2-(Methoxy­carbon­yl)anilinium chloride monohydrate

Ma, Y.-Y.; Yu, Y.; Wu, Y.-F.; Xiao, F.-P.; Jin, L.-F.

doi:10.1107/S1600536805030771

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2-(Methoxycarbonyl)anilinium chloride monohydrate

Y.-Y. Ma, Y. Yu, Y.-F. Wu, F.-P. Xiao and L.-F. Jin

The asymmetric unit of the title compound, C₈H₁₀NO₂⁺·Cl⁻·H₂O, contains two crystallographically independent 2-(methoxycarbonyl)anilinium cations related by a pseudo-inversion centre, two chloride ions and two water molecules. A three-dimensional network structure is formed via N—H

O, N—H

Cl and O—H

Cl hydrogen bonds, and π–π stacking interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805030771/ci6646sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805030771/ci6646Isup2.hkl Contains datablock I

CCDC reference: 287511

checkCIF report

Key indicators

Single-crystal X-ray study
T = 292 K
Mean (C-C) = 0.003 Å
R factor = 0.041
wR factor = 0.128
Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety         N1

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

Methyl 2-aminobenzoate is used as an intermediate for fine chemicals (Zhang, 1992). It is known that many esters of 2-aminobenzoate display a broad range of biological activities (Li et al., 1998). Synthetic esters of 2-aminobenzoate show useful properties (Ye, 2000). Furthermore, these esters can also be used as interesting ligands. These properties stimutated us to find new methods to synthesize them and study their structures and activities. We report here the crystal structure of the title compound, (I).

The asymmetric unit contains two crystallographically independent methyl 2-aminobenzoate cations related by a local inversion centre, two chloride ions and two water molecules (Fig. 1). The corresponding bond lengths and angles in the independent methyl 2-aminobenzoate molecules agree with each other (Table 1) and show normal values. The N1- and N2-containing cations are essentially planar, with r.m.s deviations of 0.074 and 0.045 Å, respectively. In the crystal structure, the molecules are linked together via N—H···O and N—H···Cl hydrogen bonds involving the amine groups, and by O—H···Cl hydrogen bonds, to form a three-dimensional network. In addition, the crystal packing is stabilized by weak π–π interactions resulting from the stacking of inversion-related C9–C14 benzene rings along the a axis. The Cg—Cg^v and Cg—Cg^vi distances are 3.781 (1) and 3.725 (1) Å, respectively, where Cg is the centroid of the C9–C14 benzene ring [symmetry codes: (v) −x, 2 − y, 1 − z; (vi) 1 − x, 2 − y, 1 − z]; similar features are observed in related structures (Du et al., 2003; Jin & Xiao, 2005).

Experimental top

Compound (I) was synthesized according to a literature procedure (Dan, 2000). Single crystals suitable for X-ray measurements were grown from a solution in methanol at room temperature by slow evaporation.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. The asymmetric unit of (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme. Dashed lines represent hydrogen bonds.
	Fig. 2. Packing diagram for (I). The hydrogen bonds are indicated by dashed lines.

2-(Methoxycarbonyl)anilinium chloride monohydrate top

Crystal data top

C₈H₁₀NO₂⁺·Cl⁻·H₂O	Z = 4
M_r = 205.64	F(000) = 432
Triclinic, P1	D_x = 1.364 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4709 (9) Å	Cell parameters from 3522 reflections
b = 11.6988 (14) Å	θ = 2.4–25.7°
c = 12.3883 (15) Å	µ = 0.36 mm⁻¹
α = 96.299 (2)°	T = 292 K
β = 101.097 (2)°	Block, colourless
γ = 106.844 (2)°	0.32 × 0.30 × 0.30 mm
V = 1001.0 (2) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	3867 independent reflections
Radiation source: fine-focus sealed tube	3433 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
ϕ and ω scans	θ_max = 26.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→8
T_min = 0.894, T_max = 0.900	k = −14→14
5444 measured reflections	l = −15→11

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0779P)² + 0.2162P] where P = (F_o² + 2F_c²)/3
3867 reflections	(Δ/σ)_max = 0.001
255 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₈H₁₀NO₂⁺·Cl⁻·H₂O	γ = 106.844 (2)°
M_r = 205.64	V = 1001.0 (2) Å³
Triclinic, P1	Z = 4
a = 7.4709 (9) Å	Mo Kα radiation
b = 11.6988 (14) Å	µ = 0.36 mm⁻¹
c = 12.3883 (15) Å	T = 292 K
α = 96.299 (2)°	0.32 × 0.30 × 0.30 mm
β = 101.097 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3867 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3433 reflections with I > 2σ(I)
T_min = 0.894, T_max = 0.900	R_int = 0.016
5444 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.33 e Å⁻³
3867 reflections	Δρ_min = −0.23 e Å⁻³
255 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.2657 (3)	0.61200 (15)	0.98457 (15)	0.0406 (4)
C2	0.2930 (3)	0.72975 (15)	1.03841 (15)	0.0383 (4)
C3	0.3387 (3)	0.75805 (18)	1.15351 (16)	0.0483 (5)
H3	0.3569	0.8364	1.1884	0.058*
C4	0.3576 (4)	0.6709 (2)	1.21686 (17)	0.0572 (5)
H4	0.3901	0.6909	1.2944	0.069*
C5	0.3283 (4)	0.5540 (2)	1.16565 (18)	0.0598 (6)
H5	0.3392	0.4948	1.2085	0.072*
C6	0.2827 (3)	0.52545 (18)	1.05041 (18)	0.0538 (5)
H6	0.2631	0.4465	1.0163	0.065*
C7	0.2256 (3)	0.58225 (16)	0.86061 (16)	0.0434 (4)
C8	0.1460 (5)	0.4297 (2)	0.7027 (2)	0.0825 (9)
H8A	0.0414	0.4547	0.6667	0.124*
H8B	0.1136	0.3433	0.6836	0.124*
H8C	0.2596	0.4684	0.6784	0.124*
C9	0.2314 (2)	1.00752 (15)	0.61787 (14)	0.0343 (4)
C10	0.2491 (2)	0.89784 (15)	0.57108 (14)	0.0350 (4)
C11	0.2631 (3)	0.87781 (16)	0.46209 (15)	0.0412 (4)
H11	0.2732	0.8043	0.4318	0.049*
C12	0.2621 (3)	0.96682 (18)	0.39747 (15)	0.0442 (4)
H12	0.2693	0.9525	0.3233	0.053*
C13	0.2505 (3)	1.07669 (17)	0.44253 (15)	0.0426 (4)
H13	0.2539	1.1374	0.3996	0.051*
C14	0.2338 (3)	1.09663 (16)	0.55155 (15)	0.0391 (4)
H14	0.2241	1.1706	0.5812	0.047*
C15	0.1997 (2)	1.02604 (16)	0.73273 (14)	0.0378 (4)
C16	0.1489 (4)	1.1601 (2)	0.87130 (18)	0.0608 (6)
H16A	0.0366	1.0982	0.8778	0.091*
H16B	0.1287	1.2376	0.8814	0.091*
H16C	0.2579	1.1611	0.9274	0.091*
Cl1	0.37394 (7)	0.07755 (4)	0.14253 (4)	0.04657 (16)
Cl2	0.18067 (8)	0.36339 (4)	0.40175 (5)	0.05799 (18)
H5A	0.880 (4)	0.720 (3)	0.803 (3)	0.070 (9)*
H6A	0.500 (6)	0.641 (3)	0.544 (3)	0.109 (13)*
H5B	0.826 (5)	0.797 (3)	0.859 (2)	0.083 (9)*
H6B	0.326 (5)	0.572 (3)	0.492 (3)	0.080 (9)*
N1	0.2718 (2)	0.82504 (13)	0.97525 (13)	0.0424 (4)
H1A	0.2942	0.8935	1.0224	0.064*
H1B	0.1528	0.8030	0.9327	0.064*
H1C	0.3557	0.8368	0.9321	0.064*
N2	0.2535 (2)	0.80099 (13)	0.63524 (13)	0.0405 (3)
H2A	0.1347	0.7618	0.6400	0.061*
H2B	0.3276	0.8327	0.7036	0.061*
H2C	0.3010	0.7494	0.6013	0.061*
O1	0.1814 (3)	0.46450 (12)	0.82347 (12)	0.0658 (5)
O2	0.2325 (3)	0.65573 (12)	0.80063 (12)	0.0618 (4)
O3	0.1842 (2)	1.13512 (11)	0.76149 (11)	0.0493 (3)
O4	0.1858 (3)	0.95180 (13)	0.79200 (12)	0.0587 (4)
O5	0.8866 (3)	0.74624 (16)	0.86478 (16)	0.0589 (4)
O6	0.3892 (3)	0.63930 (16)	0.51649 (17)	0.0646 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0443 (10)	0.0337 (8)	0.0413 (9)	0.0098 (7)	0.0083 (8)	0.0067 (7)
C2	0.0418 (9)	0.0348 (8)	0.0399 (9)	0.0121 (7)	0.0122 (7)	0.0085 (7)
C3	0.0613 (12)	0.0441 (10)	0.0404 (10)	0.0174 (9)	0.0151 (9)	0.0045 (8)
C4	0.0739 (14)	0.0619 (13)	0.0356 (10)	0.0199 (11)	0.0141 (10)	0.0104 (9)
C5	0.0802 (15)	0.0507 (11)	0.0490 (12)	0.0190 (11)	0.0122 (11)	0.0217 (10)
C6	0.0718 (14)	0.0377 (9)	0.0487 (11)	0.0161 (9)	0.0081 (10)	0.0082 (8)
C7	0.0517 (11)	0.0331 (8)	0.0431 (10)	0.0151 (8)	0.0055 (8)	0.0034 (8)
C8	0.132 (3)	0.0547 (13)	0.0511 (13)	0.0362 (16)	0.0008 (15)	−0.0090 (11)
C9	0.0322 (8)	0.0340 (8)	0.0353 (8)	0.0101 (6)	0.0065 (6)	0.0048 (7)
C10	0.0340 (8)	0.0335 (8)	0.0369 (9)	0.0107 (7)	0.0063 (7)	0.0068 (7)
C11	0.0440 (10)	0.0403 (9)	0.0387 (9)	0.0150 (8)	0.0093 (7)	0.0010 (7)
C12	0.0476 (10)	0.0536 (11)	0.0334 (9)	0.0170 (9)	0.0125 (8)	0.0082 (8)
C13	0.0433 (10)	0.0437 (9)	0.0428 (10)	0.0135 (8)	0.0096 (8)	0.0179 (8)
C14	0.0404 (9)	0.0342 (8)	0.0424 (9)	0.0124 (7)	0.0080 (7)	0.0069 (7)
C15	0.0395 (9)	0.0376 (9)	0.0377 (9)	0.0158 (7)	0.0072 (7)	0.0056 (7)
C16	0.0830 (16)	0.0617 (13)	0.0451 (11)	0.0343 (12)	0.0197 (11)	0.0009 (10)
Cl1	0.0565 (3)	0.0417 (3)	0.0408 (3)	0.0152 (2)	0.0128 (2)	0.00370 (19)
Cl2	0.0531 (3)	0.0428 (3)	0.0703 (4)	0.0139 (2)	0.0037 (2)	0.0012 (2)
N1	0.0557 (9)	0.0329 (7)	0.0398 (8)	0.0150 (7)	0.0135 (7)	0.0052 (6)
N2	0.0517 (9)	0.0337 (7)	0.0399 (8)	0.0185 (7)	0.0112 (7)	0.0077 (6)
O1	0.1103 (14)	0.0367 (7)	0.0455 (8)	0.0264 (8)	0.0063 (8)	0.0004 (6)
O2	0.1021 (13)	0.0402 (7)	0.0389 (7)	0.0211 (8)	0.0094 (8)	0.0067 (6)
O3	0.0723 (9)	0.0403 (7)	0.0394 (7)	0.0234 (7)	0.0167 (6)	0.0031 (6)
O4	0.0954 (12)	0.0563 (8)	0.0476 (8)	0.0433 (8)	0.0340 (8)	0.0230 (7)
O5	0.0653 (10)	0.0513 (9)	0.0624 (11)	0.0234 (8)	0.0127 (8)	0.0113 (8)
O6	0.0615 (11)	0.0426 (9)	0.0868 (13)	0.0220 (8)	0.0114 (9)	−0.0042 (8)

Geometric parameters (Å, º) top

C1—C6	1.387 (3)	C11—C12	1.382 (3)
C1—C2	1.403 (2)	C11—H11	0.93
C1—C7	1.488 (3)	C12—C13	1.377 (3)
C2—C3	1.379 (3)	C12—H12	0.93
C2—N1	1.458 (2)	C13—C14	1.381 (3)
C3—C4	1.375 (3)	C13—H13	0.93
C3—H3	0.93	C14—H14	0.93
C4—C5	1.380 (3)	C15—O4	1.192 (2)
C4—H4	0.93	C15—O3	1.330 (2)
C5—C6	1.381 (3)	C16—O3	1.450 (2)
C5—H5	0.93	C16—H16A	0.96
C6—H6	0.93	C16—H16B	0.96
C7—O2	1.193 (2)	C16—H16C	0.96
C7—O1	1.326 (2)	N1—H1A	0.89
C8—O1	1.457 (3)	N1—H1B	0.89
C8—H8A	0.96	N1—H1C	0.89
C8—H8B	0.96	N2—H2A	0.89
C8—H8C	0.96	N2—H2B	0.89
C9—C14	1.395 (2)	N2—H2C	0.89
C9—C10	1.402 (2)	O5—H5A	0.78 (3)
C9—C15	1.490 (2)	O5—H5B	0.84 (3)
C10—C11	1.374 (2)	O6—H6A	0.83 (4)
C10—N2	1.458 (2)	O6—H6B	0.78 (3)

C6—C1—C2	118.00 (17)	C12—C11—H11	120.0
C6—C1—C7	121.18 (16)	C13—C12—C11	120.21 (16)
C2—C1—C7	120.79 (16)	C13—C12—H12	119.9
C3—C2—C1	120.48 (17)	C11—C12—H12	119.9
C3—C2—N1	118.09 (16)	C12—C13—C14	119.89 (16)
C1—C2—N1	121.43 (15)	C12—C13—H13	120.1
C4—C3—C2	120.33 (18)	C14—C13—H13	120.1
C4—C3—H3	119.8	C13—C14—C9	120.96 (16)
C2—C3—H3	119.8	C13—C14—H14	119.5
C3—C4—C5	120.17 (19)	C9—C14—H14	119.5
C3—C4—H4	119.9	O4—C15—O3	123.32 (16)
C5—C4—H4	119.9	O4—C15—C9	124.57 (16)
C4—C5—C6	119.63 (19)	O3—C15—C9	112.10 (15)
C4—C5—H5	120.2	O3—C16—H16A	109.5
C6—C5—H5	120.2	O3—C16—H16B	109.5
C5—C6—C1	121.37 (19)	H16A—C16—H16B	109.5
C5—C6—H6	119.3	O3—C16—H16C	109.5
C1—C6—H6	119.3	H16A—C16—H16C	109.5
O2—C7—O1	123.30 (17)	H16B—C16—H16C	109.5
O2—C7—C1	124.10 (16)	C2—N1—H1A	109.5
O1—C7—C1	112.60 (16)	C2—N1—H1B	109.5
O1—C8—H8A	109.5	H1A—N1—H1B	109.5
O1—C8—H8B	109.5	C2—N1—H1C	109.5
H8A—C8—H8B	109.5	H1A—N1—H1C	109.5
O1—C8—H8C	109.5	H1B—N1—H1C	109.5
H8A—C8—H8C	109.5	C10—N2—H2A	109.5
H8B—C8—H8C	109.5	C10—N2—H2B	109.5
C14—C9—C10	118.03 (15)	H2A—N2—H2B	109.5
C14—C9—C15	120.77 (15)	C10—N2—H2C	109.5
C10—C9—C15	121.12 (15)	H2A—N2—H2C	109.5
C11—C10—C9	120.79 (16)	H2B—N2—H2C	109.5
C11—C10—N2	117.42 (15)	C7—O1—C8	115.31 (17)
C9—C10—N2	121.79 (15)	C15—O3—C16	115.88 (15)
C10—C11—C12	120.09 (16)	H5A—O5—H5B	104 (3)
C10—C11—H11	120.0	H6A—O6—H6B	109 (3)

C6—C1—C2—C3	1.1 (3)	C14—C9—C10—N2	178.21 (15)
C7—C1—C2—C3	−177.05 (18)	C15—C9—C10—N2	−5.2 (2)
C6—C1—C2—N1	−178.11 (18)	C9—C10—C11—C12	0.8 (3)
C7—C1—C2—N1	3.7 (3)	N2—C10—C11—C12	−179.20 (16)
C1—C2—C3—C4	−0.2 (3)	C10—C11—C12—C13	1.1 (3)
N1—C2—C3—C4	179.07 (19)	C11—C12—C13—C14	−2.0 (3)
C2—C3—C4—C5	−0.9 (3)	C12—C13—C14—C9	1.0 (3)
C3—C4—C5—C6	0.9 (4)	C10—C9—C14—C13	0.9 (3)
C4—C5—C6—C1	0.0 (4)	C15—C9—C14—C13	−175.69 (16)
C2—C1—C6—C5	−1.0 (3)	C14—C9—C15—O4	175.95 (18)
C7—C1—C6—C5	177.1 (2)	C10—C9—C15—O4	−0.5 (3)
C6—C1—C7—O2	−170.5 (2)	C14—C9—C15—O3	−2.7 (2)
C2—C1—C7—O2	7.6 (3)	C10—C9—C15—O3	−179.19 (15)
C6—C1—C7—O1	9.4 (3)	O2—C7—O1—C8	1.6 (3)
C2—C1—C7—O1	−172.55 (18)	C1—C7—O1—C8	−178.3 (2)
C14—C9—C10—C11	−1.8 (2)	O4—C15—O3—C16	0.0 (3)
C15—C9—C10—C11	174.81 (16)	C9—C15—O3—C16	178.72 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1ⁱ	0.89	2.33	3.2163 (16)	176
N1—H1B···O4	0.89	2.59	2.915 (2)	102
N1—H1B···O5ⁱⁱ	0.89	1.89	2.770 (3)	170
N1—H1C···O2	0.89	2.35	2.677 (2)	102
N1—H1C···Cl1ⁱⁱⁱ	0.89	2.38	3.2459 (17)	163
N2—H2A···Cl2^iv	0.89	2.31	3.1700 (17)	163
N2—H2B···O2	0.89	2.50	2.801 (2)	100
N2—H2B···O4	0.89	2.29	2.699 (2)	108
N2—H2B···Cl1ⁱⁱⁱ	0.89	2.51	3.3534 (17)	159
N2—H2C···O6	0.89	1.91	2.801 (3)	175
O5—H5A···Cl2ⁱⁱⁱ	0.78 (4)	2.52 (4)	3.295 (2)	173 (3)
O5—H5B···Cl1ⁱⁱⁱ	0.85 (4)	2.38 (4)	3.216 (2)	172 (3)
O6—H6A···Cl2ⁱⁱⁱ	0.83 (5)	2.37 (5)	3.188 (2)	172 (4)
O6—H6B···Cl2	0.78 (3)	2.41 (3)	3.177 (2)	169 (4)

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

Experimental details

Crystal data
Chemical formula	C₈H₁₀NO₂⁺·Cl⁻·H₂O
M_r	205.64
Crystal system, space group	Triclinic, P1
Temperature (K)	292
a, b, c (Å)	7.4709 (9), 11.6988 (14), 12.3883 (15)
α, β, γ (°)	96.299 (2), 101.097 (2), 106.844 (2)
V (Å³)	1001.0 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.36
Crystal size (mm)	0.32 × 0.30 × 0.30

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.894, 0.900
No. of measured, independent and observed [I > 2σ(I)] reflections	5444, 3867, 3433
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.128, 1.05
No. of reflections	3867
No. of parameters	255
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.23

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001), SHELXTL.

Selected geometric parameters (Å, º) top

C1—C7	1.488 (3)	C9—C15	1.490 (2)
C2—N1	1.458 (2)	C10—N2	1.458 (2)
C7—O2	1.193 (2)	C15—O4	1.192 (2)
C7—O1	1.326 (2)	C15—O3	1.330 (2)
C8—O1	1.457 (3)	C16—O3	1.450 (2)

O2—C7—O1	123.30 (17)	O3—C15—C9	112.10 (15)
O1—C7—C1	112.60 (16)	C7—O1—C8	115.31 (17)
O4—C15—O3	123.32 (16)	C15—O3—C16	115.88 (15)

C2—C1—C7—O2	7.6 (3)	C14—C9—C15—O3	−2.7 (2)
C6—C1—C7—O1	9.4 (3)	O2—C7—O1—C8	1.6 (3)
C10—C9—C15—O4	−0.5 (3)	C9—C15—O3—C16	178.72 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1ⁱ	0.89	2.33	3.2163 (16)	176
N1—H1B···O4	0.89	2.59	2.915 (2)	102
N1—H1B···O5ⁱⁱ	0.89	1.89	2.770 (3)	170
N1—H1C···O2	0.89	2.35	2.677 (2)	102
N1—H1C···Cl1ⁱⁱⁱ	0.89	2.38	3.2459 (17)	163
N2—H2A···Cl2^iv	0.89	2.31	3.1700 (17)	163
N2—H2B···O2	0.89	2.50	2.801 (2)	100
N2—H2B···O4	0.89	2.29	2.699 (2)	108
N2—H2B···Cl1ⁱⁱⁱ	0.89	2.51	3.3534 (17)	159
N2—H2C···O6	0.89	1.91	2.801 (3)	175
O5—H5A···Cl2ⁱⁱⁱ	0.78 (4)	2.52 (4)	3.295 (2)	173 (3)
O5—H5B···Cl1ⁱⁱⁱ	0.85 (4)	2.38 (4)	3.216 (2)	172 (3)
O6—H6A···Cl2ⁱⁱⁱ	0.83 (5)	2.37 (5)	3.188 (2)	172 (4)
O6—H6B···Cl2	0.78 (3)	2.41 (3)	3.177 (2)	169 (4)

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

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