Two-dimensional networks in 2-methyl­anilinium picrate and 2,5-dichloro­anilinium picrate

Both the title mol­ecular adducts of 2-methyl­aniline or 2,5-dichloro­aniline with picric acid are 1:1 organic salts, namely 2-methyl­anilinium picrate, C₇H₁₀N⁺·C₆H₂N₃O₇⁻, (I), and 2,5-dichloro­anilinium picrate, C₆H₆Cl₂N⁺·C₆H₂N₃O₇⁻, (II). In both structures, the phenoxide O atoms accept two N—H hydrogen bonds in a bifurcated acceptor fashion, which link the component ions by N—H...O hydrogen bonds into continuous two-dimensional zigzag layers, running parallel to the (100) plane in (I) and the (010) plane in (II). A π–π inter­action is observed between symmetry-related anilinium cations in (I), while in (II), Cl...O_nitro and Cl...Cl inter­actions are observed. This study indicates that a substitution on aniline can exert a pivotal influence on the construction of its supra­molecular structure.

Computing details

For both compounds, data collection: SMART (Bruker, 2001); cell refinement: SMART (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

(I) 2-methylanilinium picrate

Crystal data

C7H10N^+·C6H2N3O7^−	F(000) = 696
Mr = 336.27	Dx = 1.540 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1547 reflections
a = 11.6501 (3) Å	θ = 2.2–25.3°
b = 16.4813 (4) Å	µ = 0.13 mm^−1
c = 7.5754 (2) Å	T = 123 K
β = 94.269 (2)°	Block, yellow
V = 1450.51 (6) Å^3	0.16 × 0.12 × 0.10 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2852 independent reflections
Radiation source: fine focus sealed Siemens Mo tube	2267 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
0.3° wide ω exposures scans	θmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	h = −14→14
Tmin = 0.970, Tmax = 0.987	k = −20→15
9575 measured reflections	l = −9→9

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.172	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[s^2(Fo^2) + (0.0785P)^2 + 1.5344P] where P = (Fo^2 + 2Fc^2)/3
2852 reflections	(Δ/σ)max < 0.001
227 parameters	Δρmax = 0.51 e Å^−3
0 restraints	Δρmin = −0.31 e Å^−3

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. Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > σ(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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
C1	0.5876 (2)	0.24890 (17)	0.4978 (4)	0.0124 (6)
C2	0.5032 (2)	0.19308 (18)	0.5370 (4)	0.0140 (6)
C3	0.3990 (2)	0.22580 (19)	0.5852 (4)	0.0178 (7)
H3	0.3383	0.1902	0.6109	0.021*
C4	0.3824 (2)	0.30889 (19)	0.5964 (4)	0.0193 (7)
H4	0.3115	0.3292	0.6323	0.023*
C5	0.4686 (2)	0.36292 (18)	0.5556 (4)	0.0181 (7)
H5	0.4565	0.4198	0.5622	0.022*
C6	0.5728 (2)	0.33255 (18)	0.5049 (4)	0.0168 (6)
H6	0.6325	0.3683	0.4757	0.020*
C7	0.9026 (2)	0.12291 (17)	0.7829 (4)	0.0129 (6)
C8	1.0156 (2)	0.15881 (17)	0.8107 (4)	0.0144 (6)
C9	1.1170 (2)	0.11606 (18)	0.8051 (4)	0.0146 (6)
H9	1.1891	0.1430	0.8214	0.018*
C10	1.1120 (2)	0.03303 (18)	0.7752 (4)	0.0151 (6)
C11	1.0069 (2)	−0.00764 (17)	0.7478 (4)	0.0139 (6)
H11	1.0042	−0.0642	0.7243	0.017*
C12	0.9083 (2)	0.03654 (17)	0.7560 (4)	0.0128 (6)
C13	0.5217 (2)	0.10246 (18)	0.5298 (4)	0.0183 (7)
H13A	0.5460	0.0875	0.4131	0.027*
H13B	0.4496	0.0745	0.5503	0.027*
H13C	0.5813	0.0866	0.6213	0.027*
N1	0.7004 (2)	0.21749 (16)	0.4502 (4)	0.0145 (5)
H1C	0.689 (3)	0.174 (2)	0.375 (5)	0.017*
H1A	0.745 (3)	0.197 (2)	0.560 (5)	0.017*
H1B	0.741 (3)	0.258 (2)	0.403 (5)	0.017*
N2	1.0252 (2)	0.24733 (15)	0.8351 (4)	0.0189 (6)
N3	1.21805 (19)	−0.01227 (15)	0.7659 (3)	0.0174 (6)
N4	0.79761 (19)	−0.00660 (14)	0.7297 (3)	0.0133 (5)
O1	0.80771 (16)	0.16211 (12)	0.7685 (3)	0.0155 (5)
O2	0.95267 (17)	0.28171 (13)	0.9192 (3)	0.0253 (6)
O3	1.10521 (19)	0.28239 (14)	0.7711 (4)	0.0344 (7)
O4	1.31051 (16)	0.02380 (13)	0.7795 (3)	0.0204 (5)
O5	1.20952 (18)	−0.08698 (13)	0.7414 (3)	0.0286 (6)
O6	0.78077 (18)	−0.05062 (14)	0.5981 (3)	0.0251 (6)
O7	0.72885 (17)	0.00209 (13)	0.8446 (3)	0.0214 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0089 (12)	0.0148 (15)	0.0136 (15)	0.0021 (11)	0.0023 (10)	−0.0006 (12)
C2	0.0132 (13)	0.0142 (15)	0.0146 (15)	0.0006 (11)	0.0007 (11)	0.0010 (12)
C3	0.0100 (13)	0.0268 (17)	0.0168 (16)	−0.0012 (12)	0.0028 (11)	0.0023 (13)
C4	0.0132 (13)	0.0248 (17)	0.0203 (16)	0.0066 (12)	0.0033 (12)	−0.0003 (14)
C5	0.0207 (15)	0.0130 (15)	0.0204 (16)	0.0066 (12)	0.0003 (12)	−0.0004 (13)
C6	0.0152 (14)	0.0170 (16)	0.0184 (16)	−0.0030 (11)	0.0019 (11)	0.0002 (13)
C7	0.0118 (13)	0.0135 (15)	0.0137 (15)	0.0025 (11)	0.0037 (10)	0.0010 (12)
C8	0.0147 (13)	0.0113 (15)	0.0172 (15)	0.0014 (11)	0.0019 (11)	−0.0020 (12)
C9	0.0116 (13)	0.0175 (16)	0.0148 (15)	−0.0052 (11)	0.0011 (11)	0.0019 (12)
C10	0.0118 (13)	0.0181 (16)	0.0158 (15)	0.0039 (11)	0.0040 (11)	−0.0008 (12)
C11	0.0184 (14)	0.0068 (13)	0.0168 (15)	−0.0008 (11)	0.0028 (11)	−0.0005 (12)
C12	0.0125 (13)	0.0135 (15)	0.0125 (15)	−0.0028 (11)	0.0025 (11)	−0.0002 (11)
C13	0.0151 (14)	0.0158 (16)	0.0244 (18)	−0.0015 (11)	0.0041 (12)	0.0025 (13)
N1	0.0101 (11)	0.0148 (14)	0.0193 (14)	−0.0006 (10)	0.0055 (10)	0.0008 (11)
N2	0.0123 (11)	0.0144 (13)	0.0298 (16)	−0.0001 (10)	0.0003 (10)	−0.0023 (11)
N3	0.0121 (12)	0.0187 (14)	0.0214 (14)	0.0027 (10)	0.0017 (10)	−0.0023 (11)
N4	0.0116 (11)	0.0106 (12)	0.0177 (13)	−0.0001 (9)	0.0006 (9)	0.0027 (10)
O1	0.0126 (9)	0.0146 (11)	0.0197 (11)	0.0034 (8)	0.0036 (8)	0.0004 (9)
O2	0.0177 (10)	0.0179 (12)	0.0404 (15)	0.0041 (9)	0.0023 (10)	−0.0089 (10)
O3	0.0248 (12)	0.0178 (13)	0.0621 (19)	−0.0095 (10)	0.0125 (12)	0.0006 (12)
O4	0.0114 (10)	0.0255 (12)	0.0244 (12)	0.0021 (9)	0.0029 (8)	−0.0006 (10)
O5	0.0203 (11)	0.0170 (12)	0.0479 (16)	0.0061 (9)	−0.0006 (10)	−0.0101 (11)
O6	0.0236 (11)	0.0269 (13)	0.0246 (13)	−0.0074 (9)	0.0001 (9)	−0.0085 (10)
O7	0.0177 (10)	0.0215 (12)	0.0267 (13)	−0.0035 (9)	0.0120 (9)	−0.0001 (10)

Geometric parameters (Å, º)

C1—C6	1.391 (4)	C9—H9	0.9500
C1—C2	1.395 (4)	C10—C11	1.398 (4)
C1—N1	1.481 (3)	C10—N3	1.450 (3)
C2—C3	1.401 (4)	C11—C12	1.366 (4)
C2—C13	1.511 (4)	C11—H11	0.9500
C3—C4	1.386 (4)	C12—N4	1.473 (3)
C3—H3	0.9500	C13—H13A	0.9800
C4—C5	1.395 (4)	C13—H13B	0.9800
C4—H4	0.9500	C13—H13C	0.9800
C5—C6	1.392 (4)	N1—H1C	0.92 (4)
C5—H5	0.9500	N1—H1A	1.00 (3)
C6—H6	0.9500	N1—H1B	0.91 (4)
C7—O1	1.278 (3)	N2—O3	1.227 (3)
C7—C12	1.440 (4)	N2—O2	1.233 (3)
C7—C8	1.444 (4)	N3—O4	1.228 (3)
C8—C9	1.379 (4)	N3—O5	1.248 (3)
C8—N2	1.474 (4)	N4—O7	1.235 (3)
C9—C10	1.388 (4)	N4—O6	1.236 (3)
C6—C1—C2	123.6 (3)	C11—C10—N3	119.1 (3)
C6—C1—N1	118.1 (2)	C12—C11—C10	117.9 (3)
C2—C1—N1	118.3 (2)	C12—C11—H11	121.0
C1—C2—C3	116.1 (3)	C10—C11—H11	121.0
C1—C2—C13	122.7 (2)	C11—C12—C7	125.5 (2)
C3—C2—C13	121.2 (3)	C11—C12—N4	117.9 (2)
C4—C3—C2	121.6 (3)	C7—C12—N4	116.6 (2)
C4—C3—H3	119.2	C2—C13—H13A	109.5
C2—C3—H3	119.2	C2—C13—H13B	109.5
C3—C4—C5	120.7 (3)	H13A—C13—H13B	109.5
C3—C4—H4	119.6	C2—C13—H13C	109.5
C5—C4—H4	119.6	H13A—C13—H13C	109.5
C6—C5—C4	119.2 (3)	H13B—C13—H13C	109.5
C6—C5—H5	120.4	C1—N1—H1C	109 (2)
C4—C5—H5	120.4	C1—N1—H1A	109.5 (18)
C1—C6—C5	118.7 (3)	H1C—N1—H1A	107 (3)
C1—C6—H6	120.6	C1—N1—H1B	110 (2)
C5—C6—H6	120.6	H1C—N1—H1B	113 (3)
O1—C7—C12	122.4 (2)	H1A—N1—H1B	109 (3)
O1—C7—C8	125.4 (3)	O3—N2—O2	123.9 (3)
C12—C7—C8	112.0 (2)	O3—N2—C8	118.0 (2)
C9—C8—C7	124.0 (3)	O2—N2—C8	118.1 (2)
C9—C8—N2	116.9 (2)	O4—N3—O5	123.4 (2)
C7—C8—N2	118.9 (2)	O4—N3—C10	119.5 (2)
C8—C9—C10	118.9 (2)	O5—N3—C10	117.2 (2)
C8—C9—H9	120.5	O7—N4—O6	124.3 (2)
C10—C9—H9	120.5	O7—N4—C12	117.1 (2)
C9—C10—C11	121.5 (3)	O6—N4—C12	118.5 (2)
C9—C10—N3	119.4 (2)
C6—C1—C2—C3	0.1 (4)	N3—C10—C11—C12	−179.5 (3)
N1—C1—C2—C3	178.6 (3)	C10—C11—C12—C7	2.9 (4)
C6—C1—C2—C13	−179.5 (3)	C10—C11—C12—N4	−179.1 (3)
N1—C1—C2—C13	−1.1 (4)	O1—C7—C12—C11	171.5 (3)
C1—C2—C3—C4	−1.3 (4)	C8—C7—C12—C11	−3.2 (4)
C13—C2—C3—C4	178.4 (3)	O1—C7—C12—N4	−6.5 (4)
C2—C3—C4—C5	1.6 (5)	C8—C7—C12—N4	178.9 (2)
C3—C4—C5—C6	−0.7 (5)	C9—C8—N2—O3	32.8 (4)
C2—C1—C6—C5	0.7 (5)	C7—C8—N2—O3	−143.3 (3)
N1—C1—C6—C5	−177.7 (3)	C9—C8—N2—O2	−146.9 (3)
C4—C5—C6—C1	−0.4 (4)	C7—C8—N2—O2	37.1 (4)
O1—C7—C8—C9	−172.0 (3)	C9—C10—N3—O4	−2.1 (4)
C12—C7—C8—C9	2.4 (4)	C11—C10—N3—O4	175.7 (3)
O1—C7—C8—N2	3.7 (4)	C9—C10—N3—O5	179.0 (3)
C12—C7—C8—N2	178.2 (3)	C11—C10—N3—O5	−3.2 (4)
C7—C8—C9—C10	−1.6 (5)	C11—C12—N4—O7	127.0 (3)
N2—C8—C9—C10	−177.4 (3)	C7—C12—N4—O7	−54.9 (3)
C8—C9—C10—C11	1.1 (4)	C11—C12—N4—O6	−51.0 (4)
C8—C9—C10—N3	178.9 (3)	C7—C12—N4—O6	127.1 (3)
C9—C10—C11—C12	−1.7 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	1.00 (3)	1.79 (4)	2.786 (3)	172 (3)
N1—H1B···O1^i	0.91 (4)	1.86 (4)	2.767 (3)	170 (3)
N1—H1C···O5^ii	0.92 (4)	2.10 (3)	2.840 (3)	137 (3)

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

(II) 2,5-dichloroanilinium picrate

Crystal data

C6H6Cl2N^+·C6H2N3O7^−	F(000) = 792
Mr = 391.12	Dx = 1.685 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 1754 reflections
a = 4.3288 (18) Å	θ = 2.2–27.7°
b = 23.372 (10) Å	µ = 0.47 mm^−1
c = 15.292 (6) Å	T = 123 K
β = 94.606 (7)°	Plate, yellow
V = 1542.2 (11) Å^3	0.36 × 0.20 × 0.05 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2666 independent reflections
Radiation source: fine focus sealed Siemens Mo tube	2362 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.066
0.3° wide ω exposures scans	θmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	h = −5→5
Tmin = 0.840, Tmax = 0.977	k = −22→28
3948 measured reflections	l = −18→16

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.094	w = 1/[σ^2(Fo^2) + (0.0473P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.98	(Δ/σ)max = 0.001
2666 reflections	Δρmax = 0.37 e Å^−3
235 parameters	Δρmin = −0.26 e Å^−3
2 restraints	Absolute structure: Flack (1983), with 1131 Bijvoet pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (6)

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. 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 > σ(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
C1	0.9100 (8)	0.77700 (14)	0.7377 (3)	0.0165 (8)
C2	0.7887 (8)	0.74163 (15)	0.7997 (2)	0.0171 (8)
C3	0.8303 (9)	0.68291 (16)	0.7961 (3)	0.0225 (9)
H3	0.7472	0.6590	0.8386	0.027*
C4	0.9922 (9)	0.65911 (16)	0.7309 (3)	0.0234 (9)
H4	1.0268	0.6190	0.7290	0.028*
C5	1.1028 (8)	0.69482 (16)	0.6684 (3)	0.0205 (8)
C6	1.0656 (8)	0.75408 (16)	0.6707 (2)	0.0184 (8)
H6	1.1451	0.7779	0.6274	0.022*
C7	0.3468 (7)	0.93006 (15)	0.6052 (2)	0.0162 (8)
C8	0.4988 (8)	0.93024 (16)	0.5244 (2)	0.0179 (8)
C9	0.4983 (8)	0.97680 (16)	0.4662 (2)	0.0200 (8)
H9	0.5992	0.9738	0.4135	0.024*
C10	0.3502 (8)	1.02692 (15)	0.4862 (2)	0.0185 (8)
C11	0.2201 (8)	1.03260 (16)	0.5655 (2)	0.0190 (8)
H11	0.1316	1.0680	0.5812	0.023*
C12	0.2203 (8)	0.98559 (15)	0.6224 (2)	0.0179 (8)
Cl1	0.59161 (17)	0.77184 (4)	0.88212 (6)	0.0259 (2)
Cl2	1.29302 (19)	0.66517 (4)	0.58377 (6)	0.0265 (2)
N1	0.8782 (8)	0.83947 (13)	0.7437 (2)	0.0192 (7)
H1A	0.682 (10)	0.8537 (17)	0.713 (3)	0.023*
H1B	1.030 (9)	0.8585 (18)	0.715 (3)	0.023*
H1C	0.877 (9)	0.8473 (16)	0.801 (3)	0.023*
N2	0.6617 (7)	0.87856 (14)	0.4985 (2)	0.0234 (7)
N3	0.3329 (8)	1.07506 (13)	0.4235 (2)	0.0223 (7)
N4	0.0810 (7)	0.99458 (13)	0.70586 (19)	0.0204 (7)
O1	0.3370 (5)	0.88725 (10)	0.65767 (17)	0.0219 (6)
O4	0.4978 (6)	1.07395 (12)	0.36204 (18)	0.0308 (7)
O5	0.1505 (6)	1.11432 (12)	0.43352 (17)	0.0276 (6)
O2	0.6101 (8)	0.83209 (13)	0.5327 (2)	0.0437 (8)
O3	0.8421 (7)	0.88452 (12)	0.4424 (2)	0.0352 (8)
O6	0.1278 (8)	1.04068 (13)	0.74530 (19)	0.0421 (8)
O7	−0.0799 (6)	0.95665 (11)	0.7322 (2)	0.0259 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0154 (17)	0.0148 (17)	0.019 (2)	0.0009 (14)	0.0010 (15)	−0.0019 (16)
C2	0.0176 (19)	0.0198 (18)	0.0144 (19)	−0.0011 (15)	0.0042 (15)	−0.0014 (16)
C3	0.028 (2)	0.0205 (19)	0.019 (2)	−0.0048 (16)	0.0040 (17)	0.0078 (16)
C4	0.030 (2)	0.0153 (19)	0.024 (2)	−0.0020 (16)	−0.0036 (18)	0.0009 (17)
C5	0.0207 (19)	0.023 (2)	0.0175 (19)	0.0007 (15)	0.0015 (15)	−0.0013 (16)
C6	0.0190 (19)	0.0188 (19)	0.0174 (19)	−0.0003 (14)	0.0024 (15)	−0.0006 (15)
C7	0.0158 (18)	0.0180 (18)	0.0148 (19)	−0.0032 (13)	0.0016 (14)	−0.0003 (14)
C8	0.0172 (17)	0.021 (2)	0.0156 (19)	0.0026 (15)	0.0022 (14)	−0.0055 (15)
C9	0.0173 (18)	0.029 (2)	0.0145 (19)	−0.0021 (15)	0.0052 (14)	−0.0023 (15)
C10	0.0218 (18)	0.023 (2)	0.0118 (19)	−0.0032 (15)	0.0049 (15)	0.0013 (15)
C11	0.0223 (18)	0.0167 (19)	0.019 (2)	0.0019 (14)	0.0051 (15)	0.0001 (15)
C12	0.0191 (17)	0.0206 (19)	0.0149 (19)	−0.0009 (14)	0.0068 (15)	−0.0047 (16)
Cl1	0.0299 (5)	0.0306 (5)	0.0185 (5)	−0.0030 (4)	0.0100 (4)	−0.0012 (4)
Cl2	0.0345 (5)	0.0251 (5)	0.0205 (5)	0.0090 (4)	0.0053 (4)	−0.0037 (4)
N1	0.0250 (17)	0.0168 (16)	0.0166 (17)	0.0010 (13)	0.0063 (14)	−0.0003 (14)
N2	0.0247 (18)	0.0288 (19)	0.0167 (18)	0.0037 (14)	0.0017 (14)	−0.0037 (15)
N3	0.0257 (16)	0.0240 (17)	0.0177 (18)	−0.0029 (15)	0.0055 (14)	0.0016 (14)
N4	0.0268 (17)	0.0184 (17)	0.0177 (18)	0.0004 (13)	0.0117 (14)	−0.0001 (14)
O1	0.0243 (13)	0.0176 (14)	0.0244 (15)	0.0001 (11)	0.0064 (11)	0.0026 (11)
O4	0.0386 (16)	0.0336 (16)	0.0229 (16)	0.0000 (13)	0.0185 (13)	0.0046 (13)
O5	0.0346 (15)	0.0248 (15)	0.0245 (15)	0.0075 (12)	0.0091 (12)	0.0076 (12)
O2	0.073 (2)	0.0257 (17)	0.0358 (19)	0.0171 (15)	0.0269 (17)	0.0074 (14)
O3	0.0326 (15)	0.0337 (18)	0.0421 (19)	0.0033 (13)	0.0206 (15)	−0.0079 (14)
O6	0.075 (2)	0.0237 (16)	0.0316 (19)	−0.0165 (15)	0.0308 (16)	−0.0117 (13)
O7	0.0295 (14)	0.0204 (13)	0.0302 (15)	−0.0026 (12)	0.0166 (12)	0.0035 (13)

Geometric parameters (Å, º)

C1—C6	1.379 (5)	C9—C10	1.381 (5)
C1—C2	1.392 (5)	C9—H9	0.9500
C1—N1	1.470 (5)	C10—C11	1.384 (5)
C2—C3	1.386 (5)	C10—N3	1.477 (5)
C2—Cl1	1.729 (4)	C11—C12	1.401 (5)
C3—C4	1.381 (6)	C11—H11	0.9500
C3—H3	0.9500	C12—N4	1.469 (5)
C4—C5	1.383 (5)	N1—H1A	0.99 (4)
C4—H4	0.9500	N1—H1B	0.93 (4)
C5—C6	1.395 (5)	N1—H1C	0.90 (4)
C5—Cl2	1.733 (4)	N2—O3	1.213 (4)
C6—H6	0.9500	N2—O2	1.234 (4)
C7—O1	1.286 (4)	N3—O4	1.225 (4)
C7—C12	1.441 (5)	N3—O5	1.228 (4)
C7—C8	1.446 (5)	N4—O7	1.216 (4)
C8—C9	1.405 (5)	N4—O6	1.243 (4)
C8—N2	1.469 (5)
C6—C1—C2	120.6 (3)	C8—C9—H9	120.2
C6—C1—N1	119.1 (4)	C9—C10—C11	120.3 (3)
C2—C1—N1	120.3 (4)	C9—C10—N3	120.2 (3)
C3—C2—C1	120.3 (4)	C11—C10—N3	119.6 (3)
C3—C2—Cl1	120.4 (3)	C10—C11—C12	119.3 (3)
C1—C2—Cl1	119.3 (3)	C10—C11—H11	120.4
C4—C3—C2	120.2 (4)	C12—C11—H11	120.4
C4—C3—H3	119.9	C11—C12—C7	125.0 (3)
C2—C3—H3	119.9	C11—C12—N4	116.6 (3)
C3—C4—C5	118.7 (3)	C7—C12—N4	118.4 (3)
C3—C4—H4	120.7	C1—N1—H1A	113 (2)
C5—C4—H4	120.7	C1—N1—H1B	112 (3)
C4—C5—C6	122.3 (4)	H1A—N1—H1B	103 (3)
C4—C5—Cl2	119.1 (3)	C1—N1—H1C	106 (2)
C6—C5—Cl2	118.6 (3)	H1A—N1—H1C	109 (3)
C1—C6—C5	118.0 (4)	H1B—N1—H1C	115 (4)
C1—C6—H6	121.0	O3—N2—O2	123.3 (3)
C5—C6—H6	121.0	O3—N2—C8	116.5 (3)
O1—C7—C12	123.7 (3)	O2—N2—C8	120.1 (3)
O1—C7—C8	125.2 (3)	O4—N3—O5	122.2 (3)
C12—C7—C8	111.1 (3)	O4—N3—C10	118.7 (3)
C9—C8—C7	124.4 (3)	O5—N3—C10	119.2 (3)
C9—C8—N2	116.3 (3)	O7—N4—O6	123.1 (3)
C7—C8—N2	119.3 (3)	O7—N4—C12	118.0 (3)
C10—C9—C8	119.6 (3)	O6—N4—C12	118.9 (3)
C10—C9—H9	120.2
C6—C1—C2—C3	1.7 (5)	C9—C10—C11—C12	−4.6 (5)
N1—C1—C2—C3	−177.3 (3)	N3—C10—C11—C12	176.1 (3)
C6—C1—C2—Cl1	−179.4 (3)	C10—C11—C12—C7	−0.2 (5)
N1—C1—C2—Cl1	1.7 (5)	C10—C11—C12—N4	179.5 (3)
C1—C2—C3—C4	−0.1 (5)	O1—C7—C12—C11	−178.2 (3)
Cl1—C2—C3—C4	−179.0 (3)	C8—C7—C12—C11	5.0 (5)
C2—C3—C4—C5	−1.8 (5)	O1—C7—C12—N4	2.1 (5)
C3—C4—C5—C6	2.2 (5)	C8—C7—C12—N4	−174.8 (3)
C3—C4—C5—Cl2	−177.5 (3)	C9—C8—N2—O3	17.5 (4)
C2—C1—C6—C5	−1.4 (5)	C7—C8—N2—O3	−163.7 (3)
N1—C1—C6—C5	177.6 (3)	C9—C8—N2—O2	−161.8 (3)
C4—C5—C6—C1	−0.6 (5)	C7—C8—N2—O2	17.0 (5)
Cl2—C5—C6—C1	179.1 (3)	C9—C10—N3—O4	−13.3 (5)
O1—C7—C8—C9	177.7 (3)	C11—C10—N3—O4	166.0 (3)
C12—C7—C8—C9	−5.5 (5)	C9—C10—N3—O5	165.5 (3)
O1—C7—C8—N2	−1.0 (5)	C11—C10—N3—O5	−15.2 (5)
C12—C7—C8—N2	175.8 (3)	C11—C12—N4—O7	138.9 (3)
C7—C8—C9—C10	1.3 (5)	C7—C12—N4—O7	−41.3 (4)
N2—C8—C9—C10	−179.9 (3)	C11—C12—N4—O6	−39.8 (4)
C8—C9—C10—C11	4.1 (5)	C7—C12—N4—O6	140.0 (3)
C8—C9—C10—N3	−176.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.99 (4)	1.83 (4)	2.823 (4)	174 (3)
N1—H1B···O1^i	0.93 (4)	1.78 (4)	2.709 (4)	174 (4)
N1—H1C···O5^ii	0.90 (4)	2.43 (4)	3.230 (4)	148 (3)

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