2-Chloro-4-nitro­benzoic acid as a coformer with pharmaceutical cocrystals and mol­ecular salts

A series of five binary com­plexes, i.e. three cocrystals and two mol­ecular salts, using 2-chloro-4-nitro­benzoic acid as a coformer have been produced with five commonly available com­pounds, some of pharmaceutical relevance, namely, 2-chloro-4-nitro­benzoic acid–isonicotinamide (1/1), C₇H₄ClNO₄·C₆H₆N₂O, 2-chloro-4-nitro­benzoic acid–3,3-di­ethyl­pyridine-2,4(1H,3H)-dione (2/1), 2C₇H₄ClNO₄·C₉H₁₃NO₂, 2-chloro-4-nitro­benzoic acid–pyrrolidin-2-one (1/1), C₇H₄ClNO₄·C₄H₇NO, 2-carb­oxy­piperidinium 2-chloro-4-nitro­benzoate, C₆H₁₂NO₂⁻·C₇H₃ClNO₄⁻, and (2-hy­droxy­eth­yl)ammonium 2-chloro-4-nitro­benzoate, C₂H₈NO⁺·C₇H₃ClNO₄⁻. The coformer falls under the classification of a `generally regarded as safe' com­pound. All five com­plexes make use of a number of different heteromeric hydrogen-bonded inter­actions. Inter­molecular potentials were evaluated using the CSD-Materials module.

Computing details

For all structures, data collection: APEX3 (Bruker, 2016); cell refinement: SAINT-Plus (Bruker, 2016); data reduction: SAINT-Plus and XPREP (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a). Program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b) for (I), (II); SHELXL2017 (Sheldrick, 2015b) for (III), (IV), (V). For all structures, molecular graphics: ORTEP for Windows (Farrugia, 2012) and DIAMOND (Brandenburg & Berndt, 1999); software used to prepare material for publication: WinGX (Farrugia, 2012).

2-Chloro-4-nitrobenzoic acid–isonicotinamide (1/1) (I)

Crystal data

C7H4ClNO4·C6H6N2O	F(000) = 664
Mr = 323.69	Dx = 1.586 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5801 reflections
a = 21.5205 (11) Å	θ = 3.1–28.3°
b = 4.8432 (2) Å	µ = 0.31 mm^−1
c = 13.0164 (7) Å	T = 173 K
β = 92.205 (2)°	Plate, yellow
V = 1355.67 (12) Å^3	0.67 × 0.49 × 0.07 mm
Z = 4

Data collection

Bruker D8 Venture Photon CCD area detector diffractometer	2761 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.067
ω scans	θmax = 28.0°, θmin = 1.9°
Absorption correction: integration (XPREP; Bruker, 2016)	h = −28→28
Tmin = 0.881, Tmax = 0.982	k = −6→6
16040 measured reflections	l = −17→17
3284 independent reflections

Refinement

Refinement on F^2	0 constraints
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) = 0.101	w = 1/[σ^2(Fo^2) + (0.0549P)^2 + 0.228P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
3284 reflections	Δρmax = 0.44 e Å^−3
208 parameters	Δρmin = −0.29 e Å^−3
0 restraints

Special details

Experimental. Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 2016)

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

Refinement. Reflection (100) was removed as it showed a large discrepency due to the beam stop. AFIX 147 was used for OH group.

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

	x	y	z	Uiso*/Ueq
C1	0.18979 (6)	−0.0392 (3)	0.34643 (10)	0.0195 (3)
C2	0.15297 (6)	0.0029 (3)	0.43135 (10)	0.0195 (3)
C3	0.09607 (6)	−0.1290 (3)	0.43897 (11)	0.0213 (3)
H3	0.070166	−0.0939	0.49498	0.026*
C4	0.07847 (6)	−0.3130 (3)	0.36230 (11)	0.0205 (3)
C5	0.11403 (6)	−0.3698 (3)	0.27896 (11)	0.0235 (3)
H5	0.101264	−0.50352	0.229084	0.028*
C6	0.16910 (7)	−0.2245 (3)	0.27072 (11)	0.0235 (3)
H6	0.19331	−0.251906	0.212065	0.028*
C7	0.25019 (6)	0.1113 (3)	0.33253 (11)	0.0208 (3)
N1	0.01801 (5)	−0.4520 (3)	0.36911 (10)	0.0242 (3)
O1	0.25470 (5)	0.2024 (2)	0.23942 (9)	0.0295 (3)
H1	0.284685	0.313032	0.237271	0.044*
O2	0.28943 (5)	0.1372 (3)	0.40099 (9)	0.0348 (3)
O3	0.01215 (5)	−0.6795 (2)	0.32907 (9)	0.0322 (3)
O4	−0.02300 (5)	−0.3318 (3)	0.41458 (10)	0.0342 (3)
Cl1	0.17523 (2)	0.22955 (8)	0.52934 (3)	0.02756 (12)
H3A	0.4450 (9)	1.463 (4)	−0.0454 (14)	0.031 (5)*
H3S	0.3832 (10)	1.322 (4)	−0.0451 (15)	0.032 (5)*
C8	0.40463 (6)	0.9781 (3)	0.10404 (10)	0.0187 (3)
C9	0.34736 (6)	0.8975 (3)	0.06104 (11)	0.0225 (3)
H9	0.330995	0.982255	0	0.027*
C10	0.31475 (7)	0.6918 (3)	0.10879 (12)	0.0241 (3)
H10	0.275795	0.635921	0.078863	0.029*
C11	0.39022 (7)	0.6477 (3)	0.23778 (12)	0.0267 (3)
H11	0.404955	0.562727	0.299829	0.032*
C12	0.42603 (7)	0.8506 (3)	0.19419 (12)	0.0248 (3)
H12	0.464885	0.90214	0.225622	0.03*
C13	0.44533 (6)	1.1943 (3)	0.05713 (11)	0.0192 (3)
N2	0.33551 (6)	0.5672 (3)	0.19546 (10)	0.0243 (3)
N3	0.42190 (6)	1.3356 (3)	−0.02301 (10)	0.0227 (3)
O5	0.49829 (5)	1.2317 (2)	0.09422 (8)	0.0246 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0170 (6)	0.0206 (6)	0.0209 (7)	0.0006 (5)	−0.0008 (5)	0.0029 (5)
C2	0.0190 (6)	0.0196 (6)	0.0196 (6)	0.0018 (5)	−0.0031 (5)	−0.0007 (5)
C3	0.0179 (6)	0.0254 (7)	0.0207 (7)	0.0031 (5)	0.0021 (5)	0.0012 (5)
C4	0.0163 (6)	0.0202 (6)	0.0248 (7)	0.0000 (5)	−0.0008 (5)	0.0037 (5)
C5	0.0217 (7)	0.0242 (7)	0.0246 (7)	−0.0013 (6)	−0.0002 (6)	−0.0036 (6)
C6	0.0202 (7)	0.0282 (7)	0.0224 (7)	−0.0002 (5)	0.0045 (5)	−0.0014 (6)
C7	0.0182 (6)	0.0213 (6)	0.0227 (7)	0.0005 (5)	0.0012 (5)	−0.0004 (5)
N1	0.0191 (6)	0.0288 (6)	0.0247 (6)	−0.0022 (5)	−0.0008 (5)	0.0042 (5)
O1	0.0270 (6)	0.0360 (6)	0.0253 (6)	−0.0124 (4)	−0.0011 (4)	0.0067 (5)
O2	0.0214 (5)	0.0541 (7)	0.0285 (6)	−0.0101 (5)	−0.0052 (4)	0.0047 (5)
O3	0.0292 (6)	0.0280 (6)	0.0391 (7)	−0.0084 (4)	−0.0023 (5)	−0.0023 (5)
O4	0.0203 (5)	0.0415 (6)	0.0412 (7)	−0.0011 (5)	0.0078 (5)	−0.0010 (5)
Cl1	0.0231 (2)	0.0327 (2)	0.0267 (2)	−0.00001 (13)	−0.00159 (14)	−0.01053 (14)
C8	0.0169 (6)	0.0189 (6)	0.0205 (6)	−0.0003 (5)	0.0026 (5)	−0.0015 (5)
C9	0.0202 (7)	0.0258 (7)	0.0214 (7)	−0.0018 (5)	−0.0009 (5)	0.0011 (6)
C10	0.0181 (7)	0.0280 (7)	0.0262 (7)	−0.0041 (5)	0.0021 (6)	−0.0039 (6)
C11	0.0272 (8)	0.0285 (7)	0.0244 (7)	−0.0034 (6)	−0.0003 (6)	0.0055 (6)
C12	0.0211 (7)	0.0266 (7)	0.0264 (7)	−0.0038 (6)	−0.0024 (6)	0.0022 (6)
C13	0.0173 (6)	0.0184 (6)	0.0221 (7)	−0.0004 (5)	0.0018 (5)	−0.0020 (5)
N2	0.0239 (6)	0.0237 (6)	0.0255 (6)	−0.0036 (5)	0.0051 (5)	0.0003 (5)
N3	0.0162 (6)	0.0243 (6)	0.0275 (7)	−0.0028 (5)	−0.0003 (5)	0.0058 (5)
O5	0.0187 (5)	0.0265 (5)	0.0282 (5)	−0.0051 (4)	−0.0031 (4)	0.0050 (4)

Geometric parameters (Å, º)

C1—C6	1.393 (2)	O1—H1	0.84
C1—C2	1.3995 (19)	C8—C12	1.389 (2)
C1—C7	1.5071 (19)	C8—C9	1.3897 (19)
C2—C3	1.3880 (19)	C8—C13	1.5094 (18)
C2—Cl1	1.7362 (14)	C9—C10	1.380 (2)
C3—C4	1.380 (2)	C9—H9	0.95
C3—H3	0.95	C10—N2	1.341 (2)
C4—C5	1.379 (2)	C10—H10	0.95
C4—N1	1.4705 (18)	C11—N2	1.3387 (19)
C5—C6	1.386 (2)	C11—C12	1.384 (2)
C5—H5	0.95	C11—H11	0.95
C6—H6	0.95	C12—H12	0.95
C7—O2	1.2104 (18)	C13—O5	1.2338 (17)
C7—O1	1.2970 (18)	C13—N3	1.3305 (19)
N1—O3	1.2236 (17)	N3—H3A	0.85 (2)
N1—O4	1.2279 (17)	N3—H3S	0.87 (2)
C6—C1—C2	118.50 (12)	C7—O1—H1	109.5
C6—C1—C7	118.70 (12)	C12—C8—C9	118.40 (12)
C2—C1—C7	122.79 (12)	C12—C8—C13	118.13 (12)
C3—C2—C1	121.15 (12)	C9—C8—C13	123.47 (12)
C3—C2—Cl1	117.24 (10)	C10—C9—C8	118.68 (13)
C1—C2—Cl1	121.57 (10)	C10—C9—H9	120.7
C4—C3—C2	117.64 (13)	C8—C9—H9	120.7
C4—C3—H3	121.2	N2—C10—C9	123.02 (13)
C2—C3—H3	121.2	N2—C10—H10	118.5
C5—C4—C3	123.54 (13)	C9—C10—H10	118.5
C5—C4—N1	118.36 (13)	N2—C11—C12	122.20 (14)
C3—C4—N1	118.09 (12)	N2—C11—H11	118.9
C4—C5—C6	117.48 (13)	C12—C11—H11	118.9
C4—C5—H5	121.3	C11—C12—C8	119.36 (13)
C6—C5—H5	121.3	C11—C12—H12	120.3
C5—C6—C1	121.55 (13)	C8—C12—H12	120.3
C5—C6—H6	119.2	O5—C13—N3	123.21 (13)
C1—C6—H6	119.2	O5—C13—C8	119.03 (12)
O2—C7—O1	125.27 (13)	N3—C13—C8	117.76 (12)
O2—C7—C1	122.84 (13)	C11—N2—C10	118.33 (12)
O1—C7—C1	111.88 (12)	C13—N3—H3A	115.6 (12)
O3—N1—O4	124.59 (12)	C13—N3—H3S	123.2 (13)
O3—N1—C4	117.61 (12)	H3A—N3—H3S	120.3 (18)
O4—N1—C4	117.79 (12)
C6—C1—C2—C3	−2.1 (2)	C5—C4—N1—O3	28.73 (19)
C7—C1—C2—C3	176.69 (13)	C3—C4—N1—O3	−152.33 (13)
C6—C1—C2—Cl1	179.91 (11)	C5—C4—N1—O4	−151.33 (14)
C7—C1—C2—Cl1	−1.27 (19)	C3—C4—N1—O4	27.61 (19)
C1—C2—C3—C4	3.0 (2)	C12—C8—C9—C10	−1.0 (2)
Cl1—C2—C3—C4	−178.95 (10)	C13—C8—C9—C10	178.12 (13)
C2—C3—C4—C5	−0.6 (2)	C8—C9—C10—N2	0.6 (2)
C2—C3—C4—N1	−179.44 (12)	N2—C11—C12—C8	0.6 (2)
C3—C4—C5—C6	−2.7 (2)	C9—C8—C12—C11	0.4 (2)
N1—C4—C5—C6	176.21 (13)	C13—C8—C12—C11	−178.75 (13)
C4—C5—C6—C1	3.6 (2)	C12—C8—C13—O5	6.91 (19)
C2—C1—C6—C5	−1.3 (2)	C9—C8—C13—O5	−172.19 (13)
C7—C1—C6—C5	179.87 (13)	C12—C8—C13—N3	−173.19 (13)
C6—C1—C7—O2	−135.12 (16)	C9—C8—C13—N3	7.7 (2)
C2—C1—C7—O2	46.1 (2)	C12—C11—N2—C10	−1.0 (2)
C6—C1—C7—O1	43.82 (18)	C9—C10—N2—C11	0.4 (2)
C2—C1—C7—O1	−135.00 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2	0.84	1.75	2.5593 (16)	162
N3—H3A···O5^i	0.85 (2)	2.03 (2)	2.8849 (16)	178 (2)
N3—H3S···O2^ii	0.87 (2)	2.12 (2)	2.9843 (17)	171 (2)

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

2-Chloro-4-nitrobenzoic acid)–3,3–diethylpyridine-2,4(1H,3H)-dione (2/1) (II)

Crystal data

2C7H4ClNO4·C9H13NO2	Z = 4
Mr = 570.33	F(000) = 1176
Triclinic, P1	Dx = 1.507 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2016 (2) Å	Cell parameters from 9915 reflections
b = 14.0910 (5) Å	θ = 2.3–28.4°
c = 25.8120 (8) Å	µ = 0.32 mm^−1
α = 95.124 (2)°	T = 173 K
β = 96.755 (2)°	Block, colourless
γ = 103.258 (2)°	0.6 × 0.4 × 0.2 mm
V = 2513.44 (14) Å^3

Data collection

Bruker D8 Venture Photon CCD area detector diffractometer	7132 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
ω scans	θmax = 25.5°, θmin = 0.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.76, Tmax = 0.9	k = −17→17
39273 measured reflections	l = −31→31
9352 independent reflections

Refinement

Refinement on F^2	0 constraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.064	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.198	w = 1/[σ^2(Fo^2) + (0.1148P)^2 + 2.1772P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
9352 reflections	Δρmax = 1.25 e Å^−3
713 parameters	Δρmin = −0.41 e Å^−3
0 restraints

Special details

Experimental. Absorption corrections were made using the program SADABS (Sheldrick, 1996)

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

Refinement. Reflections (1–24), (003), (1–24), (010) and (005) were removed as they showed a large discrepency between calculated and measured intensities due to the beam stop.

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

	x	y	z	Uiso*/Ueq
C1	0.9068 (4)	0.3581 (2)	0.98176 (11)	0.0300 (6)
C2	1.1069 (4)	0.3936 (2)	0.98537 (11)	0.0312 (6)
C3	1.2220 (5)	0.4160 (2)	1.03358 (11)	0.0339 (7)
H3	1.357666	0.439691	1.035961	0.041*
C4	1.1358 (5)	0.4031 (2)	1.07826 (11)	0.0346 (7)
C5	0.9413 (5)	0.3676 (2)	1.07714 (11)	0.0370 (7)
H5B	0.886428	0.358639	1.10861	0.044*
C6	0.8276 (5)	0.3452 (2)	1.02840 (11)	0.0323 (6)
H6	0.692375	0.320513	1.026586	0.039*
C7	0.7760 (5)	0.3369 (2)	0.93054 (11)	0.0342 (7)
N1	1.2636 (4)	0.4300 (2)	1.12949 (10)	0.0449 (7)
O1	0.6037 (4)	0.2854 (2)	0.93320 (10)	0.0588 (8)
O2	0.8204 (4)	0.3682 (3)	0.89106 (10)	0.0789 (10)
O3	1.1874 (4)	0.4195 (2)	1.16887 (9)	0.0663 (8)
O4	1.4347 (4)	0.4624 (2)	1.12935 (10)	0.0640 (8)
Cl1	1.22532 (13)	0.40935 (6)	0.93107 (3)	0.0456 (2)
H1	0.545 (8)	0.278 (4)	0.906 (2)	0.095 (19)*
C8	0.0789 (5)	0.1430 (2)	0.02132 (11)	0.0335 (7)
C9	−0.1201 (5)	0.1087 (2)	0.01716 (11)	0.0350 (7)
C10	−0.2350 (5)	0.0909 (2)	−0.03112 (11)	0.0371 (7)
H10	−0.370967	0.067862	−0.033926	0.045*
C11	−0.1469 (5)	0.1073 (2)	−0.07493 (11)	0.0396 (8)
C12	0.0478 (5)	0.1416 (2)	−0.07321 (12)	0.0421 (8)
H12	0.103667	0.152604	−0.10436	0.051*
C13	0.1601 (5)	0.1595 (2)	−0.02452 (11)	0.0377 (7)
H13A	0.295666	0.183596	−0.022202	0.045*
C14	0.2078 (5)	0.1593 (2)	0.07257 (11)	0.0377 (7)
N2	−0.2747 (5)	0.0873 (2)	−0.12625 (10)	0.0524 (8)
O5	0.3674 (4)	0.2273 (2)	0.07527 (10)	0.0559 (7)
O6	0.1728 (4)	0.1085 (2)	0.10765 (10)	0.0672 (8)
O7	−0.4467 (5)	0.0583 (3)	−0.12692 (10)	0.0741 (9)
O8	−0.1957 (5)	0.0994 (2)	−0.16528 (9)	0.0805 (11)
Cl2	−0.23875 (14)	0.08909 (7)	0.07131 (3)	0.0516 (2)
H5	0.455 (8)	0.239 (4)	0.112 (2)	0.114 (19)*
C15	0.2176 (4)	0.4462 (2)	0.51981 (10)	0.0287 (6)
C16	0.2917 (4)	0.5454 (2)	0.51516 (10)	0.0291 (6)
C17	0.2817 (4)	0.5792 (2)	0.46655 (11)	0.0305 (6)
H17	0.329307	0.646777	0.463392	0.037*
C18	0.2014 (4)	0.5128 (2)	0.42277 (10)	0.0315 (6)
C19	0.1261 (4)	0.4150 (2)	0.42498 (11)	0.0340 (7)
H19	0.070603	0.371056	0.394071	0.041*
C20	0.1344 (4)	0.3828 (2)	0.47404 (11)	0.0321 (6)
H20	0.081752	0.315451	0.476733	0.038*
C21	0.2325 (4)	0.4058 (2)	0.57142 (11)	0.0342 (7)
N3	0.1970 (4)	0.5508 (2)	0.37127 (9)	0.0378 (6)
O9	0.0943 (3)	0.32912 (18)	0.57446 (9)	0.0483 (6)
O10	0.3705 (4)	0.4367 (2)	0.60520 (10)	0.0641 (8)
O11	0.1365 (4)	0.4925 (2)	0.33209 (9)	0.0597 (7)
O12	0.2545 (4)	0.6387 (2)	0.37041 (9)	0.0541 (7)
Cl3	0.39006 (12)	0.63153 (6)	0.56896 (3)	0.0441 (2)
H9	0.109 (6)	0.312 (3)	0.6071 (18)	0.077 (14)*
C22	0.7458 (4)	0.0198 (2)	0.47917 (11)	0.0328 (6)
C23	0.6853 (4)	−0.0809 (2)	0.48159 (11)	0.0342 (7)
C24	0.7107 (4)	−0.1193 (2)	0.52854 (12)	0.0372 (7)
H24	0.671085	−0.18804	0.530013	0.045*
C25	0.7943 (4)	−0.0563 (2)	0.57298 (12)	0.0376 (7)
C26	0.8561 (5)	0.0437 (3)	0.57309 (12)	0.0405 (7)
H26	0.913375	0.085515	0.604593	0.049*
C27	0.8317 (4)	0.0811 (2)	0.52569 (11)	0.0351 (7)
H27	0.874117	0.149837	0.524631	0.042*
C28	0.7164 (4)	0.0649 (2)	0.42952 (11)	0.0358 (7)
N4	0.8145 (4)	−0.0987 (2)	0.62293 (11)	0.0493 (7)
O13	0.8345 (4)	0.15015 (19)	0.42933 (10)	0.0574 (7)
O14	0.5878 (4)	0.0286 (2)	0.39381 (10)	0.0636 (8)
O15	0.7564 (5)	−0.1869 (2)	0.62230 (10)	0.0659 (8)
O16	0.8888 (5)	−0.0430 (2)	0.66219 (10)	0.0783 (10)
Cl4	0.58385 (14)	−0.16442 (7)	0.42674 (3)	0.0528 (3)
H13	0.804 (6)	0.167 (3)	0.3998 (18)	0.069 (13)*
C29	0.2003 (4)	0.2483 (2)	0.75856 (11)	0.0330 (6)
C30	0.3751 (4)	0.2770 (2)	0.80108 (10)	0.0316 (6)
C31	0.5448 (4)	0.3353 (2)	0.79096 (11)	0.0361 (7)
H31	0.65244	0.353672	0.817966	0.043*
C32	0.5621 (5)	0.3672 (3)	0.74314 (13)	0.0544 (10)
H32	0.682966	0.406469	0.737836	0.065*
C34	0.2388 (4)	0.2840 (2)	0.70528 (11)	0.0331 (7)
C35	0.0884 (5)	0.4050 (2)	0.78415 (13)	0.0433 (8)
H35A	0.21083	0.430277	0.807502	0.065*
H35B	−0.013681	0.428645	0.799283	0.065*
H35C	0.10034	0.428026	0.749697	0.065*
C36	0.0381 (4)	0.2932 (2)	0.77789 (11)	0.0334 (6)
H36A	−0.081296	0.268377	0.752492	0.04*
H36B	0.011667	0.270567	0.812106	0.04*
C37	0.1338 (5)	0.1369 (2)	0.75037 (13)	0.0453 (8)
H37A	0.015531	0.116812	0.724269	0.054*
H37B	0.101843	0.112807	0.783891	0.054*
C38	0.2898 (7)	0.0896 (3)	0.73105 (17)	0.0721 (13)
H38A	0.318279	0.111367	0.69721	0.108*
H38B	0.243273	0.017921	0.726833	0.108*
H38C	0.407132	0.109364	0.756805	0.108*
N5	0.4137 (4)	0.3455 (3)	0.70232 (11)	0.0560 (9)
O17	0.3584 (3)	0.24988 (18)	0.84511 (8)	0.0438 (6)
O18	0.1104 (3)	0.26123 (18)	0.66753 (8)	0.0479 (6)
H5A	0.453 (6)	0.377 (3)	0.6702 (17)	0.076 (13)*
C39	0.7090 (4)	0.2683 (2)	0.25674 (11)	0.0358 (7)
C40	0.5731 (4)	0.2239 (2)	0.20646 (11)	0.0363 (7)
C41	0.4315 (4)	0.1403 (2)	0.20719 (10)	0.0323 (6)
H41	0.339408	0.115914	0.176679	0.039*
C42	0.4188 (5)	0.0911 (2)	0.25018 (12)	0.0422 (8)
H42	0.31906	0.03303	0.248325	0.051*
C43	0.6875 (4)	0.2057 (2)	0.30185 (11)	0.0319 (6)
C44	0.6653 (5)	0.3693 (2)	0.27580 (13)	0.0421 (8)
H44A	0.755486	0.399431	0.308086	0.051*
H44B	0.690909	0.413764	0.248512	0.051*
C45	0.4612 (5)	0.3618 (3)	0.28713 (14)	0.0537 (9)
H45A	0.428925	0.312409	0.311156	0.081*
H45B	0.371721	0.342649	0.25422	0.081*
H45C	0.450869	0.425656	0.303362	0.081*
C46	0.9147 (5)	0.2846 (3)	0.24453 (14)	0.0538 (10)
H46A	0.932696	0.330833	0.217775	0.065*
H46B	1.0046	0.315502	0.276767	0.065*
C47	0.9648 (6)	0.1919 (4)	0.22477 (15)	0.0658 (12)
H47A	0.870556	0.158279	0.194398	0.099*
H47B	0.962848	0.148963	0.252665	0.099*
H47C	1.093796	0.207604	0.214302	0.099*
N6	0.5440 (4)	0.1217 (2)	0.29603 (10)	0.0441 (7)
O19	0.5867 (3)	0.26521 (19)	0.16642 (9)	0.0521 (7)
O20	0.7999 (3)	0.23354 (17)	0.34335 (8)	0.0453 (6)
H6A	0.517 (6)	0.076 (3)	0.3268 (17)	0.079 (14)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0431 (17)	0.0235 (14)	0.0265 (14)	0.0137 (13)	0.0046 (12)	0.0050 (11)
C2	0.0432 (17)	0.0245 (14)	0.0283 (14)	0.0112 (13)	0.0078 (12)	0.0047 (11)
C3	0.0379 (17)	0.0276 (15)	0.0355 (16)	0.0059 (13)	0.0049 (13)	0.0052 (12)
C4	0.0458 (18)	0.0270 (15)	0.0275 (14)	0.0060 (14)	−0.0015 (13)	0.0015 (11)
C5	0.0508 (19)	0.0334 (16)	0.0264 (15)	0.0082 (15)	0.0060 (13)	0.0065 (12)
C6	0.0384 (16)	0.0299 (15)	0.0278 (14)	0.0072 (13)	0.0032 (12)	0.0049 (11)
C7	0.0471 (19)	0.0314 (16)	0.0253 (15)	0.0127 (14)	0.0028 (13)	0.0043 (12)
N1	0.0519 (19)	0.0433 (16)	0.0323 (15)	0.0016 (14)	−0.0030 (12)	0.0040 (12)
O1	0.0378 (14)	0.102 (2)	0.0333 (13)	0.0073 (14)	−0.0049 (11)	0.0264 (14)
O2	0.0689 (19)	0.118 (3)	0.0310 (14)	−0.0140 (18)	−0.0029 (12)	0.0202 (15)
O3	0.0651 (18)	0.090 (2)	0.0277 (12)	−0.0135 (16)	−0.0011 (12)	0.0148 (13)
O4	0.0418 (16)	0.090 (2)	0.0463 (15)	−0.0029 (15)	−0.0058 (11)	−0.0004 (14)
Cl1	0.0536 (5)	0.0523 (5)	0.0347 (4)	0.0143 (4)	0.0166 (4)	0.0078 (3)
C8	0.0511 (19)	0.0236 (14)	0.0274 (14)	0.0126 (14)	0.0036 (13)	0.0044 (11)
C9	0.0526 (19)	0.0263 (15)	0.0271 (14)	0.0107 (14)	0.0076 (13)	0.0037 (11)
C10	0.0486 (19)	0.0282 (15)	0.0307 (15)	0.0045 (14)	0.0023 (13)	0.0007 (12)
C11	0.059 (2)	0.0265 (15)	0.0257 (15)	0.0006 (15)	−0.0025 (14)	−0.0008 (12)
C12	0.066 (2)	0.0292 (16)	0.0271 (15)	0.0031 (16)	0.0067 (14)	0.0030 (12)
C13	0.0517 (19)	0.0305 (16)	0.0288 (15)	0.0073 (14)	0.0028 (13)	0.0036 (12)
C14	0.055 (2)	0.0354 (17)	0.0256 (15)	0.0177 (16)	0.0022 (13)	0.0076 (12)
N2	0.077 (2)	0.0372 (16)	0.0281 (15)	−0.0090 (16)	−0.0029 (14)	−0.0001 (11)
O5	0.0470 (15)	0.0750 (19)	0.0406 (14)	0.0047 (14)	−0.0077 (11)	0.0248 (13)
O6	0.085 (2)	0.0641 (18)	0.0432 (14)	0.0013 (16)	−0.0073 (14)	0.0194 (13)
O7	0.064 (2)	0.101 (2)	0.0409 (15)	0.0002 (18)	−0.0116 (13)	−0.0039 (15)
O8	0.096 (2)	0.085 (2)	0.0254 (13)	−0.0429 (18)	−0.0034 (13)	0.0080 (13)
Cl2	0.0610 (6)	0.0631 (6)	0.0322 (4)	0.0136 (5)	0.0143 (4)	0.0068 (4)
C15	0.0212 (13)	0.0418 (17)	0.0251 (14)	0.0100 (12)	0.0043 (10)	0.0064 (12)
C16	0.0192 (13)	0.0433 (17)	0.0233 (13)	0.0065 (12)	0.0027 (10)	0.0002 (12)
C17	0.0252 (14)	0.0361 (16)	0.0294 (14)	0.0047 (12)	0.0054 (11)	0.0051 (12)
C18	0.0229 (14)	0.0485 (19)	0.0244 (14)	0.0084 (13)	0.0066 (11)	0.0085 (12)
C19	0.0282 (15)	0.0434 (18)	0.0269 (14)	0.0042 (13)	0.0026 (11)	0.0000 (12)
C20	0.0296 (15)	0.0380 (16)	0.0272 (14)	0.0069 (13)	0.0010 (11)	0.0039 (12)
C21	0.0300 (15)	0.0511 (19)	0.0227 (14)	0.0138 (15)	0.0003 (11)	0.0047 (13)
N3	0.0322 (14)	0.0534 (18)	0.0273 (13)	0.0060 (13)	0.0074 (10)	0.0095 (12)
O9	0.0483 (14)	0.0526 (15)	0.0346 (12)	−0.0051 (12)	−0.0084 (10)	0.0192 (11)
O10	0.0545 (16)	0.084 (2)	0.0413 (14)	−0.0057 (15)	−0.0098 (12)	0.0209 (13)
O11	0.0700 (18)	0.0697 (18)	0.0254 (12)	−0.0088 (14)	−0.0001 (11)	0.0079 (11)
O12	0.0754 (18)	0.0534 (17)	0.0365 (13)	0.0128 (14)	0.0164 (12)	0.0178 (11)
Cl3	0.0470 (5)	0.0480 (5)	0.0296 (4)	0.0033 (4)	−0.0017 (3)	−0.0054 (3)
C22	0.0247 (14)	0.0430 (18)	0.0310 (15)	0.0091 (13)	0.0054 (11)	0.0011 (12)
C23	0.0278 (15)	0.0406 (18)	0.0320 (15)	0.0058 (13)	0.0055 (12)	−0.0025 (12)
C24	0.0318 (16)	0.0387 (17)	0.0391 (17)	0.0027 (14)	0.0094 (13)	0.0030 (13)
C25	0.0304 (16)	0.0478 (19)	0.0319 (15)	−0.0006 (14)	0.0099 (12)	0.0091 (13)
C26	0.0360 (17)	0.049 (2)	0.0300 (15)	−0.0003 (15)	0.0051 (13)	−0.0006 (13)
C27	0.0323 (16)	0.0388 (17)	0.0318 (15)	0.0035 (13)	0.0052 (12)	0.0035 (12)
C28	0.0348 (16)	0.0428 (19)	0.0292 (15)	0.0122 (15)	0.0004 (12)	−0.0016 (13)
N4	0.0505 (18)	0.054 (2)	0.0341 (15)	−0.0072 (15)	0.0063 (13)	0.0104 (13)
O13	0.0708 (18)	0.0464 (15)	0.0435 (14)	0.0009 (13)	−0.0196 (13)	0.0155 (12)
O14	0.0600 (17)	0.0713 (19)	0.0477 (15)	0.0008 (14)	−0.0119 (13)	0.0099 (13)
O15	0.090 (2)	0.0517 (17)	0.0458 (15)	−0.0075 (15)	0.0117 (14)	0.0160 (12)
O16	0.107 (2)	0.0672 (19)	0.0327 (14)	−0.0276 (18)	−0.0061 (14)	0.0080 (13)
Cl4	0.0675 (6)	0.0455 (5)	0.0383 (4)	0.0086 (4)	−0.0001 (4)	−0.0084 (4)
C29	0.0314 (15)	0.0391 (17)	0.0276 (14)	0.0063 (13)	0.0006 (12)	0.0100 (12)
C30	0.0356 (16)	0.0413 (17)	0.0210 (13)	0.0159 (14)	0.0005 (11)	0.0076 (12)
C31	0.0249 (15)	0.053 (2)	0.0255 (14)	0.0054 (14)	−0.0063 (11)	0.0043 (13)
C32	0.0263 (16)	0.093 (3)	0.0377 (18)	−0.0006 (18)	0.0026 (13)	0.0202 (18)
C34	0.0306 (16)	0.0433 (17)	0.0251 (14)	0.0083 (14)	0.0009 (12)	0.0085 (12)
C35	0.0377 (18)	0.0429 (19)	0.0492 (19)	0.0096 (15)	0.0044 (14)	0.0076 (15)
C36	0.0302 (15)	0.0402 (17)	0.0308 (15)	0.0072 (13)	0.0068 (12)	0.0099 (12)
C37	0.053 (2)	0.0412 (19)	0.0378 (17)	0.0075 (16)	0.0005 (15)	0.0051 (14)
C38	0.077 (3)	0.072 (3)	0.067 (3)	0.044 (2)	−0.017 (2)	−0.027 (2)
N5	0.0439 (17)	0.092 (3)	0.0291 (14)	0.0043 (17)	0.0061 (12)	0.0230 (15)
O17	0.0371 (12)	0.0628 (15)	0.0304 (11)	0.0074 (11)	−0.0008 (9)	0.0195 (10)
O18	0.0417 (13)	0.0620 (16)	0.0302 (11)	−0.0036 (11)	−0.0112 (10)	0.0168 (10)
C39	0.0313 (16)	0.0386 (17)	0.0323 (15)	−0.0005 (13)	−0.0032 (12)	0.0105 (13)
C40	0.0376 (17)	0.0413 (18)	0.0289 (15)	0.0103 (15)	−0.0031 (12)	0.0064 (13)
C41	0.0314 (15)	0.0383 (17)	0.0209 (13)	0.0024 (13)	−0.0055 (11)	−0.0023 (11)
C42	0.0451 (19)	0.0367 (17)	0.0347 (16)	−0.0057 (15)	0.0012 (14)	−0.0025 (13)
C43	0.0373 (16)	0.0318 (16)	0.0261 (14)	0.0100 (13)	−0.0017 (12)	0.0045 (11)
C44	0.0484 (19)	0.0314 (17)	0.0394 (17)	−0.0004 (15)	−0.0045 (14)	0.0068 (13)
C45	0.061 (2)	0.045 (2)	0.055 (2)	0.0216 (18)	−0.0055 (18)	−0.0005 (16)
C46	0.0367 (19)	0.079 (3)	0.0429 (19)	0.0061 (19)	0.0055 (15)	0.0130 (18)
C47	0.044 (2)	0.110 (4)	0.045 (2)	0.025 (2)	0.0075 (17)	−0.001 (2)
N6	0.0626 (19)	0.0372 (15)	0.0329 (14)	0.0117 (14)	0.0070 (13)	0.0067 (12)
O19	0.0494 (14)	0.0613 (16)	0.0369 (12)	−0.0025 (12)	−0.0101 (10)	0.0236 (11)
O20	0.0484 (14)	0.0449 (13)	0.0335 (12)	0.0010 (11)	−0.0126 (10)	0.0082 (10)

Geometric parameters (Å, º)

C1—C6	1.400 (4)	C25—N4	1.475 (4)
C1—C2	1.402 (4)	C26—C27	1.383 (4)
C1—C7	1.494 (4)	C26—H26	0.95
C2—C3	1.379 (4)	C27—H27	0.95
C2—Cl1	1.729 (3)	C28—O14	1.211 (4)
C3—C4	1.379 (4)	C28—O13	1.304 (4)
C3—H3	0.95	N4—O16	1.211 (4)
C4—C5	1.371 (5)	N4—O15	1.215 (4)
C4—N1	1.485 (4)	O13—H13	0.84 (4)
C5—C6	1.386 (4)	C29—C37	1.520 (5)
C5—H5B	0.95	C29—C30	1.521 (4)
C6—H6	0.95	C29—C34	1.540 (4)
C7—O2	1.195 (4)	C29—C36	1.561 (4)
C7—O1	1.299 (4)	C30—O17	1.241 (3)
N1—O4	1.212 (4)	C30—C31	1.375 (4)
N1—O3	1.215 (4)	C31—C32	1.361 (4)
O1—H1	0.75 (5)	C31—H31	0.95
C8—C9	1.392 (5)	C32—N5	1.369 (4)
C8—C13	1.395 (4)	C32—H32	0.95
C8—C14	1.491 (4)	C34—O18	1.226 (3)
C9—C10	1.381 (4)	C34—N5	1.370 (4)
C9—Cl2	1.732 (3)	C35—C36	1.522 (4)
C10—C11	1.372 (4)	C35—H35A	0.98
C10—H10	0.95	C35—H35B	0.98
C11—C12	1.368 (5)	C35—H35C	0.98
C11—N2	1.486 (4)	C36—H36A	0.99
C12—C13	1.381 (4)	C36—H36B	0.99
C12—H12	0.95	C37—C38	1.539 (5)
C13—H13A	0.95	C37—H37A	0.99
C14—O6	1.217 (4)	C37—H37B	0.99
C14—O5	1.307 (4)	C38—H38A	0.98
N2—O7	1.209 (4)	C38—H38B	0.98
N2—O8	1.220 (4)	C38—H38C	0.98
O5—H5	1.04 (6)	N5—H5A	1.02 (4)
C15—C20	1.397 (4)	C39—C40	1.519 (4)
C15—C16	1.399 (4)	C39—C46	1.521 (5)
C15—C21	1.496 (4)	C39—C43	1.523 (4)
C16—C17	1.381 (4)	C39—C44	1.575 (5)
C16—Cl3	1.725 (3)	C40—O19	1.233 (4)
C17—C18	1.377 (4)	C40—C41	1.374 (5)
C17—H17	0.95	C41—C42	1.361 (4)
C18—C19	1.370 (4)	C41—H41	0.95
C18—N3	1.477 (4)	C42—N6	1.371 (4)
C19—C20	1.382 (4)	C42—H42	0.95
C19—H19	0.95	C43—O20	1.238 (3)
C20—H20	0.95	C43—N6	1.364 (4)
C21—O10	1.211 (4)	C44—C45	1.514 (5)
C21—O9	1.306 (4)	C44—H44A	0.99
N3—O11	1.213 (4)	C44—H44B	0.99
N3—O12	1.215 (4)	C45—H45A	0.98
O9—H9	0.90 (5)	C45—H45B	0.98
C22—C23	1.396 (4)	C45—H45C	0.98
C22—C27	1.402 (4)	C46—C47	1.496 (6)
C22—C28	1.494 (4)	C46—H46A	0.99
C23—C24	1.380 (4)	C46—H46B	0.99
C23—Cl4	1.728 (3)	C47—H47A	0.98
C24—C25	1.370 (4)	C47—H47B	0.98
C24—H24	0.95	C47—H47C	0.98
C25—C26	1.376 (5)	N6—H6A	1.08 (5)
C6—C1—C2	118.1 (3)	O13—C28—C22	113.9 (3)
C6—C1—C7	119.3 (3)	O16—N4—O15	124.0 (3)
C2—C1—C7	122.5 (3)	O16—N4—C25	117.6 (3)
C3—C2—C1	120.8 (3)	O15—N4—C25	118.4 (3)
C3—C2—Cl1	116.0 (2)	C28—O13—H13	105 (3)
C1—C2—Cl1	123.2 (2)	C37—C29—C30	108.1 (2)
C2—C3—C4	118.5 (3)	C37—C29—C34	108.2 (2)
C2—C3—H3	120.7	C30—C29—C34	114.2 (2)
C4—C3—H3	120.7	C37—C29—C36	110.0 (3)
C5—C4—C3	123.3 (3)	C30—C29—C36	108.3 (2)
C5—C4—N1	119.7 (3)	C34—C29—C36	108.1 (2)
C3—C4—N1	117.0 (3)	O17—C30—C31	121.3 (3)
C4—C5—C6	117.5 (3)	O17—C30—C29	118.7 (3)
C4—C5—H5B	121.2	C31—C30—C29	119.9 (2)
C6—C5—H5B	121.2	C32—C31—C30	121.5 (3)
C5—C6—C1	121.7 (3)	C32—C31—H31	119.2
C5—C6—H6	119.1	C30—C31—H31	119.2
C1—C6—H6	119.1	C31—C32—N5	123.1 (3)
O2—C7—O1	122.2 (3)	C31—C32—H32	118.4
O2—C7—C1	123.8 (3)	N5—C32—H32	118.4
O1—C7—C1	113.8 (3)	O18—C34—N5	121.7 (3)
O4—N1—O3	124.6 (3)	O18—C34—C29	119.7 (3)
O4—N1—C4	118.3 (3)	N5—C34—C29	118.5 (2)
O3—N1—C4	117.0 (3)	C36—C35—H35A	109.5
C7—O1—H1	109 (4)	C36—C35—H35B	109.5
C9—C8—C13	118.4 (3)	H35A—C35—H35B	109.5
C9—C8—C14	122.4 (3)	C36—C35—H35C	109.5
C13—C8—C14	119.2 (3)	H35A—C35—H35C	109.5
C10—C9—C8	121.0 (3)	H35B—C35—H35C	109.5
C10—C9—Cl2	116.2 (3)	C35—C36—C29	113.5 (3)
C8—C9—Cl2	122.8 (2)	C35—C36—H36A	108.9
C11—C10—C9	118.0 (3)	C29—C36—H36A	108.9
C11—C10—H10	121	C35—C36—H36B	108.9
C9—C10—H10	121	C29—C36—H36B	108.9
C12—C11—C10	123.6 (3)	H36A—C36—H36B	107.7
C12—C11—N2	119.8 (3)	C29—C37—C38	111.6 (3)
C10—C11—N2	116.6 (3)	C29—C37—H37A	109.3
C11—C12—C13	117.6 (3)	C38—C37—H37A	109.3
C11—C12—H12	121.2	C29—C37—H37B	109.3
C13—C12—H12	121.2	C38—C37—H37B	109.3
C12—C13—C8	121.5 (3)	H37A—C37—H37B	108
C12—C13—H13A	119.3	C37—C38—H38A	109.5
C8—C13—H13A	119.3	C37—C38—H38B	109.5
O6—C14—O5	122.8 (3)	H38A—C38—H38B	109.5
O6—C14—C8	122.4 (3)	C37—C38—H38C	109.5
O5—C14—C8	114.6 (3)	H38A—C38—H38C	109.5
O7—N2—O8	124.6 (3)	H38B—C38—H38C	109.5
O7—N2—C11	118.9 (3)	C32—N5—C34	122.4 (3)
O8—N2—C11	116.5 (3)	C32—N5—H5A	112 (3)
C14—O5—H5	114 (3)	C34—N5—H5A	126 (3)
C20—C15—C16	118.1 (2)	C40—C39—C46	108.2 (3)
C20—C15—C21	119.6 (3)	C40—C39—C43	114.4 (3)
C16—C15—C21	122.2 (3)	C46—C39—C43	108.8 (3)
C17—C16—C15	120.6 (3)	C40—C39—C44	108.1 (2)
C17—C16—Cl3	116.9 (2)	C46—C39—C44	110.2 (3)
C15—C16—Cl3	122.5 (2)	C43—C39—C44	107.1 (2)
C18—C17—C16	118.6 (3)	O19—C40—C41	121.2 (3)
C18—C17—H17	120.7	O19—C40—C39	119.8 (3)
C16—C17—H17	120.7	C41—C40—C39	118.9 (3)
C19—C18—C17	123.3 (3)	C42—C41—C40	122.2 (3)
C19—C18—N3	119.3 (3)	C42—C41—H41	118.9
C17—C18—N3	117.3 (3)	C40—C41—H41	118.9
C18—C19—C20	117.2 (3)	C41—C42—N6	122.7 (3)
C18—C19—H19	121.4	C41—C42—H42	118.6
C20—C19—H19	121.4	N6—C42—H42	118.6
C19—C20—C15	122.1 (3)	O20—C43—N6	121.7 (3)
C19—C20—H20	118.9	O20—C43—C39	118.7 (3)
C15—C20—H20	118.9	N6—C43—C39	119.6 (2)
O10—C21—O9	123.4 (3)	C45—C44—C39	114.6 (3)
O10—C21—C15	122.2 (3)	C45—C44—H44A	108.6
O9—C21—C15	114.0 (2)	C39—C44—H44A	108.6
O11—N3—O12	123.6 (3)	C45—C44—H44B	108.6
O11—N3—C18	118.1 (3)	C39—C44—H44B	108.6
O12—N3—C18	118.3 (3)	H44A—C44—H44B	107.6
C21—O9—H9	108 (3)	C44—C45—H45A	109.5
C23—C22—C27	118.3 (3)	C44—C45—H45B	109.5
C23—C22—C28	122.6 (3)	H45A—C45—H45B	109.5
C27—C22—C28	119.0 (3)	C44—C45—H45C	109.5
C24—C23—C22	120.8 (3)	H45A—C45—H45C	109.5
C24—C23—Cl4	116.4 (2)	H45B—C45—H45C	109.5
C22—C23—Cl4	122.7 (2)	C47—C46—C39	113.2 (3)
C25—C24—C23	118.6 (3)	C47—C46—H46A	108.9
C25—C24—H24	120.7	C39—C46—H46A	108.9
C23—C24—H24	120.7	C47—C46—H46B	108.9
C24—C25—C26	123.2 (3)	C39—C46—H46B	108.9
C24—C25—N4	117.6 (3)	H46A—C46—H46B	107.8
C26—C25—N4	119.2 (3)	C46—C47—H47A	109.5
C25—C26—C27	117.6 (3)	C46—C47—H47B	109.5
C25—C26—H26	121.2	H47A—C47—H47B	109.5
C27—C26—H26	121.2	C46—C47—H47C	109.5
C26—C27—C22	121.4 (3)	H47A—C47—H47C	109.5
C26—C27—H27	119.3	H47B—C47—H47C	109.5
C22—C27—H27	119.3	C43—N6—C42	121.7 (3)
O14—C28—O13	122.7 (3)	C43—N6—H6A	123 (2)
O14—C28—C22	123.3 (3)	C42—N6—H6A	115 (2)
C6—C1—C2—C3	−0.5 (4)	C28—C22—C23—Cl4	4.1 (4)
C7—C1—C2—C3	177.5 (3)	C22—C23—C24—C25	0.9 (4)
C6—C1—C2—Cl1	177.8 (2)	Cl4—C23—C24—C25	178.7 (2)
C7—C1—C2—Cl1	−4.2 (4)	C23—C24—C25—C26	−0.6 (5)
C1—C2—C3—C4	−0.4 (4)	C23—C24—C25—N4	178.2 (3)
Cl1—C2—C3—C4	−178.8 (2)	C24—C25—C26—C27	−0.1 (5)
C2—C3—C4—C5	1.1 (4)	N4—C25—C26—C27	−178.8 (3)
C2—C3—C4—N1	−178.6 (3)	C25—C26—C27—C22	0.5 (5)
C3—C4—C5—C6	−0.9 (5)	C23—C22—C27—C26	−0.2 (4)
N1—C4—C5—C6	178.8 (3)	C28—C22—C27—C26	177.7 (3)
C4—C5—C6—C1	0.0 (4)	C23—C22—C28—O14	26.4 (5)
C2—C1—C6—C5	0.7 (4)	C27—C22—C28—O14	−151.4 (3)
C7—C1—C6—C5	−177.3 (3)	C23—C22—C28—O13	−157.7 (3)
C6—C1—C7—O2	160.2 (3)	C27—C22—C28—O13	24.5 (4)
C2—C1—C7—O2	−17.7 (5)	C24—C25—N4—O16	179.8 (3)
C6—C1—C7—O1	−16.1 (4)	C26—C25—N4—O16	−1.4 (5)
C2—C1—C7—O1	166.0 (3)	C24—C25—N4—O15	0.0 (5)
C5—C4—N1—O4	−179.0 (3)	C26—C25—N4—O15	178.8 (3)
C3—C4—N1—O4	0.7 (4)	C37—C29—C30—O17	−58.3 (4)
C5—C4—N1—O3	−0.4 (4)	C34—C29—C30—O17	−178.8 (3)
C3—C4—N1—O3	179.4 (3)	C36—C29—C30—O17	60.8 (3)
C13—C8—C9—C10	0.2 (4)	C37—C29—C30—C31	124.4 (3)
C14—C8—C9—C10	−177.5 (3)	C34—C29—C30—C31	3.9 (4)
C13—C8—C9—Cl2	−177.9 (2)	C36—C29—C30—C31	−116.6 (3)
C14—C8—C9—Cl2	4.3 (4)	O17—C30—C31—C32	−178.3 (3)
C8—C9—C10—C11	0.5 (4)	C29—C30—C31—C32	−1.0 (5)
Cl2—C9—C10—C11	178.7 (2)	C30—C31—C32—N5	1.1 (6)
C9—C10—C11—C12	−0.9 (5)	C37—C29—C34—O18	56.3 (4)
C9—C10—C11—N2	179.9 (3)	C30—C29—C34—O18	176.7 (3)
C10—C11—C12—C13	0.5 (5)	C36—C29—C34—O18	−62.8 (4)
N2—C11—C12—C13	179.7 (3)	C37—C29—C34—N5	−127.4 (3)
C11—C12—C13—C8	0.3 (5)	C30—C29—C34—N5	−7.0 (4)
C9—C8—C13—C12	−0.6 (4)	C36—C29—C34—N5	113.5 (3)
C14—C8—C13—C12	177.2 (3)	C37—C29—C36—C35	−176.7 (3)
C9—C8—C14—O6	32.9 (5)	C30—C29—C36—C35	65.4 (3)
C13—C8—C14—O6	−144.9 (3)	C34—C29—C36—C35	−58.8 (3)
C9—C8—C14—O5	−151.9 (3)	C30—C29—C37—C38	−62.2 (3)
C13—C8—C14—O5	30.4 (4)	C34—C29—C37—C38	61.9 (3)
C12—C11—N2—O7	−179.1 (3)	C36—C29—C37—C38	179.8 (3)
C10—C11—N2—O7	0.2 (5)	C31—C32—N5—C34	−4.6 (6)
C12—C11—N2—O8	2.7 (5)	O18—C34—N5—C32	−176.2 (4)
C10—C11—N2—O8	−178.0 (3)	C29—C34—N5—C32	7.6 (5)
C20—C15—C16—C17	0.2 (4)	C46—C39—C40—O19	−53.7 (4)
C21—C15—C16—C17	177.5 (3)	C43—C39—C40—O19	−175.2 (3)
C20—C15—C16—Cl3	177.6 (2)	C44—C39—C40—O19	65.6 (4)
C21—C15—C16—Cl3	−5.1 (4)	C46—C39—C40—C41	129.0 (3)
C15—C16—C17—C18	−1.5 (4)	C43—C39—C40—C41	7.5 (4)
Cl3—C16—C17—C18	−179.0 (2)	C44—C39—C40—C41	−111.7 (3)
C16—C17—C18—C19	1.7 (4)	O19—C40—C41—C42	177.1 (3)
C16—C17—C18—N3	−178.6 (2)	C39—C40—C41—C42	−5.7 (5)
C17—C18—C19—C20	−0.6 (4)	C40—C41—C42—N6	0.9 (5)
N3—C18—C19—C20	179.7 (2)	C40—C39—C43—O20	175.9 (3)
C18—C19—C20—C15	−0.8 (4)	C46—C39—C43—O20	54.8 (4)
C16—C15—C20—C19	0.9 (4)	C44—C39—C43—O20	−64.3 (3)
C21—C15—C20—C19	−176.4 (3)	C40—C39—C43—N6	−5.2 (4)
C20—C15—C21—O10	142.7 (3)	C46—C39—C43—N6	−126.3 (3)
C16—C15—C21—O10	−34.5 (4)	C44—C39—C43—N6	114.6 (3)
C20—C15—C21—O9	−30.9 (4)	C40—C39—C44—C45	59.8 (3)
C16—C15—C21—O9	151.8 (3)	C46—C39—C44—C45	177.8 (3)
C19—C18—N3—O11	−4.3 (4)	C43—C39—C44—C45	−63.9 (3)
C17—C18—N3—O11	176.0 (3)	C40—C39—C46—C47	−60.4 (4)
C19—C18—N3—O12	175.9 (3)	C43—C39—C46—C47	64.4 (4)
C17—C18—N3—O12	−3.8 (4)	C44—C39—C46—C47	−178.5 (3)
C27—C22—C23—C24	−0.5 (4)	O20—C43—N6—C42	179.7 (3)
C28—C22—C23—C24	−178.3 (3)	C39—C43—N6—C42	0.8 (5)
C27—C22—C23—Cl4	−178.1 (2)	C41—C42—N6—C43	1.7 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O17	0.75 (5)	1.90 (5)	2.643 (3)	170 (6)
C31—H31···O2	0.95	2.08	2.998 (4)	161
O5—H5···O19	1.04 (6)	1.57 (6)	2.613 (3)	176 (5)
C41—H41···O6	0.95	2.01	2.926 (4)	162
O9—H9···O18	0.90 (5)	1.77 (5)	2.664 (3)	171 (5)
O13—H13···O20	0.84 (4)	1.80 (5)	2.615 (3)	163 (4)
N5—H5A···O10	1.02 (4)	2.03 (4)	2.933 (4)	147 (4)
N6—H6A···O14	1.08 (5)	1.96 (4)	2.964 (4)	154 (4)

2-Chloro-4-nitrobenzoic acid–2-oxopyrrolidine (1/1) (III)

Crystal data

C7H4ClNO4·C4H7NO	F(000) = 592
Mr = 286.67	Dx = 1.536 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 676 reflections
a = 8.2013 (18) Å	θ = 2.5–25.5°
b = 5.8069 (14) Å	µ = 0.33 mm^−1
c = 26.043 (5) Å	T = 173 K
β = 91.355 (6)°	Plate, colourless
V = 1239.9 (5) Å^3	0.48 × 0.28 × 0.08 mm
Z = 4

Data collection

Bruker D8 Venture Photon CCD area detector diffractometer	Rint = 0.050
Graphite monochromator	θmax = 25.5°, θmin = 1.6°
ω scans	h = −9→6
2378 measured reflections	k = −2→7
1933 independent reflections	l = −30→17
1425 reflections with I > 2σ(I)

Refinement

Refinement on F^2	0 constraints
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) = 0.089	w = 1/[σ^2(Fo^2) + (0.0344P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.96	(Δ/σ)max = 0.001
1933 reflections	Δρmax = 0.17 e Å^−3
177 parameters	Δρmin = −0.21 e Å^−3
0 restraints

Special details

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

Refinement. AFIX 147 was used for OH group.

Reflections listed below were removed as they showed a large discrepency between calculated and measured intensities

(1 0 12) (-1 2 14) (0 2 19) (-5 4 17) (1 2 25) (2 0 22) (0 3 25) (-4 3 14) (-4 4 19) (-1 2 13) (0 1 9)

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

	x	y	z	Uiso*/Ueq
C1	0.2206 (3)	0.9284 (4)	0.51362 (9)	0.0284 (5)
C2	0.3026 (3)	1.1370 (4)	0.50755 (9)	0.0295 (6)
C3	0.3489 (3)	1.2109 (4)	0.45979 (9)	0.0323 (6)
H3	0.402881	1.354323	0.455787	0.039*
C4	0.3150 (3)	1.0716 (5)	0.41784 (9)	0.0342 (6)
C5	0.2341 (3)	0.8625 (4)	0.42183 (9)	0.0353 (6)
H5	0.212809	0.769064	0.392493	0.042*
C6	0.1858 (3)	0.7955 (4)	0.47000 (9)	0.0330 (6)
H6	0.12732	0.655348	0.473584	0.04*
C7	0.1766 (3)	0.8383 (4)	0.56538 (9)	0.0304 (6)
N1	0.3659 (3)	1.1507 (5)	0.36683 (8)	0.0443 (6)
O1	0.04156 (19)	0.7153 (3)	0.56398 (6)	0.0380 (5)
H1	0.026377	0.657709	0.593059	0.057*
O2	0.2599 (2)	0.8693 (3)	0.60410 (6)	0.0423 (5)
O3	0.3471 (3)	1.0164 (4)	0.33098 (7)	0.0648 (6)
O4	0.4227 (2)	1.3434 (4)	0.36279 (7)	0.0535 (6)
Cl1	0.34666 (8)	1.31801 (11)	0.55895 (2)	0.0385 (2)
C8	0.0820 (3)	0.4101 (5)	0.67321 (9)	0.0379 (6)
C9	0.3410 (4)	0.3208 (6)	0.70741 (11)	0.0563 (8)
H9A	0.401972	0.400962	0.735379	0.068*
H9B	0.419713	0.246529	0.684382	0.068*
C10	0.2241 (4)	0.1457 (6)	0.72880 (11)	0.0621 (9)
H10A	0.213874	0.1666	0.766314	0.074*
H10B	0.263032	−0.012671	0.722194	0.074*
C11	0.0615 (4)	0.1877 (5)	0.70137 (11)	0.0492 (7)
H11A	0.035645	0.060927	0.677095	0.059*
H11B	−0.027255	0.199758	0.726342	0.059*
O5	−0.0269 (2)	0.5114 (3)	0.64749 (7)	0.0471 (5)
N2	0.2352 (3)	0.4800 (4)	0.67907 (8)	0.0425 (6)
H2	0.272 (4)	0.599 (6)	0.6621 (11)	0.065 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0227 (12)	0.0294 (13)	0.0331 (13)	0.0033 (11)	0.0032 (11)	0.0018 (11)
C2	0.0247 (13)	0.0328 (14)	0.0310 (14)	0.0033 (11)	0.0010 (11)	0.0005 (11)
C3	0.0237 (13)	0.0331 (14)	0.0403 (15)	0.0007 (11)	0.0028 (12)	0.0017 (11)
C4	0.0268 (13)	0.0424 (16)	0.0337 (14)	0.0071 (12)	0.0051 (12)	0.0082 (12)
C5	0.0363 (15)	0.0378 (16)	0.0319 (14)	0.0052 (12)	0.0013 (12)	−0.0028 (12)
C6	0.0305 (14)	0.0291 (14)	0.0393 (15)	−0.0008 (11)	0.0008 (12)	−0.0021 (11)
C7	0.0270 (13)	0.0273 (13)	0.0373 (15)	0.0026 (11)	0.0073 (12)	0.0007 (11)
N1	0.0391 (14)	0.0563 (17)	0.0376 (14)	0.0064 (12)	0.0052 (11)	0.0087 (12)
O1	0.0269 (9)	0.0439 (11)	0.0434 (11)	−0.0033 (8)	0.0063 (9)	0.0093 (9)
O2	0.0479 (11)	0.0453 (12)	0.0336 (9)	−0.0116 (9)	−0.0023 (9)	0.0035 (9)
O3	0.0872 (17)	0.0695 (16)	0.0382 (11)	0.0025 (13)	0.0130 (12)	−0.0008 (11)
O4	0.0480 (12)	0.0635 (15)	0.0493 (12)	−0.0080 (11)	0.0056 (10)	0.0192 (11)
Cl1	0.0431 (4)	0.0317 (4)	0.0406 (4)	−0.0043 (3)	0.0004 (3)	−0.0037 (3)
C8	0.0466 (17)	0.0402 (16)	0.0275 (14)	−0.0051 (14)	0.0137 (13)	−0.0041 (12)
C9	0.0530 (19)	0.075 (2)	0.0407 (17)	0.0013 (18)	0.0089 (15)	0.0104 (16)
C10	0.086 (2)	0.054 (2)	0.0456 (17)	−0.0119 (18)	−0.0123 (17)	0.0047 (15)
C11	0.0560 (18)	0.0452 (17)	0.0471 (17)	−0.0067 (16)	0.0174 (15)	0.0083 (14)
O5	0.0409 (11)	0.0556 (13)	0.0454 (11)	−0.0050 (10)	0.0120 (9)	0.0097 (10)
N2	0.0447 (15)	0.0475 (15)	0.0356 (13)	−0.0093 (12)	0.0064 (11)	−0.0005 (11)

Geometric parameters (Å, º)

C1—C2	1.396 (3)	N1—O3	1.223 (3)
C1—C6	1.398 (3)	O1—H1	0.84
C1—C7	1.498 (3)	C8—O5	1.250 (3)
C2—C3	1.377 (3)	C8—N2	1.326 (3)
C2—Cl1	1.733 (2)	C8—C11	1.496 (4)
C3—C4	1.382 (3)	C9—N2	1.457 (4)
C3—H3	0.95	C9—C10	1.513 (4)
C4—C5	1.389 (4)	C9—H9A	0.99
C4—N1	1.475 (3)	C9—H9B	0.99
C5—C6	1.381 (4)	C10—C11	1.518 (4)
C5—H5	0.95	C10—H10A	0.99
C6—H6	0.95	C10—H10B	0.99
C7—O2	1.218 (3)	C11—H11A	0.99
C7—O1	1.317 (3)	C11—H11B	0.99
N1—O4	1.218 (3)	N2—H2	0.88 (3)
C2—C1—C6	118.5 (2)	O5—C8—N2	125.5 (2)
C2—C1—C7	122.2 (2)	O5—C8—C11	125.6 (3)
C6—C1—C7	119.3 (2)	N2—C8—C11	108.9 (2)
C3—C2—C1	121.1 (2)	N2—C9—C10	103.8 (2)
C3—C2—Cl1	116.83 (19)	N2—C9—H9A	111
C1—C2—Cl1	122.05 (19)	C10—C9—H9A	111
C2—C3—C4	118.5 (2)	N2—C9—H9B	111
C2—C3—H3	120.8	C10—C9—H9B	111
C4—C3—H3	120.8	H9A—C9—H9B	109
C3—C4—C5	122.7 (2)	C9—C10—C11	106.0 (2)
C3—C4—N1	118.3 (2)	C9—C10—H10A	110.5
C5—C4—N1	119.0 (2)	C11—C10—H10A	110.5
C6—C5—C4	117.6 (2)	C9—C10—H10B	110.5
C6—C5—H5	121.2	C11—C10—H10B	110.5
C4—C5—H5	121.2	H10A—C10—H10B	108.7
C5—C6—C1	121.7 (2)	C8—C11—C10	105.2 (2)
C5—C6—H6	119.2	C8—C11—H11A	110.7
C1—C6—H6	119.2	C10—C11—H11A	110.7
O2—C7—O1	123.9 (2)	C8—C11—H11B	110.7
O2—C7—C1	123.4 (2)	C10—C11—H11B	110.7
O1—C7—C1	112.6 (2)	H11A—C11—H11B	108.8
O4—N1—O3	124.1 (2)	C8—N2—C9	114.6 (3)
O4—N1—C4	118.7 (2)	C8—N2—H2	121 (2)
O3—N1—C4	117.1 (2)	C9—N2—H2	123 (2)
C7—O1—H1	109.5
C6—C1—C2—C3	−0.2 (3)	C6—C1—C7—O2	143.5 (2)
C7—C1—C2—C3	176.8 (2)	C2—C1—C7—O1	148.9 (2)
C6—C1—C2—Cl1	178.24 (17)	C6—C1—C7—O1	−34.2 (3)
C7—C1—C2—Cl1	−4.9 (3)	C3—C4—N1—O4	−6.3 (3)
C1—C2—C3—C4	−1.2 (3)	C5—C4—N1—O4	173.1 (2)
Cl1—C2—C3—C4	−179.67 (18)	C3—C4—N1—O3	174.0 (2)
C2—C3—C4—C5	1.1 (4)	C5—C4—N1—O3	−6.6 (3)
C2—C3—C4—N1	−179.6 (2)	N2—C9—C10—C11	12.2 (3)
C3—C4—C5—C6	0.4 (4)	O5—C8—C11—C10	−176.7 (3)
N1—C4—C5—C6	−178.9 (2)	N2—C8—C11—C10	4.6 (3)
C4—C5—C6—C1	−1.9 (4)	C9—C10—C11—C8	−10.5 (3)
C2—C1—C6—C5	1.7 (3)	O5—C8—N2—C9	−175.1 (2)
C7—C1—C6—C5	−175.3 (2)	C11—C8—N2—C9	3.6 (3)
C2—C1—C7—O2	−33.4 (4)	C10—C9—N2—C8	−10.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O5	0.84	1.72	2.550 (2)	171
N2—H2···O2	0.88 (3)	2.18 (3)	2.997 (3)	155 (3)

2-Carboxypiperidinium 2-chloro-4-nitrobenzoate (IV)

Crystal data

C6H12NO2^+·C7H3ClNO4^−	F(000) = 688
Mr = 330.72	Dx = 1.468 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5383 reflections
a = 13.4355 (7) Å	θ = 2.5–28.1°
b = 10.3411 (6) Å	µ = 0.29 mm^−1
c = 10.8206 (6) Å	T = 173 K
β = 95.479 (2)°	Block, yellow
V = 1496.52 (14) Å^3	0.57 × 0.46 × 0.10 mm
Z = 4

Data collection

Bruker D8 Venture Photon CCD area detector diffractometer	2795 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.074
ω scans	θmax = 28.0°, θmin = 2.7°
Absorption correction: integration (XPREP; Bruker, 2016)	h = −17→17
Tmin = 0.89, Tmax = 0.975	k = −13→13
19868 measured reflections	l = −14→14
3616 independent reflections

Refinement

Refinement on F^2	0 constraints
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) = 0.106	w = 1/[σ^2(Fo^2) + (0.0572P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
3616 reflections	Δρmax = 0.33 e Å^−3
211 parameters	Δρmin = −0.25 e Å^−3
0 restraints

Special details

Experimental. Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 2016)

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

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

	x	y	z	Uiso*/Ueq
C1	0.24647 (10)	0.40338 (13)	0.24877 (13)	0.0250 (3)
C2	0.14877 (11)	0.44707 (13)	0.21820 (13)	0.0250 (3)
C3	0.07435 (11)	0.42564 (14)	0.29488 (14)	0.0278 (3)
H3	0.007947	0.454472	0.27244	0.033*
C4	0.09881 (11)	0.36132 (14)	0.40493 (14)	0.0292 (3)
C5	0.19407 (12)	0.31641 (15)	0.44010 (15)	0.0335 (4)
H5	0.209052	0.27238	0.516673	0.04*
C6	0.26694 (11)	0.33746 (14)	0.36054 (14)	0.0308 (3)
H6A	0.332715	0.30616	0.382635	0.037*
C7	0.33137 (10)	0.42914 (14)	0.16905 (13)	0.0261 (3)
N1	0.01939 (10)	0.34146 (13)	0.48816 (14)	0.0372 (3)
O1	0.39000 (8)	0.33568 (10)	0.15427 (11)	0.0363 (3)
O2	0.33919 (9)	0.53867 (10)	0.12596 (11)	0.0368 (3)
O3	0.04292 (11)	0.29564 (15)	0.59018 (14)	0.0649 (4)
O4	−0.06565 (9)	0.37364 (12)	0.45151 (12)	0.0461 (3)
Cl1	0.11440 (3)	0.52691 (4)	0.08028 (3)	0.03972 (14)
C8	0.63469 (11)	0.40891 (14)	0.19751 (13)	0.0270 (3)
H8	0.613534	0.358657	0.269505	0.032*
C9	0.74709 (11)	0.39440 (15)	0.19369 (15)	0.0320 (3)
H9A	0.781861	0.42342	0.273672	0.038*
H9B	0.76942	0.449955	0.127123	0.038*
C10	0.77489 (12)	0.25419 (16)	0.16992 (15)	0.0376 (4)
H10A	0.847389	0.248388	0.16092	0.045*
H10B	0.76057	0.20034	0.241768	0.045*
C11	0.71644 (12)	0.20307 (15)	0.05332 (15)	0.0354 (4)
H11A	0.736649	0.25036	−0.019807	0.042*
H11B	0.732128	0.110393	0.042932	0.042*
C12	0.60514 (12)	0.21901 (14)	0.06018 (15)	0.0336 (3)
H12A	0.568481	0.188621	−0.018155	0.04*
H12B	0.58369	0.165965	0.129043	0.04*
C14	0.60560 (11)	0.54922 (14)	0.21123 (14)	0.0289 (3)
O5	0.56148 (8)	0.61059 (10)	0.12885 (11)	0.0368 (3)
O6	0.63789 (10)	0.59527 (12)	0.32072 (11)	0.0418 (3)
N2	0.58092 (10)	0.35835 (11)	0.08101 (12)	0.0250 (3)
H6	0.6262 (17)	0.689 (2)	0.322 (2)	0.071 (7)*
H2A	0.5147 (14)	0.3670 (16)	0.0849 (16)	0.034 (5)*
H2B	0.5993 (12)	0.4060 (16)	0.0165 (16)	0.031 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0249 (7)	0.0234 (6)	0.0277 (7)	−0.0010 (5)	0.0068 (6)	−0.0003 (6)
C2	0.0265 (7)	0.0260 (7)	0.0224 (7)	−0.0031 (5)	0.0024 (6)	0.0003 (5)
C3	0.0224 (7)	0.0288 (7)	0.0325 (8)	−0.0002 (6)	0.0043 (6)	−0.0004 (6)
C4	0.0296 (8)	0.0273 (7)	0.0326 (8)	0.0003 (6)	0.0131 (6)	0.0018 (6)
C5	0.0368 (9)	0.0323 (8)	0.0325 (8)	0.0074 (6)	0.0087 (7)	0.0102 (6)
C6	0.0270 (8)	0.0328 (7)	0.0334 (8)	0.0065 (6)	0.0066 (6)	0.0080 (6)
C7	0.0229 (7)	0.0302 (7)	0.0259 (7)	−0.0013 (6)	0.0048 (6)	0.0022 (6)
N1	0.0394 (8)	0.0312 (7)	0.0444 (8)	0.0033 (6)	0.0214 (6)	0.0073 (6)
O1	0.0317 (6)	0.0329 (6)	0.0470 (7)	0.0051 (5)	0.0180 (5)	0.0108 (5)
O2	0.0378 (6)	0.0315 (6)	0.0435 (7)	0.0006 (5)	0.0166 (5)	0.0095 (5)
O3	0.0618 (9)	0.0795 (10)	0.0595 (9)	0.0294 (8)	0.0372 (7)	0.0411 (8)
O4	0.0306 (6)	0.0557 (8)	0.0545 (8)	−0.0016 (5)	0.0175 (6)	0.0025 (6)
Cl1	0.0316 (2)	0.0586 (3)	0.0282 (2)	−0.00049 (17)	−0.00138 (15)	0.01214 (17)
C8	0.0282 (7)	0.0302 (7)	0.0229 (7)	0.0024 (6)	0.0040 (6)	0.0014 (6)
C9	0.0265 (8)	0.0386 (8)	0.0308 (8)	0.0041 (6)	0.0021 (6)	0.0025 (6)
C10	0.0345 (8)	0.0412 (9)	0.0379 (9)	0.0140 (7)	0.0073 (7)	0.0079 (7)
C11	0.0395 (9)	0.0304 (8)	0.0380 (9)	0.0097 (7)	0.0132 (7)	0.0045 (7)
C12	0.0395 (9)	0.0243 (7)	0.0383 (9)	0.0012 (6)	0.0102 (7)	0.0004 (6)
C14	0.0233 (7)	0.0322 (8)	0.0316 (8)	−0.0008 (6)	0.0043 (6)	−0.0024 (6)
O5	0.0363 (6)	0.0295 (5)	0.0424 (7)	0.0010 (5)	−0.0078 (5)	−0.0013 (5)
O6	0.0545 (8)	0.0383 (6)	0.0316 (6)	0.0058 (6)	−0.0012 (5)	−0.0077 (5)
N2	0.0236 (6)	0.0254 (6)	0.0267 (6)	0.0008 (5)	0.0053 (5)	0.0009 (5)

Geometric parameters (Å, º)

C1—C6	1.393 (2)	C8—H8	1
C1—C2	1.398 (2)	C9—C10	1.525 (2)
C1—C7	1.5180 (19)	C9—H9A	0.99
C2—C3	1.377 (2)	C9—H9B	0.99
C2—Cl1	1.7292 (14)	C10—C11	1.516 (2)
C3—C4	1.376 (2)	C10—H10A	0.99
C3—H3	0.95	C10—H10B	0.99
C4—C5	1.381 (2)	C11—C12	1.513 (2)
C4—N1	1.4749 (19)	C11—H11A	0.99
C5—C6	1.381 (2)	C11—H11B	0.99
C5—H5	0.95	C12—N2	1.4990 (18)
C6—H6A	0.95	C12—H12A	0.99
C7—O2	1.2331 (17)	C12—H12B	0.99
C7—O1	1.2665 (18)	C14—O5	1.2032 (18)
N1—O3	1.2151 (19)	C14—O6	1.3116 (18)
N1—O4	1.2193 (18)	O6—H6	0.98 (2)
C8—N2	1.4868 (18)	N2—H2A	0.900 (18)
C8—C14	1.514 (2)	N2—H2B	0.908 (18)
C8—C9	1.522 (2)
C6—C1—C2	117.83 (13)	C10—C9—H9A	109.4
C6—C1—C7	118.85 (13)	C8—C9—H9B	109.4
C2—C1—C7	123.26 (13)	C10—C9—H9B	109.4
C3—C2—C1	121.66 (13)	H9A—C9—H9B	108
C3—C2—Cl1	116.59 (11)	C11—C10—C9	110.86 (12)
C1—C2—Cl1	121.73 (11)	C11—C10—H10A	109.5
C4—C3—C2	118.18 (14)	C9—C10—H10A	109.5
C4—C3—H3	120.9	C11—C10—H10B	109.5
C2—C3—H3	120.9	C9—C10—H10B	109.5
C3—C4—C5	122.66 (14)	H10A—C10—H10B	108.1
C3—C4—N1	117.96 (13)	C12—C11—C10	110.91 (13)
C5—C4—N1	119.38 (14)	C12—C11—H11A	109.5
C4—C5—C6	117.96 (14)	C10—C11—H11A	109.5
C4—C5—H5	121	C12—C11—H11B	109.5
C6—C5—H5	121	C10—C11—H11B	109.5
C5—C6—C1	121.70 (14)	H11A—C11—H11B	108
C5—C6—H6A	119.2	N2—C12—C11	109.98 (12)
C1—C6—H6A	119.2	N2—C12—H12A	109.7
O2—C7—O1	125.22 (13)	C11—C12—H12A	109.7
O2—C7—C1	118.15 (13)	N2—C12—H12B	109.7
O1—C7—C1	116.61 (12)	C11—C12—H12B	109.7
O3—N1—O4	123.80 (14)	H12A—C12—H12B	108.2
O3—N1—C4	117.93 (14)	O5—C14—O6	125.08 (14)
O4—N1—C4	118.26 (14)	O5—C14—C8	123.12 (13)
N2—C8—C14	108.13 (11)	O6—C14—C8	111.74 (13)
N2—C8—C9	110.20 (12)	C14—O6—H6	109.1 (13)
C14—C8—C9	111.30 (12)	C8—N2—C12	111.76 (11)
N2—C8—H8	109.1	C8—N2—H2A	109.2 (11)
C14—C8—H8	109.1	C12—N2—H2A	109.4 (10)
C9—C8—H8	109.1	C8—N2—H2B	108.4 (10)
C8—C9—C10	110.97 (13)	C12—N2—H2B	109.1 (10)
C8—C9—H9A	109.4	H2A—N2—H2B	108.9 (15)
C6—C1—C2—C3	−0.4 (2)	C3—C4—N1—O3	−173.24 (15)
C7—C1—C2—C3	−177.76 (13)	C5—C4—N1—O3	6.2 (2)
C6—C1—C2—Cl1	−178.59 (11)	C3—C4—N1—O4	5.7 (2)
C7—C1—C2—Cl1	4.0 (2)	C5—C4—N1—O4	−174.89 (14)
C1—C2—C3—C4	1.1 (2)	N2—C8—C9—C10	−55.70 (16)
Cl1—C2—C3—C4	179.42 (11)	C14—C8—C9—C10	−175.65 (12)
C2—C3—C4—C5	−0.9 (2)	C8—C9—C10—C11	54.49 (17)
C2—C3—C4—N1	178.52 (13)	C9—C10—C11—C12	−55.22 (17)
C3—C4—C5—C6	−0.1 (2)	C10—C11—C12—N2	56.88 (17)
N1—C4—C5—C6	−179.49 (13)	N2—C8—C14—O5	−12.23 (19)
C4—C5—C6—C1	0.9 (2)	C9—C8—C14—O5	108.94 (16)
C2—C1—C6—C5	−0.7 (2)	N2—C8—C14—O6	170.35 (12)
C7—C1—C6—C5	176.84 (14)	C9—C8—C14—O6	−68.47 (16)
C6—C1—C7—O2	−133.68 (15)	C14—C8—N2—C12	−179.76 (12)
C2—C1—C7—O2	43.7 (2)	C9—C8—N2—C12	58.38 (15)
C6—C1—C7—O1	45.00 (19)	C11—C12—N2—C8	−59.03 (16)
C2—C1—C7—O1	−137.64 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.900 (18)	1.927 (19)	2.7662 (17)	154 (2)
N2—H2B···O2^i	0.908 (18)	1.906 (18)	2.7859 (17)	163 (2)
O6—H6···O1^ii	0.98 (2)	1.56 (2)	2.5325 (16)	171 (2)

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

(2-Hydroxyethyl)ammonium 2-chloro-4-nitrobenzoate (V)

Crystal data

C2H8NO^+·C7H3ClNO4^−	F(000) = 544
Mr = 262.65	Dx = 1.626 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5804 reflections
a = 4.9315 (2) Å	θ = 2.2–28.3°
b = 20.8047 (8) Å	µ = 0.37 mm^−1
c = 10.7325 (4) Å	T = 173 K
β = 103.022 (2)°	Needle, yellow
V = 1072.82 (7) Å^3	0.70 × 0.14 × 0.13 mm
Z = 4

Data collection

Bruker D8 Venture Photon CCD area detector diffractometer	2279 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.070
ω scans	θmax = 28.0°, θmin = 2.0°
Absorption correction: integration (XPREP; Bruker, 2016)	h = −6→6
Tmin = 0.854, Tmax = 0.971	k = −27→25
10481 measured reflections	l = −14→14
2578 independent reflections

Refinement

Refinement on F^2	0 constraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.090	w = 1/[σ^2(Fo^2) + (0.0433P)^2 + 0.2218P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.001
2578 reflections	Δρmax = 0.45 e Å^−3
170 parameters	Δρmin = −0.30 e Å^−3
0 restraints

Special details

Experimental. Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 2016)

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

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

	x	y	z	Uiso*/Ueq
C1	0.6913 (2)	0.59701 (6)	0.82604 (11)	0.0155 (2)
C2	0.5742 (3)	0.65654 (6)	0.78341 (11)	0.0166 (2)
C3	0.4014 (3)	0.68919 (6)	0.84749 (11)	0.0181 (3)
H3	0.317545	0.728848	0.816107	0.022*
C4	0.3552 (2)	0.66209 (6)	0.95866 (11)	0.0171 (3)
C5	0.4778 (3)	0.60526 (6)	1.00888 (11)	0.0193 (3)
H5A	0.448166	0.588683	1.087216	0.023*
C6	0.6453 (3)	0.57317 (6)	0.94152 (11)	0.0182 (3)
H6	0.731113	0.533967	0.974555	0.022*
C7	0.8565 (2)	0.55514 (6)	0.75450 (11)	0.0161 (2)
N1	0.1713 (2)	0.69620 (5)	1.02671 (11)	0.0202 (2)
O1	0.79411 (17)	0.55801 (4)	0.63250 (8)	0.0175 (2)
O2	1.0356 (2)	0.51933 (5)	0.81899 (9)	0.0259 (2)
O3	0.0332 (2)	0.74120 (5)	0.97276 (10)	0.0279 (2)
O4	0.1656 (2)	0.67791 (6)	1.13504 (10)	0.0335 (3)
Cl1	0.66077 (7)	0.69606 (2)	0.65485 (3)	0.02359 (11)
C8	0.1436 (2)	0.61112 (6)	0.38808 (12)	0.0184 (3)
H8A	0.21835	0.597784	0.313834	0.022*
H8B	0.220188	0.654069	0.41604	0.022*
C9	−0.1717 (2)	0.61478 (6)	0.34897 (12)	0.0192 (3)
H9A	−0.242137	0.63687	0.417044	0.023*
H9B	−0.226078	0.640738	0.269965	0.023*
N2	0.2313 (2)	0.56410 (5)	0.49433 (10)	0.0168 (2)
O5	−0.29747 (19)	0.55317 (5)	0.32720 (9)	0.0211 (2)
H2A	0.413 (4)	0.5710 (9)	0.5378 (17)	0.034 (5)*
H2B	0.220 (3)	0.5246 (9)	0.4603 (16)	0.026 (4)*
H2C	0.120 (4)	0.5666 (8)	0.5506 (17)	0.028 (4)*
H5	−0.223 (4)	0.5322 (10)	0.280 (2)	0.047 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0162 (5)	0.0179 (6)	0.0126 (5)	−0.0006 (4)	0.0034 (4)	−0.0017 (4)
C2	0.0203 (6)	0.0176 (6)	0.0128 (5)	−0.0014 (4)	0.0054 (4)	0.0007 (4)
C3	0.0217 (6)	0.0157 (6)	0.0173 (6)	0.0009 (5)	0.0053 (5)	0.0005 (4)
C4	0.0183 (5)	0.0190 (6)	0.0156 (5)	−0.0017 (5)	0.0074 (4)	−0.0042 (4)
C5	0.0253 (6)	0.0209 (6)	0.0130 (5)	−0.0015 (5)	0.0069 (5)	0.0005 (4)
C6	0.0228 (6)	0.0169 (6)	0.0151 (5)	0.0018 (5)	0.0045 (5)	0.0013 (4)
C7	0.0159 (5)	0.0174 (6)	0.0151 (5)	−0.0010 (4)	0.0041 (4)	−0.0024 (4)
N1	0.0232 (5)	0.0195 (6)	0.0204 (5)	−0.0030 (4)	0.0104 (4)	−0.0042 (4)
O1	0.0195 (4)	0.0209 (5)	0.0128 (4)	0.0024 (3)	0.0051 (3)	−0.0010 (3)
O2	0.0281 (5)	0.0306 (5)	0.0173 (4)	0.0129 (4)	0.0015 (4)	−0.0018 (4)
O3	0.0310 (5)	0.0250 (5)	0.0302 (5)	0.0078 (4)	0.0122 (4)	−0.0018 (4)
O4	0.0512 (7)	0.0317 (6)	0.0262 (5)	0.0041 (5)	0.0266 (5)	0.0029 (4)
Cl1	0.0354 (2)	0.02037 (19)	0.01907 (16)	0.00404 (12)	0.01472 (13)	0.00562 (11)
C8	0.0183 (5)	0.0183 (6)	0.0194 (6)	0.0016 (5)	0.0063 (5)	0.0040 (5)
C9	0.0184 (6)	0.0194 (6)	0.0200 (6)	0.0032 (5)	0.0049 (5)	0.0013 (5)
N2	0.0159 (5)	0.0178 (6)	0.0172 (5)	0.0013 (4)	0.0044 (4)	0.0001 (4)
O5	0.0187 (4)	0.0223 (5)	0.0237 (5)	0.0004 (4)	0.0074 (4)	−0.0029 (4)

Geometric parameters (Å, º)

C1—C2	1.3990 (17)	N1—O3	1.2238 (15)
C1—C6	1.4001 (17)	N1—O4	1.2298 (15)
C1—C7	1.5147 (17)	C8—N2	1.4907 (15)
C2—C3	1.3873 (19)	C8—C9	1.5182 (17)
C2—Cl1	1.7400 (13)	C8—H8A	0.99
C3—C4	1.3841 (18)	C8—H8B	0.99
C3—H3	0.95	C9—O5	1.4204 (16)
C4—C5	1.3808 (18)	C9—H9A	0.99
C4—N1	1.4689 (17)	C9—H9B	0.99
C5—C6	1.3855 (18)	N2—H2A	0.922 (19)
C5—H5A	0.95	N2—H2B	0.897 (18)
C6—H6	0.95	N2—H2C	0.904 (19)
C7—O2	1.2405 (15)	O5—H5	0.82 (2)
C7—O1	1.2771 (14)
C2—C1—C6	117.77 (11)	O3—N1—C4	118.32 (11)
C2—C1—C7	124.94 (11)	O4—N1—C4	117.95 (11)
C6—C1—C7	117.26 (11)	N2—C8—C9	110.30 (10)
C3—C2—C1	121.71 (11)	N2—C8—H8A	109.6
C3—C2—Cl1	116.72 (9)	C9—C8—H8A	109.6
C1—C2—Cl1	121.38 (10)	N2—C8—H8B	109.6
C4—C3—C2	117.82 (11)	C9—C8—H8B	109.6
C4—C3—H3	121.1	H8A—C8—H8B	108.1
C2—C3—H3	121.1	O5—C9—C8	112.48 (10)
C5—C4—C3	122.87 (12)	O5—C9—H9A	109.1
C5—C4—N1	118.98 (11)	C8—C9—H9A	109.1
C3—C4—N1	118.14 (11)	O5—C9—H9B	109.1
C4—C5—C6	117.96 (11)	C8—C9—H9B	109.1
C4—C5—H5A	121	H9A—C9—H9B	107.8
C6—C5—H5A	121	C8—N2—H2A	111.4 (11)
C5—C6—C1	121.71 (11)	C8—N2—H2B	108.1 (11)
C5—C6—H6	119.1	H2A—N2—H2B	108.4 (16)
C1—C6—H6	119.1	C8—N2—H2C	110.9 (11)
O2—C7—O1	125.23 (11)	H2A—N2—H2C	108.5 (16)
O2—C7—C1	117.34 (10)	H2B—N2—H2C	109.4 (15)
O1—C7—C1	117.39 (10)	C9—O5—H5	110.0 (15)
O3—N1—O4	123.72 (12)
C6—C1—C2—C3	−4.58 (18)	C2—C1—C6—C5	3.37 (18)
C7—C1—C2—C3	173.25 (11)	C7—C1—C6—C5	−174.64 (11)
C6—C1—C2—Cl1	170.21 (9)	C2—C1—C7—O2	151.61 (12)
C7—C1—C2—Cl1	−11.96 (16)	C6—C1—C7—O2	−30.55 (16)
C1—C2—C3—C4	2.28 (18)	C2—C1—C7—O1	−30.61 (17)
Cl1—C2—C3—C4	−172.74 (9)	C6—C1—C7—O1	147.24 (11)
C2—C3—C4—C5	1.41 (19)	C5—C4—N1—O3	−169.72 (11)
C2—C3—C4—N1	−179.69 (11)	C3—C4—N1—O3	11.33 (17)
C3—C4—C5—C6	−2.57 (19)	C5—C4—N1—O4	10.44 (18)
N1—C4—C5—C6	178.54 (11)	C3—C4—N1—O4	−168.50 (12)
C4—C5—C6—C1	0.08 (19)	N2—C8—C9—O5	−49.89 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.922 (19)	1.945 (19)	2.8396 (13)	163 (2)
N2—H2B···O1^i	0.897 (18)	1.979 (19)	2.8714 (15)	173 (2)
N2—H2C···O1^ii	0.904 (19)	2.006 (19)	2.8818 (15)	163 (2)
O5—H5···O2^i	0.82 (2)	1.89 (2)	2.7052 (14)	176 (2)

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