
H2	0.430 (3)	0.756 (3)	0.5107 (9)	0.101 (9)*
C10	0.53807 (16)	1.04602 (18)	0.24302 (5)	0.0256 (3)
C6	0.05306 (18)	1.06539 (18)	0.35047 (5)	0.0285 (3)
H6	0.0564	1.1116	0.3195	0.034*
N1	0.36271 (16)	1.00046 (19)	0.35755 (4)	0.0354 (3)
C1	0.35091 (17)	0.85760 (17)	0.45119 (5)	0.0269 (3)
C9	0.49966 (16)	0.97326 (17)	0.28558 (5)	0.0241 (3)
C7	0.20633 (17)	1.00183 (17)	0.37628 (5)	0.0253 (3)
C15	0.59130 (19)	0.57089 (18)	0.57860 (5)	0.0293 (3)
C3	0.03625 (18)	0.92933 (18)	0.44017 (5)	0.0304 (3)
H3	0.0297	0.8817	0.4709	0.036*
C8	0.40072 (17)	1.06929 (18)	0.31414 (5)	0.0260 (3)
C5	−0.10205 (18)	1.06137 (18)	0.36973 (5)	0.0319 (3)
H5	−0.2037	1.1057	0.3518	0.038*
C13	0.34757 (17)	1.22897 (19)	0.30006 (5)	0.0316 (3)
H13	0.2828	1.2932	0.3199	0.038*
C12	0.38844 (18)	1.29440 (19)	0.25739 (6)	0.0340 (3)
H12	0.3510	1.4030	0.2480	0.041*
C20	0.4158 (2)	0.5506 (2)	0.59506 (6)	0.0396 (4)
H20A	0.3574	0.4539	0.5793	0.059*
H20C	0.3459	0.6500	0.5867	0.059*
H20B	0.4296	0.5348	0.6300	0.059*
C14	0.55494 (19)	0.80070 (18)	0.30056 (5)	0.0324 (3)
H14C	0.6016	0.7448	0.2739	0.049*
H14B	0.4546	0.7388	0.3091	0.049*
H14A	0.6448	0.8058	0.3284	0.049*
C16	0.7395 (2)	0.49485 (19)	0.60177 (5)	0.0339 (3)
H16	0.7324	0.4270	0.6291	0.041*
C4	−0.11259 (18)	0.9940 (2)	0.41473 (6)	0.0349 (3)
H4	−0.2198	0.9925	0.4278	0.042*
C17	0.8974 (2)	0.5184 (2)	0.58481 (5)	0.0360 (3)
H17	0.9995	0.4669	0.6004	0.043*
C19	0.75305 (19)	0.6887 (2)	0.52354 (5)	0.0343 (3)
H19	0.7573	0.7567	0.4961	0.041*
C11	0.48339 (17)	1.20283 (19)	0.22832 (5)	0.0312 (3)
H11	0.5106	1.2469	0.1988	0.037*
C18	0.90534 (19)	0.6176 (2)	0.54500 (6)	0.0355 (3)
H18	1.0124	0.6364	0.5328	0.043*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0416 (2)	0.0442 (2)	0.03322 (19)	−0.00067 (16)	0.01696 (15)	−0.00518 (15)
O1	0.0244 (5)	0.0467 (6)	0.0331 (5)	0.0033 (4)	0.0064 (4)	0.0103 (5)
O2	0.0314 (5)	0.0503 (7)	0.0271 (5)	0.0048 (5)	0.0077 (4)	0.0090 (5)
C2	0.0242 (6)	0.0236 (6)	0.0268 (6)	−0.0008 (5)	0.0053 (5)	−0.0030 (5)
N2	0.0299 (6)	0.0321 (7)	0.0279 (6)	−0.0014 (5)	0.0025 (5)	0.0000 (5)
C10	0.0199 (6)	0.0330 (7)	0.0242 (6)	−0.0029 (5)	0.0042 (5)	−0.0018 (5)
C6	0.0277 (7)	0.0303 (7)	0.0273 (6)	0.0024 (6)	0.0029 (5)	−0.0017 (5)
N1	0.0262 (6)	0.0539 (8)	0.0274 (6)	0.0142 (6)	0.0086 (5)	0.0115 (6)
C1	0.0280 (7)	0.0276 (7)	0.0256 (6)	−0.0018 (5)	0.0053 (5)	0.0002 (5)
C9	0.0193 (6)	0.0274 (7)	0.0252 (6)	−0.0005 (5)	0.0017 (5)	0.0009 (5)
C7	0.0239 (6)	0.0258 (7)	0.0267 (6)	0.0014 (5)	0.0055 (5)	−0.0035 (5)
C15	0.0323 (7)	0.0286 (7)	0.0269 (6)	−0.0016 (6)	0.0038 (5)	−0.0037 (5)
C3	0.0276 (7)	0.0307 (7)	0.0345 (7)	−0.0026 (6)	0.0105 (6)	0.0013 (6)
C8	0.0209 (6)	0.0333 (7)	0.0237 (6)	0.0013 (5)	0.0024 (5)	0.0007 (5)
C5	0.0230 (7)	0.0306 (7)	0.0411 (8)	0.0012 (5)	0.0009 (6)	−0.0017 (6)
C13	0.0249 (7)	0.0335 (8)	0.0365 (7)	0.0046 (6)	0.0047 (5)	−0.0040 (6)
C12	0.0252 (7)	0.0301 (8)	0.0457 (8)	0.0020 (6)	0.0011 (6)	0.0091 (6)
C20	0.0353 (8)	0.0457 (9)	0.0395 (8)	0.0018 (7)	0.0111 (6)	0.0070 (7)
C14	0.0302 (7)	0.0306 (8)	0.0376 (8)	0.0044 (6)	0.0090 (6)	0.0055 (6)
C16	0.0403 (8)	0.0309 (8)	0.0299 (7)	0.0024 (6)	0.0024 (6)	0.0006 (6)
C4	0.0239 (7)	0.0365 (8)	0.0462 (9)	−0.0023 (6)	0.0116 (6)	0.0006 (7)
C17	0.0330 (8)	0.0362 (8)	0.0369 (8)	0.0054 (6)	−0.0024 (6)	−0.0062 (6)
C19	0.0339 (8)	0.0372 (8)	0.0322 (7)	−0.0044 (6)	0.0058 (6)	0.0005 (6)
C11	0.0256 (7)	0.0373 (8)	0.0305 (7)	−0.0023 (6)	0.0033 (5)	0.0088 (6)
C18	0.0290 (7)	0.0399 (9)	0.0380 (8)	−0.0041 (6)	0.0053 (6)	−0.0069 (7)

Geometric parameters (Å, º)

Cl1—C10	1.7494 (14)	N1—C8	1.4036 (18)
O1—C1	1.2296 (17)	C9—C8	1.4098 (19)
O2—C1	1.3116 (16)	C9—C14	1.5014 (19)
C2—C3	1.4004 (19)	C15—C16	1.390 (2)
C2—C7	1.4166 (19)	C15—C20	1.501 (2)
C2—C1	1.4865 (19)	C3—C4	1.381 (2)
N2—C19	1.3411 (19)	C8—C13	1.395 (2)
N2—C15	1.3415 (18)	C5—C4	1.386 (2)
C10—C11	1.381 (2)	C13—C12	1.382 (2)
C10—C9	1.3963 (18)	C12—C11	1.381 (2)
C6—C5	1.381 (2)	C16—C17	1.382 (2)
C6—C7	1.4083 (19)	C17—C18	1.382 (2)
N1—C7	1.3820 (17)	C19—C18	1.381 (2)
C3—C2—C7	119.09 (13)	C6—C7—C2	118.25 (12)
C3—C2—C1	119.15 (12)	N2—C15—C16	120.75 (13)
C7—C2—C1	121.74 (12)	N2—C15—C20	116.77 (13)
C19—N2—C15	119.28 (13)	C16—C15—C20	122.48 (13)
C11—C10—C9	123.36 (13)	C4—C3—C2	122.04 (13)
C11—C10—Cl1	117.21 (10)	C13—C8—N1	121.62 (13)
C9—C10—Cl1	119.42 (11)	C13—C8—C9	120.63 (12)
C5—C6—C7	120.75 (13)	N1—C8—C9	117.72 (12)
C7—N1—C8	128.17 (12)	C6—C5—C4	121.37 (13)
O1—C1—O2	122.23 (13)	C12—C13—C8	120.43 (13)
O1—C1—C2	123.14 (12)	C11—C12—C13	120.37 (14)
O2—C1—C2	114.62 (12)	C17—C16—C15	119.68 (14)
C10—C9—C8	116.46 (12)	C3—C4—C5	118.49 (13)
C10—C9—C14	123.02 (12)	C18—C17—C16	119.34 (14)
C8—C9—C14	120.50 (12)	N2—C19—C18	122.92 (14)
N1—C7—C6	122.15 (12)	C12—C11—C10	118.73 (13)
N1—C7—C2	119.56 (12)	C19—C18—C17	118.03 (14)
C3—C2—C1—O1	174.80 (14)	C7—N1—C8—C9	−135.99 (15)
C7—C2—C1—O1	−3.9 (2)	C10—C9—C8—C13	−0.76 (19)
C3—C2—C1—O2	−4.43 (19)	C14—C9—C8—C13	−179.30 (12)
C7—C2—C1—O2	176.86 (12)	C10—C9—C8—N1	−178.91 (12)
C11—C10—C9—C8	−0.44 (19)	C14—C9—C8—N1	2.56 (19)
Cl1—C10—C9—C8	−179.90 (9)	C7—C6—C5—C4	−0.4 (2)
C11—C10—C9—C14	178.05 (13)	N1—C8—C13—C12	179.26 (13)
Cl1—C10—C9—C14	−1.41 (18)	C9—C8—C13—C12	1.2 (2)
C8—N1—C7—C6	5.5 (2)	C8—C13—C12—C11	−0.4 (2)
C8—N1—C7—C2	−176.98 (14)	N2—C15—C16—C17	0.5 (2)
C5—C6—C7—N1	178.44 (14)	C20—C15—C16—C17	179.98 (14)
C5—C6—C7—C2	0.9 (2)	C2—C3—C4—C5	0.8 (2)
C3—C2—C7—N1	−178.11 (13)	C6—C5—C4—C3	−0.4 (2)
C1—C2—C7—N1	0.6 (2)	C15—C16—C17—C18	0.0 (2)
C3—C2—C7—C6	−0.5 (2)	C15—N2—C19—C18	0.3 (2)
C1—C2—C7—C6	178.24 (13)	C13—C12—C11—C10	−0.8 (2)
C19—N2—C15—C16	−0.7 (2)	C9—C10—C11—C12	1.2 (2)
C19—N2—C15—C20	179.83 (14)	Cl1—C10—C11—C12	−179.32 (11)
C7—C2—C3—C4	−0.4 (2)	N2—C19—C18—C17	0.2 (2)
C1—C2—C3—C4	−179.11 (14)	C16—C17—C18—C19	−0.4 (2)
C7—N1—C8—C13	45.9 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H7···O1	0.842 (17)	1.938 (17)	2.6370 (17)	139.6 (15)
O2—H2···N2	0.98 (3)	1.63 (3)	2.6088 (17)	177 (3)

(tfa3pic) 2-[(3-chloro-2-methylphenyl)amino]benzoic acid) 3-methylpyridine solvate

Crystal data

C20H19ClN2O2	Dx = 1.341 Mg m^−3
Mr = 354.82	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 51960 reflections
a = 7.8069 (16) Å	θ = 1.3–28.4°
b = 13.987 (3) Å	µ = 0.23 mm^−1
c = 32.185 (6) Å	T = 173 K
V = 3514.5 (12) Å^3	Platelet, colourless
Z = 8	0.24 × 0.12 × 0.08 mm
F(000) = 1488

Data collection

Bruker Kappa Duo Apex II diffractometer	4397 independent reflections
Radiation source: fine-focus sealed tube	3281 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.063
1.2° φ scans and ω scans	θmax = 28.4°, θmin = 1.3°
Absorption correction: multi-scan SADABS	h = −10→10
Tmin = 0.898, Tmax = 0.982	k = −18→18
51960 measured reflections	l = −42→42

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.046P)^2 + 1.5661P] where P = (Fo^2 + 2Fc^2)/3
4397 reflections	(Δ/σ)max = 0.001
236 parameters	Δρmax = 0.28 e Å^−3
0 restraints	Δρmin = −0.30 e Å^−3

Special details

Experimental. 'SADABS (Sheldrick, 1996)'

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
Cl1	0.01395 (6)	0.85841 (3)	0.449816 (12)	0.03870 (13)
O1	−0.44507 (16)	0.82314 (10)	0.62910 (3)	0.0384 (3)
N2	−0.78777 (17)	0.74218 (9)	0.68041 (4)	0.0283 (3)
N1	−0.15088 (18)	0.90005 (10)	0.60302 (4)	0.0289 (3)
H7	−0.247 (2)	0.8671 (13)	0.5987 (6)	0.034 (5)*
H2	−0.604 (4)	0.7922 (19)	0.6894 (8)	0.082 (8)*
C10	0.0616 (2)	0.86761 (11)	0.50270 (5)	0.0271 (3)
C3	−0.2470 (2)	0.95402 (11)	0.71286 (4)	0.0264 (3)
H3	−0.3302	0.9382	0.7333	0.032*
O2	−0.50295 (16)	0.83080 (10)	0.69654 (4)	0.0383 (3)
C9	−0.0688 (2)	0.88339 (10)	0.53137 (5)	0.0243 (3)
C2	−0.26218 (19)	0.91527 (11)	0.67308 (4)	0.0237 (3)
C14	−0.2531 (2)	0.89472 (13)	0.51910 (5)	0.0338 (4)
H14A	−0.2601	0.9100	0.4894	0.051*
H14C	−0.3048	0.9466	0.5353	0.051*
H14B	−0.3147	0.8350	0.5246	0.051*
C13	0.1510 (2)	0.87984 (11)	0.58479 (5)	0.0294 (3)
H13	0.1827	0.8837	0.6132	0.035*
C7	−0.1378 (2)	0.93778 (11)	0.64259 (5)	0.0247 (3)
C8	−0.02002 (19)	0.88924 (11)	0.57355 (4)	0.0246 (3)
C1	−0.4105 (2)	0.85241 (12)	0.66386 (5)	0.0269 (3)
C15	−0.8131 (2)	0.69616 (11)	0.64465 (5)	0.0281 (3)
H15	−0.7203	0.6920	0.6256	0.034*
C19	−0.9170 (2)	0.74782 (12)	0.70734 (5)	0.0306 (3)
H19	−0.9000	0.7808	0.7328	0.037*
C17	−1.0992 (2)	0.66056 (12)	0.66217 (5)	0.0339 (4)
H17	−1.2073	0.6327	0.6561	0.041*
C11	0.2319 (2)	0.85857 (12)	0.51363 (5)	0.0323 (4)
H11	0.3173	0.8482	0.4931	0.039*
C5	0.0035 (2)	1.03899 (12)	0.69313 (5)	0.0317 (3)
H5	0.0937	1.0819	0.6998	0.038*
C4	−0.1148 (2)	1.01470 (12)	0.72337 (5)	0.0302 (3)
H4	−0.1050	1.0393	0.7508	0.036*
C12	0.2751 (2)	0.86491 (12)	0.55505 (5)	0.0332 (4)
H12	0.3916	0.8589	0.5632	0.040*
C6	−0.0072 (2)	1.00201 (11)	0.65347 (5)	0.0294 (3)
H6	0.0750	1.0203	0.6332	0.035*
C18	−1.0740 (2)	0.70742 (12)	0.69938 (5)	0.0341 (4)
H18	−1.1639	0.7117	0.7192	0.041*
C16	−0.9669 (2)	0.65417 (12)	0.63372 (5)	0.0306 (3)
C20	−0.9879 (3)	0.60588 (17)	0.59246 (7)	0.0565 (6)
H20C	−0.9046	0.5538	0.5900	0.085*
H20B	−0.9687	0.6524	0.5702	0.085*
H20A	−1.1042	0.5799	0.5902	0.085*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0478 (3)	0.0468 (3)	0.02147 (19)	−0.0049 (2)	0.00098 (17)	−0.00275 (16)
O1	0.0327 (6)	0.0588 (8)	0.0238 (6)	−0.0145 (6)	−0.0012 (5)	−0.0074 (5)
N2	0.0252 (7)	0.0317 (7)	0.0280 (7)	−0.0020 (5)	−0.0025 (5)	0.0019 (5)
N1	0.0257 (7)	0.0389 (8)	0.0222 (6)	−0.0053 (6)	0.0018 (5)	−0.0032 (5)
C10	0.0349 (8)	0.0256 (8)	0.0207 (7)	−0.0029 (6)	0.0011 (6)	0.0006 (6)
C3	0.0261 (8)	0.0302 (8)	0.0230 (7)	0.0006 (6)	−0.0010 (6)	0.0011 (6)
O2	0.0337 (6)	0.0579 (8)	0.0234 (5)	−0.0198 (6)	0.0008 (5)	−0.0004 (5)
C9	0.0270 (8)	0.0231 (7)	0.0227 (7)	−0.0009 (6)	−0.0007 (6)	0.0008 (6)
C2	0.0222 (7)	0.0266 (7)	0.0224 (7)	−0.0002 (6)	−0.0017 (6)	0.0015 (6)
C14	0.0287 (8)	0.0420 (10)	0.0307 (8)	0.0011 (7)	−0.0045 (7)	−0.0044 (7)
C13	0.0316 (8)	0.0314 (8)	0.0251 (8)	0.0027 (7)	−0.0026 (6)	0.0019 (6)
C7	0.0247 (7)	0.0266 (7)	0.0228 (7)	0.0009 (6)	−0.0005 (6)	0.0014 (6)
C8	0.0277 (8)	0.0241 (7)	0.0218 (7)	−0.0008 (6)	0.0016 (6)	0.0021 (5)
C1	0.0237 (7)	0.0331 (8)	0.0240 (7)	−0.0004 (6)	−0.0025 (6)	0.0013 (6)
C15	0.0269 (8)	0.0316 (8)	0.0257 (7)	−0.0005 (6)	0.0022 (6)	0.0020 (6)
C19	0.0362 (9)	0.0305 (8)	0.0249 (8)	0.0009 (7)	0.0004 (6)	−0.0005 (6)
C17	0.0258 (8)	0.0308 (9)	0.0451 (10)	−0.0051 (7)	−0.0021 (7)	0.0022 (7)
C11	0.0292 (8)	0.0362 (9)	0.0315 (8)	0.0001 (7)	0.0077 (7)	−0.0017 (7)
C5	0.0293 (8)	0.0310 (8)	0.0348 (8)	−0.0061 (7)	−0.0037 (7)	−0.0019 (7)
C4	0.0324 (8)	0.0337 (9)	0.0245 (7)	−0.0007 (7)	−0.0047 (6)	−0.0037 (6)
C12	0.0255 (8)	0.0380 (9)	0.0360 (9)	0.0034 (7)	−0.0006 (7)	0.0013 (7)
C6	0.0279 (8)	0.0307 (8)	0.0297 (8)	−0.0038 (7)	0.0014 (6)	0.0023 (6)
C18	0.0313 (9)	0.0346 (9)	0.0365 (9)	0.0017 (7)	0.0097 (7)	0.0024 (7)
C16	0.0335 (8)	0.0292 (8)	0.0291 (8)	−0.0012 (7)	−0.0031 (7)	−0.0002 (6)
C20	0.0583 (14)	0.0687 (15)	0.0425 (11)	−0.0088 (11)	−0.0065 (10)	−0.0210 (10)

Geometric parameters (Å, º)

Cl1—C10	1.7470 (16)	C2—C7	1.416 (2)
O1—C1	1.2214 (18)	C2—C1	1.484 (2)
N2—C19	1.332 (2)	C13—C12	1.378 (2)
N2—C15	1.334 (2)	C13—C8	1.390 (2)
N1—C7	1.3822 (19)	C7—C6	1.403 (2)
N1—C8	1.402 (2)	C15—C16	1.382 (2)
C10—C11	1.381 (2)	C19—C18	1.374 (2)
C10—C9	1.392 (2)	C17—C18	1.380 (2)
C3—C4	1.379 (2)	C17—C16	1.383 (2)
C3—C2	1.395 (2)	C11—C12	1.378 (2)
O2—C1	1.3106 (19)	C5—C6	1.380 (2)
C9—C8	1.412 (2)	C5—C4	1.384 (2)
C9—C14	1.500 (2)	C16—C20	1.499 (2)
C19—N2—C15	118.53 (14)	C13—C8—C9	120.25 (14)
C7—N1—C8	127.62 (14)	N1—C8—C9	117.39 (14)
C11—C10—C9	123.36 (15)	O1—C1—O2	122.42 (15)
C11—C10—Cl1	116.52 (12)	O1—C1—C2	123.65 (14)
C9—C10—Cl1	120.12 (13)	O2—C1—C2	113.94 (13)
C4—C3—C2	121.84 (14)	N2—C15—C16	123.61 (15)
C10—C9—C8	116.70 (14)	N2—C19—C18	122.00 (15)
C10—C9—C14	122.93 (14)	C18—C17—C16	119.95 (16)
C8—C9—C14	120.37 (14)	C12—C11—C10	118.44 (15)
C3—C2—C7	119.43 (14)	C6—C5—C4	121.21 (15)
C3—C2—C1	118.67 (13)	C3—C4—C5	118.57 (14)
C7—C2—C1	121.89 (13)	C13—C12—C11	120.64 (16)
C12—C13—C8	120.61 (15)	C5—C6—C7	120.99 (15)
N1—C7—C6	121.89 (14)	C19—C18—C17	118.97 (15)
N1—C7—C2	120.18 (14)	C15—C16—C17	116.93 (15)
C6—C7—C2	117.88 (14)	C15—C16—C20	120.78 (16)
C13—C8—N1	122.29 (14)	C17—C16—C20	122.28 (16)
C11—C10—C9—C8	−0.6 (2)	C7—C2—C1—O1	−7.0 (2)
Cl1—C10—C9—C8	179.53 (11)	C3—C2—C1—O2	−7.7 (2)
C11—C10—C9—C14	178.96 (16)	C7—C2—C1—O2	173.14 (14)
Cl1—C10—C9—C14	−0.9 (2)	C19—N2—C15—C16	0.4 (2)
C4—C3—C2—C7	0.7 (2)	C15—N2—C19—C18	0.3 (2)
C4—C3—C2—C1	−178.52 (14)	C9—C10—C11—C12	0.4 (3)
C8—N1—C7—C6	24.1 (2)	Cl1—C10—C11—C12	−179.69 (13)
C8—N1—C7—C2	−158.62 (15)	C2—C3—C4—C5	1.4 (2)
C3—C2—C7—N1	−179.96 (14)	C6—C5—C4—C3	−1.5 (3)
C1—C2—C7—N1	−0.8 (2)	C8—C13—C12—C11	−0.3 (3)
C3—C2—C7—C6	−2.6 (2)	C10—C11—C12—C13	0.1 (3)
C1—C2—C7—C6	176.52 (14)	C4—C5—C6—C7	−0.6 (3)
C12—C13—C8—N1	176.98 (15)	N1—C7—C6—C5	179.90 (15)
C12—C13—C8—C9	0.1 (2)	C2—C7—C6—C5	2.6 (2)
C7—N1—C8—C13	26.2 (2)	N2—C19—C18—C17	−0.8 (3)
C7—N1—C8—C9	−156.88 (15)	C16—C17—C18—C19	0.5 (3)
C10—C9—C8—C13	0.3 (2)	N2—C15—C16—C17	−0.6 (2)
C14—C9—C8—C13	−179.24 (15)	N2—C15—C16—C20	178.28 (17)
C10—C9—C8—N1	−176.71 (14)	C18—C17—C16—C15	0.1 (2)
C14—C9—C8—N1	3.7 (2)	C18—C17—C16—C20	−178.74 (18)
C3—C2—C1—O1	172.11 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H7···O1	0.889 (19)	1.933 (19)	2.6715 (19)	139.4 (16)
O2—H2···N2	0.98 (3)	1.62 (3)	2.5981 (18)	171 (2)
C12—H12···O1^i	0.95	2.53	3.285 (2)	137
C19—H19···O2^ii	0.95	2.51	3.372 (2)	151

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