Five solvates of a multicom­ponent pharmaceutical salt formed by berberine and diclofenac

Sun, W.; Zuo, L.; Zhao, T.; Zhu, Z.; Shan, G.

doi:10.1107/S2053229619015432

Five solvates of a multicomponent pharmaceutical salt formed by berberine and diclofenac

W. Sun, L. Zuo, T. Zhao, Z. Zhu and G. Shan

A multicomponent pharmaceutical salt formed by the isoquinoline alkaloid berberine (5,6-dihydro-9,10-dimethoxybenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium, BBR) and the nonsteroidal anti-inflammatory drug diclofenac {2-[2-(2,6-dichloroanilino)phenyl]acetic acid, DIC} was discovered. Five solvates of the pharmaceutical salt form were obtained by solid-form screening. These five multicomponent solvates are the dihydrate (BBR–DIC·2H₂O or C₂₀H₁₈NO₄⁺·C₁₄H₁₀Cl₂NO₂⁻·2H₂O), the dichloromethane hemisolvate dihydrate (BBR–DIC·0.5CH₂Cl₂·2H₂O or C₂₀H₁₈NO₄⁺·C₁₄H₁₀Cl₂NO₂⁻·0.5CH₂Cl₂·2H₂O), the ethanol monosolvate (BBR–DIC·C₂H₅OH or C₂₀H₁₈NO₄⁺·C₁₄H₁₀Cl₂NO₂⁻·C₂H₅OH), the methanol monosolvate (BBR–DIC·CH₃OH or C₂₀H₁₈NO₄⁺·C₁₄H₁₀Cl₂NO₂⁻·CH₃OH) and the methanol disolvate (BBR–DIC·2CH₃OH or C₂₀H₁₈NO₄⁺·C₁₄H₁₀Cl₂NO₂⁻·2CH₃OH), and their crystal structures were determined. All five solvates of BBR–DIC (1:1 molar ratio) were crystallized from different organic solvents. Solvent molecules in a pharmaceutical salt are essential components for the formation of crystalline structures and stabilization of the crystal lattices. These solvates have strong intermolecular O

H hydrogen bonds between the DIC anions and solvent molecules. The intermolecular hydrogen-bond interactions were visualized by two-dimensional fingerprint plots. All the multicomponent solvates contained intramolecular N—H

O hydrogen bonds. Various π–π interactions dominate the packing structures of the solvates.

Keywords: berberine; diclofenac; solvate; pharmaceutical salt; crystal structure; hydrogen bonding.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229619015432/fp3076sup1.cif Contains datablocks I, II, III, IV, V, global
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229619015432/fp3076Isup2.hkl Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229619015432/fp3076IIsup3.hkl Contains datablock II
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229619015432/fp3076IIIsup4.hkl Contains datablock III
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229619015432/fp3076IVsup5.hkl Contains datablock IV
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229619015432/fp3076Vsup6.hkl Contains datablock V
	Portable Document Format (PDF) file https://doi.org/10.1107/S2053229619015432/fp3076sup7.pdf PXRD patterns and an overlay plot

CCDC references: 1965859; 1965858; 1965857; 1965856; 1965855

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2017) for (I), (III), (IV), (V); CrysAlis PRO (Rigaku OD, 2018) for (II). Cell refinement: CrysAlis PRO (Rigaku OD, 2017) for (I), (III), (IV), (V); CrysAlis PRO (Rigaku OD, 2018) for (II). Data reduction: CrysAlis PRO (Rigaku OD, 2017) for (I), (III), (IV), (V); CrysAlis PRO (Rigaku OD, 2018) for (II). For all structures, program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009), PLATON (Spek, 2009), Mercury (Macrae et al., 2008) and publCIF (Westrip, 2010).

5,6-Dihydro-9,10-dimethoxybenzo[g][1,3]benzodioxolo[5,6-a]quinolizinium 2-[2-(2,6-dichloroanilino)phenyl]acetate dihydrate (I) top

Crystal data top

C₂₀H₁₈NO₄⁺·C₁₄H₁₀Cl₂NO₂⁻·2H₂O	D_x = 1.405 Mg m⁻³
M_r = 667.51	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, Pbca	Cell parameters from 8118 reflections
a = 20.8602 (3) Å	θ = 4.2–66.8°
b = 8.76477 (12) Å	µ = 2.32 mm⁻¹
c = 34.5299 (7) Å	T = 293 K
V = 6313.29 (18) Å³	Needle, clear yellowish colourless
Z = 8	0.21 × 0.13 × 0.1 mm
F(000) = 2784

Data collection top

Rigaku Xcalibur Atlas Gemini ultra diffractometer	5569 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance Ultra (Cu) X-ray Source	4442 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.036
Detector resolution: 10.4674 pixels mm^-1	θ_max = 66.7°, θ_min = 4.2°
ω scans	h = −24→23
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2017)	k = −10→8
T_min = 0.584, T_max = 1.000	l = −35→40
26375 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.119	w = 1/[σ²(F_o²) + (0.0548P)² + 2.9645P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
5569 reflections	Δρ_max = 0.59 e Å⁻³
456 parameters	Δρ_min = −0.43 e Å⁻³
1 restraint

Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.20653 (9)	0.7466 (2)	0.28745 (5)	0.0743 (5)
N1	0.31989 (8)	0.3725 (2)	0.43172 (6)	0.0546 (5)
C1	0.13861 (15)	0.7503 (4)	0.29117 (9)	0.0790 (8)
H1A	0.1185	0.7261	0.2666	0.095*
H1B	0.1246	0.8511	0.2991	0.095*
O2	0.12120 (9)	0.6399 (3)	0.31969 (7)	0.0931 (7)
C2	0.22818 (12)	0.6637 (3)	0.31864 (7)	0.0597 (6)
O3	0.36147 (8)	0.1664 (2)	0.53532 (5)	0.0634 (4)
C3	0.28923 (13)	0.6410 (4)	0.33074 (8)	0.0731 (8)
H3	0.3237	0.6828	0.3173	0.088*
O4	0.26778 (9)	0.0309 (3)	0.57805 (6)	0.0835 (6)
C4	0.29886 (11)	0.5529 (3)	0.36404 (8)	0.0613 (6)
C5	0.3646 (2)	0.5486 (10)	0.38207 (16)	0.0646 (15)	0.754 (15)
H5A	0.3969	0.5584	0.3620	0.078*	0.754 (15)
H5B	0.3694	0.6339	0.3998	0.078*	0.754 (15)
C6	0.37436 (18)	0.4021 (9)	0.40355 (18)	0.0603 (14)	0.754 (15)
H6A	0.4145	0.4066	0.4176	0.072*	0.754 (15)
H6B	0.3770	0.3186	0.3852	0.072*	0.754 (15)
C5'	0.3652 (6)	0.469 (3)	0.3740 (5)	0.062 (4)	0.246 (15)
H5'A	0.3644	0.3644	0.3647	0.074*	0.246 (15)
H5'B	0.4008	0.5215	0.3618	0.074*	0.246 (15)
C6'	0.3720 (5)	0.472 (2)	0.4171 (5)	0.053 (4)	0.246 (15)
H6'A	0.4136	0.4336	0.4249	0.064*	0.246 (15)
H6'B	0.3671	0.5755	0.4268	0.064*	0.246 (15)
C7	0.33290 (10)	0.3004 (3)	0.46449 (7)	0.0541 (6)
H7	0.3754	0.2895	0.4720	0.065*
C8	0.28479 (10)	0.2404 (3)	0.48808 (7)	0.0501 (5)
C9	0.29935 (11)	0.1645 (3)	0.52303 (7)	0.0547 (6)
C10	0.25014 (12)	0.1001 (3)	0.54435 (7)	0.0615 (6)
C11	0.18636 (12)	0.1099 (3)	0.53090 (8)	0.0656 (7)
H11	0.1537	0.0633	0.5449	0.079*
C12	0.17175 (11)	0.1865 (3)	0.49775 (8)	0.0619 (6)
H12	0.1293	0.1931	0.4897	0.074*
C13	0.22017 (10)	0.2558 (3)	0.47552 (7)	0.0524 (5)
C14	0.20888 (10)	0.3415 (3)	0.44178 (7)	0.0544 (6)
H14	0.1667	0.3591	0.4343	0.065*
C15	0.25738 (10)	0.4002 (2)	0.41950 (7)	0.0507 (5)
C16	0.24759 (11)	0.4897 (3)	0.38397 (7)	0.0512 (5)
C17	0.18472 (12)	0.5143 (3)	0.37036 (9)	0.0684 (7)
H17	0.1495	0.4729	0.3831	0.082*
C18	0.17740 (12)	0.6005 (3)	0.33809 (8)	0.0633 (6)
C19	0.39266 (13)	0.0211 (3)	0.53690 (9)	0.0694 (7)
H19A	0.3870	−0.0309	0.5127	0.104*
H19B	0.3743	−0.0388	0.5574	0.104*
H19C	0.4376	0.0355	0.5417	0.104*
C20	0.21992 (17)	−0.0310 (5)	0.60255 (10)	0.1038 (12)
H20A	0.1932	−0.0992	0.5879	0.156*
H20B	0.1942	0.0501	0.6129	0.156*
H20C	0.2399	−0.0859	0.6234	0.156*
Cl1	0.67249 (3)	0.52358 (10)	0.28717 (2)	0.0869 (3)
Cl2	0.52752 (3)	0.16717 (7)	0.37853 (2)	0.0698 (2)
N2	0.57486 (9)	0.4642 (2)	0.34953 (5)	0.0453 (4)
H2	0.5653 (12)	0.455 (3)	0.3728 (8)	0.059 (7)*
O5	0.47800 (8)	0.71321 (19)	0.44586 (5)	0.0578 (4)
O6	0.53268 (10)	0.51079 (18)	0.42563 (5)	0.0650 (5)
C21	0.60135 (9)	0.3355 (2)	0.33154 (6)	0.0435 (5)
C22	0.64774 (10)	0.3456 (3)	0.30255 (7)	0.0546 (6)
C23	0.67595 (11)	0.2167 (4)	0.28633 (7)	0.0660 (7)
H23	0.7061	0.2269	0.2667	0.079*
C24	0.65913 (13)	0.0750 (4)	0.29941 (8)	0.0692 (7)
H24	0.6783	−0.0112	0.2888	0.083*
C25	0.61447 (12)	0.0598 (3)	0.32783 (8)	0.0631 (6)
H25	0.6033	−0.0365	0.3369	0.076*
C26	0.58573 (11)	0.1888 (3)	0.34325 (6)	0.0492 (5)
C27	0.53372 (9)	0.5663 (2)	0.33049 (6)	0.0414 (4)
C28	0.51014 (11)	0.5380 (3)	0.29349 (6)	0.0530 (5)
H28	0.5216	0.4487	0.2807	0.064*
C29	0.46983 (12)	0.6415 (3)	0.27558 (7)	0.0623 (7)
H29	0.4550	0.6223	0.2507	0.075*
C30	0.45164 (12)	0.7723 (3)	0.29445 (7)	0.0613 (6)
H30	0.4240	0.8412	0.2825	0.074*
C31	0.47466 (11)	0.8011 (3)	0.33132 (7)	0.0529 (5)
H31	0.4622	0.8899	0.3440	0.063*
C32	0.51597 (10)	0.7007 (2)	0.34994 (6)	0.0426 (5)
C33	0.54318 (11)	0.7399 (2)	0.38930 (6)	0.0476 (5)
H33A	0.5357	0.8475	0.3942	0.057*
H33B	0.5892	0.7241	0.3886	0.057*
C34	0.51536 (11)	0.6480 (2)	0.42320 (6)	0.0470 (5)
O2W	0.43186 (9)	0.0137 (3)	0.43829 (6)	0.0701 (5)
O1W	0.50921 (10)	0.7218 (2)	0.52578 (6)	0.0649 (5)
H1WA	0.4930 (15)	0.647 (4)	0.5385 (9)	0.081 (10)*
H2WA	0.4542 (16)	0.079 (4)	0.4491 (10)	0.086 (11)*
H1WB	0.4975 (16)	0.713 (4)	0.5027 (11)	0.090 (11)*
H2WB	0.4495 (17)	−0.076 (2)	0.4399 (11)	0.114 (14)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0730 (12)	0.0856 (13)	0.0645 (11)	−0.0028 (10)	0.0086 (9)	0.0006 (10)
N1	0.0351 (9)	0.0562 (11)	0.0726 (13)	−0.0052 (8)	0.0060 (8)	−0.0078 (10)
C1	0.0784 (19)	0.091 (2)	0.0672 (17)	0.0131 (17)	0.0137 (14)	0.0058 (16)
O2	0.0567 (11)	0.1235 (18)	0.0990 (15)	0.0064 (11)	0.0032 (10)	0.0357 (14)
C2	0.0607 (15)	0.0588 (14)	0.0596 (14)	−0.0021 (12)	0.0104 (11)	−0.0121 (12)
O3	0.0468 (9)	0.0689 (10)	0.0743 (11)	−0.0066 (8)	−0.0065 (8)	−0.0113 (9)
C3	0.0574 (16)	0.091 (2)	0.0707 (17)	−0.0161 (14)	0.0149 (13)	0.0007 (15)
O4	0.0610 (11)	0.1184 (17)	0.0711 (12)	−0.0047 (11)	0.0116 (9)	0.0099 (12)
C4	0.0459 (13)	0.0706 (15)	0.0674 (15)	−0.0072 (12)	0.0105 (11)	−0.0113 (13)
C5	0.0462 (19)	0.072 (4)	0.076 (3)	−0.011 (2)	0.0097 (17)	−0.010 (2)
C6	0.0378 (17)	0.069 (4)	0.074 (3)	−0.0051 (19)	0.0119 (17)	−0.011 (3)
C5'	0.048 (6)	0.060 (9)	0.078 (10)	−0.007 (7)	0.020 (6)	−0.010 (8)
C6'	0.037 (5)	0.051 (7)	0.071 (9)	−0.010 (5)	0.009 (5)	−0.011 (6)
C7	0.0353 (11)	0.0552 (13)	0.0720 (15)	−0.0026 (10)	0.0025 (10)	−0.0140 (12)
C8	0.0381 (11)	0.0477 (11)	0.0646 (14)	−0.0018 (9)	0.0055 (10)	−0.0170 (11)
C9	0.0426 (12)	0.0564 (13)	0.0651 (15)	−0.0028 (10)	0.0034 (10)	−0.0163 (11)
C10	0.0533 (13)	0.0696 (16)	0.0616 (14)	−0.0013 (12)	0.0070 (12)	−0.0095 (13)
C11	0.0456 (13)	0.0742 (16)	0.0769 (17)	−0.0025 (12)	0.0157 (12)	−0.0061 (14)
C12	0.0387 (12)	0.0692 (15)	0.0777 (17)	0.0008 (11)	0.0097 (11)	−0.0066 (14)
C13	0.0384 (11)	0.0503 (12)	0.0686 (15)	0.0002 (10)	0.0090 (10)	−0.0156 (11)
C14	0.0355 (11)	0.0563 (13)	0.0713 (15)	0.0010 (10)	0.0056 (10)	−0.0095 (12)
C15	0.0363 (11)	0.0462 (12)	0.0695 (14)	−0.0020 (9)	0.0063 (10)	−0.0140 (11)
C16	0.0419 (11)	0.0474 (12)	0.0644 (13)	−0.0030 (9)	0.0073 (10)	−0.0133 (11)
C17	0.0437 (13)	0.0764 (17)	0.0850 (18)	−0.0021 (12)	0.0099 (12)	0.0120 (15)
C18	0.0511 (14)	0.0665 (15)	0.0723 (17)	0.0033 (12)	0.0090 (12)	−0.0026 (13)
C19	0.0532 (14)	0.0758 (17)	0.0791 (18)	0.0019 (13)	−0.0113 (13)	−0.0098 (14)
C20	0.085 (2)	0.152 (4)	0.075 (2)	−0.018 (2)	0.0217 (17)	0.012 (2)
Cl1	0.0634 (4)	0.0979 (5)	0.0993 (5)	−0.0176 (4)	0.0135 (4)	0.0421 (4)
Cl2	0.0839 (4)	0.0485 (3)	0.0771 (4)	−0.0023 (3)	0.0342 (3)	0.0083 (3)
N2	0.0530 (11)	0.0461 (10)	0.0367 (9)	−0.0020 (8)	−0.0048 (8)	0.0060 (8)
O5	0.0641 (10)	0.0598 (9)	0.0495 (9)	−0.0032 (8)	0.0053 (8)	0.0009 (7)
O6	0.1025 (14)	0.0458 (9)	0.0466 (9)	−0.0011 (9)	0.0110 (8)	0.0095 (7)
C21	0.0386 (10)	0.0535 (12)	0.0385 (10)	−0.0013 (9)	−0.0038 (8)	0.0038 (9)
C22	0.0402 (11)	0.0753 (16)	0.0482 (12)	−0.0064 (11)	−0.0024 (9)	0.0124 (11)
C23	0.0405 (12)	0.106 (2)	0.0520 (13)	0.0089 (13)	0.0064 (10)	−0.0005 (14)
C24	0.0548 (14)	0.0791 (18)	0.0737 (17)	0.0129 (13)	0.0052 (12)	−0.0125 (15)
C25	0.0614 (15)	0.0551 (14)	0.0730 (16)	0.0065 (12)	0.0063 (13)	−0.0048 (12)
C26	0.0484 (12)	0.0501 (12)	0.0491 (12)	−0.0005 (10)	0.0034 (10)	0.0004 (10)
C27	0.0386 (10)	0.0469 (11)	0.0386 (10)	−0.0098 (9)	−0.0020 (8)	0.0082 (9)
C28	0.0496 (12)	0.0659 (14)	0.0435 (11)	−0.0051 (11)	−0.0054 (9)	−0.0001 (10)
C29	0.0540 (14)	0.0884 (19)	0.0446 (12)	−0.0048 (13)	−0.0119 (10)	0.0101 (13)
C30	0.0516 (13)	0.0757 (17)	0.0565 (14)	0.0022 (12)	−0.0073 (11)	0.0226 (13)
C31	0.0518 (13)	0.0514 (12)	0.0556 (13)	−0.0005 (10)	0.0020 (10)	0.0132 (10)
C32	0.0435 (11)	0.0436 (11)	0.0408 (10)	−0.0093 (9)	0.0002 (8)	0.0111 (9)
C33	0.0586 (13)	0.0388 (10)	0.0454 (11)	−0.0098 (10)	−0.0031 (10)	0.0027 (9)
C34	0.0568 (13)	0.0464 (12)	0.0378 (11)	−0.0095 (10)	−0.0060 (9)	0.0010 (9)
O2W	0.0473 (10)	0.0803 (14)	0.0827 (13)	−0.0017 (10)	−0.0077 (9)	0.0020 (11)
O1W	0.0757 (12)	0.0674 (11)	0.0515 (10)	−0.0184 (9)	−0.0014 (9)	0.0079 (9)

Geometric parameters (Å, º) top

O1—C1	1.423 (4)	C15—C16	1.470 (3)
O1—C2	1.376 (3)	C16—C17	1.410 (3)
N1—C6	1.518 (4)	C17—H17	0.9300
N1—C6'	1.484 (11)	C17—C18	1.355 (4)
N1—C7	1.324 (3)	C19—H19A	0.9600
N1—C15	1.392 (3)	C19—H19B	0.9600
C1—H1A	0.9700	C19—H19C	0.9600
C1—H1B	0.9700	C20—H20A	0.9600
C1—O2	1.428 (4)	C20—H20B	0.9600
O2—C18	1.377 (3)	C20—H20C	0.9600
C2—C3	1.355 (4)	Cl1—C22	1.727 (2)
C2—C18	1.371 (3)	Cl2—C26	1.730 (2)
O3—C9	1.364 (3)	N2—H2	0.83 (3)
O3—C19	1.431 (3)	N2—C21	1.402 (3)
C3—H3	0.9300	N2—C27	1.403 (3)
C3—C4	1.400 (4)	O5—C34	1.244 (3)
O4—C10	1.363 (3)	O6—C34	1.258 (3)
O4—C20	1.417 (4)	C21—C22	1.395 (3)
C4—C5	1.506 (5)	C21—C26	1.387 (3)
C4—C5'	1.604 (15)	C22—C23	1.392 (4)
C4—C16	1.387 (3)	C23—H23	0.9300
C5—H5A	0.9700	C23—C24	1.367 (4)
C5—H5B	0.9700	C24—H24	0.9300
C5—C6	1.497 (11)	C24—C25	1.360 (4)
C6—H6A	0.9700	C25—H25	0.9300
C6—H6B	0.9700	C25—C26	1.386 (3)
C5'—H5'A	0.9700	C27—C28	1.391 (3)
C5'—H5'B	0.9700	C27—C32	1.405 (3)
C5'—C6'	1.50 (3)	C28—H28	0.9300
C6'—H6'A	0.9700	C28—C29	1.382 (3)
C6'—H6'B	0.9700	C29—H29	0.9300
C7—H7	0.9300	C29—C30	1.373 (4)
C7—C8	1.395 (3)	C30—H30	0.9300
C8—C9	1.411 (4)	C30—C31	1.384 (3)
C8—C13	1.423 (3)	C31—H31	0.9300
C9—C10	1.384 (3)	C31—C32	1.389 (3)
C10—C11	1.412 (4)	C32—C33	1.513 (3)
C11—H11	0.9300	C33—H33A	0.9700
C11—C12	1.362 (4)	C33—H33B	0.9700
C12—H12	0.9300	C33—C34	1.535 (3)
C12—C13	1.407 (3)	O2W—H2WA	0.83 (3)
C13—C14	1.406 (4)	O2W—H2WB	0.868 (10)
C14—H14	0.9300	O1W—H1WA	0.86 (3)
C14—C15	1.371 (3)	O1W—H1WB	0.84 (4)

C2—O1—C1	105.6 (2)	N1—C15—C16	118.42 (19)
C7—N1—C6	118.4 (2)	C14—C15—N1	117.1 (2)
C7—N1—C6'	115.0 (6)	C14—C15—C16	124.5 (2)
C7—N1—C15	122.29 (19)	C4—C16—C15	121.3 (2)
C15—N1—C6	118.5 (3)	C4—C16—C17	119.4 (2)
C15—N1—C6'	118.7 (5)	C17—C16—C15	119.3 (2)
O1—C1—H1A	110.2	C16—C17—H17	121.2
O1—C1—H1B	110.2	C18—C17—C16	117.7 (2)
O1—C1—O2	107.5 (2)	C18—C17—H17	121.2
H1A—C1—H1B	108.5	C2—C18—O2	109.3 (2)
O2—C1—H1A	110.2	C17—C18—O2	128.0 (2)
O2—C1—H1B	110.2	C17—C18—C2	122.7 (2)
C18—O2—C1	105.8 (2)	O3—C19—H19A	109.5
C3—C2—O1	128.9 (2)	O3—C19—H19B	109.5
C3—C2—C18	121.1 (3)	O3—C19—H19C	109.5
C18—C2—O1	110.1 (2)	H19A—C19—H19B	109.5
C9—O3—C19	115.64 (18)	H19A—C19—H19C	109.5
C2—C3—H3	121.0	H19B—C19—H19C	109.5
C2—C3—C4	118.0 (2)	O4—C20—H20A	109.5
C4—C3—H3	121.0	O4—C20—H20B	109.5
C10—O4—C20	119.3 (2)	O4—C20—H20C	109.5
C3—C4—C5	118.9 (3)	H20A—C20—H20B	109.5
C3—C4—C5'	123.5 (6)	H20A—C20—H20C	109.5
C16—C4—C3	121.2 (2)	H20B—C20—H20C	109.5
C16—C4—C5	119.1 (3)	C21—N2—H2	116.4 (18)
C16—C4—C5'	112.1 (6)	C21—N2—C27	123.15 (18)
C4—C5—H5A	109.6	C27—N2—H2	111.6 (18)
C4—C5—H5B	109.6	C22—C21—N2	122.7 (2)
H5A—C5—H5B	108.1	C26—C21—N2	121.65 (18)
C6—C5—C4	110.5 (5)	C26—C21—C22	115.6 (2)
C6—C5—H5A	109.6	C21—C22—Cl1	119.07 (19)
C6—C5—H5B	109.6	C23—C22—Cl1	118.89 (18)
N1—C6—H6A	109.4	C23—C22—C21	122.0 (2)
N1—C6—H6B	109.4	C22—C23—H23	120.1
C5—C6—N1	111.2 (5)	C24—C23—C22	119.7 (2)
C5—C6—H6A	109.4	C24—C23—H23	120.1
C5—C6—H6B	109.4	C23—C24—H24	119.9
H6A—C6—H6B	108.0	C25—C24—C23	120.2 (3)
C4—C5'—H5'A	110.4	C25—C24—H24	119.9
C4—C5'—H5'B	110.4	C24—C25—H25	120.2
H5'A—C5'—H5'B	108.6	C24—C25—C26	119.6 (3)
C6'—C5'—C4	106.6 (14)	C26—C25—H25	120.2
C6'—C5'—H5'A	110.4	C21—C26—Cl2	118.13 (16)
C6'—C5'—H5'B	110.4	C25—C26—Cl2	119.01 (18)
N1—C6'—C5'	104.9 (15)	C25—C26—C21	122.9 (2)
N1—C6'—H6'A	110.8	N2—C27—C32	118.14 (18)
N1—C6'—H6'B	110.8	C28—C27—N2	122.2 (2)
C5'—C6'—H6'A	110.8	C28—C27—C32	119.6 (2)
C5'—C6'—H6'B	110.8	C27—C28—H28	119.7
H6'A—C6'—H6'B	108.8	C29—C28—C27	120.6 (2)
N1—C7—H7	119.0	C29—C28—H28	119.7
N1—C7—C8	122.1 (2)	C28—C29—H29	119.9
C8—C7—H7	119.0	C30—C29—C28	120.3 (2)
C7—C8—C9	121.5 (2)	C30—C29—H29	119.9
C7—C8—C13	117.9 (2)	C29—C30—H30	120.2
C9—C8—C13	120.6 (2)	C29—C30—C31	119.5 (2)
O3—C9—C8	117.7 (2)	C31—C30—H30	120.2
O3—C9—C10	123.0 (2)	C30—C31—H31	119.2
C10—C9—C8	119.2 (2)	C30—C31—C32	121.7 (2)
O4—C10—C9	115.8 (2)	C32—C31—H31	119.2
O4—C10—C11	124.2 (2)	C27—C32—C33	121.40 (18)
C9—C10—C11	119.9 (2)	C31—C32—C27	118.25 (19)
C10—C11—H11	119.4	C31—C32—C33	120.3 (2)
C12—C11—C10	121.2 (2)	C32—C33—H33A	108.5
C12—C11—H11	119.4	C32—C33—H33B	108.5
C11—C12—H12	119.6	C32—C33—C34	115.09 (17)
C11—C12—C13	120.7 (2)	H33A—C33—H33B	107.5
C13—C12—H12	119.6	C34—C33—H33A	108.5
C12—C13—C8	118.2 (2)	C34—C33—H33B	108.5
C14—C13—C8	117.5 (2)	O5—C34—O6	125.3 (2)
C14—C13—C12	124.2 (2)	O5—C34—C33	118.37 (19)
C13—C14—H14	118.6	O6—C34—C33	116.4 (2)
C15—C14—C13	122.8 (2)	H2WA—O2W—H2WB	111 (3)
C15—C14—H14	118.6	H1WA—O1W—H1WB	108 (3)

O1—C1—O2—C18	13.4 (3)	C11—C12—C13—C14	−177.6 (2)
O1—C2—C3—C4	179.0 (2)	C12—C13—C14—C15	−176.1 (2)
O1—C2—C18—O2	0.6 (3)	C13—C8—C9—O3	−173.79 (19)
O1—C2—C18—C17	−179.1 (2)	C13—C8—C9—C10	2.3 (3)
N1—C7—C8—C9	−179.7 (2)	C13—C14—C15—N1	−0.4 (3)
N1—C7—C8—C13	1.3 (3)	C13—C14—C15—C16	179.7 (2)
N1—C15—C16—C4	−3.6 (3)	C14—C15—C16—C4	176.3 (2)
N1—C15—C16—C17	177.8 (2)	C14—C15—C16—C17	−2.3 (3)
C1—O1—C2—C3	−172.1 (3)	C15—N1—C6—C5	42.9 (8)
C1—O1—C2—C18	7.8 (3)	C15—N1—C6'—C5'	−52.9 (19)
C1—O2—C18—C2	−8.7 (3)	C15—N1—C7—C8	3.3 (3)
C1—O2—C18—C17	171.0 (3)	C15—C16—C17—C18	178.4 (2)
C2—O1—C1—O2	−13.0 (3)	C16—C4—C5—C6	37.0 (8)
C2—C3—C4—C5	−169.4 (4)	C16—C4—C5'—C6'	−54.2 (18)
C2—C3—C4—C5'	158.4 (11)	C16—C17—C18—O2	−179.9 (3)
C2—C3—C4—C16	0.4 (4)	C16—C17—C18—C2	−0.2 (4)
O3—C9—C10—O4	−3.1 (4)	C18—C2—C3—C4	−0.9 (4)
O3—C9—C10—C11	176.3 (2)	C19—O3—C9—C8	−115.9 (2)
C3—C2—C18—O2	−179.5 (3)	C19—O3—C9—C10	68.2 (3)
C3—C2—C18—C17	0.8 (4)	C20—O4—C10—C9	176.8 (3)
C3—C4—C5—C6	−153.0 (5)	C20—O4—C10—C11	−2.6 (4)
C3—C4—C5'—C6'	146.0 (10)	Cl1—C22—C23—C24	177.0 (2)
C3—C4—C16—C15	−178.5 (2)	N2—C21—C22—Cl1	−1.6 (3)
C3—C4—C16—C17	0.2 (4)	N2—C21—C22—C23	176.7 (2)
O4—C10—C11—C12	177.2 (3)	N2—C21—C26—Cl2	4.9 (3)
C4—C5—C6—N1	−51.9 (9)	N2—C21—C26—C25	−175.4 (2)
C4—C5'—C6'—N1	67 (2)	N2—C27—C28—C29	−179.8 (2)
C4—C16—C17—C18	−0.3 (4)	N2—C27—C32—C31	−179.28 (18)
C5—C4—C16—C15	−8.7 (5)	N2—C27—C32—C33	3.5 (3)
C5—C4—C16—C17	170.0 (4)	C21—N2—C27—C28	7.5 (3)
C6—N1—C7—C8	−166.3 (4)	C21—N2—C27—C32	−172.76 (18)
C6—N1—C15—C14	165.8 (4)	C21—C22—C23—C24	−1.3 (4)
C6—N1—C15—C16	−14.2 (5)	C22—C21—C26—Cl2	−178.90 (16)
C5'—C4—C16—C15	21.2 (10)	C22—C21—C26—C25	0.8 (3)
C5'—C4—C16—C17	−160.1 (10)	C22—C23—C24—C25	0.8 (4)
C6'—N1—C7—C8	160.4 (10)	C23—C24—C25—C26	0.5 (4)
C6'—N1—C15—C14	−160.1 (10)	C24—C25—C26—Cl2	178.4 (2)
C6'—N1—C15—C16	19.8 (11)	C24—C25—C26—C21	−1.4 (4)
C7—N1—C6—C5	−147.1 (5)	C26—C21—C22—Cl1	−177.79 (16)
C7—N1—C6'—C5'	149.1 (11)	C26—C21—C22—C23	0.5 (3)
C7—N1—C15—C14	−3.8 (3)	C27—N2—C21—C22	69.4 (3)
C7—N1—C15—C16	176.1 (2)	C27—N2—C21—C26	−114.6 (2)
C7—C8—C9—O3	7.3 (3)	C27—C28—C29—C30	−1.2 (4)
C7—C8—C9—C10	−176.7 (2)	C27—C32—C33—C34	−75.2 (3)
C7—C8—C13—C12	175.7 (2)	C28—C27—C32—C31	0.4 (3)
C7—C8—C13—C14	−5.1 (3)	C28—C27—C32—C33	−176.77 (19)
C8—C9—C10—O4	−179.0 (2)	C28—C29—C30—C31	0.9 (4)
C8—C9—C10—C11	0.5 (4)	C29—C30—C31—C32	0.0 (4)
C8—C13—C14—C15	4.7 (3)	C30—C31—C32—C27	−0.7 (3)
C9—C8—C13—C12	−3.3 (3)	C30—C31—C32—C33	176.5 (2)
C9—C8—C13—C14	175.9 (2)	C31—C32—C33—C34	107.6 (2)
C9—C10—C11—C12	−2.2 (4)	C32—C27—C28—C29	0.5 (3)
C10—C11—C12—C13	1.2 (4)	C32—C33—C34—O5	−107.0 (2)
C11—C12—C13—C8	1.5 (4)	C32—C33—C34—O6	72.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O6	0.83 (3)	2.01 (3)	2.801 (2)	159 (3)
O1W—H1WA···O6ⁱ	0.86 (3)	1.94 (4)	2.781 (3)	170 (3)
O2W—H2WA···O1Wⁱ	0.83 (3)	2.09 (4)	2.902 (3)	166 (3)
O1W—H1WB···O5	0.84 (4)	2.00 (4)	2.836 (3)	172 (3)
O2W—H2WB···O5ⁱⁱ	0.87 (1)	1.95 (1)	2.816 (3)	172 (4)

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

5,6-Dihydro-9,10-dimethoxybenzo[g][1,3]benzodioxolo[5,6-a]quinolizinium 2-[2-(2,6-dichloroanilino)phenyl]acetate dichloromethane hemisolvate dihydrate (II) top

Crystal data top

C₂₀H₁₈NO₄⁺·C₁₄H₁₀Cl₂NO₂⁻·0.5CH₂Cl₂·2H₂O	F(000) = 2952
M_r = 709.98	D_x = 1.455 Mg m⁻³
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54184 Å
a = 24.0513 (3) Å	Cell parameters from 15996 reflections
b = 7.23787 (8) Å	θ = 3.6–66.6°
c = 37.2921 (4) Å	µ = 3.04 mm⁻¹
β = 93.1167 (10)°	T = 114 K
V = 6482.22 (12) Å³	Block, clear yellowish yellow
Z = 8	0.22 × 0.18 × 0.15 mm

Data collection top

Rigaku Xcalibur Atlas Gemini ultra diffractometer	5684 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance Ultra (Cu) X-ray Source	5282 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.031
Detector resolution: 10.4674 pixels mm^-1	θ_max = 66.7°, θ_min = 3.7°
ω scans	h = −28→28
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2018)	k = −6→8
T_min = 0.196, T_max = 1.000	l = −44→42
29742 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.085	w = 1/[σ²(F_o²) + (0.0413P)² + 7.2555P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
5684 reflections	Δρ_max = 0.36 e Å⁻³
460 parameters	Δρ_min = −0.64 e Å⁻³
0 restraints

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.32070 (5)	0.86503 (19)	0.62460 (3)	0.0320 (3)
N1	0.55134 (5)	0.80135 (17)	0.54724 (3)	0.0158 (3)
C1	0.27599 (7)	0.8633 (3)	0.59709 (5)	0.0319 (4)
H1A	0.2548	0.7463	0.5981	0.038*
H1B	0.2502	0.9673	0.6007	0.038*
O2	0.30026 (5)	0.88025 (19)	0.56316 (3)	0.0303 (3)
C2	0.36855 (7)	0.8474 (2)	0.60664 (4)	0.0224 (3)
O3	0.68437 (4)	0.69752 (15)	0.48353 (3)	0.0210 (2)
C3	0.42211 (7)	0.8278 (2)	0.62077 (4)	0.0220 (3)
H3	0.4302	0.8243	0.6460	0.026*
O4	0.66652 (4)	0.63053 (18)	0.41309 (3)	0.0271 (3)
C4	0.46430 (6)	0.8131 (2)	0.59649 (4)	0.0184 (3)
C5	0.52376 (6)	0.7804 (2)	0.60969 (4)	0.0205 (3)
H5A	0.5310	0.6459	0.6112	0.025*
H5B	0.5301	0.8334	0.6340	0.025*
C6	0.56319 (6)	0.8685 (2)	0.58454 (4)	0.0191 (3)
H6A	0.5590	1.0045	0.5852	0.023*
H6B	0.6021	0.8379	0.5924	0.023*
C7	0.59376 (6)	0.7653 (2)	0.52714 (4)	0.0165 (3)
H7	0.6306	0.7717	0.5376	0.020*
C8	0.58555 (6)	0.7180 (2)	0.49082 (4)	0.0164 (3)
C9	0.63095 (6)	0.6855 (2)	0.46906 (4)	0.0177 (3)
C10	0.62092 (6)	0.6540 (2)	0.43281 (4)	0.0196 (3)
C11	0.56544 (6)	0.6449 (2)	0.41815 (4)	0.0203 (3)
H11	0.5589	0.6203	0.3933	0.024*
C12	0.52100 (6)	0.6709 (2)	0.43903 (4)	0.0183 (3)
H12	0.4842	0.6615	0.4286	0.022*
C13	0.52969 (6)	0.7116 (2)	0.47593 (4)	0.0163 (3)
C14	0.48614 (6)	0.7448 (2)	0.49871 (4)	0.0162 (3)
H14	0.4488	0.7357	0.4892	0.019*
C15	0.49590 (6)	0.7899 (2)	0.53415 (4)	0.0157 (3)
C16	0.45192 (6)	0.8210 (2)	0.55937 (4)	0.0167 (3)
C17	0.39638 (6)	0.8452 (2)	0.54551 (4)	0.0188 (3)
H17	0.3874	0.8534	0.5204	0.023*
C18	0.35648 (6)	0.8560 (2)	0.56992 (4)	0.0209 (3)
C19	0.70655 (7)	0.5251 (2)	0.49746 (5)	0.0284 (4)
H19A	0.7053	0.4324	0.4783	0.043*
H19B	0.6842	0.4826	0.5171	0.043*
H19C	0.7452	0.5432	0.5065	0.043*
C20	0.65902 (7)	0.6365 (3)	0.37471 (4)	0.0274 (4)
H20A	0.6954	0.6309	0.3642	0.041*
H20B	0.6402	0.7516	0.3674	0.041*
H20C	0.6363	0.5309	0.3663	0.041*
Cl1	0.36052 (2)	0.58891 (5)	0.23298 (2)	0.02558 (11)
Cl2	0.30026 (2)	0.03455 (6)	0.32016 (2)	0.03537 (12)
N2	0.34918 (5)	0.40033 (19)	0.30521 (4)	0.0209 (3)
H2	0.3332 (9)	0.366 (3)	0.3241 (6)	0.032 (5)*
O5	0.37696 (5)	0.53379 (17)	0.42094 (3)	0.0300 (3)
O6	0.32836 (5)	0.37124 (17)	0.37911 (3)	0.0268 (3)
C21	0.33443 (6)	0.2961 (2)	0.27474 (4)	0.0198 (3)
C22	0.31037 (6)	0.1205 (2)	0.27748 (4)	0.0232 (3)
C23	0.29387 (7)	0.0148 (2)	0.24791 (5)	0.0283 (4)
H23	0.2778	−0.1037	0.2510	0.034*
C24	0.30102 (7)	0.0834 (3)	0.21383 (5)	0.0317 (4)
H24	0.2907	0.0108	0.1933	0.038*
C25	0.32319 (7)	0.2579 (3)	0.20969 (4)	0.0274 (4)
H25	0.3278	0.3059	0.1863	0.033*
C26	0.33872 (6)	0.3625 (2)	0.23965 (4)	0.0218 (3)
C27	0.40312 (6)	0.4730 (2)	0.31203 (4)	0.0187 (3)
C28	0.44843 (7)	0.4113 (2)	0.29359 (4)	0.0224 (3)
H28	0.4433	0.3168	0.2760	0.027*
C29	0.50098 (7)	0.4869 (3)	0.30063 (4)	0.0259 (4)
H29	0.5317	0.4430	0.2881	0.031*
C30	0.50880 (7)	0.6255 (3)	0.32584 (4)	0.0281 (4)
H30	0.5445	0.6801	0.3302	0.034*
C31	0.46386 (7)	0.6843 (2)	0.34483 (4)	0.0249 (3)
H31	0.4694	0.7788	0.3624	0.030*
C32	0.41097 (7)	0.6087 (2)	0.33888 (4)	0.0207 (3)
C33	0.36386 (7)	0.6630 (2)	0.36182 (4)	0.0237 (3)
H33A	0.3292	0.6791	0.3465	0.028*
H33B	0.3726	0.7818	0.3740	0.028*
C34	0.35550 (6)	0.5118 (2)	0.38989 (4)	0.0231 (3)
Cl3	0.5479 (2)	0.0034 (6)	0.27154 (11)	0.0624 (12)	0.5
Cl3'	0.55312 (16)	0.0168 (5)	0.27550 (7)	0.0303 (5)	0.5
C35	0.5000	−0.1100 (5)	0.2500	0.120 (3)
H35B	0.4812	−0.1913	0.2669	0.144*	0.5
H35A	0.5188	−0.1913	0.2331	0.144*	0.5
O2W	0.36144 (6)	0.85088 (19)	0.45863 (3)	0.0291 (3)
O1W	0.28849 (5)	1.1056 (2)	0.42261 (4)	0.0357 (3)
H2WA	0.3648 (9)	0.750 (4)	0.4452 (6)	0.042 (6)*
H1WA	0.3000 (11)	1.193 (4)	0.4084 (7)	0.054 (7)*
H2WB	0.3367 (11)	0.916 (4)	0.4483 (7)	0.047 (7)*
H1WB	0.2552 (12)	1.134 (4)	0.4285 (7)	0.054 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0210 (6)	0.0531 (8)	0.0225 (6)	0.0085 (5)	0.0073 (5)	0.0030 (5)
N1	0.0158 (6)	0.0158 (6)	0.0156 (6)	−0.0003 (5)	−0.0012 (5)	0.0011 (5)
C1	0.0193 (8)	0.0508 (11)	0.0262 (8)	0.0047 (8)	0.0061 (7)	0.0004 (8)
O2	0.0158 (5)	0.0515 (8)	0.0239 (6)	0.0096 (5)	0.0036 (4)	0.0057 (5)
C2	0.0204 (8)	0.0252 (8)	0.0222 (8)	0.0034 (6)	0.0072 (6)	0.0021 (6)
O3	0.0133 (5)	0.0249 (6)	0.0246 (5)	−0.0018 (4)	−0.0018 (4)	0.0012 (4)
C3	0.0247 (8)	0.0251 (8)	0.0164 (7)	0.0026 (6)	0.0019 (6)	0.0017 (6)
O4	0.0174 (5)	0.0458 (7)	0.0183 (5)	0.0019 (5)	0.0044 (4)	−0.0019 (5)
C4	0.0194 (7)	0.0170 (7)	0.0187 (7)	0.0000 (6)	0.0003 (6)	0.0010 (6)
C5	0.0197 (8)	0.0257 (8)	0.0159 (7)	0.0013 (6)	−0.0006 (6)	0.0000 (6)
C6	0.0180 (7)	0.0237 (8)	0.0153 (7)	−0.0003 (6)	−0.0021 (6)	−0.0028 (6)
C7	0.0138 (7)	0.0165 (7)	0.0191 (7)	−0.0009 (5)	−0.0009 (5)	0.0024 (6)
C8	0.0170 (7)	0.0138 (7)	0.0183 (7)	−0.0018 (6)	−0.0003 (6)	0.0025 (6)
C9	0.0144 (7)	0.0174 (7)	0.0210 (7)	−0.0018 (6)	−0.0009 (6)	0.0022 (6)
C10	0.0173 (7)	0.0219 (8)	0.0200 (7)	0.0005 (6)	0.0040 (6)	0.0003 (6)
C11	0.0207 (8)	0.0224 (8)	0.0176 (7)	0.0001 (6)	−0.0004 (6)	−0.0002 (6)
C12	0.0167 (7)	0.0197 (7)	0.0182 (7)	0.0002 (6)	−0.0020 (6)	0.0005 (6)
C13	0.0162 (7)	0.0143 (7)	0.0182 (7)	0.0002 (5)	−0.0008 (6)	0.0030 (6)
C14	0.0146 (7)	0.0157 (7)	0.0181 (7)	−0.0004 (6)	−0.0012 (6)	0.0022 (6)
C15	0.0149 (7)	0.0138 (7)	0.0183 (7)	0.0005 (5)	−0.0011 (6)	0.0034 (6)
C16	0.0183 (7)	0.0143 (7)	0.0176 (7)	0.0003 (6)	0.0011 (6)	0.0013 (6)
C17	0.0191 (7)	0.0195 (7)	0.0176 (7)	0.0024 (6)	0.0000 (6)	0.0025 (6)
C18	0.0171 (7)	0.0229 (8)	0.0225 (8)	0.0046 (6)	0.0007 (6)	0.0029 (6)
C19	0.0185 (8)	0.0319 (9)	0.0342 (9)	−0.0001 (7)	−0.0054 (7)	0.0088 (7)
C20	0.0241 (8)	0.0401 (10)	0.0185 (8)	0.0000 (7)	0.0062 (6)	−0.0021 (7)
Cl1	0.0275 (2)	0.0258 (2)	0.02382 (19)	0.00025 (15)	0.00468 (15)	0.00455 (15)
Cl2	0.0402 (2)	0.0317 (2)	0.0337 (2)	−0.00777 (18)	−0.00187 (18)	0.01303 (18)
N2	0.0186 (6)	0.0265 (7)	0.0180 (6)	−0.0012 (5)	0.0042 (5)	0.0002 (5)
O5	0.0383 (7)	0.0329 (7)	0.0188 (6)	0.0114 (5)	0.0017 (5)	0.0011 (5)
O6	0.0240 (6)	0.0327 (7)	0.0243 (6)	0.0016 (5)	0.0067 (5)	0.0038 (5)
C21	0.0141 (7)	0.0227 (8)	0.0227 (8)	0.0035 (6)	0.0009 (6)	−0.0005 (6)
C22	0.0164 (7)	0.0244 (8)	0.0287 (8)	0.0024 (6)	0.0016 (6)	0.0036 (7)
C23	0.0187 (8)	0.0249 (9)	0.0412 (10)	−0.0008 (6)	0.0013 (7)	−0.0040 (7)
C24	0.0252 (8)	0.0380 (10)	0.0318 (9)	−0.0004 (8)	0.0013 (7)	−0.0132 (8)
C25	0.0246 (8)	0.0354 (10)	0.0224 (8)	0.0022 (7)	0.0031 (6)	−0.0035 (7)
C26	0.0177 (7)	0.0234 (8)	0.0245 (8)	0.0014 (6)	0.0034 (6)	0.0008 (6)
C27	0.0186 (7)	0.0219 (8)	0.0156 (7)	0.0007 (6)	0.0000 (6)	0.0054 (6)
C28	0.0227 (8)	0.0263 (8)	0.0184 (7)	0.0017 (6)	0.0024 (6)	0.0023 (6)
C29	0.0191 (8)	0.0382 (10)	0.0205 (7)	0.0005 (7)	0.0029 (6)	0.0075 (7)
C30	0.0240 (8)	0.0397 (10)	0.0202 (8)	−0.0097 (7)	−0.0013 (6)	0.0086 (7)
C31	0.0326 (9)	0.0257 (8)	0.0161 (7)	−0.0053 (7)	−0.0027 (6)	0.0034 (6)
C32	0.0257 (8)	0.0200 (8)	0.0164 (7)	0.0028 (6)	0.0001 (6)	0.0057 (6)
C33	0.0272 (8)	0.0239 (8)	0.0200 (7)	0.0068 (7)	0.0009 (6)	0.0000 (6)
C34	0.0194 (8)	0.0281 (9)	0.0224 (8)	0.0115 (7)	0.0075 (6)	0.0016 (7)
Cl3	0.0406 (11)	0.0478 (18)	0.097 (2)	−0.0065 (10)	−0.0146 (12)	0.0341 (15)
Cl3'	0.0374 (13)	0.0262 (9)	0.0272 (6)	−0.0051 (7)	0.0000 (6)	0.0000 (6)
C35	0.221 (7)	0.0301 (18)	0.094 (3)	0.000	−0.119 (4)	0.000
O2W	0.0341 (7)	0.0266 (7)	0.0254 (6)	−0.0001 (5)	−0.0086 (5)	0.0006 (5)
O1W	0.0190 (6)	0.0453 (8)	0.0429 (7)	0.0027 (6)	0.0035 (5)	0.0176 (6)

Geometric parameters (Å, º) top

O1—C1	1.445 (2)	C20—H20A	0.9800
O1—C2	1.3686 (19)	C20—H20B	0.9800
N1—C6	1.4862 (18)	C20—H20C	0.9800
N1—C7	1.324 (2)	Cl1—C26	1.7423 (17)
N1—C15	1.3972 (19)	Cl2—C22	1.7383 (17)
C1—H1A	0.9900	N2—H2	0.86 (2)
C1—H1B	0.9900	N2—C21	1.394 (2)
C1—O2	1.427 (2)	N2—C27	1.410 (2)
O2—C18	1.3733 (19)	O5—C34	1.252 (2)
C2—C3	1.372 (2)	O6—C34	1.263 (2)
C2—C18	1.386 (2)	C21—C22	1.403 (2)
O3—C9	1.3691 (18)	C21—C26	1.403 (2)
O3—C19	1.443 (2)	C22—C23	1.382 (2)
C3—H3	0.9500	C23—H23	0.9500
C3—C4	1.400 (2)	C23—C24	1.384 (3)
O4—C10	1.3640 (19)	C24—H24	0.9500
O4—C20	1.4333 (19)	C24—C25	1.383 (3)
C4—C5	1.506 (2)	C25—H25	0.9500
C4—C16	1.401 (2)	C25—C26	1.384 (2)
C5—H5A	0.9900	C27—C28	1.393 (2)
C5—H5B	0.9900	C27—C32	1.408 (2)
C5—C6	1.511 (2)	C28—H28	0.9500
C6—H6A	0.9900	C28—C29	1.389 (2)
C6—H6B	0.9900	C29—H29	0.9500
C7—H7	0.9500	C29—C30	1.381 (3)
C7—C8	1.401 (2)	C30—H30	0.9500
C8—C9	1.415 (2)	C30—C31	1.391 (3)
C8—C13	1.426 (2)	C31—H31	0.9500
C9—C10	1.379 (2)	C31—C32	1.392 (2)
C10—C11	1.416 (2)	C32—C33	1.508 (2)
C11—H11	0.9500	C33—H33A	0.9900
C11—C12	1.369 (2)	C33—H33B	0.9900
C12—H12	0.9500	C33—C34	1.535 (2)
C12—C13	1.412 (2)	Cl3—C35	1.595 (5)
C13—C14	1.405 (2)	Cl3'—C35	1.802 (4)
C14—H14	0.9500	C35—Cl3ⁱ	1.595 (5)
C14—C15	1.369 (2)	C35—Cl3'ⁱ	1.802 (4)
C15—C16	1.471 (2)	C35—H35B	0.9900
C16—C17	1.417 (2)	C35—H35A	0.9900
C17—H17	0.9500	O2W—H2WA	0.89 (3)
C17—C18	1.360 (2)	O2W—H2WB	0.83 (3)
C19—H19A	0.9800	O1W—H1WA	0.88 (3)
C19—H19B	0.9800	O1W—H1WB	0.87 (3)
C19—H19C	0.9800

C2—O1—C1	105.36 (12)	O3—C19—H19A	109.5
C7—N1—C6	118.65 (12)	O3—C19—H19B	109.5
C7—N1—C15	122.70 (12)	O3—C19—H19C	109.5
C15—N1—C6	118.52 (12)	H19A—C19—H19B	109.5
O1—C1—H1A	110.2	H19A—C19—H19C	109.5
O1—C1—H1B	110.2	H19B—C19—H19C	109.5
H1A—C1—H1B	108.5	O4—C20—H20A	109.5
O2—C1—O1	107.71 (13)	O4—C20—H20B	109.5
O2—C1—H1A	110.2	O4—C20—H20C	109.5
O2—C1—H1B	110.2	H20A—C20—H20B	109.5
C18—O2—C1	105.79 (12)	H20A—C20—H20C	109.5
O1—C2—C3	128.20 (14)	H20B—C20—H20C	109.5
O1—C2—C18	110.05 (14)	C21—N2—H2	114.2 (14)
C3—C2—C18	121.73 (14)	C21—N2—C27	122.67 (13)
C9—O3—C19	114.04 (12)	C27—N2—H2	114.1 (14)
C2—C3—H3	121.4	N2—C21—C22	121.25 (14)
C2—C3—C4	117.24 (14)	N2—C21—C26	123.13 (15)
C4—C3—H3	121.4	C22—C21—C26	115.48 (14)
C10—O4—C20	118.25 (12)	C21—C22—Cl2	118.02 (12)
C3—C4—C5	120.63 (13)	C23—C22—Cl2	118.95 (13)
C3—C4—C16	120.87 (14)	C23—C22—C21	123.03 (15)
C16—C4—C5	118.44 (13)	C22—C23—H23	120.4
C4—C5—H5A	109.6	C22—C23—C24	119.29 (16)
C4—C5—H5B	109.6	C24—C23—H23	120.4
C4—C5—C6	110.36 (12)	C23—C24—H24	120.1
H5A—C5—H5B	108.1	C25—C24—C23	119.89 (16)
C6—C5—H5A	109.6	C25—C24—H24	120.1
C6—C5—H5B	109.6	C24—C25—H25	120.1
N1—C6—C5	110.35 (12)	C24—C25—C26	119.89 (16)
N1—C6—H6A	109.6	C26—C25—H25	120.1
N1—C6—H6B	109.6	C21—C26—Cl1	119.57 (12)
C5—C6—H6A	109.6	C25—C26—Cl1	117.99 (13)
C5—C6—H6B	109.6	C25—C26—C21	122.34 (15)
H6A—C6—H6B	108.1	C28—C27—N2	121.89 (14)
N1—C7—H7	119.2	C28—C27—C32	119.75 (14)
N1—C7—C8	121.54 (13)	C32—C27—N2	118.35 (14)
C8—C7—H7	119.2	C27—C28—H28	119.7
C7—C8—C9	121.51 (13)	C29—C28—C27	120.58 (15)
C7—C8—C13	117.69 (13)	C29—C28—H28	119.7
C9—C8—C13	120.74 (13)	C28—C29—H29	119.9
O3—C9—C8	120.01 (13)	C30—C29—C28	120.24 (16)
O3—C9—C10	120.49 (13)	C30—C29—H29	119.9
C10—C9—C8	119.36 (13)	C29—C30—H30	120.4
O4—C10—C9	116.49 (13)	C29—C30—C31	119.22 (15)
O4—C10—C11	123.69 (13)	C31—C30—H30	120.4
C9—C10—C11	119.81 (14)	C30—C31—H31	119.1
C10—C11—H11	119.2	C30—C31—C32	121.82 (15)
C12—C11—C10	121.52 (14)	C32—C31—H31	119.1
C12—C11—H11	119.2	C27—C32—C33	120.62 (14)
C11—C12—H12	119.9	C31—C32—C27	118.30 (15)
C11—C12—C13	120.26 (14)	C31—C32—C33	121.00 (14)
C13—C12—H12	119.9	C32—C33—H33A	109.8
C12—C13—C8	118.22 (13)	C32—C33—H33B	109.8
C14—C13—C8	118.45 (13)	C32—C33—C34	109.33 (13)
C14—C13—C12	123.33 (13)	H33A—C33—H33B	108.3
C13—C14—H14	119.0	C34—C33—H33A	109.8
C15—C14—C13	122.02 (13)	C34—C33—H33B	109.8
C15—C14—H14	119.0	O5—C34—O6	125.23 (15)
N1—C15—C16	118.25 (12)	O5—C34—C33	118.51 (15)
C14—C15—N1	117.51 (13)	O6—C34—C33	116.23 (14)
C14—C15—C16	124.21 (13)	Cl3ⁱ—C35—Cl3	118.1 (4)
C4—C16—C15	120.27 (13)	Cl3'—C35—Cl3'ⁱ	118.8 (3)
C4—C16—C17	120.73 (14)	Cl3'ⁱ—C35—H35B	107.6
C17—C16—C15	118.84 (13)	Cl3'—C35—H35B	107.6
C16—C17—H17	121.7	Cl3'ⁱ—C35—H35A	107.6
C18—C17—C16	116.64 (14)	Cl3'—C35—H35A	107.6
C18—C17—H17	121.7	H35B—C35—H35A	107.1
O2—C18—C2	109.78 (13)	H2WA—O2W—H2WB	107 (2)
C17—C18—O2	127.43 (14)	H1WA—O1W—H1WB	108 (2)
C17—C18—C2	122.77 (14)

O1—C1—O2—C18	11.20 (19)	C13—C14—C15—N1	−0.2 (2)
O1—C2—C3—C4	−179.69 (16)	C13—C14—C15—C16	−178.25 (14)
O1—C2—C18—O2	0.2 (2)	C14—C15—C16—C4	161.35 (15)
O1—C2—C18—C17	178.95 (15)	C14—C15—C16—C17	−14.0 (2)
N1—C7—C8—C9	177.90 (14)	C15—N1—C6—C5	43.91 (17)
N1—C7—C8—C13	0.6 (2)	C15—N1—C7—C8	1.9 (2)
N1—C15—C16—C4	−16.7 (2)	C15—C16—C17—C18	173.97 (14)
N1—C15—C16—C17	167.99 (13)	C16—C4—C5—C6	33.28 (19)
C1—O1—C2—C3	−174.66 (18)	C16—C17—C18—O2	179.56 (15)
C1—O1—C2—C18	6.72 (19)	C16—C17—C18—C2	1.1 (2)
C1—O2—C18—C2	−7.18 (19)	C18—C2—C3—C4	−1.2 (2)
C1—O2—C18—C17	174.18 (17)	C19—O3—C9—C8	91.12 (17)
C2—O1—C1—O2	−11.04 (19)	C19—O3—C9—C10	−93.26 (17)
C2—C3—C4—C5	−176.48 (15)	C20—O4—C10—C9	−167.06 (15)
C2—C3—C4—C16	0.9 (2)	C20—O4—C10—C11	13.8 (2)
O3—C9—C10—O4	1.9 (2)	Cl2—C22—C23—C24	179.04 (13)
O3—C9—C10—C11	−178.94 (14)	N2—C21—C22—Cl2	−0.85 (19)
C3—C2—C18—O2	−178.50 (15)	N2—C21—C22—C23	178.32 (15)
C3—C2—C18—C17	0.2 (3)	N2—C21—C26—Cl1	−2.9 (2)
C3—C4—C5—C6	−149.29 (15)	N2—C21—C26—C25	−179.14 (15)
C3—C4—C16—C15	−174.86 (14)	N2—C27—C28—C29	179.32 (14)
C3—C4—C16—C17	0.4 (2)	N2—C27—C32—C31	−178.06 (14)
O4—C10—C11—C12	−179.46 (15)	N2—C27—C32—C33	5.1 (2)
C4—C5—C6—N1	−54.87 (17)	C21—N2—C27—C28	−15.2 (2)
C4—C16—C17—C18	−1.4 (2)	C21—N2—C27—C32	166.19 (14)
C5—C4—C16—C15	2.6 (2)	C21—C22—C23—C24	−0.1 (2)
C5—C4—C16—C17	177.83 (14)	C22—C21—C26—Cl1	172.75 (11)
C6—N1—C7—C8	−174.04 (13)	C22—C21—C26—C25	−3.5 (2)
C6—N1—C15—C14	173.85 (13)	C22—C23—C24—C25	−1.6 (2)
C6—N1—C15—C16	−8.01 (19)	C23—C24—C25—C26	0.7 (3)
C7—N1—C6—C5	−140.01 (13)	C24—C25—C26—Cl1	−174.32 (13)
C7—N1—C15—C14	−2.1 (2)	C24—C25—C26—C21	2.0 (2)
C7—N1—C15—C16	176.07 (13)	C26—C21—C22—Cl2	−176.60 (11)
C7—C8—C9—O3	0.9 (2)	C26—C21—C22—C23	2.6 (2)
C7—C8—C9—C10	−174.80 (14)	C27—N2—C21—C22	126.08 (16)
C7—C8—C13—C12	177.65 (14)	C27—N2—C21—C26	−58.5 (2)
C7—C8—C13—C14	−2.7 (2)	C27—C28—C29—C30	−0.6 (2)
C8—C9—C10—O4	177.57 (14)	C27—C32—C33—C34	75.84 (18)
C8—C9—C10—C11	−3.3 (2)	C28—C27—C32—C31	3.3 (2)
C8—C13—C14—C15	2.6 (2)	C28—C27—C32—C33	−173.56 (14)
C9—C8—C13—C12	0.3 (2)	C28—C29—C30—C31	2.0 (2)
C9—C8—C13—C14	179.96 (14)	C29—C30—C31—C32	−0.7 (2)
C9—C10—C11—C12	1.5 (2)	C30—C31—C32—C27	−1.9 (2)
C10—C11—C12—C13	1.3 (2)	C30—C31—C32—C33	174.93 (14)
C11—C12—C13—C8	−2.2 (2)	C31—C32—C33—C34	−100.95 (17)
C11—C12—C13—C14	178.21 (15)	C32—C27—C28—C29	−2.1 (2)
C12—C13—C14—C15	−177.82 (14)	C32—C33—C34—O5	97.98 (16)
C13—C8—C9—O3	178.08 (13)	C32—C33—C34—O6	−80.09 (17)
C13—C8—C9—C10	2.4 (2)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O6	0.86 (2)	2.06 (2)	2.8354 (18)	150.0 (19)
O2W—H2WA···O5	0.89 (3)	1.84 (3)	2.7275 (18)	174 (2)
O1W—H1WA···O6ⁱⁱ	0.88 (3)	1.84 (3)	2.7233 (18)	177 (3)
O2W—H2WB···O1W	0.83 (3)	2.01 (3)	2.8330 (19)	170 (2)
O1W—H1WB···O4ⁱⁱⁱ	0.87 (3)	2.18 (3)	2.9412 (17)	147 (2)

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

5,6-Dihydro-9,10-dimethoxybenzo[g][1,3]benzodioxolo[5,6-a]quinolizinium 2-[2-(2,6-dichloroanilino)phenyl]acetate ethanol monosolvate (III) top

Crystal data top

C₂₀H₁₈NO₄⁺·C₁₄H₁₀Cl₂NO₂⁻·C₂H₆O	F(000) = 1416
M_r = 677.55	D_x = 1.365 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54184 Å
a = 8.15748 (18) Å	Cell parameters from 8049 reflections
b = 15.9353 (3) Å	θ = 4.4–66.5°
c = 25.4325 (5) Å	µ = 2.21 mm⁻¹
β = 93.9667 (18)°	T = 293 K
V = 3298.10 (12) Å³	Needle, clear yellowish yellow
Z = 4	0.23 × 0.15 × 0.11 mm

Data collection top

Rigaku Xcalibur Atlas Gemini ultra diffractometer	5818 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance Ultra (Cu) X-ray Source	4598 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.033
Detector resolution: 10.4674 pixels mm^-1	θ_max = 66.6°, θ_min = 3.3°
ω scans	h = −8→9
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2017)	k = −18→18
T_min = 0.645, T_max = 1.000	l = −30→30
23478 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.048	w = 1/[σ²(F_o²) + (0.0663P)² + 1.0854P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.136	(Δ/σ)_max < 0.001
S = 1.04	Δρ_max = 0.31 e Å⁻³
5818 reflections	Δρ_min = −0.47 e Å⁻³
456 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
4 restraints	Extinction coefficient: 0.00143 (14)
Primary atom site location: structure-invariant direct methods

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.6126 (2)	0.28269 (11)	0.62870 (7)	0.0716 (5)
N1	0.2266 (3)	0.44547 (12)	0.42647 (7)	0.0632 (5)
C1	0.5916 (3)	0.33501 (16)	0.67324 (9)	0.0661 (6)
H1A	0.5297	0.3056	0.6987	0.079*
H1B	0.6978	0.3502	0.6901	0.079*
O2	0.5056 (3)	0.40807 (12)	0.65514 (6)	0.0786 (5)
C2	0.5271 (3)	0.32068 (14)	0.58681 (9)	0.0539 (5)
O3	0.0010 (2)	0.58510 (12)	0.30732 (6)	0.0695 (5)
C3	0.5069 (3)	0.29431 (15)	0.53588 (9)	0.0652 (6)
H3	0.5520	0.2440	0.5253	0.078*
O4	−0.1415 (3)	0.73645 (12)	0.32815 (7)	0.0802 (5)
C4	0.4161 (3)	0.34553 (13)	0.49995 (8)	0.0523 (5)
C5	0.4137 (8)	0.3268 (5)	0.4420 (3)	0.0560 (15)	0.649 (9)
H5A	0.5003	0.3577	0.4263	0.067*	0.649 (9)
H5B	0.4317	0.2674	0.4366	0.067*	0.649 (9)
C6	0.2494 (6)	0.3522 (2)	0.41695 (15)	0.0565 (14)	0.649 (9)
H6A	0.1628	0.3207	0.4323	0.068*	0.649 (9)
H6B	0.2444	0.3408	0.3794	0.068*	0.649 (9)
C5'	0.3468 (17)	0.3124 (10)	0.4448 (7)	0.063 (3)	0.351 (9)
H5'A	0.4095	0.2643	0.4344	0.076*	0.351 (9)
H5'B	0.2328	0.2957	0.4463	0.076*	0.351 (9)
C6'	0.3606 (12)	0.3815 (5)	0.4070 (3)	0.059 (3)	0.351 (9)
H6'A	0.3335	0.3631	0.3711	0.071*	0.351 (9)
H6'B	0.4698	0.4059	0.4096	0.071*	0.351 (9)
C7	0.1476 (3)	0.48997 (14)	0.38888 (9)	0.0611 (6)
H7	0.1347	0.4677	0.3550	0.073*
C8	0.0832 (2)	0.56891 (12)	0.39828 (8)	0.0471 (4)
C9	0.0005 (3)	0.61605 (14)	0.35723 (8)	0.0531 (5)
C10	−0.0658 (3)	0.69267 (14)	0.36907 (9)	0.0567 (5)
C11	−0.0473 (3)	0.72283 (14)	0.42110 (9)	0.0617 (6)
H11	−0.0924	0.7747	0.4287	0.074*
C12	0.0343 (3)	0.67895 (13)	0.46084 (9)	0.0557 (5)
H12	0.0453	0.7013	0.4947	0.067*
C13	0.1019 (2)	0.59978 (12)	0.45061 (8)	0.0444 (4)
C14	0.1877 (2)	0.55063 (12)	0.48908 (7)	0.0439 (4)
H14	0.2011	0.5708	0.5234	0.053*
C15	0.2525 (2)	0.47404 (12)	0.47788 (7)	0.0436 (4)
C16	0.3468 (2)	0.42019 (12)	0.51616 (8)	0.0436 (4)
C17	0.3694 (3)	0.44569 (13)	0.56919 (8)	0.0552 (5)
H17	0.3232	0.4951	0.5808	0.066*
C18	0.4612 (3)	0.39531 (14)	0.60256 (8)	0.0521 (5)
C19	−0.1546 (4)	0.5637 (2)	0.28161 (11)	0.0877 (9)
H19A	−0.1384	0.5393	0.2479	0.132*
H19B	−0.2207	0.6133	0.2769	0.132*
H19C	−0.2093	0.5240	0.3028	0.132*
C20	−0.2235 (4)	0.81244 (17)	0.33918 (13)	0.0852 (8)
H20A	−0.2769	0.8342	0.3072	0.128*
H20B	−0.1450	0.8526	0.3536	0.128*
H20C	−0.3040	0.8018	0.3642	0.128*
Cl1	0.88185 (10)	0.86519 (5)	0.52455 (3)	0.0853 (2)
Cl2	0.95883 (12)	0.98783 (5)	0.72228 (3)	0.1005 (3)
N2	0.9841 (2)	0.85550 (11)	0.64005 (7)	0.0567 (5)
H2	1.0191	0.8284	0.6138	0.068*
O5	1.1848 (3)	0.60343 (12)	0.61693 (8)	0.1022 (7)
O6	1.1660 (3)	0.73197 (13)	0.58597 (8)	0.0908 (6)
C21	0.9145 (3)	0.93147 (13)	0.62222 (8)	0.0520 (5)
C22	0.8960 (3)	0.99896 (15)	0.65599 (10)	0.0670 (6)
C23	0.8344 (4)	1.07547 (17)	0.63810 (12)	0.0848 (9)
H23	0.8211	1.1190	0.6618	0.102*
C24	0.7932 (4)	1.08698 (17)	0.58564 (12)	0.0808 (8)
H24	0.7523	1.1385	0.5736	0.097*
C25	0.8115 (3)	1.02357 (17)	0.55105 (11)	0.0705 (7)
H25	0.7857	1.0318	0.5152	0.085*
C26	0.8691 (3)	0.94637 (14)	0.56941 (9)	0.0570 (5)
C27	0.9057 (3)	0.79984 (13)	0.67251 (8)	0.0519 (5)
C28	0.7453 (3)	0.81278 (19)	0.68572 (9)	0.0709 (7)
H28	0.6894	0.8611	0.6744	0.085*
C29	0.6685 (5)	0.7541 (3)	0.71556 (12)	0.1005 (12)
H29	0.5611	0.7633	0.7243	0.121*
C30	0.7490 (7)	0.6829 (3)	0.73239 (12)	0.1132 (15)
H30	0.6957	0.6429	0.7516	0.136*
C31	0.9102 (5)	0.67081 (17)	0.72062 (9)	0.0915 (11)
H31	0.9647	0.6225	0.7327	0.110*
C32	0.9935 (3)	0.72859 (13)	0.69122 (8)	0.0604 (6)
C33	1.1678 (4)	0.71380 (15)	0.67851 (9)	0.0711 (7)
H33A	1.2189	0.6744	0.7037	0.085*
H33B	1.2282	0.7662	0.6818	0.085*
C34	1.1779 (3)	0.67926 (15)	0.62274 (10)	0.0648 (6)
O7	0.6770 (4)	1.13564 (18)	0.45216 (12)	0.1235 (9)
H7A	0.7269	1.1741	0.4390	0.185*
C35	0.5785 (6)	1.0971 (4)	0.4142 (3)	0.154 (2)
H35A	0.549 (7)	1.125 (3)	0.3808 (12)	0.26 (4)*
H35B	0.461 (2)	1.091 (4)	0.418 (2)	0.23 (3)*
C36	0.6324 (6)	1.0227 (4)	0.3935 (3)	0.171 (2)
H36A	0.7401	1.0306	0.3813	0.257*
H36B	0.5580	1.0057	0.3645	0.257*
H36C	0.6365	0.9801	0.4202	0.257*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0849 (11)	0.0706 (10)	0.0578 (9)	0.0246 (9)	−0.0062 (8)	0.0098 (8)
N1	0.0888 (14)	0.0511 (10)	0.0470 (10)	0.0183 (9)	−0.0146 (9)	−0.0143 (8)
C1	0.0710 (15)	0.0739 (15)	0.0524 (13)	0.0080 (12)	−0.0023 (11)	0.0128 (11)
O2	0.1109 (14)	0.0750 (11)	0.0468 (9)	0.0276 (10)	−0.0156 (9)	−0.0018 (8)
C2	0.0559 (12)	0.0526 (12)	0.0529 (12)	0.0064 (9)	0.0021 (9)	0.0076 (9)
O3	0.0790 (11)	0.0841 (12)	0.0440 (8)	0.0113 (9)	−0.0064 (7)	−0.0062 (8)
C3	0.0792 (16)	0.0554 (13)	0.0605 (14)	0.0218 (11)	0.0005 (11)	−0.0020 (11)
O4	0.1104 (14)	0.0678 (11)	0.0594 (10)	0.0212 (10)	−0.0160 (9)	0.0107 (8)
C4	0.0575 (12)	0.0483 (11)	0.0507 (12)	0.0065 (9)	0.0007 (9)	−0.0044 (9)
C5	0.060 (4)	0.055 (3)	0.053 (2)	0.016 (3)	0.001 (3)	−0.010 (2)
C6	0.075 (3)	0.0417 (19)	0.050 (2)	0.0048 (19)	−0.0083 (19)	−0.0109 (15)
C5'	0.070 (8)	0.059 (6)	0.061 (5)	0.010 (6)	0.003 (7)	−0.017 (4)
C6'	0.073 (6)	0.058 (4)	0.046 (4)	0.009 (4)	0.001 (3)	−0.016 (3)
C7	0.0803 (15)	0.0572 (13)	0.0435 (11)	0.0104 (11)	−0.0115 (10)	−0.0109 (10)
C8	0.0498 (11)	0.0468 (11)	0.0441 (10)	−0.0036 (8)	−0.0008 (8)	−0.0010 (8)
C9	0.0588 (12)	0.0577 (12)	0.0422 (10)	−0.0019 (10)	−0.0018 (9)	0.0013 (9)
C10	0.0644 (13)	0.0530 (12)	0.0517 (12)	0.0004 (10)	−0.0034 (10)	0.0096 (10)
C11	0.0802 (16)	0.0456 (11)	0.0586 (13)	0.0090 (10)	0.0004 (11)	0.0014 (10)
C12	0.0723 (14)	0.0468 (11)	0.0477 (11)	0.0052 (10)	0.0015 (10)	−0.0027 (9)
C13	0.0495 (11)	0.0398 (10)	0.0441 (10)	−0.0041 (8)	0.0040 (8)	0.0002 (8)
C14	0.0511 (11)	0.0412 (10)	0.0393 (10)	−0.0028 (8)	0.0030 (8)	−0.0024 (8)
C15	0.0467 (10)	0.0422 (10)	0.0417 (10)	−0.0041 (8)	0.0011 (8)	−0.0046 (8)
C16	0.0454 (10)	0.0405 (10)	0.0447 (10)	−0.0014 (8)	0.0013 (8)	−0.0016 (8)
C17	0.0693 (13)	0.0466 (11)	0.0486 (11)	0.0118 (10)	−0.0038 (10)	−0.0049 (9)
C18	0.0585 (12)	0.0537 (12)	0.0436 (11)	0.0009 (9)	−0.0004 (9)	0.0012 (9)
C19	0.097 (2)	0.094 (2)	0.0681 (17)	0.0049 (16)	−0.0259 (15)	−0.0174 (15)
C20	0.098 (2)	0.0652 (16)	0.088 (2)	0.0175 (14)	−0.0204 (16)	0.0155 (14)
Cl1	0.1157 (6)	0.0811 (5)	0.0593 (4)	0.0125 (4)	0.0070 (3)	−0.0088 (3)
Cl2	0.1561 (8)	0.0754 (5)	0.0648 (4)	0.0421 (5)	−0.0289 (4)	−0.0153 (3)
N2	0.0707 (12)	0.0429 (9)	0.0581 (11)	0.0105 (8)	0.0160 (9)	0.0069 (8)
O5	0.178 (2)	0.0530 (11)	0.0782 (13)	0.0262 (12)	0.0241 (13)	−0.0111 (9)
O6	0.1374 (18)	0.0710 (12)	0.0644 (11)	0.0077 (11)	0.0100 (11)	0.0062 (9)
C21	0.0554 (12)	0.0438 (11)	0.0568 (12)	0.0055 (9)	0.0042 (9)	0.0050 (9)
C22	0.0858 (17)	0.0548 (13)	0.0585 (14)	0.0163 (12)	−0.0076 (12)	−0.0038 (10)
C23	0.117 (2)	0.0529 (14)	0.0813 (18)	0.0267 (14)	−0.0166 (16)	−0.0056 (13)
C24	0.099 (2)	0.0525 (14)	0.088 (2)	0.0179 (13)	−0.0101 (15)	0.0154 (13)
C25	0.0783 (16)	0.0684 (15)	0.0637 (15)	0.0047 (12)	−0.0023 (12)	0.0188 (13)
C26	0.0612 (13)	0.0537 (12)	0.0564 (13)	−0.0011 (10)	0.0067 (10)	0.0049 (10)
C27	0.0706 (14)	0.0456 (11)	0.0396 (10)	−0.0068 (9)	0.0040 (9)	−0.0042 (8)
C28	0.0738 (16)	0.0859 (18)	0.0536 (13)	−0.0157 (13)	0.0073 (11)	−0.0092 (12)
C29	0.103 (2)	0.137 (3)	0.0630 (17)	−0.058 (2)	0.0213 (16)	−0.018 (2)
C30	0.183 (4)	0.110 (3)	0.0489 (16)	−0.086 (3)	0.022 (2)	−0.0030 (17)
C31	0.184 (4)	0.0522 (14)	0.0375 (12)	−0.0343 (18)	0.0024 (17)	−0.0013 (10)
C32	0.1049 (19)	0.0412 (11)	0.0344 (10)	−0.0063 (11)	−0.0012 (10)	−0.0052 (8)
C33	0.107 (2)	0.0500 (12)	0.0539 (13)	0.0219 (12)	−0.0139 (13)	−0.0045 (10)
C34	0.0870 (17)	0.0493 (13)	0.0579 (13)	0.0136 (11)	0.0041 (12)	−0.0018 (11)
O7	0.127 (2)	0.109 (2)	0.130 (2)	−0.0102 (16)	−0.0186 (17)	0.0411 (16)
C35	0.091 (3)	0.130 (4)	0.232 (7)	0.004 (3)	−0.051 (3)	−0.013 (4)
C36	0.113 (4)	0.209 (7)	0.191 (6)	0.001 (4)	0.013 (3)	−0.059 (5)

Geometric parameters (Å, º) top

O1—C1	1.426 (3)	C17—H17	0.9300
O1—C2	1.373 (3)	C17—C18	1.356 (3)
N1—C6	1.519 (4)	C19—H19A	0.9600
N1—C6'	1.598 (7)	C19—H19B	0.9600
N1—C7	1.322 (3)	C19—H19C	0.9600
N1—C15	1.387 (3)	C20—H20A	0.9600
C1—H1A	0.9700	C20—H20B	0.9600
C1—H1B	0.9700	C20—H20C	0.9600
C1—O2	1.420 (3)	Cl1—C26	1.733 (2)
O2—C18	1.376 (3)	Cl2—C22	1.737 (3)
C2—C3	1.361 (3)	N2—H2	0.8600
C2—C18	1.376 (3)	N2—C21	1.399 (3)
O3—C9	1.362 (3)	N2—C27	1.396 (3)
O3—C19	1.428 (3)	O5—C34	1.219 (3)
C3—H3	0.9300	O6—C34	1.256 (3)
C3—C4	1.399 (3)	C21—C22	1.391 (3)
O4—C10	1.365 (3)	C21—C26	1.389 (3)
O4—C20	1.421 (3)	C22—C23	1.384 (3)
C4—C5	1.502 (8)	C23—H23	0.9300
C4—C5'	1.566 (16)	C23—C24	1.366 (4)
C4—C16	1.392 (3)	C24—H24	0.9300
C5—H5A	0.9700	C24—C25	1.355 (4)
C5—H5B	0.9700	C25—H25	0.9300
C5—C6	1.500 (10)	C25—C26	1.386 (3)
C6—H6A	0.9700	C27—C28	1.388 (4)
C6—H6B	0.9700	C27—C32	1.408 (3)
C5'—H5'A	0.9700	C28—H28	0.9300
C5'—H5'B	0.9700	C28—C29	1.381 (4)
C5'—C6'	1.47 (2)	C29—H29	0.9300
C6'—H6'A	0.9700	C29—C30	1.365 (6)
C6'—H6'B	0.9700	C30—H30	0.9300
C7—H7	0.9300	C30—C31	1.382 (6)
C7—C8	1.390 (3)	C31—H31	0.9300
C8—C9	1.418 (3)	C31—C32	1.393 (4)
C8—C13	1.417 (3)	C32—C33	1.498 (4)
C9—C10	1.377 (3)	C33—H33A	0.9700
C10—C11	1.406 (3)	C33—H33B	0.9700
C11—H11	0.9300	C33—C34	1.529 (3)
C11—C12	1.364 (3)	O7—H7A	0.8200
C12—H12	0.9300	O7—C35	1.360 (6)
C12—C13	1.408 (3)	C35—H35A	0.977 (10)
C13—C14	1.402 (3)	C35—H35B	0.974 (10)
C14—H14	0.9300	C35—C36	1.381 (8)
C14—C15	1.368 (3)	C36—H36A	0.9600
C15—C16	1.474 (3)	C36—H36B	0.9600
C16—C17	1.408 (3)	C36—H36C	0.9600

C2—O1—C1	106.02 (17)	C16—C17—H17	121.4
C7—N1—C6	117.9 (2)	C18—C17—C16	117.30 (19)
C7—N1—C6'	115.3 (3)	C18—C17—H17	121.4
C7—N1—C15	122.74 (18)	C2—C18—O2	109.20 (18)
C15—N1—C6	117.3 (2)	C17—C18—O2	128.2 (2)
C15—N1—C6'	116.0 (3)	C17—C18—C2	122.6 (2)
O1—C1—H1A	110.1	O3—C19—H19A	109.5
O1—C1—H1B	110.1	O3—C19—H19B	109.5
H1A—C1—H1B	108.5	O3—C19—H19C	109.5
O2—C1—O1	107.79 (17)	H19A—C19—H19B	109.5
O2—C1—H1A	110.1	H19A—C19—H19C	109.5
O2—C1—H1B	110.1	H19B—C19—H19C	109.5
C18—O2—C1	106.56 (18)	O4—C20—H20A	109.5
O1—C2—C18	110.05 (19)	O4—C20—H20B	109.5
C3—C2—O1	128.6 (2)	O4—C20—H20C	109.5
C3—C2—C18	121.3 (2)	H20A—C20—H20B	109.5
C9—O3—C19	117.0 (2)	H20A—C20—H20C	109.5
C2—C3—H3	121.1	H20B—C20—H20C	109.5
C2—C3—C4	117.7 (2)	C21—N2—H2	109.3
C4—C3—H3	121.1	C27—N2—H2	109.3
C10—O4—C20	118.6 (2)	C27—N2—C21	123.31 (18)
C3—C4—C5	119.7 (4)	C22—C21—N2	121.8 (2)
C3—C4—C5'	122.0 (7)	C26—C21—N2	122.5 (2)
C16—C4—C3	120.8 (2)	C26—C21—C22	115.58 (19)
C16—C4—C5	118.8 (4)	C21—C22—Cl2	118.88 (17)
C16—C4—C5'	115.1 (6)	C23—C22—Cl2	119.0 (2)
C4—C5—H5A	110.0	C23—C22—C21	122.1 (2)
C4—C5—H5B	110.0	C22—C23—H23	120.0
H5A—C5—H5B	108.4	C24—C23—C22	119.9 (3)
C6—C5—C4	108.3 (5)	C24—C23—H23	120.0
C6—C5—H5A	110.0	C23—C24—H24	119.9
C6—C5—H5B	110.0	C25—C24—C23	120.2 (2)
N1—C6—H6A	110.1	C25—C24—H24	119.9
N1—C6—H6B	110.1	C24—C25—H25	120.2
C5—C6—N1	108.2 (4)	C24—C25—C26	119.6 (2)
C5—C6—H6A	110.1	C26—C25—H25	120.2
C5—C6—H6B	110.1	C21—C26—Cl1	119.00 (17)
H6A—C6—H6B	108.4	C25—C26—Cl1	118.37 (19)
C4—C5'—H5'A	110.3	C25—C26—C21	122.6 (2)
C4—C5'—H5'B	110.3	N2—C27—C32	118.0 (2)
H5'A—C5'—H5'B	108.5	C28—C27—N2	121.8 (2)
C6'—C5'—C4	107.1 (10)	C28—C27—C32	120.3 (2)
C6'—C5'—H5'A	110.3	C27—C28—H28	119.9
C6'—C5'—H5'B	110.3	C29—C28—C27	120.2 (3)
N1—C6'—H6'A	111.6	C29—C28—H28	119.9
N1—C6'—H6'B	111.6	C28—C29—H29	119.7
C5'—C6'—N1	100.9 (8)	C30—C29—C28	120.6 (4)
C5'—C6'—H6'A	111.6	C30—C29—H29	119.7
C5'—C6'—H6'B	111.6	C29—C30—H30	120.3
H6'A—C6'—H6'B	109.4	C29—C30—C31	119.5 (3)
N1—C7—H7	118.9	C31—C30—H30	120.3
N1—C7—C8	122.16 (19)	C30—C31—H31	119.0
C8—C7—H7	118.9	C30—C31—C32	122.1 (3)
C7—C8—C9	121.26 (19)	C32—C31—H31	119.0
C7—C8—C13	117.27 (18)	C27—C32—C33	121.5 (2)
C13—C8—C9	121.46 (19)	C31—C32—C27	117.3 (3)
O3—C9—C8	117.53 (19)	C31—C32—C33	121.2 (3)
O3—C9—C10	123.45 (19)	C32—C33—H33A	109.3
C10—C9—C8	118.87 (19)	C32—C33—H33B	109.3
O4—C10—C9	116.8 (2)	C32—C33—C34	111.7 (2)
O4—C10—C11	123.8 (2)	H33A—C33—H33B	107.9
C9—C10—C11	119.37 (19)	C34—C33—H33A	109.3
C10—C11—H11	118.8	C34—C33—H33B	109.3
C12—C11—C10	122.5 (2)	O5—C34—O6	125.1 (2)
C12—C11—H11	118.8	O5—C34—C33	118.4 (2)
C11—C12—H12	120.0	O6—C34—C33	116.3 (2)
C11—C12—C13	120.0 (2)	C35—O7—H7A	109.5
C13—C12—H12	120.0	O7—C35—H35A	120.3 (13)
C12—C13—C8	117.81 (18)	O7—C35—H35B	120 (4)
C14—C13—C8	118.51 (17)	O7—C35—C36	118.1 (5)
C14—C13—C12	123.67 (18)	H35A—C35—H35B	87.4 (11)
C13—C14—H14	118.8	C36—C35—H35A	97 (4)
C15—C14—C13	122.32 (18)	C36—C35—H35B	108 (4)
C15—C14—H14	118.8	C35—C36—H36A	109.5
N1—C15—C16	118.06 (17)	C35—C36—H36B	109.5
C14—C15—N1	116.95 (18)	C35—C36—H36C	109.5
C14—C15—C16	124.99 (17)	H36A—C36—H36B	109.5
C4—C16—C15	120.39 (17)	H36A—C36—H36C	109.5
C4—C16—C17	120.10 (18)	H36B—C36—H36C	109.5
C17—C16—C15	119.49 (17)

O1—C1—O2—C18	6.3 (3)	C11—C12—C13—C14	179.9 (2)
O1—C2—C3—C4	−178.7 (2)	C12—C13—C14—C15	−179.8 (2)
O1—C2—C18—O2	1.1 (3)	C13—C8—C9—O3	174.25 (18)
O1—C2—C18—C17	−179.5 (2)	C13—C8—C9—C10	−1.4 (3)
N1—C7—C8—C9	179.3 (2)	C13—C14—C15—N1	−1.4 (3)
N1—C7—C8—C13	−1.5 (3)	C13—C14—C15—C16	178.66 (18)
N1—C15—C16—C4	4.0 (3)	C14—C15—C16—C4	−176.05 (19)
N1—C15—C16—C17	−177.30 (19)	C14—C15—C16—C17	2.6 (3)
C1—O1—C2—C3	−178.6 (2)	C15—N1—C6—C5	−51.2 (5)
C1—O1—C2—C18	2.8 (3)	C15—N1—C6'—C5'	60.0 (9)
C1—O2—C18—C2	−4.6 (3)	C15—N1—C7—C8	−0.5 (4)
C1—O2—C18—C17	176.0 (2)	C15—C16—C17—C18	−178.02 (19)
C2—O1—C1—O2	−5.6 (3)	C16—C4—C5—C6	−41.2 (6)
C2—C3—C4—C5	169.9 (4)	C16—C4—C5'—C6'	53.1 (10)
C2—C3—C4—C5'	−164.0 (6)	C16—C17—C18—O2	177.3 (2)
C2—C3—C4—C16	−1.0 (4)	C16—C17—C18—C2	−2.0 (3)
O3—C9—C10—O4	3.4 (3)	C18—C2—C3—C4	−0.3 (4)
O3—C9—C10—C11	−174.2 (2)	C19—O3—C9—C8	117.3 (2)
C3—C2—C18—O2	−177.6 (2)	C19—O3—C9—C10	−67.2 (3)
C3—C2—C18—C17	1.9 (4)	C20—O4—C10—C9	174.8 (2)
C3—C4—C5—C6	147.7 (4)	C20—O4—C10—C11	−7.7 (4)
C3—C4—C5'—C6'	−142.9 (7)	Cl2—C22—C23—C24	176.3 (3)
C3—C4—C16—C15	179.5 (2)	N2—C21—C22—Cl2	−0.8 (3)
C3—C4—C16—C17	0.8 (3)	N2—C21—C22—C23	176.9 (3)
O4—C10—C11—C12	−177.5 (2)	N2—C21—C26—Cl1	5.8 (3)
C4—C5—C6—N1	59.7 (6)	N2—C21—C26—C25	−175.1 (2)
C4—C5'—C6'—N1	−69.1 (10)	N2—C27—C28—C29	176.5 (2)
C4—C16—C17—C18	0.6 (3)	N2—C27—C32—C31	−175.81 (19)
C5—C4—C16—C15	8.5 (4)	N2—C27—C32—C33	2.1 (3)
C5—C4—C16—C17	−170.2 (3)	C21—N2—C27—C28	5.8 (3)
C6—N1—C7—C8	162.9 (3)	C21—N2—C27—C32	−175.1 (2)
C6—N1—C15—C14	−161.6 (3)	C21—C22—C23—C24	−1.5 (5)
C6—N1—C15—C16	18.3 (4)	C22—C21—C26—Cl1	−178.08 (19)
C5'—C4—C16—C15	−16.4 (6)	C22—C21—C26—C25	1.0 (3)
C5'—C4—C16—C17	164.9 (6)	C22—C23—C24—C25	0.3 (5)
C6'—N1—C7—C8	−152.3 (4)	C23—C24—C25—C26	1.4 (5)
C6'—N1—C15—C14	153.6 (4)	C24—C25—C26—Cl1	177.0 (2)
C6'—N1—C15—C16	−26.5 (5)	C24—C25—C26—C21	−2.1 (4)
C7—N1—C6—C5	144.5 (4)	C26—C21—C22—Cl2	−176.96 (18)
C7—N1—C6'—C5'	−146.2 (7)	C26—C21—C22—C23	0.8 (4)
C7—N1—C15—C14	2.0 (3)	C27—N2—C21—C22	70.5 (3)
C7—N1—C15—C16	−178.1 (2)	C27—N2—C21—C26	−113.7 (2)
C7—C8—C9—O3	−6.6 (3)	C27—C28—C29—C30	0.0 (4)
C7—C8—C9—C10	177.8 (2)	C27—C32—C33—C34	−78.5 (3)
C7—C8—C13—C12	−178.7 (2)	C28—C27—C32—C31	3.3 (3)
C7—C8—C13—C14	2.0 (3)	C28—C27—C32—C33	−178.8 (2)
C8—C9—C10—O4	178.8 (2)	C28—C29—C30—C31	1.8 (5)
C8—C9—C10—C11	1.2 (3)	C29—C30—C31—C32	−1.0 (4)
C8—C13—C14—C15	−0.5 (3)	C30—C31—C32—C27	−1.5 (3)
C9—C8—C13—C12	0.5 (3)	C30—C31—C32—C33	−179.4 (2)
C9—C8—C13—C14	−178.81 (18)	C31—C32—C33—C34	99.3 (2)
C9—C10—C11—C12	−0.1 (4)	C32—C27—C28—C29	−2.6 (3)
C10—C11—C12—C13	−0.9 (4)	C32—C33—C34—O5	−94.1 (3)
C11—C12—C13—C8	0.7 (3)	C32—C33—C34—O6	80.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O6	0.86	2.10	2.873 (3)	149
O7—H7A···O6ⁱ	0.82	1.87	2.684 (3)	175

Symmetry code: (i) −x+2, −y+2, −z+1.

5,6-Dihydro-9,10-dimethoxybenzo[g][1,3]benzodioxolo[5,6-a]quinolizinium 2-[2-(2,6-dichloroanilino)phenyl]acetate methanol monosolvate (IV) top

Crystal data top

C₂₀H₁₈NO₄⁺·C₁₄H₁₀Cl₂NO₂⁻·CH₄O	F(000) = 1384
M_r = 663.52	D_x = 1.401 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54184 Å
a = 20.8841 (7) Å	Cell parameters from 7302 reflections
b = 7.44641 (19) Å	θ = 4.4–66.7°
c = 21.5399 (7) Å	µ = 2.30 mm⁻¹
β = 110.049 (4)°	T = 293 K
V = 3146.70 (17) Å³	Needle, clear yellowish yellow
Z = 4	0.27 × 0.14 × 0.09 mm

Data collection top

Rigaku Xcalibur Atlas Gemini ultra diffractometer	5546 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance Ultra (Cu) X-ray Source	4162 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.040
Detector resolution: 10.4674 pixels mm^-1	θ_max = 66.7°, θ_min = 3.6°
ω scans	h = −24→24
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2017)	k = −8→5
T_min = 0.653, T_max = 1.000	l = −25→25
23314 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.123	w = 1/[σ²(F_o²) + (0.0635P)² + 0.7365P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
5546 reflections	Δρ_max = 0.30 e Å⁻³
431 parameters	Δρ_min = −0.33 e Å⁻³
0 restraints

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.70603 (9)	0.5181 (3)	0.35371 (8)	0.0826 (6)
N1	0.96669 (9)	0.3386 (2)	0.58317 (8)	0.0441 (4)
C1	0.64604 (16)	0.5736 (6)	0.36444 (16)	0.0833 (9)
H1A	0.6085 (18)	0.507 (5)	0.3365 (17)	0.101 (11)*
H1B	0.642 (2)	0.709 (6)	0.356 (2)	0.143 (16)*
O2	0.65552 (8)	0.5505 (3)	0.43305 (9)	0.0748 (5)
C2	0.72195 (11)	0.4969 (3)	0.46200 (11)	0.0553 (5)
O3	1.16738 (8)	0.1781 (2)	0.65218 (8)	0.0617 (4)
C3	0.75685 (11)	0.4652 (3)	0.52741 (11)	0.0559 (5)
H3	0.7361	0.4788	0.5591	0.067*
O4	1.22972 (9)	0.0667 (3)	0.56895 (9)	0.0726 (5)
C4	0.82478 (11)	0.4115 (3)	0.54484 (10)	0.0490 (5)
C5	0.86521 (11)	0.3643 (3)	0.61515 (10)	0.0558 (5)
H5A	0.8462	0.4259	0.6446	0.067*
H5B	0.8622	0.2361	0.6216	0.067*
C6	0.93830 (11)	0.4165 (3)	0.63173 (10)	0.0529 (5)
H6A	0.9420	0.5464	0.6315	0.063*
H6B	0.9644	0.3740	0.6757	0.063*
C7	1.03070 (10)	0.2830 (3)	0.60502 (10)	0.0464 (5)
H7	1.0549	0.2859	0.6502	0.056*
C8	1.06306 (10)	0.2201 (3)	0.56242 (10)	0.0447 (5)
C9	1.13182 (11)	0.1653 (3)	0.58632 (11)	0.0504 (5)
C10	1.16262 (12)	0.1106 (3)	0.54237 (12)	0.0555 (5)
C11	1.12439 (13)	0.1047 (3)	0.47441 (12)	0.0584 (6)
H11	1.1454	0.0663	0.4450	0.070*
C12	1.05740 (12)	0.1536 (3)	0.45042 (11)	0.0546 (5)
H12	1.0330	0.1457	0.4054	0.065*
C13	1.02507 (11)	0.2164 (3)	0.49420 (10)	0.0462 (5)
C14	0.95682 (11)	0.2738 (3)	0.47329 (10)	0.0468 (5)
H14	0.9311	0.2697	0.4285	0.056*
C15	0.92709 (10)	0.3351 (3)	0.51654 (9)	0.0430 (4)
C16	0.85586 (10)	0.3949 (3)	0.49741 (10)	0.0454 (5)
C17	0.81834 (11)	0.4281 (3)	0.43022 (10)	0.0537 (5)
H17	0.8381	0.4164	0.3978	0.064*
C18	0.75226 (12)	0.4777 (3)	0.41495 (11)	0.0576 (6)
C19	1.17107 (16)	0.0132 (5)	0.68733 (15)	0.0893 (9)
H19A	1.1949	−0.0749	0.6710	0.134*
H19B	1.1258	−0.0289	0.6810	0.134*
H19C	1.1950	0.0328	0.7336	0.134*
C20	1.26507 (14)	0.0154 (4)	0.52583 (16)	0.0791 (8)
H20A	1.2618	0.1098	0.4945	0.119*
H20B	1.2452	−0.0923	0.5027	0.119*
H20C	1.3121	−0.0059	0.5511	0.119*
Cl1	0.34997 (3)	0.83343 (10)	0.41121 (3)	0.0740 (2)
Cl2	0.54709 (4)	1.12811 (11)	0.33456 (4)	0.0822 (2)
N2	0.43795 (9)	0.8633 (3)	0.32552 (9)	0.0532 (5)
H2	0.4708 (15)	0.840 (4)	0.3114 (14)	0.074 (8)*
O5	0.49580 (11)	0.4676 (3)	0.19387 (10)	0.0810 (5)
O6	0.51083 (8)	0.7242 (2)	0.24777 (9)	0.0704 (5)
C21	0.44634 (10)	0.9960 (3)	0.37268 (10)	0.0489 (5)
C22	0.40887 (11)	1.0009 (3)	0.41550 (11)	0.0545 (5)
C23	0.41875 (13)	1.1301 (4)	0.46331 (12)	0.0652 (6)
H23	0.3920	1.1305	0.4901	0.078*
C24	0.46798 (15)	1.2586 (4)	0.47160 (13)	0.0735 (7)
H24	0.4746	1.3466	0.5038	0.088*
C25	0.50765 (14)	1.2569 (4)	0.43192 (13)	0.0685 (7)
H25	0.5417	1.3422	0.4377	0.082*
C26	0.49636 (11)	1.1281 (3)	0.38382 (11)	0.0543 (5)
C27	0.37556 (10)	0.8330 (3)	0.27353 (10)	0.0495 (5)
C28	0.32292 (11)	0.9562 (4)	0.25762 (11)	0.0585 (6)
H28	0.3279	1.0620	0.2817	0.070*
C29	0.26265 (12)	0.9227 (4)	0.20581 (12)	0.0698 (7)
H29	0.2270	1.0047	0.1960	0.084*
C30	0.25570 (12)	0.7698 (5)	0.16930 (12)	0.0721 (8)
H30	0.2158	0.7490	0.1339	0.087*
C31	0.30800 (12)	0.6459 (4)	0.18504 (12)	0.0644 (6)
H31	0.3027	0.5418	0.1599	0.077*
C32	0.36837 (11)	0.6731 (3)	0.23758 (10)	0.0521 (5)
C33	0.42335 (12)	0.5335 (3)	0.25515 (12)	0.0590 (6)
H33A	0.4035	0.4190	0.2369	0.071*
H33B	0.4417	0.5212	0.3029	0.071*
C34	0.48150 (11)	0.5767 (3)	0.22997 (10)	0.0526 (5)
O7	0.40857 (9)	0.1186 (3)	0.81069 (9)	0.0752 (5)
H7A	0.4329	0.1738	0.7944	0.113*
C35	0.34978 (15)	0.0620 (4)	0.76074 (14)	0.0802 (8)
H35A	0.3620	−0.0108	0.7298	0.120*
H35B	0.3246	0.1649	0.7384	0.120*
H35C	0.3222	−0.0069	0.7796	0.120*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0610 (11)	0.1247 (17)	0.0491 (9)	−0.0011 (10)	0.0024 (8)	0.0127 (10)
N1	0.0523 (10)	0.0462 (9)	0.0358 (8)	−0.0060 (7)	0.0177 (7)	−0.0020 (7)
C1	0.0656 (18)	0.104 (3)	0.0670 (18)	−0.0029 (17)	0.0054 (14)	0.0172 (17)
O2	0.0526 (9)	0.0935 (14)	0.0701 (11)	0.0013 (9)	0.0106 (8)	0.0128 (10)
C2	0.0490 (12)	0.0537 (13)	0.0576 (13)	−0.0058 (10)	0.0112 (10)	0.0029 (10)
O3	0.0567 (9)	0.0735 (11)	0.0536 (9)	−0.0069 (7)	0.0172 (7)	−0.0053 (8)
C3	0.0561 (13)	0.0607 (14)	0.0530 (13)	−0.0019 (10)	0.0211 (10)	−0.0009 (10)
O4	0.0620 (10)	0.0820 (12)	0.0829 (12)	0.0048 (9)	0.0366 (9)	−0.0044 (10)
C4	0.0555 (12)	0.0473 (11)	0.0451 (11)	−0.0032 (9)	0.0182 (9)	−0.0005 (9)
C5	0.0603 (13)	0.0691 (14)	0.0425 (11)	0.0039 (11)	0.0233 (10)	0.0028 (10)
C6	0.0603 (13)	0.0627 (14)	0.0375 (11)	0.0019 (10)	0.0193 (9)	−0.0067 (10)
C7	0.0501 (11)	0.0480 (11)	0.0410 (10)	−0.0074 (9)	0.0155 (9)	−0.0011 (9)
C8	0.0524 (11)	0.0405 (10)	0.0457 (11)	−0.0094 (9)	0.0225 (9)	−0.0007 (9)
C9	0.0554 (12)	0.0461 (12)	0.0528 (12)	−0.0087 (9)	0.0225 (10)	−0.0019 (10)
C10	0.0589 (13)	0.0473 (12)	0.0696 (15)	−0.0043 (10)	0.0340 (12)	−0.0019 (10)
C11	0.0748 (16)	0.0518 (13)	0.0630 (14)	−0.0035 (11)	0.0421 (12)	−0.0056 (11)
C12	0.0736 (15)	0.0506 (12)	0.0479 (12)	−0.0085 (11)	0.0317 (11)	−0.0040 (10)
C13	0.0592 (12)	0.0393 (10)	0.0454 (11)	−0.0098 (9)	0.0246 (9)	−0.0005 (8)
C14	0.0586 (12)	0.0463 (11)	0.0370 (10)	−0.0101 (9)	0.0185 (9)	−0.0022 (9)
C15	0.0543 (11)	0.0390 (10)	0.0366 (10)	−0.0078 (8)	0.0167 (9)	0.0008 (8)
C16	0.0527 (11)	0.0429 (11)	0.0405 (10)	−0.0090 (9)	0.0159 (9)	0.0007 (8)
C17	0.0591 (13)	0.0605 (13)	0.0414 (11)	−0.0099 (10)	0.0170 (10)	0.0010 (10)
C18	0.0583 (13)	0.0616 (14)	0.0453 (12)	−0.0114 (11)	0.0078 (10)	0.0052 (10)
C19	0.085 (2)	0.110 (2)	0.0645 (17)	−0.0124 (17)	0.0149 (15)	0.0217 (17)
C20	0.0724 (17)	0.0744 (17)	0.109 (2)	−0.0007 (13)	0.0552 (16)	−0.0162 (16)
Cl1	0.0681 (4)	0.0956 (5)	0.0647 (4)	−0.0221 (3)	0.0308 (3)	−0.0065 (3)
Cl2	0.0808 (4)	0.0964 (5)	0.0841 (5)	−0.0244 (4)	0.0472 (4)	−0.0129 (4)
N2	0.0417 (10)	0.0682 (12)	0.0491 (10)	−0.0004 (8)	0.0147 (8)	−0.0134 (9)
O5	0.1090 (15)	0.0721 (12)	0.0821 (13)	0.0029 (10)	0.0589 (12)	−0.0104 (10)
O6	0.0553 (9)	0.0773 (12)	0.0888 (12)	−0.0110 (8)	0.0379 (9)	−0.0206 (10)
C21	0.0463 (11)	0.0564 (12)	0.0402 (11)	0.0023 (9)	0.0099 (9)	−0.0024 (9)
C22	0.0504 (12)	0.0665 (14)	0.0456 (12)	−0.0014 (10)	0.0150 (9)	−0.0011 (10)
C23	0.0700 (15)	0.0804 (17)	0.0501 (13)	0.0013 (13)	0.0267 (11)	−0.0099 (12)
C24	0.0893 (19)	0.0708 (17)	0.0605 (15)	−0.0043 (14)	0.0257 (14)	−0.0187 (13)
C25	0.0772 (17)	0.0606 (15)	0.0660 (15)	−0.0131 (12)	0.0222 (13)	−0.0089 (12)
C26	0.0555 (13)	0.0584 (13)	0.0498 (12)	−0.0016 (10)	0.0191 (10)	0.0011 (10)
C27	0.0415 (11)	0.0691 (14)	0.0410 (11)	−0.0041 (10)	0.0182 (9)	−0.0014 (10)
C28	0.0507 (12)	0.0808 (16)	0.0478 (12)	0.0061 (11)	0.0220 (10)	0.0004 (11)
C29	0.0455 (13)	0.114 (2)	0.0528 (14)	0.0082 (13)	0.0204 (11)	0.0175 (15)
C30	0.0464 (13)	0.121 (2)	0.0470 (13)	−0.0220 (14)	0.0133 (10)	0.0013 (15)
C31	0.0549 (14)	0.0891 (18)	0.0516 (13)	−0.0220 (13)	0.0215 (11)	−0.0098 (12)
C32	0.0481 (11)	0.0684 (14)	0.0449 (11)	−0.0123 (10)	0.0227 (9)	−0.0045 (10)
C33	0.0681 (14)	0.0596 (14)	0.0528 (13)	−0.0093 (11)	0.0252 (11)	−0.0065 (11)
C34	0.0549 (12)	0.0583 (14)	0.0437 (11)	0.0060 (11)	0.0160 (10)	0.0010 (10)
O7	0.0659 (11)	0.0928 (14)	0.0668 (11)	0.0001 (9)	0.0226 (9)	0.0142 (10)
C35	0.0721 (17)	0.101 (2)	0.0695 (17)	−0.0083 (15)	0.0264 (14)	0.0078 (16)

Geometric parameters (Å, º) top

O1—C1	1.412 (4)	C19—H19A	0.9600
O1—C18	1.374 (3)	C19—H19B	0.9600
N1—C6	1.486 (3)	C19—H19C	0.9600
N1—C7	1.322 (3)	C20—H20A	0.9600
N1—C15	1.389 (3)	C20—H20B	0.9600
C1—H1A	0.95 (4)	C20—H20C	0.9600
C1—H1B	1.02 (5)	Cl1—C22	1.732 (2)
C1—O2	1.433 (4)	Cl2—C26	1.738 (2)
O2—C2	1.371 (3)	N2—H2	0.86 (3)
C2—C3	1.367 (3)	N2—C21	1.385 (3)
C2—C18	1.374 (3)	N2—C27	1.415 (3)
O3—C9	1.360 (3)	O5—C34	1.230 (3)
O3—C19	1.430 (3)	O6—C34	1.252 (3)
C3—H3	0.9300	C21—C22	1.400 (3)
C3—C4	1.395 (3)	C21—C26	1.395 (3)
O4—C10	1.360 (3)	C22—C23	1.372 (3)
O4—C20	1.423 (3)	C23—H23	0.9300
C4—C5	1.501 (3)	C23—C24	1.371 (4)
C4—C16	1.391 (3)	C24—H24	0.9300
C5—H5A	0.9700	C24—C25	1.379 (4)
C5—H5B	0.9700	C25—H25	0.9300
C5—C6	1.495 (3)	C25—C26	1.371 (3)
C6—H6A	0.9700	C27—C28	1.382 (3)
C6—H6B	0.9700	C27—C32	1.400 (3)
C7—H7	0.9300	C28—H28	0.9300
C7—C8	1.394 (3)	C28—C29	1.389 (3)
C8—C9	1.409 (3)	C29—H29	0.9300
C8—C13	1.411 (3)	C29—C30	1.363 (4)
C9—C10	1.376 (3)	C30—H30	0.9300
C10—C11	1.407 (3)	C30—C31	1.380 (4)
C11—H11	0.9300	C31—H31	0.9300
C11—C12	1.364 (3)	C31—C32	1.390 (3)
C12—H12	0.9300	C32—C33	1.498 (3)
C12—C13	1.414 (3)	C33—H33A	0.9700
C13—C14	1.406 (3)	C33—H33B	0.9700
C14—H14	0.9300	C33—C34	1.525 (3)
C14—C15	1.363 (3)	O7—H7A	0.8200
C15—C16	1.470 (3)	O7—C35	1.392 (3)
C16—C17	1.411 (3)	C35—H35A	0.9600
C17—H17	0.9300	C35—H35B	0.9600
C17—C18	1.356 (3)	C35—H35C	0.9600

C18—O1—C1	106.1 (2)	C17—C18—C2	122.5 (2)
C7—N1—C6	118.06 (16)	O3—C19—H19A	109.5
C7—N1—C15	122.19 (17)	O3—C19—H19B	109.5
C15—N1—C6	119.66 (17)	O3—C19—H19C	109.5
O1—C1—H1A	109 (2)	H19A—C19—H19B	109.5
O1—C1—H1B	106 (2)	H19A—C19—H19C	109.5
O1—C1—O2	108.5 (2)	H19B—C19—H19C	109.5
H1A—C1—H1B	114 (3)	O4—C20—H20A	109.5
O2—C1—H1A	113 (2)	O4—C20—H20B	109.5
O2—C1—H1B	107 (2)	O4—C20—H20C	109.5
C2—O2—C1	105.3 (2)	H20A—C20—H20B	109.5
O2—C2—C18	110.2 (2)	H20A—C20—H20C	109.5
C3—C2—O2	128.2 (2)	H20B—C20—H20C	109.5
C3—C2—C18	121.6 (2)	C21—N2—H2	119.3 (19)
C9—O3—C19	113.77 (19)	C21—N2—C27	123.01 (18)
C2—C3—H3	121.3	C27—N2—H2	108.5 (19)
C2—C3—C4	117.4 (2)	N2—C21—C22	122.9 (2)
C4—C3—H3	121.3	N2—C21—C26	121.9 (2)
C10—O4—C20	118.7 (2)	C26—C21—C22	115.0 (2)
C3—C4—C5	120.46 (19)	C21—C22—Cl1	119.58 (17)
C16—C4—C3	121.00 (19)	C23—C22—Cl1	117.78 (18)
C16—C4—C5	118.50 (19)	C23—C22—C21	122.6 (2)
C4—C5—H5A	109.5	C22—C23—H23	120.0
C4—C5—H5B	109.5	C24—C23—C22	120.0 (2)
H5A—C5—H5B	108.1	C24—C23—H23	120.0
C6—C5—C4	110.82 (18)	C23—C24—H24	120.1
C6—C5—H5A	109.5	C23—C24—C25	119.7 (2)
C6—C5—H5B	109.5	C25—C24—H24	120.1
N1—C6—C5	110.57 (17)	C24—C25—H25	120.3
N1—C6—H6A	109.5	C26—C25—C24	119.4 (2)
N1—C6—H6B	109.5	C26—C25—H25	120.3
C5—C6—H6A	109.5	C21—C26—Cl2	118.19 (17)
C5—C6—H6B	109.5	C25—C26—Cl2	118.59 (19)
H6A—C6—H6B	108.1	C25—C26—C21	123.2 (2)
N1—C7—H7	119.0	C28—C27—N2	122.0 (2)
N1—C7—C8	122.02 (19)	C28—C27—C32	120.1 (2)
C8—C7—H7	119.0	C32—C27—N2	117.92 (19)
C7—C8—C9	121.33 (19)	C27—C28—H28	119.8
C7—C8—C13	117.75 (19)	C27—C28—C29	120.3 (2)
C9—C8—C13	120.91 (18)	C29—C28—H28	119.8
O3—C9—C8	118.97 (19)	C28—C29—H29	119.9
O3—C9—C10	121.4 (2)	C30—C29—C28	120.1 (3)
C10—C9—C8	119.5 (2)	C30—C29—H29	119.9
O4—C10—C9	116.0 (2)	C29—C30—H30	120.1
O4—C10—C11	124.5 (2)	C29—C30—C31	119.9 (2)
C9—C10—C11	119.5 (2)	C31—C30—H30	120.1
C10—C11—H11	119.1	C30—C31—H31	119.2
C12—C11—C10	121.9 (2)	C30—C31—C32	121.5 (2)
C12—C11—H11	119.1	C32—C31—H31	119.2
C11—C12—H12	120.1	C27—C32—C33	121.52 (19)
C11—C12—C13	119.8 (2)	C31—C32—C27	118.0 (2)
C13—C12—H12	120.1	C31—C32—C33	120.5 (2)
C8—C13—C12	118.3 (2)	C32—C33—H33A	108.9
C14—C13—C8	118.31 (18)	C32—C33—H33B	108.9
C14—C13—C12	123.4 (2)	C32—C33—C34	113.50 (19)
C13—C14—H14	118.9	H33A—C33—H33B	107.7
C15—C14—C13	122.14 (19)	C34—C33—H33A	108.9
C15—C14—H14	118.9	C34—C33—H33B	108.9
N1—C15—C16	118.07 (17)	O5—C34—O6	125.0 (2)
C14—C15—N1	117.58 (19)	O5—C34—C33	118.8 (2)
C14—C15—C16	124.34 (18)	O6—C34—C33	116.22 (19)
C4—C16—C15	120.22 (18)	C35—O7—H7A	109.5
C4—C16—C17	120.2 (2)	O7—C35—H35A	109.5
C17—C16—C15	119.56 (18)	O7—C35—H35B	109.5
C16—C17—H17	121.4	O7—C35—H35C	109.5
C18—C17—C16	117.2 (2)	H35A—C35—H35B	109.5
C18—C17—H17	121.4	H35A—C35—H35C	109.5
C2—C18—O1	109.6 (2)	H35B—C35—H35C	109.5
C17—C18—O1	127.9 (2)

O1—C1—O2—C2	4.9 (3)	C13—C14—C15—C16	−179.35 (18)
N1—C7—C8—C9	178.43 (18)	C14—C15—C16—C4	163.5 (2)
N1—C7—C8—C13	−0.3 (3)	C14—C15—C16—C17	−13.9 (3)
N1—C15—C16—C4	−15.5 (3)	C15—N1—C6—C5	40.0 (3)
N1—C15—C16—C17	167.16 (18)	C15—N1—C7—C8	1.2 (3)
C1—O1—C18—C2	3.2 (3)	C15—C16—C17—C18	178.1 (2)
C1—O1—C18—C17	−176.0 (3)	C16—C4—C5—C6	35.8 (3)
C1—O2—C2—C3	176.8 (3)	C16—C17—C18—O1	179.5 (2)
C1—O2—C2—C18	−2.9 (3)	C16—C17—C18—C2	0.4 (3)
O2—C2—C3—C4	−179.9 (2)	C18—O1—C1—O2	−5.0 (4)
O2—C2—C18—O1	−0.2 (3)	C18—C2—C3—C4	−0.3 (3)
O2—C2—C18—C17	179.1 (2)	C19—O3—C9—C8	97.9 (3)
C2—C3—C4—C5	−176.6 (2)	C19—O3—C9—C10	−86.1 (3)
C2—C3—C4—C16	1.3 (3)	C20—O4—C10—C9	−177.7 (2)
O3—C9—C10—O4	1.5 (3)	C20—O4—C10—C11	1.7 (3)
O3—C9—C10—C11	−178.0 (2)	Cl1—C22—C23—C24	175.7 (2)
C3—C2—C18—O1	−179.9 (2)	N2—C21—C22—Cl1	1.0 (3)
C3—C2—C18—C17	−0.6 (4)	N2—C21—C22—C23	178.2 (2)
C3—C4—C5—C6	−146.3 (2)	N2—C21—C26—Cl2	2.3 (3)
C3—C4—C16—C15	−178.9 (2)	N2—C21—C26—C25	−177.3 (2)
C3—C4—C16—C17	−1.5 (3)	N2—C27—C28—C29	179.4 (2)
O4—C10—C11—C12	−178.7 (2)	N2—C27—C32—C31	−177.85 (19)
C4—C5—C6—N1	−53.4 (3)	N2—C27—C32—C33	2.8 (3)
C4—C16—C17—C18	0.7 (3)	C21—N2—C27—C28	14.0 (3)
C5—C4—C16—C15	−1.0 (3)	C21—N2—C27—C32	−166.4 (2)
C5—C4—C16—C17	176.4 (2)	C21—C22—C23—C24	−1.6 (4)
C6—N1—C7—C8	−175.34 (19)	C22—C21—C26—Cl2	178.11 (16)
C6—N1—C15—C14	175.61 (18)	C22—C21—C26—C25	−1.5 (3)
C6—N1—C15—C16	−5.3 (3)	C22—C23—C24—C25	−0.3 (4)
C7—N1—C6—C5	−143.37 (19)	C23—C24—C25—C26	1.2 (4)
C7—N1—C15—C14	−0.8 (3)	C24—C25—C26—Cl2	−179.8 (2)
C7—N1—C15—C16	178.21 (18)	C24—C25—C26—C21	−0.3 (4)
C7—C8—C9—O3	−1.4 (3)	C26—C21—C22—Cl1	−174.83 (17)
C7—C8—C9—C10	−177.5 (2)	C26—C21—C22—C23	2.4 (3)
C7—C8—C13—C12	179.71 (18)	C27—N2—C21—C22	61.0 (3)
C7—C8—C13—C14	−0.9 (3)	C27—N2—C21—C26	−123.5 (2)
C8—C9—C10—O4	177.46 (18)	C27—C28—C29—C30	−1.6 (4)
C8—C9—C10—C11	−2.0 (3)	C27—C32—C33—C34	−79.8 (3)
C8—C13—C14—C15	1.2 (3)	C28—C27—C32—C31	1.7 (3)
C9—C8—C13—C12	1.0 (3)	C28—C27—C32—C33	−177.6 (2)
C9—C8—C13—C14	−179.59 (18)	C28—C29—C30—C31	1.7 (4)
C9—C10—C11—C12	0.7 (3)	C29—C30—C31—C32	−0.2 (4)
C10—C11—C12—C13	1.5 (3)	C30—C31—C32—C27	−1.5 (3)
C11—C12—C13—C8	−2.3 (3)	C30—C31—C32—C33	177.8 (2)
C11—C12—C13—C14	178.3 (2)	C31—C32—C33—C34	100.9 (2)
C12—C13—C14—C15	−179.42 (19)	C32—C27—C28—C29	−0.2 (3)
C13—C8—C9—O3	177.27 (18)	C32—C33—C34—O5	−123.0 (2)
C13—C8—C9—C10	1.2 (3)	C32—C33—C34—O6	56.4 (3)
C13—C14—C15—N1	−0.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O6	0.86 (3)	2.02 (3)	2.818 (2)	153 (3)
O7—H7A···O6ⁱ	0.82	1.87	2.691 (2)	174

Symmetry code: (i) −x+1, −y+1, −z+1.

5,6-Dihydro-9,10-dimethoxybenzo[g][1,3]benzodioxolo[5,6-a]quinolizinium 2-[2-(2,6-dichloroanilino)phenyl]acetate methanol disolvate (V) top

Crystal data top

C₂₀H₁₈NO₄⁺·C₁₄H₁₀Cl₂NO₂⁻·2CH₄O	Z = 2
M_r = 695.57	F(000) = 728
Triclinic, P1	D_x = 1.401 Mg m⁻³
a = 8.1183 (3) Å	Cu Kα radiation, λ = 1.54184 Å
b = 13.7384 (6) Å	Cell parameters from 6387 reflections
c = 15.0469 (6) Å	θ = 4.1–66.5°
α = 97.102 (4)°	µ = 2.25 mm⁻¹
β = 97.620 (3)°	T = 293 K
γ = 91.886 (3)°	Block, clear yellowish yellow
V = 1648.57 (12) Å³	0.26 × 0.22 × 0.15 mm

Data collection top

Rigaku Xcalibur Atlas Gemini ultra diffractometer	5751 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance Ultra (Cu) X-ray Source	4614 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.039
Detector resolution: 10.4674 pixels mm^-1	θ_max = 66.6°, θ_min = 4.1°
ω scans	h = −8→9
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2017)	k = −16→16
T_min = 0.125, T_max = 1.000	l = −17→17
16859 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.146	w = 1/[σ²(F_o²) + (0.0813P)² + 0.3484P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
5751 reflections	Δρ_max = 0.32 e Å⁻³
462 parameters	Δρ_min = −0.33 e Å⁻³
0 restraints

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	−0.0485 (3)	0.25365 (14)	0.76395 (13)	0.0760 (5)
N1	0.2357 (2)	0.60657 (12)	0.57757 (12)	0.0491 (4)
C1	−0.0356 (4)	0.1635 (2)	0.70746 (19)	0.0726 (7)
H1A	0.0288	0.1185	0.7412	0.087*
H1B	−0.1455	0.1329	0.6860	0.087*
O2	0.0437 (3)	0.18485 (13)	0.63343 (14)	0.0857 (6)
C2	0.0099 (3)	0.32608 (18)	0.71966 (15)	0.0542 (5)
O3	0.3916 (2)	0.80020 (11)	0.41523 (12)	0.0603 (4)
C3	0.0166 (3)	0.4248 (2)	0.74396 (16)	0.0624 (6)
H3	−0.0238	0.4519	0.7961	0.075*
O4	0.4944 (2)	0.73234 (13)	0.25337 (12)	0.0647 (4)
C4	0.0860 (3)	0.48460 (17)	0.68830 (14)	0.0504 (5)
C5	0.0731 (9)	0.5951 (4)	0.7035 (4)	0.0514 (12)	0.680 (13)
H5A	−0.0270	0.6134	0.6680	0.062*	0.680 (13)
H5B	0.0664	0.6163	0.7668	0.062*	0.680 (13)
C6	0.2242 (9)	0.6445 (3)	0.6761 (3)	0.0519 (14)	0.680 (13)
H6A	0.3239	0.6299	0.7143	0.062*	0.680 (13)
H6B	0.2145	0.7151	0.6830	0.062*	0.680 (13)
C5'	0.154 (2)	0.5917 (8)	0.7229 (8)	0.055 (3)	0.320 (13)
H5'A	0.0957	0.6191	0.7719	0.066*	0.320 (13)
H5'B	0.2713	0.5926	0.7452	0.066*	0.320 (13)
C6'	0.1259 (17)	0.6495 (6)	0.6471 (7)	0.052 (3)	0.320 (13)
H6'A	0.1575	0.7182	0.6672	0.062*	0.320 (13)
H6'B	0.0096	0.6441	0.6209	0.062*	0.320 (13)
C7	0.2940 (3)	0.66827 (15)	0.52702 (15)	0.0489 (5)
H7	0.3032	0.7351	0.5480	0.059*
C8	0.3424 (2)	0.63586 (15)	0.44289 (13)	0.0420 (4)
C9	0.3994 (3)	0.70231 (15)	0.38758 (14)	0.0464 (5)
C10	0.4476 (3)	0.66512 (17)	0.30590 (15)	0.0500 (5)
C11	0.4439 (3)	0.56286 (17)	0.28038 (15)	0.0529 (5)
H11	0.4810	0.5388	0.2264	0.064*
C12	0.3874 (3)	0.49800 (17)	0.33281 (14)	0.0494 (5)
H12	0.3845	0.4308	0.3139	0.059*
C13	0.3337 (2)	0.53326 (15)	0.41551 (13)	0.0407 (4)
C14	0.2712 (2)	0.47077 (14)	0.47135 (13)	0.0404 (4)
H14	0.2659	0.4033	0.4535	0.048*
C15	0.2178 (2)	0.50552 (14)	0.55133 (13)	0.0395 (4)
C16	0.1453 (2)	0.44312 (15)	0.61012 (13)	0.0408 (4)
C17	0.1332 (3)	0.34076 (17)	0.58612 (16)	0.0571 (6)
H17	0.1705	0.3119	0.5337	0.069*
C18	0.0655 (3)	0.28534 (16)	0.64184 (16)	0.0535 (5)
C19	0.5437 (4)	0.8578 (2)	0.4287 (2)	0.0776 (8)
H19A	0.5932	0.8509	0.3738	0.116*
H19B	0.6184	0.8359	0.4763	0.116*
H19C	0.5223	0.9255	0.4449	0.116*
C20	0.5551 (4)	0.6972 (2)	0.17154 (18)	0.0717 (7)
H20A	0.4685	0.6586	0.1316	0.108*
H20B	0.6481	0.6574	0.1845	0.108*
H20C	0.5897	0.7519	0.1432	0.108*
Cl1	−0.20904 (8)	−0.09056 (5)	0.08844 (5)	0.0694 (2)
Cl2	−0.00842 (10)	0.28108 (5)	0.05698 (5)	0.0803 (2)
N2	−0.0265 (2)	0.10661 (16)	0.15542 (12)	0.0518 (4)
H2	0.059 (4)	0.146 (2)	0.1597 (18)	0.064 (8)*
O5	0.3420 (3)	0.25592 (14)	0.37666 (14)	0.0816 (6)
O6	0.2630 (3)	0.2294 (2)	0.23027 (15)	0.1094 (9)
C21	−0.1252 (2)	0.09840 (17)	0.07122 (13)	0.0479 (5)
C22	−0.2182 (3)	0.01198 (18)	0.03236 (15)	0.0537 (5)
C23	−0.3139 (3)	0.0042 (2)	−0.05167 (17)	0.0666 (7)
H23	−0.3765	−0.0535	−0.0746	0.080*
C24	−0.3162 (3)	0.0817 (3)	−0.10100 (17)	0.0745 (8)
H24	−0.3817	0.0771	−0.1571	0.089*
C25	−0.2217 (3)	0.1664 (2)	−0.06751 (17)	0.0692 (7)
H25	−0.2204	0.2183	−0.1017	0.083*
C26	−0.1285 (3)	0.17412 (19)	0.01726 (16)	0.0568 (6)
C27	−0.0886 (2)	0.09709 (14)	0.23707 (13)	0.0409 (4)
C28	−0.2583 (3)	0.08901 (16)	0.24236 (15)	0.0483 (5)
H28	−0.3348	0.0901	0.1907	0.058*
C29	−0.3139 (3)	0.07936 (17)	0.32417 (17)	0.0559 (6)
H29	−0.4275	0.0729	0.3267	0.067*
C30	−0.2034 (3)	0.07926 (17)	0.40138 (17)	0.0569 (6)
H30	−0.2415	0.0735	0.4562	0.068*
C31	−0.0348 (3)	0.08789 (16)	0.39669 (15)	0.0513 (5)
H31	0.0401	0.0885	0.4492	0.062*
C32	0.0259 (2)	0.09559 (14)	0.31563 (14)	0.0424 (4)
C33	0.2115 (3)	0.10067 (16)	0.31338 (15)	0.0482 (5)
H33A	0.2365	0.0567	0.2619	0.058*
H33B	0.2674	0.0783	0.3677	0.058*
C34	0.2795 (3)	0.20444 (17)	0.30694 (16)	0.0522 (5)
O7	0.4318 (3)	0.35185 (14)	0.15097 (13)	0.0723 (5)
H7A	0.3841	0.3175	0.1815	0.108*
C35	0.5100 (5)	0.2927 (3)	0.0899 (2)	0.0926 (10)
H35A	0.4279	0.2585	0.0438	0.139*
H35B	0.5727	0.2459	0.1209	0.139*
H35C	0.5835	0.3325	0.0628	0.139*
O8	0.2390 (6)	0.4938 (4)	0.0783 (3)	0.1757 (18)
H8	0.3253	0.4714	0.1003	0.264*
C36	0.2274 (7)	0.4796 (4)	−0.0149 (3)	0.1331 (16)
H36A	0.1723	0.5332	−0.0392	0.200*
H36B	0.1648	0.4192	−0.0381	0.200*
H36C	0.3370	0.4765	−0.0321	0.200*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.1059 (15)	0.0655 (12)	0.0631 (11)	−0.0035 (10)	0.0237 (10)	0.0230 (9)
N1	0.0665 (11)	0.0355 (9)	0.0453 (10)	0.0030 (8)	0.0174 (8)	−0.0054 (7)
C1	0.099 (2)	0.0558 (15)	0.0648 (16)	−0.0022 (14)	0.0085 (14)	0.0212 (12)
O2	0.1379 (19)	0.0435 (10)	0.0836 (13)	−0.0050 (10)	0.0439 (13)	0.0107 (9)
C2	0.0601 (13)	0.0578 (14)	0.0465 (12)	0.0023 (10)	0.0047 (10)	0.0168 (10)
O3	0.0685 (10)	0.0387 (8)	0.0763 (11)	0.0023 (7)	0.0225 (8)	0.0042 (7)
C3	0.0815 (17)	0.0637 (15)	0.0442 (12)	0.0035 (12)	0.0184 (11)	0.0055 (10)
O4	0.0817 (11)	0.0582 (10)	0.0587 (10)	−0.0027 (8)	0.0229 (8)	0.0131 (8)
C4	0.0595 (13)	0.0493 (12)	0.0413 (11)	0.0035 (10)	0.0083 (9)	−0.0008 (9)
C5	0.057 (3)	0.051 (2)	0.044 (2)	0.003 (2)	0.012 (2)	−0.0060 (16)
C6	0.066 (4)	0.0456 (19)	0.041 (2)	0.0010 (18)	0.012 (2)	−0.0118 (14)
C5'	0.064 (7)	0.051 (5)	0.046 (5)	0.001 (5)	0.011 (5)	−0.013 (4)
C6'	0.056 (6)	0.045 (4)	0.051 (5)	0.007 (4)	0.013 (5)	−0.012 (3)
C7	0.0595 (12)	0.0328 (10)	0.0543 (12)	0.0007 (9)	0.0150 (10)	−0.0023 (9)
C8	0.0396 (10)	0.0407 (11)	0.0439 (10)	0.0023 (8)	0.0042 (8)	0.0001 (8)
C9	0.0470 (11)	0.0393 (11)	0.0528 (12)	0.0029 (8)	0.0076 (9)	0.0042 (9)
C10	0.0484 (11)	0.0538 (13)	0.0482 (12)	−0.0008 (9)	0.0076 (9)	0.0089 (9)
C11	0.0583 (13)	0.0543 (13)	0.0455 (11)	0.0003 (10)	0.0136 (9)	−0.0023 (9)
C12	0.0555 (12)	0.0459 (12)	0.0448 (11)	0.0001 (9)	0.0104 (9)	−0.0053 (9)
C13	0.0371 (9)	0.0415 (11)	0.0412 (10)	0.0023 (8)	0.0027 (8)	−0.0010 (8)
C14	0.0425 (10)	0.0354 (10)	0.0404 (10)	0.0019 (8)	0.0030 (8)	−0.0030 (8)
C15	0.0405 (10)	0.0357 (10)	0.0398 (10)	0.0036 (8)	0.0018 (8)	−0.0010 (8)
C16	0.0407 (10)	0.0405 (10)	0.0392 (10)	0.0042 (8)	0.0017 (8)	0.0013 (8)
C17	0.0782 (16)	0.0423 (12)	0.0532 (13)	0.0041 (11)	0.0221 (11)	0.0010 (10)
C18	0.0645 (14)	0.0414 (12)	0.0552 (13)	0.0031 (10)	0.0073 (10)	0.0095 (9)
C19	0.0855 (19)	0.0505 (15)	0.094 (2)	−0.0139 (13)	0.0215 (16)	−0.0062 (13)
C20	0.0755 (17)	0.087 (2)	0.0587 (15)	0.0019 (14)	0.0238 (13)	0.0181 (13)
Cl1	0.0674 (4)	0.0559 (4)	0.0807 (4)	−0.0018 (3)	0.0041 (3)	−0.0005 (3)
Cl2	0.0985 (5)	0.0648 (4)	0.0808 (5)	−0.0081 (4)	0.0288 (4)	0.0072 (3)
N2	0.0411 (9)	0.0685 (12)	0.0440 (10)	−0.0095 (9)	0.0080 (7)	0.0010 (8)
O5	0.1060 (15)	0.0505 (10)	0.0786 (13)	−0.0104 (10)	−0.0049 (11)	−0.0076 (9)
O6	0.1154 (18)	0.133 (2)	0.0734 (14)	−0.0737 (16)	−0.0129 (12)	0.0372 (14)
C21	0.0394 (10)	0.0624 (14)	0.0418 (11)	0.0047 (9)	0.0113 (8)	−0.0009 (9)
C22	0.0442 (11)	0.0615 (14)	0.0532 (12)	0.0039 (10)	0.0086 (9)	−0.0037 (10)
C23	0.0505 (13)	0.0881 (19)	0.0541 (14)	0.0042 (12)	0.0025 (10)	−0.0134 (13)
C24	0.0634 (16)	0.112 (3)	0.0454 (13)	0.0187 (16)	0.0041 (11)	−0.0003 (14)
C25	0.0729 (16)	0.092 (2)	0.0497 (13)	0.0252 (15)	0.0217 (12)	0.0161 (13)
C26	0.0557 (13)	0.0662 (15)	0.0510 (12)	0.0071 (11)	0.0207 (10)	0.0018 (10)
C27	0.0408 (10)	0.0361 (10)	0.0456 (11)	0.0014 (8)	0.0109 (8)	−0.0003 (8)
C28	0.0411 (10)	0.0468 (12)	0.0564 (12)	0.0020 (9)	0.0090 (9)	0.0026 (9)
C29	0.0473 (12)	0.0472 (12)	0.0773 (16)	0.0014 (9)	0.0262 (11)	0.0054 (11)
C30	0.0682 (15)	0.0487 (13)	0.0593 (14)	0.0022 (11)	0.0298 (12)	0.0068 (10)
C31	0.0618 (13)	0.0437 (12)	0.0487 (12)	0.0015 (10)	0.0104 (10)	0.0047 (9)
C32	0.0467 (11)	0.0318 (10)	0.0478 (11)	0.0016 (8)	0.0096 (8)	−0.0013 (8)
C33	0.0434 (11)	0.0452 (11)	0.0526 (12)	0.0033 (9)	0.0050 (9)	−0.0053 (9)
C34	0.0428 (11)	0.0533 (13)	0.0577 (13)	−0.0043 (9)	0.0031 (9)	0.0020 (10)
O7	0.0885 (13)	0.0619 (11)	0.0671 (11)	−0.0103 (9)	0.0251 (9)	−0.0012 (8)
C35	0.116 (3)	0.087 (2)	0.0760 (19)	−0.0059 (19)	0.0365 (18)	−0.0079 (16)
O8	0.218 (5)	0.159 (4)	0.124 (3)	0.059 (3)	−0.039 (3)	−0.031 (2)
C36	0.166 (5)	0.122 (4)	0.111 (4)	0.004 (3)	0.012 (3)	0.025 (3)

Geometric parameters (Å, º) top

O1—C1	1.428 (3)	C17—C18	1.355 (3)
O1—C2	1.370 (3)	C19—H19A	0.9600
N1—C6	1.525 (4)	C19—H19B	0.9600
N1—C6'	1.539 (7)	C19—H19C	0.9600
N1—C7	1.323 (3)	C20—H20A	0.9600
N1—C15	1.393 (3)	C20—H20B	0.9600
C1—H1A	0.9700	C20—H20C	0.9600
C1—H1B	0.9700	Cl1—C22	1.728 (3)
C1—O2	1.415 (3)	Cl2—C26	1.732 (3)
O2—C18	1.374 (3)	N2—H2	0.86 (3)
C2—C3	1.358 (4)	N2—C21	1.396 (3)
C2—C18	1.372 (3)	N2—C27	1.407 (3)
O3—C9	1.364 (3)	O5—C34	1.229 (3)
O3—C19	1.422 (3)	O6—C34	1.235 (3)
C3—H3	0.9300	C21—C22	1.405 (3)
C3—C4	1.399 (3)	C21—C26	1.395 (3)
O4—C10	1.364 (3)	C22—C23	1.384 (3)
O4—C20	1.422 (3)	C23—H23	0.9300
C4—C5	1.516 (5)	C23—C24	1.371 (4)
C4—C5'	1.555 (11)	C24—H24	0.9300
C4—C16	1.394 (3)	C24—C25	1.374 (4)
C5—H5A	0.9700	C25—H25	0.9300
C5—H5B	0.9700	C25—C26	1.384 (4)
C5—C6	1.512 (10)	C27—C28	1.392 (3)
C6—H6A	0.9700	C27—C32	1.406 (3)
C6—H6B	0.9700	C28—H28	0.9300
C5'—H5'A	0.9700	C28—C29	1.386 (3)
C5'—H5'B	0.9700	C29—H29	0.9300
C5'—C6'	1.47 (2)	C29—C30	1.370 (4)
C6'—H6'A	0.9700	C30—H30	0.9300
C6'—H6'B	0.9700	C30—C31	1.382 (3)
C7—H7	0.9300	C31—H31	0.9300
C7—C8	1.400 (3)	C31—C32	1.389 (3)
C8—C9	1.415 (3)	C32—C33	1.511 (3)
C8—C13	1.416 (3)	C33—H33A	0.9700
C9—C10	1.382 (3)	C33—H33B	0.9700
C10—C11	1.408 (3)	C33—C34	1.531 (3)
C11—H11	0.9300	O7—H7A	0.8200
C11—C12	1.367 (3)	O7—C35	1.382 (3)
C12—H12	0.9300	C35—H35A	0.9600
C12—C13	1.408 (3)	C35—H35B	0.9600
C13—C14	1.401 (3)	C35—H35C	0.9600
C14—H14	0.9300	O8—H8	0.8200
C14—C15	1.369 (3)	O8—C36	1.381 (6)
C15—C16	1.469 (3)	C36—H36A	0.9600
C16—C17	1.405 (3)	C36—H36B	0.9600
C17—H17	0.9300	C36—H36C	0.9600

C2—O1—C1	105.90 (19)	C16—C17—H17	121.1
C7—N1—C6	117.9 (2)	C18—C17—C16	117.9 (2)
C7—N1—C6'	116.6 (3)	C18—C17—H17	121.1
C7—N1—C15	122.81 (17)	C2—C18—O2	109.5 (2)
C15—N1—C6	117.9 (2)	C17—C18—O2	128.3 (2)
C15—N1—C6'	116.6 (3)	C17—C18—C2	122.2 (2)
O1—C1—H1A	110.1	O3—C19—H19A	109.5
O1—C1—H1B	110.1	O3—C19—H19B	109.5
H1A—C1—H1B	108.4	O3—C19—H19C	109.5
O2—C1—O1	108.0 (2)	H19A—C19—H19B	109.5
O2—C1—H1A	110.1	H19A—C19—H19C	109.5
O2—C1—H1B	110.1	H19B—C19—H19C	109.5
C18—O2—C1	106.38 (19)	O4—C20—H20A	109.5
O1—C2—C18	110.0 (2)	O4—C20—H20B	109.5
C3—C2—O1	128.5 (2)	O4—C20—H20C	109.5
C3—C2—C18	121.5 (2)	H20A—C20—H20B	109.5
C9—O3—C19	116.86 (19)	H20A—C20—H20C	109.5
C2—C3—H3	121.0	H20B—C20—H20C	109.5
C2—C3—C4	118.1 (2)	C21—N2—H2	113.2 (18)
C4—C3—H3	121.0	C21—N2—C27	124.07 (18)
C10—O4—C20	118.1 (2)	C27—N2—H2	115.5 (19)
C3—C4—C5	120.5 (3)	N2—C21—C22	122.8 (2)
C3—C4—C5'	122.2 (5)	C26—C21—N2	121.6 (2)
C16—C4—C3	120.4 (2)	C26—C21—C22	115.5 (2)
C16—C4—C5	118.4 (3)	C21—C22—Cl1	119.71 (17)
C16—C4—C5'	114.5 (5)	C23—C22—Cl1	117.9 (2)
C4—C5—H5A	109.8	C23—C22—C21	122.3 (2)
C4—C5—H5B	109.8	C22—C23—H23	120.1
H5A—C5—H5B	108.2	C24—C23—C22	119.8 (3)
C6—C5—C4	109.5 (4)	C24—C23—H23	120.1
C6—C5—H5A	109.8	C23—C24—H24	120.0
C6—C5—H5B	109.8	C23—C24—C25	120.0 (2)
N1—C6—H6A	110.0	C25—C24—H24	120.0
N1—C6—H6B	110.0	C24—C25—H25	120.1
C5—C6—N1	108.6 (4)	C24—C25—C26	119.8 (3)
C5—C6—H6A	110.0	C26—C25—H25	120.1
C5—C6—H6B	110.0	C21—C26—Cl2	118.76 (18)
H6A—C6—H6B	108.3	C25—C26—Cl2	118.7 (2)
C4—C5'—H5'A	110.1	C25—C26—C21	122.5 (3)
C4—C5'—H5'B	110.1	C28—C27—N2	122.31 (19)
H5'A—C5'—H5'B	108.4	C28—C27—C32	119.33 (18)
C6'—C5'—C4	108.0 (10)	C32—C27—N2	118.36 (17)
C6'—C5'—H5'A	110.1	C27—C28—H28	119.8
C6'—C5'—H5'B	110.1	C29—C28—C27	120.4 (2)
N1—C6'—H6'A	110.5	C29—C28—H28	119.8
N1—C6'—H6'B	110.5	C28—C29—H29	119.6
C5'—C6'—N1	105.9 (10)	C30—C29—C28	120.8 (2)
C5'—C6'—H6'A	110.5	C30—C29—H29	119.6
C5'—C6'—H6'B	110.5	C29—C30—H30	120.4
H6'A—C6'—H6'B	108.7	C29—C30—C31	119.1 (2)
N1—C7—H7	119.1	C31—C30—H30	120.4
N1—C7—C8	121.86 (19)	C30—C31—H31	119.1
C8—C7—H7	119.1	C30—C31—C32	121.8 (2)
C7—C8—C9	121.75 (19)	C32—C31—H31	119.1
C7—C8—C13	117.18 (19)	C27—C32—C33	121.66 (18)
C9—C8—C13	121.07 (18)	C31—C32—C27	118.57 (19)
O3—C9—C8	117.53 (18)	C31—C32—C33	119.76 (19)
O3—C9—C10	123.60 (19)	C32—C33—H33A	109.1
C10—C9—C8	118.7 (2)	C32—C33—H33B	109.1
O4—C10—C9	116.3 (2)	C32—C33—C34	112.66 (17)
O4—C10—C11	123.7 (2)	H33A—C33—H33B	107.8
C9—C10—C11	120.0 (2)	C34—C33—H33A	109.1
C10—C11—H11	119.1	C34—C33—H33B	109.1
C12—C11—C10	121.82 (19)	O5—C34—O6	125.7 (2)
C12—C11—H11	119.1	O5—C34—C33	118.7 (2)
C11—C12—H12	120.1	O6—C34—C33	115.6 (2)
C11—C12—C13	119.8 (2)	C35—O7—H7A	109.5
C13—C12—H12	120.1	O7—C35—H35A	109.5
C12—C13—C8	118.62 (19)	O7—C35—H35B	109.5
C14—C13—C8	118.85 (17)	O7—C35—H35C	109.5
C14—C13—C12	122.52 (19)	H35A—C35—H35B	109.5
C13—C14—H14	118.9	H35A—C35—H35C	109.5
C15—C14—C13	122.27 (18)	H35B—C35—H35C	109.5
C15—C14—H14	118.9	C36—O8—H8	109.5
N1—C15—C16	118.99 (16)	O8—C36—H36A	109.5
C14—C15—N1	116.89 (18)	O8—C36—H36B	109.5
C14—C15—C16	124.12 (18)	O8—C36—H36C	109.5
C4—C16—C15	120.65 (19)	H36A—C36—H36B	109.5
C4—C16—C17	119.9 (2)	H36A—C36—H36C	109.5
C17—C16—C15	119.40 (18)	H36B—C36—H36C	109.5

O1—C1—O2—C18	−4.5 (3)	C11—C12—C13—C14	178.6 (2)
O1—C2—C3—C4	178.5 (2)	C12—C13—C14—C15	−179.42 (19)
O1—C2—C18—O2	0.3 (3)	C13—C8—C9—O3	174.85 (18)
O1—C2—C18—C17	−178.5 (2)	C13—C8—C9—C10	−0.3 (3)
N1—C7—C8—C9	177.8 (2)	C13—C14—C15—N1	−3.1 (3)
N1—C7—C8—C13	−2.9 (3)	C13—C14—C15—C16	177.41 (17)
N1—C15—C16—C4	3.8 (3)	C14—C15—C16—C4	−176.71 (19)
N1—C15—C16—C17	−177.3 (2)	C14—C15—C16—C17	2.2 (3)
C1—O1—C2—C3	176.9 (3)	C15—N1—C6—C5	−47.4 (6)
C1—O1—C2—C18	−3.1 (3)	C15—N1—C6'—C5'	52.5 (13)
C1—O2—C18—C2	2.7 (3)	C15—N1—C7—C8	0.0 (3)
C1—O2—C18—C17	−178.6 (3)	C15—C16—C17—C18	−179.9 (2)
C2—O1—C1—O2	4.7 (3)	C16—C4—C5—C6	−40.8 (7)
C2—C3—C4—C5	170.5 (4)	C16—C4—C5'—C6'	51.6 (13)
C2—C3—C4—C5'	−159.3 (8)	C16—C17—C18—O2	−178.7 (2)
C2—C3—C4—C16	0.3 (4)	C16—C17—C18—C2	−0.1 (4)
O3—C9—C10—O4	2.3 (3)	C18—C2—C3—C4	−1.5 (4)
O3—C9—C10—C11	−176.7 (2)	C19—O3—C9—C8	121.8 (2)
C3—C2—C18—O2	−179.7 (2)	C19—O3—C9—C10	−63.3 (3)
C3—C2—C18—C17	1.5 (4)	C20—O4—C10—C9	176.0 (2)
C3—C4—C5—C6	148.8 (4)	C20—O4—C10—C11	−5.1 (3)
C3—C4—C5'—C6'	−147.6 (8)	Cl1—C22—C23—C24	−175.86 (19)
C3—C4—C16—C15	179.8 (2)	N2—C21—C22—Cl1	−1.4 (3)
C3—C4—C16—C17	0.9 (3)	N2—C21—C22—C23	−179.14 (19)
O4—C10—C11—C12	−176.3 (2)	N2—C21—C26—Cl2	−0.7 (3)
C4—C5—C6—N1	57.1 (7)	N2—C21—C26—C25	178.1 (2)
C4—C5'—C6'—N1	−65.2 (14)	N2—C27—C28—C29	179.7 (2)
C4—C16—C17—C18	−1.0 (3)	N2—C27—C32—C31	178.92 (19)
C5—C4—C16—C15	9.5 (4)	N2—C27—C32—C33	−2.0 (3)
C5—C4—C16—C17	−169.4 (4)	C21—N2—C27—C28	−7.2 (3)
C6—N1—C7—C8	166.1 (4)	C21—N2—C27—C32	172.7 (2)
C6—N1—C15—C14	−163.2 (4)	C21—C22—C23—C24	1.9 (3)
C6—N1—C15—C16	16.4 (4)	C22—C21—C26—Cl2	−176.53 (15)
C5'—C4—C16—C15	−19.0 (7)	C22—C21—C26—C25	2.3 (3)
C5'—C4—C16—C17	162.1 (7)	C22—C23—C24—C25	0.9 (4)
C6'—N1—C7—C8	−156.8 (6)	C23—C24—C25—C26	−2.0 (4)
C6'—N1—C15—C14	159.8 (6)	C24—C25—C26—Cl2	179.13 (19)
C6'—N1—C15—C16	−20.7 (7)	C24—C25—C26—C21	0.3 (4)
C7—N1—C6—C5	145.7 (4)	C26—C21—C22—Cl1	174.31 (15)
C7—N1—C6'—C5'	−149.3 (8)	C26—C21—C22—C23	−3.4 (3)
C7—N1—C15—C14	3.0 (3)	C27—N2—C21—C22	−61.8 (3)
C7—N1—C15—C16	−177.42 (19)	C27—N2—C21—C26	122.7 (2)
C7—C8—C9—O3	−5.8 (3)	C27—C28—C29—C30	1.1 (3)
C7—C8—C9—C10	179.0 (2)	C27—C32—C33—C34	76.6 (2)
C7—C8—C13—C12	−177.62 (19)	C28—C27—C32—C31	−1.2 (3)
C7—C8—C13—C14	2.7 (3)	C28—C27—C32—C33	177.93 (18)
C8—C9—C10—O4	177.15 (19)	C28—C29—C30—C31	−0.7 (3)
C8—C9—C10—C11	−1.8 (3)	C29—C30—C31—C32	−0.7 (3)
C8—C13—C14—C15	0.2 (3)	C30—C31—C32—C27	1.6 (3)
C9—C8—C13—C12	1.7 (3)	C30—C31—C32—C33	−177.49 (19)
C9—C8—C13—C14	−177.95 (18)	C31—C32—C33—C34	−104.3 (2)
C9—C10—C11—C12	2.6 (3)	C32—C27—C28—C29	−0.1 (3)
C10—C11—C12—C13	−1.1 (3)	C32—C33—C34—O5	97.1 (3)
C11—C12—C13—C8	−1.0 (3)	C32—C33—C34—O6	−81.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O6	0.86 (3)	2.07 (3)	2.864 (3)	154 (3)
O7—H7A···O6	0.82	1.82	2.629 (3)	170
O8—H8···O7	0.82	2.06	2.779 (5)	146

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Five solvates of a multicom­ponent pharmaceutical salt formed by berberine and diclofenac

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Five solvates of a multicomponent pharmaceutical salt formed by berberine and diclofenac