Structural variety of clofaziminium salts: effect of the counter-ion on clofaziminium conformation and crystal packing

Bodart, L.; Tumanov, N.; Wouters, J.

doi:10.1107/S2052520619007649

Structural variety of clofaziminium salts: effect of the counter-ion on clofaziminium conformation and crystal packing

Clofazimine is a water-insoluble antimycobacterial agent gaining attention as a treatment for multi-drug resistant and extensively drug-resistant tuberculosis. Novel salts of clofazimine are reported with fumaric, succinic, 2,4-dihydroxybenzoic and terephthalic acids and with saccharin. The salt structures were obtained by single-crystal X-ray diffraction. The salts with 2,4-dihydroxybenzoic acid and with saccharin are solvated (methanol and acetonitrile, respectively). The reaction of clofazimine with terephthalic acid led to two salt cocrystals, one solvated and one non-solvated. These new clofaziminium salts are compared with the currently known ones in terms of crystal packing and clofazimine/ium conformation. Clofaziminium hydrogen succinate presents isostructurality with clofaziminium hydrogen malonate, an already described salt. In the structure of clofaziminium terephthalate terephthalic acid salt cocrystal, solvent evaporation leads to packing and hydrogen-bonding modifications. In all the new structures, the clofaziminium conformation is quite well conserved and steric hindrance is observed around the protonated site. Conformational optimization of clofaziminium reveals that this steric-hindrance energy penalty is compensated for by hydrogen-bond interactions with the salt counter-ions.

Keywords: clofazimine; salts; conformational comparison; crystal packing comparison; counter-ion effect on clofaziminium conformation; tuberculosis.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520619007649/aw5025sup1.cif Contains datablocks global, lb0211_CLZ-FA, lb_CLZ-SA, lb0276_CLZ_SAC, lb0587_CFZ-SACC_LAG_MeCN_dried, lb0214_CLZ-24DHBA, lb0221_clz-trpta_100k_remo_sq, lb0329_CLZ-TRPTA_reMo
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520619007649/aw5025lb0211_CLZ-FAsup2.hkl Contains datablock lb0211_CLZ-FA
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520619007649/aw5025lb_CLZ-SAsup3.hkl Contains datablock lb_CLZ-SA
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520619007649/aw5025lb0276_CLZ_SACsup4.hkl Contains datablock lb0276_CLZ_SAC
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520619007649/aw5025lb0587_CFZ-SACC_LAG_MeCN_driedsup5.hkl Contains datablock lb0587_CFZ-SACC_LAG_MeCN_dried
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520619007649/aw5025lb0214_CLZ-24DHBAsup6.hkl Contains datablock lb0214_CLZ-24DHBA
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520619007649/aw5025lb0221_clz-trpta_100k_remo_sqsup7.hkl Contains datablock lb0221_clz-trpta_100k_remo_sq
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520619007649/aw5025lb0329_CLZ-TRPTA_reMosup8.hkl Contains datablock lb0329_CLZ-TRPTA_reMo
	Portable Document Format (PDF) file https://doi.org/10.1107/S2052520619007649/aw5025sup9.pdf Additional figures and tables

CCDC references: 1918685; 1918686; 1918687; 1918688; 1918689; 1918690; 1918691

Computing details top

Data collection: CrysAlis PRO 1.171.38.46 (Rigaku Oxford Diffraction, 2015) for lb0211_CLZ-FA, lb0276_CLZ_SAC, lb0221_clz-trpta_100k_remo_sq; CrysAlis PRO 1.171.39.46 (Rigaku Oxford Diffraction, 2018) for lb_CLZ-SA, lb0587_CFZ-SACC_LAG_MeCN_dried, lb0214_CLZ-24DHBA, lb0329_CLZ-TRPTA_reMo. Cell refinement: CrysAlis PRO 1.171.38.46 (Rigaku Oxford Diffraction, 2015) for lb0211_CLZ-FA, lb0276_CLZ_SAC, lb0221_clz-trpta_100k_remo_sq; CrysAlis PRO 1.171.39.46 (Rigaku Oxford Diffraction, 2018) for lb_CLZ-SA, lb0587_CFZ-SACC_LAG_MeCN_dried, lb0214_CLZ-24DHBA, lb0329_CLZ-TRPTA_reMo. Data reduction: CrysAlis PRO 1.171.38.46 (Rigaku Oxford Diffraction, 2015) for lb0211_CLZ-FA, lb0276_CLZ_SAC, lb0221_clz-trpta_100k_remo_sq; CrysAlis PRO 1.171.39.46 (Rigaku Oxford Diffraction, 2018) for lb_CLZ-SA, lb0214_CLZ-24DHBA, lb0329_CLZ-TRPTA_reMo; CrysAlis PRO 1.171.39.46 (Rigaku Oxford DiffractionO 2018) for lb0587_CFZ-SACC_LAG_MeCN_dried. Program(s) used to solve structure: SHELXT (Sheldrick, 2015) for lb0211_CLZ-FA, lb_CLZ-SA; SHELXT 2014/5 (Sheldrick, 2014) for lb0276_CLZ_SAC, lb0587_CFZ-SACC_LAG_MeCN_dried, lb0214_CLZ-24DHBA, lb0221_clz-trpta_100k_remo_sq, lb0329_CLZ-TRPTA_reMo. For all structures, program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2016).

N-[(2E)-10-(4-chlorophenyl)-3-[(4-chlorophenyl)amino]-2,10-dihydrophenazin- 2-ylidene]propan-2-aminium (2E)-3-carboxyprop-2-enoate (lb0211_CLZ-FA) top

Crystal data top

C₂₇H₂₃Cl₂N₄⁺·C₄H₃O₄⁻	F(000) = 1224
M_r = 589.46	D_x = 1.395 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
a = 7.47882 (9) Å	Cell parameters from 8175 reflections
b = 26.0041 (3) Å	θ = 3.5–67.1°
c = 14.78241 (16) Å	µ = 2.45 mm⁻¹
β = 102.5075 (12)°	T = 295 K
V = 2806.65 (6) Å³	Plate, metallic dark red
Z = 4	0.57 × 0.13 × 0.04 mm

Data collection top

Xcalibur Ruby Gemini ultra diffractometer	4944 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance Ultra (Cu) X-ray Source	4394 reflections with I > 2σ(I)
Detector resolution: 5.1856 pixels mm^-1	R_int = 0.021
ω scans	θ_max = 67.1°, θ_min = 3.5°
Absorption correction: analytical CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R. C. Clark & J. S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −8→7
T_min = 0.502, T_max = 0.915	k = −30→31
15078 measured reflections	l = −17→16

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: dual
R[F² > 2σ(F²)] = 0.049	Hydrogen site location: mixed
wR(F²) = 0.136	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0701P)² + 1.5073P] where P = (F_o² + 2F_c²)/3
4944 reflections	(Δ/σ)_max = 0.001
383 parameters	Δρ_max = 0.46 e Å⁻³
0 restraints	Δρ_min = −0.51 e Å⁻³

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
Cl1	0.03334 (13)	0.65011 (4)	0.06217 (5)	0.1055 (4)
Cl2	0.74223 (13)	0.50537 (4)	1.12083 (5)	0.0985 (3)
N1	0.2143 (2)	0.54445 (6)	0.42371 (10)	0.0372 (3)
N2	0.3161 (2)	0.47961 (6)	0.57696 (11)	0.0407 (4)
N3	0.5666 (3)	0.62149 (7)	0.76846 (11)	0.0464 (4)
H3	0.538 (4)	0.6517 (11)	0.7772 (18)	0.062 (8)*
N4	0.5107 (2)	0.68259 (6)	0.61406 (12)	0.0456 (4)
H4	0.555 (4)	0.6929 (10)	0.6683 (19)	0.059 (7)*
C1	0.0626 (3)	0.47190 (8)	0.33333 (14)	0.0438 (4)
H1	0.023411	0.492797	0.281793	0.053*
C2	0.0204 (3)	0.42039 (8)	0.32882 (15)	0.0489 (5)
H2	−0.049397	0.406777	0.274308	0.059*
C3	0.0805 (3)	0.38834 (8)	0.40467 (15)	0.0501 (5)
H3A	0.052421	0.353471	0.400142	0.060*
C4	0.1809 (3)	0.40787 (8)	0.48587 (15)	0.0463 (5)
H4A	0.221835	0.386147	0.536061	0.056*
C5	0.2226 (2)	0.46084 (7)	0.49382 (13)	0.0385 (4)
C6	0.3544 (2)	0.52923 (7)	0.58394 (12)	0.0362 (4)
C7	0.4416 (3)	0.54946 (8)	0.67130 (12)	0.0394 (4)
H7	0.469334	0.527308	0.721788	0.047*
C8	0.4863 (2)	0.60009 (7)	0.68431 (12)	0.0376 (4)
C9	0.4512 (2)	0.63457 (7)	0.60334 (12)	0.0371 (4)
C10	0.3579 (3)	0.61558 (7)	0.51697 (12)	0.0385 (4)
H10	0.329556	0.637737	0.466508	0.046*
C11	0.3080 (2)	0.56470 (7)	0.50604 (12)	0.0355 (4)
C12	0.1648 (2)	0.49282 (7)	0.41571 (13)	0.0371 (4)
C13	0.1737 (3)	0.57586 (7)	0.34052 (12)	0.0384 (4)
C14	0.3115 (3)	0.58554 (9)	0.29434 (15)	0.0521 (5)
H14	0.431313	0.575514	0.319615	0.063*
C15	0.2688 (4)	0.61039 (11)	0.20983 (17)	0.0661 (7)
H15	0.360296	0.617896	0.178127	0.079*
C16	0.0902 (3)	0.62398 (9)	0.17281 (15)	0.0588 (6)
C17	−0.0444 (3)	0.61669 (9)	0.22071 (16)	0.0567 (6)
H17	−0.162930	0.628135	0.196485	0.068*
C18	−0.0030 (3)	0.59211 (9)	0.30564 (14)	0.0491 (5)
H18	−0.093603	0.586619	0.338868	0.059*
C19	0.6088 (3)	0.59306 (8)	0.85210 (13)	0.0438 (4)
C24	0.7214 (3)	0.55030 (10)	0.86174 (15)	0.0550 (5)
H24	0.770213	0.539643	0.812091	0.066*
C23	0.7623 (3)	0.52321 (11)	0.94390 (17)	0.0626 (6)
H23	0.836159	0.494118	0.949399	0.075*
C22	0.6928 (4)	0.53969 (11)	1.01711 (15)	0.0626 (7)
C21	0.5844 (4)	0.58229 (13)	1.00990 (16)	0.0717 (8)
H21	0.539924	0.593422	1.060651	0.086*
C20	0.5403 (4)	0.60904 (10)	0.92684 (15)	0.0594 (6)
H20	0.464591	0.637745	0.921575	0.071*
C25	0.4847 (4)	0.72226 (9)	0.54181 (16)	0.0613 (6)
H25	0.475304	0.705297	0.481758	0.074*
C27	0.6534 (6)	0.75708 (14)	0.5594 (2)	0.1113 (15)
H27A	0.657531	0.776730	0.614763	0.167*
H27B	0.646596	0.779996	0.507808	0.167*
H27C	0.761843	0.736400	0.566534	0.167*
C26	0.3078 (7)	0.74964 (17)	0.5409 (3)	0.1235 (17)
H26A	0.210360	0.724980	0.534589	0.185*
H26B	0.282430	0.773189	0.489690	0.185*
H26C	0.317395	0.768278	0.597798	0.185*
O1	1.2580 (2)	0.75835 (7)	0.80784 (13)	0.0628 (5)
H1A	1.379 (5)	0.7504 (13)	0.806 (2)	0.094*
O2	1.2146 (2)	0.67748 (8)	0.7663 (2)	0.1027 (9)
O3	0.58454 (18)	0.73747 (6)	0.79466 (11)	0.0548 (4)
O4	0.6550 (2)	0.81593 (8)	0.85067 (17)	0.0829 (6)
C28	1.1580 (3)	0.71777 (9)	0.78816 (17)	0.0542 (5)
C29	0.9631 (3)	0.72381 (9)	0.79386 (17)	0.0535 (5)
H29	0.885494	0.695829	0.777270	0.064*
C30	0.8936 (3)	0.76568 (9)	0.82053 (15)	0.0490 (5)
H30	0.973923	0.792797	0.839842	0.059*
C31	0.6970 (3)	0.77421 (9)	0.82301 (15)	0.0496 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1046 (6)	0.1288 (7)	0.0688 (5)	−0.0407 (5)	−0.0126 (4)	0.0539 (5)
Cl2	0.1121 (6)	0.1185 (7)	0.0488 (4)	−0.0492 (5)	−0.0181 (4)	0.0293 (4)
N1	0.0371 (8)	0.0392 (8)	0.0345 (8)	0.0014 (6)	0.0060 (6)	−0.0014 (6)
N2	0.0423 (8)	0.0407 (9)	0.0398 (8)	0.0025 (7)	0.0106 (7)	0.0010 (7)
N3	0.0587 (11)	0.0429 (10)	0.0356 (8)	0.0039 (8)	0.0058 (7)	−0.0042 (7)
N4	0.0553 (10)	0.0390 (9)	0.0383 (9)	0.0010 (7)	0.0010 (8)	−0.0025 (7)
C1	0.0400 (10)	0.0475 (11)	0.0427 (10)	0.0005 (8)	0.0063 (8)	−0.0044 (8)
C2	0.0443 (11)	0.0498 (12)	0.0522 (12)	−0.0038 (9)	0.0096 (9)	−0.0127 (9)
C3	0.0493 (11)	0.0412 (11)	0.0630 (13)	−0.0058 (9)	0.0191 (10)	−0.0095 (10)
C4	0.0490 (11)	0.0418 (10)	0.0515 (11)	0.0019 (9)	0.0186 (9)	−0.0002 (9)
C5	0.0354 (9)	0.0414 (10)	0.0408 (10)	0.0028 (7)	0.0127 (8)	−0.0017 (8)
C6	0.0328 (9)	0.0388 (9)	0.0380 (9)	0.0038 (7)	0.0101 (7)	0.0008 (7)
C7	0.0412 (10)	0.0441 (10)	0.0327 (9)	0.0044 (8)	0.0077 (7)	0.0037 (8)
C8	0.0336 (9)	0.0455 (10)	0.0341 (9)	0.0058 (7)	0.0080 (7)	−0.0025 (8)
C9	0.0334 (9)	0.0389 (10)	0.0389 (9)	0.0057 (7)	0.0078 (7)	−0.0017 (8)
C10	0.0406 (10)	0.0384 (10)	0.0353 (9)	0.0040 (8)	0.0054 (7)	0.0019 (7)
C11	0.0310 (8)	0.0418 (10)	0.0342 (9)	0.0038 (7)	0.0078 (7)	−0.0021 (7)
C12	0.0322 (9)	0.0394 (10)	0.0411 (10)	0.0015 (7)	0.0109 (7)	−0.0031 (8)
C13	0.0424 (10)	0.0382 (9)	0.0333 (9)	0.0001 (8)	0.0053 (7)	−0.0019 (7)
C14	0.0448 (11)	0.0640 (14)	0.0478 (11)	−0.0003 (10)	0.0106 (9)	0.0065 (10)
C15	0.0646 (15)	0.0818 (18)	0.0548 (13)	−0.0132 (13)	0.0191 (11)	0.0136 (12)
C16	0.0693 (15)	0.0543 (13)	0.0457 (12)	−0.0159 (11)	−0.0028 (10)	0.0110 (10)
C17	0.0514 (12)	0.0550 (13)	0.0566 (13)	0.0023 (10)	−0.0035 (10)	0.0100 (10)
C18	0.0447 (11)	0.0555 (12)	0.0465 (11)	0.0046 (9)	0.0084 (9)	0.0025 (9)
C19	0.0447 (10)	0.0516 (11)	0.0337 (9)	−0.0049 (9)	0.0053 (8)	−0.0034 (8)
C24	0.0512 (12)	0.0689 (15)	0.0437 (11)	0.0091 (11)	0.0073 (9)	0.0040 (10)
C23	0.0563 (13)	0.0711 (16)	0.0524 (13)	0.0005 (11)	−0.0059 (10)	0.0077 (11)
C22	0.0631 (14)	0.0771 (17)	0.0391 (11)	−0.0239 (13)	−0.0074 (10)	0.0076 (11)
C21	0.0803 (18)	0.101 (2)	0.0357 (11)	−0.0127 (16)	0.0165 (11)	−0.0099 (12)
C20	0.0693 (15)	0.0670 (15)	0.0422 (11)	0.0028 (12)	0.0129 (10)	−0.0121 (10)
C25	0.0912 (18)	0.0402 (11)	0.0452 (12)	0.0024 (11)	−0.0012 (11)	0.0034 (9)
C27	0.160 (4)	0.075 (2)	0.080 (2)	−0.053 (2)	−0.015 (2)	0.0230 (17)
C26	0.171 (4)	0.120 (3)	0.076 (2)	0.091 (3)	0.017 (2)	0.021 (2)
O1	0.0376 (8)	0.0626 (10)	0.0920 (12)	−0.0042 (7)	0.0224 (8)	−0.0210 (9)
O2	0.0446 (10)	0.0714 (13)	0.193 (3)	−0.0030 (9)	0.0283 (13)	−0.0563 (15)
O3	0.0340 (7)	0.0618 (9)	0.0696 (10)	−0.0059 (6)	0.0133 (7)	−0.0198 (8)
O4	0.0509 (10)	0.0713 (12)	0.1305 (17)	−0.0046 (8)	0.0289 (10)	−0.0430 (12)
C28	0.0373 (11)	0.0565 (13)	0.0673 (14)	0.0009 (9)	0.0080 (10)	−0.0159 (11)
C29	0.0350 (10)	0.0538 (12)	0.0702 (14)	−0.0057 (9)	0.0083 (10)	−0.0135 (11)
C30	0.0350 (10)	0.0523 (12)	0.0597 (12)	−0.0062 (9)	0.0101 (9)	−0.0078 (10)
C31	0.0378 (10)	0.0553 (13)	0.0567 (12)	−0.0023 (9)	0.0122 (9)	−0.0134 (10)

Geometric parameters (Å, º) top

Cl1—C16	1.737 (2)	C15—C16	1.375 (4)
Cl2—C22	1.743 (2)	C15—H15	0.9300
N1—C11	1.371 (2)	C16—C17	1.364 (4)
N1—C12	1.391 (2)	C17—C18	1.383 (3)
N1—C13	1.453 (2)	C17—H17	0.9300
N2—C6	1.321 (2)	C18—H18	0.9300
N2—C5	1.366 (2)	C19—C20	1.379 (3)
N3—C8	1.376 (2)	C19—C24	1.383 (3)
N3—C19	1.416 (3)	C24—C23	1.380 (3)
N3—H3	0.83 (3)	C24—H24	0.9300
N4—C9	1.324 (3)	C23—C22	1.367 (4)
N4—C25	1.467 (3)	C23—H23	0.9300
N4—H4	0.84 (3)	C22—C21	1.363 (4)
C1—C2	1.374 (3)	C21—C20	1.387 (4)
C1—C12	1.400 (3)	C21—H21	0.9300
C1—H1	0.9300	C20—H20	0.9300
C2—C3	1.391 (3)	C25—C26	1.500 (5)
C2—H2	0.9300	C25—C27	1.529 (4)
C3—C4	1.368 (3)	C25—H25	0.9800
C3—H3A	0.9300	C27—H27A	0.9600
C4—C5	1.411 (3)	C27—H27B	0.9600
C4—H4A	0.9300	C27—H27C	0.9600
C5—C12	1.413 (3)	C26—H26A	0.9600
C6—C7	1.416 (3)	C26—H26B	0.9600
C6—C11	1.457 (3)	C26—H26C	0.9600
C7—C8	1.362 (3)	O1—C28	1.290 (3)
C7—H7	0.9300	O1—H1A	0.94 (4)
C8—C9	1.473 (3)	O2—C28	1.200 (3)
C9—C10	1.405 (3)	O3—C31	1.282 (3)
C10—C11	1.375 (3)	O4—C31	1.224 (3)
C10—H10	0.9300	C28—C29	1.486 (3)
C13—C18	1.377 (3)	C29—C30	1.304 (3)
C13—C14	1.377 (3)	C29—H29	0.9300
C14—C15	1.381 (3)	C30—C31	1.495 (3)
C14—H14	0.9300	C30—H30	0.9300

C11—N1—C12	121.44 (15)	C15—C16—Cl1	119.6 (2)
C11—N1—C13	120.56 (15)	C16—C17—C18	119.4 (2)
C12—N1—C13	117.89 (15)	C16—C17—H17	120.3
C6—N2—C5	118.66 (16)	C18—C17—H17	120.3
C8—N3—C19	123.30 (18)	C13—C18—C17	119.3 (2)
C8—N3—H3	116.6 (19)	C13—C18—H18	120.3
C19—N3—H3	111.9 (18)	C17—C18—H18	120.3
C9—N4—C25	126.02 (18)	C20—C19—C24	118.9 (2)
C9—N4—H4	117.7 (18)	C20—C19—N3	119.4 (2)
C25—N4—H4	115.7 (18)	C24—C19—N3	121.67 (18)
C2—C1—C12	119.82 (19)	C23—C24—C19	121.0 (2)
C2—C1—H1	120.1	C23—C24—H24	119.5
C12—C1—H1	120.1	C19—C24—H24	119.5
C1—C2—C3	120.92 (19)	C22—C23—C24	119.1 (2)
C1—C2—H2	119.5	C22—C23—H23	120.4
C3—C2—H2	119.5	C24—C23—H23	120.4
C4—C3—C2	120.33 (19)	C21—C22—C23	121.0 (2)
C4—C3—H3A	119.8	C21—C22—Cl2	119.6 (2)
C2—C3—H3A	119.8	C23—C22—Cl2	119.4 (2)
C3—C4—C5	120.3 (2)	C22—C21—C20	120.0 (2)
C3—C4—H4A	119.9	C22—C21—H21	120.0
C5—C4—H4A	119.9	C20—C21—H21	120.0
N2—C5—C4	118.98 (18)	C19—C20—C21	120.0 (2)
N2—C5—C12	122.10 (17)	C19—C20—H20	120.0
C4—C5—C12	118.91 (18)	C21—C20—H20	120.0
N2—C6—C7	118.91 (17)	N4—C25—C26	108.5 (3)
N2—C6—C11	123.09 (17)	N4—C25—C27	108.6 (2)
C7—C6—C11	117.99 (17)	C26—C25—C27	114.5 (3)
C8—C7—C6	122.58 (17)	N4—C25—H25	108.4
C8—C7—H7	118.7	C26—C25—H25	108.4
C6—C7—H7	118.7	C27—C25—H25	108.4
C7—C8—N3	124.35 (17)	C25—C27—H27A	109.5
C7—C8—C9	118.60 (16)	C25—C27—H27B	109.5
N3—C8—C9	117.03 (17)	H27A—C27—H27B	109.5
N4—C9—C10	121.88 (17)	C25—C27—H27C	109.5
N4—C9—C8	118.74 (17)	H27A—C27—H27C	109.5
C10—C9—C8	119.37 (17)	H27B—C27—H27C	109.5
C11—C10—C9	120.91 (17)	C25—C26—H26A	109.5
C11—C10—H10	119.5	C25—C26—H26B	109.5
C9—C10—H10	119.5	H26A—C26—H26B	109.5
N1—C11—C10	123.19 (17)	C25—C26—H26C	109.5
N1—C11—C6	116.54 (16)	H26A—C26—H26C	109.5
C10—C11—C6	120.27 (16)	H26B—C26—H26C	109.5
N1—C12—C1	122.29 (17)	C28—O1—H1A	109 (2)
N1—C12—C5	118.04 (16)	O2—C28—O1	123.6 (2)
C1—C12—C5	119.67 (18)	O2—C28—C29	121.0 (2)
C18—C13—C14	121.27 (19)	O1—C28—C29	115.38 (19)
C18—C13—N1	119.83 (17)	C30—C29—C28	124.4 (2)
C14—C13—N1	118.73 (17)	C30—C29—H29	117.8
C13—C14—C15	118.8 (2)	C28—C29—H29	117.8
C13—C14—H14	120.6	C29—C30—C31	126.1 (2)
C15—C14—H14	120.6	C29—C30—H30	116.9
C16—C15—C14	119.7 (2)	C31—C30—H30	116.9
C16—C15—H15	120.2	O4—C31—O3	124.88 (19)
C14—C15—H15	120.2	O4—C31—C30	117.69 (19)
C17—C16—C15	121.3 (2)	O3—C31—C30	117.42 (18)
C17—C16—Cl1	119.05 (19)

C12—C1—C2—C3	−1.1 (3)	C2—C1—C12—C5	−0.5 (3)
C1—C2—C3—C4	1.0 (3)	N2—C5—C12—N1	3.4 (3)
C2—C3—C4—C5	0.7 (3)	C4—C5—C12—N1	−177.15 (16)
C6—N2—C5—C4	−179.91 (16)	N2—C5—C12—C1	−177.30 (17)
C6—N2—C5—C12	−0.4 (3)	C4—C5—C12—C1	2.2 (3)
C3—C4—C5—N2	177.18 (18)	C11—N1—C13—C18	−107.6 (2)
C3—C4—C5—C12	−2.3 (3)	C12—N1—C13—C18	76.1 (2)
C5—N2—C6—C7	176.24 (16)	C11—N1—C13—C14	77.1 (2)
C5—N2—C6—C11	−2.5 (3)	C12—N1—C13—C14	−99.2 (2)
N2—C6—C7—C8	179.76 (17)	C18—C13—C14—C15	−2.4 (3)
C11—C6—C7—C8	−1.4 (3)	N1—C13—C14—C15	172.8 (2)
C6—C7—C8—N3	178.23 (17)	C13—C14—C15—C16	−1.3 (4)
C6—C7—C8—C9	−3.2 (3)	C14—C15—C16—C17	4.6 (4)
C19—N3—C8—C7	−1.3 (3)	C14—C15—C16—Cl1	−174.4 (2)
C19—N3—C8—C9	−179.85 (17)	C15—C16—C17—C18	−4.2 (4)
C25—N4—C9—C10	2.1 (3)	Cl1—C16—C17—C18	174.80 (18)
C25—N4—C9—C8	−178.7 (2)	C14—C13—C18—C17	2.8 (3)
C7—C8—C9—N4	−173.46 (17)	N1—C13—C18—C17	−172.32 (19)
N3—C8—C9—N4	5.2 (3)	C16—C17—C18—C13	0.5 (3)
C7—C8—C9—C10	5.8 (3)	C8—N3—C19—C20	−124.4 (2)
N3—C8—C9—C10	−175.57 (17)	C8—N3—C19—C24	57.4 (3)
N4—C9—C10—C11	175.65 (18)	C20—C19—C24—C23	1.3 (3)
C8—C9—C10—C11	−3.6 (3)	N3—C19—C24—C23	179.5 (2)
C12—N1—C11—C10	−179.39 (17)	C19—C24—C23—C22	−1.2 (4)
C13—N1—C11—C10	4.4 (3)	C24—C23—C22—C21	0.0 (4)
C12—N1—C11—C6	0.7 (2)	C24—C23—C22—Cl2	179.46 (19)
C13—N1—C11—C6	−175.49 (15)	C23—C22—C21—C20	1.2 (4)
C9—C10—C11—N1	178.91 (16)	Cl2—C22—C21—C20	−178.3 (2)
C9—C10—C11—C6	−1.2 (3)	C24—C19—C20—C21	−0.1 (4)
N2—C6—C11—N1	2.4 (2)	N3—C19—C20—C21	−178.4 (2)
C7—C6—C11—N1	−176.34 (15)	C22—C21—C20—C19	−1.1 (4)
N2—C6—C11—C10	−177.49 (17)	C9—N4—C25—C26	89.0 (3)
C7—C6—C11—C10	3.7 (2)	C9—N4—C25—C27	−146.0 (3)
C11—N1—C12—C1	177.30 (16)	O2—C28—C29—C30	177.2 (3)
C13—N1—C12—C1	−6.4 (2)	O1—C28—C29—C30	−3.0 (4)
C11—N1—C12—C5	−3.4 (2)	C28—C29—C30—C31	176.9 (2)
C13—N1—C12—C5	172.86 (15)	C29—C30—C31—O4	179.5 (3)
C2—C1—C12—N1	178.81 (17)	C29—C30—C31—O3	−1.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O2ⁱ	0.83 (3)	2.48 (3)	3.003 (3)	122 (2)
N3—H3···O3	0.83 (3)	2.26 (3)	3.040 (3)	156 (3)
N4—H4···O3	0.84 (3)	2.17 (3)	2.972 (2)	160 (2)
O1—H1A···O3ⁱⁱ	0.94 (4)	1.62 (4)	2.550 (2)	176 (3)

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

N-[10-(4-chlorophenyl)-3-[(4-chlorophenyl)amino]-2,10-dihydrophenazin -2-ylidene]propan-2-aminium 3-carboxypropanoate (lb_CLZ-SA) top

Crystal data top

C₂₇H₂₃Cl₂N₄⁺·C₄H₅O₄⁻	Z = 2
M_r = 591.47	F(000) = 616
Triclinic, P1	D_x = 1.361 Mg m⁻³
a = 10.6376 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.2781 (5) Å	Cell parameters from 4129 reflections
c = 12.7975 (8) Å	θ = 2.7–27.7°
α = 90.079 (4)°	µ = 0.27 mm⁻¹
β = 113.211 (6)°	T = 295 K
γ = 108.284 (4)°	Plate, metallic dark red
V = 1443.57 (15) Å³	0.57 × 0.42 × 0.03 mm

Data collection top

Xcalibur Ruby Gemini ultra diffractometer	5090 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	3520 reflections with I > 2σ(I)
Detector resolution: 5.1856 pixels mm^-1	R_int = 0.022
ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: analytical CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R. C. Clark & J. S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −12→12
T_min = 0.897, T_max = 0.990	k = −14→14
10778 measured reflections	l = −15→15

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: dual
R[F² > 2σ(F²)] = 0.045	Hydrogen site location: mixed
wR(F²) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0526P)² + 0.2632P] where P = (F_o² + 2F_c²)/3
5090 reflections	(Δ/σ)_max < 0.001
412 parameters	Δρ_max = 0.24 e Å⁻³
4 restraints	Δρ_min = −0.24 e Å⁻³

Special details top

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cl1	0.10868 (8)	0.96608 (5)	0.40866 (7)	0.0858 (3)
Cl2	0.96625 (11)	0.28301 (9)	0.08165 (9)	0.1255 (4)
N1	0.29449 (17)	0.56699 (13)	0.37313 (14)	0.0440 (4)
N2	0.38500 (19)	0.37948 (13)	0.35805 (16)	0.0537 (5)
N3	0.6655 (2)	0.58336 (17)	0.16145 (19)	0.0644 (6)
H3	0.676 (3)	0.638 (2)	0.124 (2)	0.085 (9)*
N4	0.6134 (2)	0.77908 (15)	0.20823 (18)	0.0582 (5)
H4	0.674 (3)	0.779 (2)	0.180 (2)	0.073 (8)*
C1	0.1469 (2)	0.45683 (18)	0.46802 (19)	0.0554 (6)
H1	0.114783	0.517805	0.474079	0.067*
C2	0.1000 (3)	0.35657 (19)	0.5096 (2)	0.0650 (6)
H2	0.035602	0.349846	0.543557	0.078*
C3	0.1474 (3)	0.2644 (2)	0.5017 (2)	0.0673 (7)
H3A	0.114731	0.196743	0.530337	0.081*
C4	0.2414 (3)	0.27357 (18)	0.4521 (2)	0.0623 (6)
H4A	0.272866	0.211875	0.447337	0.075*
C5	0.2918 (2)	0.37468 (16)	0.40807 (18)	0.0493 (5)
C6	0.4314 (2)	0.47517 (16)	0.31684 (18)	0.0475 (5)
C7	0.5231 (2)	0.47973 (17)	0.26041 (19)	0.0540 (5)
H7	0.545466	0.413978	0.251047	0.065*
C8	0.5801 (2)	0.57608 (17)	0.21922 (19)	0.0511 (5)
C9	0.5467 (2)	0.68132 (16)	0.23669 (18)	0.0488 (5)
C10	0.4465 (2)	0.67422 (16)	0.28347 (18)	0.0487 (5)
H10	0.417512	0.737593	0.287268	0.058*
C11	0.3897 (2)	0.57585 (16)	0.32401 (17)	0.0433 (5)
C12	0.2427 (2)	0.46729 (16)	0.41681 (17)	0.0463 (5)
C14	0.1315 (2)	0.67684 (17)	0.29143 (18)	0.0508 (5)
H14	0.081813	0.622390	0.225413	0.061*
C15	0.0887 (2)	0.77072 (18)	0.2995 (2)	0.0558 (6)
H15	0.010154	0.780496	0.239025	0.067*
C16	0.1643 (2)	0.84910 (17)	0.3981 (2)	0.0548 (6)
C17	0.2811 (3)	0.83790 (19)	0.4880 (2)	0.0631 (6)
H17	0.331292	0.892824	0.553681	0.076*
C19	0.7283 (2)	0.50413 (18)	0.1441 (2)	0.0545 (5)
C20	0.7553 (3)	0.5062 (2)	0.0463 (2)	0.0636 (6)
H20	0.724223	0.554130	−0.006934	0.076*
C21	0.8271 (3)	0.4385 (2)	0.0271 (2)	0.0753 (7)
H21	0.845250	0.441260	−0.038425	0.090*
C22	0.8719 (3)	0.3671 (2)	0.1041 (3)	0.0729 (7)
C23	0.8455 (3)	0.3622 (2)	0.2012 (2)	0.0692 (7)
H23	0.875075	0.312583	0.252916	0.083*
C24	0.7749 (3)	0.43123 (19)	0.2212 (2)	0.0619 (6)
H24	0.758304	0.428814	0.287471	0.074*
C25	0.5824 (3)	0.88817 (17)	0.2102 (2)	0.0613 (6)
H25	0.556124	0.895611	0.274484	0.074*
C27	0.4543 (4)	0.8814 (3)	0.0989 (3)	0.1017 (10)
H27A	0.477326	0.869815	0.035234	0.153*
H27B	0.433880	0.952280	0.097588	0.153*
H27C	0.370590	0.817728	0.093184	0.153*
C26	0.7180 (3)	0.9897 (2)	0.2276 (3)	0.0999 (10)
H26A	0.796535	0.989189	0.298164	0.150*
H26B	0.699227	1.060872	0.230978	0.150*
H26C	0.744177	0.983337	0.164693	0.150*
O2	0.3911 (2)	0.25381 (18)	0.05936 (18)	0.1051 (7)
O1	0.1973 (2)	0.20161 (18)	−0.09912 (17)	0.0913 (6)
O4	0.4906 (2)	0.15854 (19)	0.23035 (18)	0.0864 (6)
C28	0.2640 (3)	0.1944 (2)	0.0032 (2)	0.0637 (6)
C29A	0.1821 (6)	0.0962 (5)	0.0485 (4)	0.0659 (15)	0.739 (9)
H29A	0.080159	0.089177	0.014881	0.079*	0.739 (9)
H29B	0.188493	0.024605	0.022814	0.079*	0.739 (9)
C30A	0.2352 (4)	0.1096 (6)	0.1775 (4)	0.0745 (15)	0.739 (9)
H30A	0.160605	0.056576	0.196443	0.089*	0.739 (9)
H30B	0.247780	0.187700	0.204742	0.089*	0.739 (9)
O3A	0.3990 (10)	0.0104 (7)	0.3032 (6)	0.120 (2)	0.739 (9)
C29B	0.2040 (16)	0.1456 (12)	0.0925 (15)	0.069 (4)	0.261 (9)
H29C	0.242509	0.207391	0.155720	0.082*	0.261 (9)
H29D	0.099285	0.126883	0.056702	0.082*	0.261 (9)
C30B	0.2341 (10)	0.0406 (11)	0.1427 (11)	0.069 (4)	0.261 (9)
H30C	0.159708	−0.001711	0.167753	0.083*	0.261 (9)
H30D	0.236358	−0.010844	0.086402	0.083*	0.261 (9)
O3B	0.3849 (19)	0.0492 (18)	0.3322 (13)	0.106 (6)	0.261 (9)
C31	0.3797 (3)	0.0870 (3)	0.2427 (2)	0.0927 (9)
H4B	0.455 (4)	0.194 (3)	0.165 (3)	0.114 (12)*
C18	0.3239 (2)	0.74403 (18)	0.48023 (19)	0.0570 (6)
H18	0.402835	0.734780	0.540699	0.068*
C13	0.2485 (2)	0.66488 (16)	0.38234 (17)	0.0440 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1041 (5)	0.0550 (3)	0.1354 (7)	0.0475 (3)	0.0710 (5)	0.0288 (4)
Cl2	0.1238 (7)	0.1392 (8)	0.1530 (9)	0.0844 (6)	0.0666 (7)	−0.0046 (6)
N1	0.0526 (10)	0.0400 (8)	0.0464 (10)	0.0207 (7)	0.0239 (8)	0.0071 (8)
N2	0.0654 (11)	0.0389 (9)	0.0685 (12)	0.0218 (8)	0.0365 (10)	0.0118 (9)
N3	0.0868 (15)	0.0543 (11)	0.0839 (15)	0.0353 (10)	0.0587 (13)	0.0228 (11)
N4	0.0723 (13)	0.0493 (10)	0.0738 (13)	0.0290 (9)	0.0445 (12)	0.0230 (10)
C1	0.0652 (14)	0.0542 (12)	0.0629 (14)	0.0277 (11)	0.0369 (12)	0.0149 (11)
C2	0.0755 (16)	0.0631 (14)	0.0754 (16)	0.0266 (12)	0.0480 (14)	0.0227 (13)
C3	0.0840 (17)	0.0536 (13)	0.0790 (17)	0.0234 (12)	0.0483 (15)	0.0237 (13)
C4	0.0764 (16)	0.0439 (11)	0.0771 (16)	0.0234 (11)	0.0402 (14)	0.0172 (12)
C5	0.0567 (13)	0.0410 (10)	0.0554 (13)	0.0184 (9)	0.0274 (11)	0.0078 (10)
C6	0.0549 (12)	0.0402 (10)	0.0521 (13)	0.0190 (9)	0.0248 (11)	0.0067 (10)
C7	0.0686 (14)	0.0410 (11)	0.0676 (14)	0.0258 (10)	0.0378 (12)	0.0094 (11)
C8	0.0590 (13)	0.0492 (11)	0.0577 (13)	0.0250 (10)	0.0317 (11)	0.0102 (10)
C9	0.0556 (13)	0.0437 (11)	0.0531 (13)	0.0211 (9)	0.0252 (11)	0.0122 (10)
C10	0.0575 (13)	0.0419 (10)	0.0564 (13)	0.0243 (9)	0.0279 (11)	0.0102 (10)
C11	0.0487 (12)	0.0419 (10)	0.0427 (11)	0.0186 (9)	0.0198 (10)	0.0070 (9)
C12	0.0537 (12)	0.0413 (10)	0.0458 (12)	0.0176 (9)	0.0215 (10)	0.0094 (9)
C14	0.0524 (13)	0.0511 (11)	0.0506 (13)	0.0204 (10)	0.0210 (11)	0.0089 (10)
C15	0.0531 (13)	0.0577 (13)	0.0661 (15)	0.0286 (11)	0.0268 (12)	0.0232 (12)
C16	0.0632 (14)	0.0417 (11)	0.0765 (16)	0.0252 (10)	0.0405 (13)	0.0183 (12)
C17	0.0736 (16)	0.0517 (12)	0.0643 (15)	0.0266 (11)	0.0250 (13)	−0.0027 (11)
C19	0.0541 (13)	0.0515 (12)	0.0636 (14)	0.0177 (10)	0.0304 (11)	0.0007 (11)
C20	0.0617 (15)	0.0713 (15)	0.0631 (15)	0.0246 (12)	0.0297 (13)	0.0055 (12)
C21	0.0714 (17)	0.0942 (19)	0.0695 (17)	0.0313 (15)	0.0361 (14)	−0.0084 (15)
C22	0.0636 (16)	0.0756 (16)	0.0823 (19)	0.0310 (13)	0.0274 (14)	−0.0127 (15)
C23	0.0637 (15)	0.0636 (14)	0.0808 (18)	0.0280 (12)	0.0257 (14)	0.0032 (13)
C24	0.0695 (15)	0.0588 (13)	0.0667 (15)	0.0263 (11)	0.0344 (13)	0.0061 (12)
C25	0.0760 (16)	0.0470 (11)	0.0772 (16)	0.0285 (11)	0.0423 (14)	0.0191 (12)
C27	0.124 (3)	0.0783 (18)	0.099 (2)	0.0611 (18)	0.023 (2)	0.0221 (17)
C26	0.103 (2)	0.0532 (14)	0.162 (3)	0.0237 (14)	0.076 (2)	0.0187 (18)
O2	0.0938 (15)	0.0978 (14)	0.0885 (14)	−0.0155 (12)	0.0399 (12)	0.0106 (12)
O1	0.0854 (13)	0.1208 (16)	0.0890 (14)	0.0525 (12)	0.0441 (11)	0.0557 (13)
O4	0.0639 (12)	0.1052 (15)	0.0767 (13)	0.0238 (11)	0.0198 (10)	0.0023 (12)
C28	0.0682 (17)	0.0607 (14)	0.0742 (18)	0.0267 (13)	0.0380 (15)	0.0179 (14)
C29A	0.058 (3)	0.066 (3)	0.060 (3)	0.009 (2)	0.021 (2)	0.017 (2)
C30A	0.075 (3)	0.091 (4)	0.064 (3)	0.024 (2)	0.039 (2)	0.021 (3)
O3A	0.134 (4)	0.162 (5)	0.086 (3)	0.075 (3)	0.051 (3)	0.054 (4)
C29B	0.036 (7)	0.072 (9)	0.085 (12)	0.010 (7)	0.019 (8)	0.012 (8)
C30B	0.066 (6)	0.059 (7)	0.076 (8)	0.024 (5)	0.022 (6)	0.017 (6)
O3B	0.071 (7)	0.140 (12)	0.075 (9)	0.018 (7)	0.014 (6)	0.042 (9)
C31	0.082 (2)	0.124 (3)	0.0578 (18)	0.0228 (19)	0.0234 (16)	0.0189 (18)
C18	0.0621 (14)	0.0548 (12)	0.0516 (13)	0.0290 (11)	0.0140 (11)	0.0021 (11)
C13	0.0512 (12)	0.0410 (10)	0.0495 (12)	0.0214 (9)	0.0263 (10)	0.0104 (10)

Geometric parameters (Å, º) top

Cl1—C16	1.740 (2)	C14—C15	1.382 (3)
Cl2—C22	1.741 (2)	C15—C16	1.370 (3)
N1—C11	1.366 (2)	C16—C17	1.367 (3)
N1—C12	1.391 (2)	C17—C18	1.382 (3)
N1—C13	1.453 (2)	C19—C24	1.384 (3)
N2—C6	1.321 (2)	C19—C20	1.389 (3)
N2—C5	1.364 (3)	C20—C21	1.371 (3)
N3—C8	1.363 (3)	C21—C22	1.364 (4)
N3—C19	1.402 (3)	C22—C23	1.375 (4)
N4—C9	1.322 (3)	C23—C24	1.379 (3)
N4—C25	1.479 (3)	C25—C27	1.514 (4)
C1—C2	1.369 (3)	C25—C26	1.518 (3)
C1—C12	1.388 (3)	O2—C28	1.221 (3)
C2—C3	1.394 (3)	O1—C28	1.238 (3)
C3—C4	1.358 (3)	O4—C31	1.299 (3)
C4—C5	1.403 (3)	C28—C29A	1.513 (5)
C5—C12	1.413 (3)	C28—C29B	1.553 (13)
C6—C7	1.414 (3)	C29A—C30A	1.509 (6)
C6—C11	1.452 (3)	C30A—C31	1.547 (5)
C7—C8	1.360 (3)	O3A—C31	1.235 (6)
C8—C9	1.482 (3)	C29B—C30B	1.508 (14)
C9—C10	1.395 (3)	C30B—C31	1.498 (10)
C10—C11	1.373 (3)	O3B—C31	1.224 (13)
C14—C13	1.378 (3)	C18—C13	1.369 (3)

C11—N1—C12	121.60 (15)	C15—C16—Cl1	118.63 (17)
C11—N1—C13	119.30 (15)	C16—C17—C18	119.3 (2)
C12—N1—C13	119.09 (16)	C24—C19—C20	118.2 (2)
C6—N2—C5	118.27 (17)	C24—C19—N3	124.7 (2)
C8—N3—C19	129.5 (2)	C20—C19—N3	116.9 (2)
C9—N4—C25	125.5 (2)	C21—C20—C19	120.9 (2)
C2—C1—C12	119.8 (2)	C22—C21—C20	120.0 (3)
C1—C2—C3	120.9 (2)	C21—C22—C23	120.5 (2)
C4—C3—C2	119.9 (2)	C21—C22—Cl2	120.3 (2)
C3—C4—C5	121.1 (2)	C23—C22—Cl2	119.2 (2)
N2—C5—C4	118.96 (18)	C22—C23—C24	119.5 (2)
N2—C5—C12	122.70 (17)	C23—C24—C19	120.9 (2)
C4—C5—C12	118.3 (2)	N4—C25—C27	108.1 (2)
N2—C6—C7	118.97 (18)	N4—C25—C26	109.2 (2)
N2—C6—C11	123.10 (19)	C27—C25—C26	112.6 (2)
C7—C6—C11	117.91 (17)	O2—C28—O1	122.4 (2)
C8—C7—C6	122.83 (19)	O2—C28—C29A	122.5 (3)
C7—C8—N3	124.83 (19)	O1—C28—C29A	114.7 (3)
C7—C8—C9	118.27 (19)	O2—C28—C29B	105.5 (7)
N3—C8—C9	116.90 (18)	O1—C28—C29B	129.5 (6)
N4—C9—C10	122.12 (19)	C30A—C29A—C28	115.0 (5)
N4—C9—C8	119.0 (2)	C29A—C30A—C31	115.0 (5)
C10—C9—C8	118.92 (17)	C30B—C29B—C28	118.7 (12)
C11—C10—C9	121.51 (18)	C31—C30B—C29B	105.4 (12)
N1—C11—C10	123.06 (17)	O3B—C31—O4	124.4 (9)
N1—C11—C6	116.84 (16)	O3A—C31—O4	118.4 (5)
C10—C11—C6	120.09 (18)	O3B—C31—C30B	115.1 (10)
C1—C12—N1	122.56 (18)	O4—C31—C30B	120.5 (5)
C1—C12—C5	119.98 (18)	O3A—C31—C30A	127.4 (5)
N1—C12—C5	117.46 (18)	O4—C31—C30A	114.2 (3)
C13—C14—C15	119.3 (2)	C13—C18—C17	119.11 (19)
C16—C15—C14	118.77 (19)	C18—C13—C14	121.55 (18)
C17—C16—C15	122.06 (19)	C18—C13—N1	119.27 (17)
C17—C16—Cl1	119.31 (19)	C14—C13—N1	119.17 (18)

C12—C1—C2—C3	0.2 (4)	N2—C5—C12—N1	−0.8 (3)
C1—C2—C3—C4	0.0 (4)	C4—C5—C12—N1	179.68 (19)
C2—C3—C4—C5	−0.2 (4)	C13—C14—C15—C16	−0.1 (3)
C6—N2—C5—C4	179.9 (2)	C14—C15—C16—C17	0.7 (3)
C6—N2—C5—C12	0.4 (3)	C14—C15—C16—Cl1	−179.17 (16)
C3—C4—C5—N2	−179.4 (2)	C15—C16—C17—C18	−0.8 (3)
C3—C4—C5—C12	0.2 (3)	Cl1—C16—C17—C18	179.07 (18)
C5—N2—C6—C7	−177.4 (2)	C8—N3—C19—C24	−32.2 (4)
C5—N2—C6—C11	1.0 (3)	C8—N3—C19—C20	153.0 (2)
N2—C6—C7—C8	−177.5 (2)	C24—C19—C20—C21	−0.5 (3)
C11—C6—C7—C8	4.0 (3)	N3—C19—C20—C21	174.7 (2)
C6—C7—C8—N3	−178.0 (2)	C19—C20—C21—C22	0.6 (4)
C6—C7—C8—C9	1.3 (3)	C20—C21—C22—C23	0.1 (4)
C19—N3—C8—C7	−9.0 (4)	C20—C21—C22—Cl2	−178.8 (2)
C19—N3—C8—C9	171.7 (2)	C21—C22—C23—C24	−0.9 (4)
C25—N4—C9—C10	−6.5 (3)	Cl2—C22—C23—C24	177.98 (19)
C25—N4—C9—C8	174.0 (2)	C22—C23—C24—C19	1.0 (4)
C7—C8—C9—N4	172.9 (2)	C20—C19—C24—C23	−0.3 (3)
N3—C8—C9—N4	−7.8 (3)	N3—C19—C24—C23	−175.1 (2)
C7—C8—C9—C10	−6.7 (3)	C9—N4—C25—C27	−83.6 (3)
N3—C8—C9—C10	172.7 (2)	C9—N4—C25—C26	153.6 (3)
N4—C9—C10—C11	−172.9 (2)	O2—C28—C29A—C30A	27.5 (7)
C8—C9—C10—C11	6.6 (3)	O1—C28—C29A—C30A	−159.8 (5)
C12—N1—C11—C10	−177.84 (18)	C28—C29A—C30A—C31	−75.0 (7)
C13—N1—C11—C10	0.8 (3)	O2—C28—C29B—C30B	−81.5 (14)
C12—N1—C11—C6	1.5 (3)	O1—C28—C29B—C30B	116.6 (12)
C13—N1—C11—C6	−179.81 (17)	C28—C29B—C30B—C31	86.1 (18)
C9—C10—C11—N1	178.18 (19)	C29B—C30B—C31—O3B	131.0 (17)
C9—C10—C11—C6	−1.2 (3)	C29B—C30B—C31—O4	−51.5 (14)
N2—C6—C11—N1	−2.0 (3)	C29A—C30A—C31—O3A	−117.2 (7)
C7—C6—C11—N1	176.40 (19)	C29A—C30A—C31—O4	62.8 (6)
N2—C6—C11—C10	177.4 (2)	C16—C17—C18—C13	0.3 (3)
C7—C6—C11—C10	−4.2 (3)	C17—C18—C13—C14	0.2 (3)
C2—C1—C12—N1	−179.9 (2)	C17—C18—C13—N1	179.08 (19)
C2—C1—C12—C5	−0.2 (3)	C15—C14—C13—C18	−0.3 (3)
C11—N1—C12—C1	179.39 (19)	C15—C14—C13—N1	−179.18 (17)
C13—N1—C12—C1	0.7 (3)	C11—N1—C13—C18	−92.4 (2)
C11—N1—C12—C5	−0.3 (3)	C12—N1—C13—C18	86.3 (2)
C13—N1—C12—C5	−178.92 (18)	C11—N1—C13—C14	86.5 (2)
N2—C5—C12—C1	179.6 (2)	C12—N1—C13—C14	−94.8 (2)
C4—C5—C12—C1	0.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O1ⁱ	0.85 (3)	1.98 (3)	2.824 (3)	170 (2)
C15—H15···O1ⁱⁱ	0.93	2.31	3.233 (3)	175
C29B—H29D···Cl2ⁱⁱⁱ	0.97	2.80	3.416 (14)	122
O4—H4B···O2	0.94 (3)	1.56 (3)	2.497 (3)	177 (3)

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

1,1,3-trioxo-2,3-dihydro-1,2-benzothiazol-2-ide; N-[(2E)-10-(4-chlorophenyl)-3-[(4-chlorophenyl)amino] -2,10-dihydrophenazin-2-ylidene]propan-2-aminium; acetonitrile (lb0276_CLZ_SAC) top

Crystal data top

C₂₇H₂₃Cl₂N₄⁺·C₇H₄NO₃S⁻·1.393(C₂H₃N)	Z = 2
M_r = 713.78	F(000) = 741
Triclinic, P1	D_x = 1.355 Mg m⁻³
a = 7.9970 (3) Å	Cu Kα radiation, λ = 1.54184 Å
b = 13.5824 (3) Å	Cell parameters from 7454 reflections
c = 16.6638 (7) Å	θ = 3.3–66.9°
α = 80.214 (3)°	µ = 2.61 mm⁻¹
β = 80.034 (4)°	T = 100 K
γ = 83.036 (3)°	Plate, metallic dark red
V = 1748.87 (11) Å³	0.70 × 0.26 × 0.05 mm

Data collection top

Xcalibur Ruby Gemini ultra diffractometer	6202 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance Ultra (Cu) X-ray Source	5378 reflections with I > 2σ(I)
Detector resolution: 5.1856 pixels mm^-1	R_int = 0.033
ω scans	θ_max = 67.2°, θ_min = 2.7°
Absorption correction: gaussian CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −9→9
T_min = 0.295, T_max = 1.000	k = −11→16
17257 measured reflections	l = −18→19

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: dual
R[F² > 2σ(F²)] = 0.053	Hydrogen site location: mixed
wR(F²) = 0.142	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0656P)² + 1.3374P] where P = (F_o² + 2F_c²)/3
6202 reflections	(Δ/σ)_max < 0.001
594 parameters	Δρ_max = 0.61 e Å⁻³
137 restraints	Δρ_min = −0.67 e Å⁻³

Special details top

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C18A	−0.083 (3)	0.757 (2)	0.354 (2)	0.048 (5)	0.411 (18)
H18A	−0.009343	0.740921	0.394484	0.058*	0.411 (18)
C17A	−0.083 (3)	0.8500 (14)	0.3011 (13)	0.061 (5)	0.411 (18)
H17A	−0.009993	0.898698	0.304484	0.073*	0.411 (18)
C16A	−0.193 (3)	0.8671 (14)	0.2448 (12)	0.047 (3)	0.411 (18)
C15A	−0.2946 (11)	0.8012 (9)	0.2339 (8)	0.044 (2)	0.411 (18)
H15A	−0.366024	0.817284	0.192566	0.053*	0.411 (18)
C14A	−0.2940 (13)	0.7080 (10)	0.2846 (8)	0.037 (2)	0.411 (18)
H14A	−0.361447	0.658946	0.275998	0.044*	0.411 (18)
C13A	−0.198 (5)	0.6870 (17)	0.346 (2)	0.029 (3)	0.411 (18)
Cl1A	−0.1956 (14)	0.9863 (4)	0.1802 (6)	0.0777 (19)	0.411 (18)
C18B	−0.0435 (18)	0.7458 (13)	0.3557 (12)	0.031 (2)	0.589 (18)
H18B	0.044455	0.718926	0.387069	0.037*	0.589 (18)
C17B	−0.0376 (13)	0.8387 (9)	0.3090 (6)	0.0357 (18)	0.589 (18)
H17B	0.057057	0.875862	0.306169	0.043*	0.589 (18)
C16B	−0.1708 (16)	0.8791 (8)	0.2654 (8)	0.036 (2)	0.589 (18)
C15B	−0.3080 (8)	0.8246 (5)	0.2680 (6)	0.0401 (17)	0.589 (18)
H15B	−0.398319	0.852104	0.238224	0.048*	0.589 (18)
C14B	−0.3126 (9)	0.7300 (5)	0.3141 (6)	0.0339 (16)	0.589 (18)
H14B	−0.405390	0.691379	0.317064	0.041*	0.589 (18)
C13B	−0.176 (3)	0.6931 (11)	0.3564 (14)	0.027 (3)	0.589 (18)
Cl1B	−0.1650 (3)	0.9973 (2)	0.2081 (4)	0.0516 (10)	0.589 (18)
Cl2	0.26863 (8)	−0.15736 (4)	0.45761 (5)	0.0508 (2)
S1	0.24712 (8)	0.69123 (6)	0.79920 (5)	0.0536 (2)
N2	−0.1685 (2)	0.40658 (12)	0.50519 (11)	0.0282 (4)
N3	0.2486 (2)	0.26865 (13)	0.30223 (12)	0.0306 (4)
H3	0.345 (4)	0.285 (2)	0.2724 (17)	0.037*
N1	−0.1858 (2)	0.59243 (12)	0.40340 (12)	0.0290 (4)
N4	0.2032 (3)	0.44258 (15)	0.19569 (14)	0.0430 (5)
H4N	0.262 (4)	0.389 (3)	0.1832 (19)	0.052*
O3	0.5895 (3)	0.7366 (2)	0.90021 (14)	0.0694 (7)
C12	−0.2879 (3)	0.58095 (15)	0.47992 (14)	0.0293 (5)
C5	−0.2756 (3)	0.48600 (15)	0.52995 (14)	0.0284 (4)
C6	−0.0778 (3)	0.41886 (15)	0.43078 (13)	0.0269 (4)
N5	0.4411 (3)	0.69191 (18)	0.81114 (14)	0.0477 (5)
C7	0.0349 (3)	0.33741 (15)	0.40438 (13)	0.0278 (4)
H7	0.040969	0.275383	0.440520	0.033*
C19	0.2519 (3)	0.16821 (15)	0.34225 (14)	0.0300 (5)
C10	0.0171 (3)	0.52253 (15)	0.29861 (14)	0.0307 (5)
H10	0.015667	0.585425	0.263477	0.037*
C11	−0.0815 (3)	0.51390 (15)	0.37493 (14)	0.0273 (4)
O1	0.2154 (3)	0.7531 (2)	0.72364 (14)	0.0873 (9)
C9	0.1203 (3)	0.43955 (16)	0.27174 (14)	0.0308 (5)
C8	0.1343 (3)	0.34522 (15)	0.32921 (13)	0.0276 (4)
C24	0.1029 (3)	0.12083 (16)	0.36502 (14)	0.0323 (5)
H24	−0.003122	0.156834	0.355473	0.039*
C34	0.1512 (3)	0.75030 (16)	0.88378 (15)	0.0329 (5)
C29	0.2813 (3)	0.76984 (17)	0.92157 (15)	0.0364 (5)
C3	−0.4887 (3)	0.54922 (17)	0.63525 (15)	0.0342 (5)
H3A	−0.557790	0.539163	0.687848	0.041*
C4	−0.3762 (3)	0.47245 (16)	0.60844 (14)	0.0319 (5)
H4A	−0.366250	0.409589	0.643216	0.038*
C2	−0.5007 (3)	0.64266 (17)	0.58436 (15)	0.0346 (5)
H2	−0.579359	0.695365	0.602906	0.042*
C23	0.1081 (3)	0.02123 (16)	0.40162 (15)	0.0342 (5)
H23	0.005873	−0.010904	0.418443	0.041*
C1	−0.4014 (3)	0.65948 (16)	0.50845 (15)	0.0334 (5)
H1	−0.409208	0.723667	0.475426	0.040*
C20	0.4085 (3)	0.11491 (17)	0.35461 (15)	0.0350 (5)
H20	0.510766	0.147163	0.338832	0.042*
C21	0.4140 (3)	0.01453 (17)	0.39008 (16)	0.0394 (5)
H21	0.520025	−0.022423	0.398206	0.047*
C22	0.2643 (3)	−0.03114 (16)	0.41344 (15)	0.0364 (5)
O2	0.2009 (4)	0.5899 (2)	0.8110 (2)	0.1070 (12)
C28	0.4522 (3)	0.7324 (2)	0.87769 (17)	0.0442 (6)
C33	−0.0185 (3)	0.7750 (2)	0.91196 (18)	0.0467 (6)
H33	−0.106794	0.759927	0.885799	0.056*
C30	0.2450 (5)	0.8167 (3)	0.99038 (19)	0.0650 (8)
H30	0.333496	0.830010	1.017297	0.078*
C32	−0.0527 (4)	0.8231 (3)	0.9807 (2)	0.0705 (10)
H32	−0.167728	0.842433	1.002159	0.085*
C31	0.0768 (6)	0.8438 (3)	1.0190 (2)	0.0850 (13)
H31	0.048815	0.877363	1.065830	0.102*
N6	0.3720 (9)	0.7146 (5)	0.2025 (4)	0.0663 (18)	0.440 (5)
C36	0.4991 (10)	0.6938 (5)	0.1610 (4)	0.0567 (18)	0.440 (5)
C35	0.6644 (11)	0.6696 (6)	0.1087 (5)	0.064 (2)	0.440 (5)
H35A	0.651742	0.687667	0.050450	0.097*	0.440 (5)
H35B	0.699050	0.597539	0.120559	0.097*	0.440 (5)
H35C	0.751454	0.707540	0.120684	0.097*	0.440 (5)
C38	0.4408 (8)	0.9765 (5)	0.1055 (4)	0.0509 (18)	0.464 (7)
N7	0.5378 (8)	0.9402 (6)	0.0553 (5)	0.082 (2)	0.464 (7)
C37	0.3288 (14)	1.0319 (11)	0.1680 (5)	0.057 (3)	0.464 (7)
H37A	0.211662	1.013948	0.174130	0.085*	0.464 (7)
H37B	0.330988	1.104276	0.149812	0.085*	0.464 (7)
H37C	0.370137	1.013732	0.221121	0.085*	0.464 (7)
N7A	0.3148 (10)	0.8524 (7)	0.1844 (6)	0.100 (3)	0.489 (7)
C38A	0.3259 (11)	0.9392 (9)	0.1734 (5)	0.082 (3)	0.489 (7)
C37A	0.326 (3)	1.0241 (19)	0.1641 (14)	0.171 (12)	0.489 (7)
H37D	0.218547	1.053208	0.192962	0.256*	0.489 (7)
H37E	0.335909	1.050345	0.105096	0.256*	0.489 (7)
H37F	0.421836	1.041804	0.186201	0.256*	0.489 (7)
C25A	0.213 (2)	0.5373 (11)	0.1352 (9)	0.054 (3)	0.560 (5)
H25A	0.105698	0.581761	0.147950	0.065*	0.560 (5)
C27A	0.2089 (9)	0.5001 (4)	0.0542 (3)	0.0623 (16)	0.560 (5)
H27A	0.209451	0.557256	0.009553	0.093*	0.560 (5)
H27B	0.105302	0.466343	0.058851	0.093*	0.560 (5)
H27C	0.309343	0.452821	0.042306	0.093*	0.560 (5)
C26A	0.3514 (13)	0.5894 (5)	0.1395 (4)	0.098 (3)	0.560 (5)
H26A	0.349964	0.651831	0.100170	0.147*	0.560 (5)
H26B	0.458179	0.547645	0.125955	0.147*	0.560 (5)
H26C	0.342965	0.605080	0.195424	0.147*	0.560 (5)
C25B	0.195 (2)	0.5233 (16)	0.1241 (12)	0.041 (3)	0.440 (5)
H25B	0.205041	0.586718	0.145148	0.049*	0.440 (5)
C26B	0.3554 (12)	0.5106 (5)	0.0578 (4)	0.067 (2)	0.440 (5)
H26D	0.353189	0.567388	0.012817	0.100*	0.440 (5)
H26E	0.355519	0.448001	0.035947	0.100*	0.440 (5)
H26F	0.458403	0.508508	0.082651	0.100*	0.440 (5)
C27B	0.0361 (11)	0.5401 (5)	0.0897 (5)	0.061 (2)	0.440 (5)
H27D	0.040578	0.598774	0.046325	0.092*	0.440 (5)
H27E	−0.059811	0.551906	0.133379	0.092*	0.440 (5)
H27F	0.020726	0.480909	0.066293	0.092*	0.440 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C18A	0.058 (12)	0.034 (8)	0.058 (7)	−0.010 (8)	−0.025 (9)	−0.004 (5)
C17A	0.087 (13)	0.018 (5)	0.085 (8)	−0.012 (7)	−0.030 (8)	−0.004 (4)
C16A	0.065 (8)	0.023 (5)	0.048 (8)	0.009 (4)	−0.006 (5)	−0.002 (5)
C15A	0.035 (4)	0.052 (5)	0.038 (5)	0.007 (3)	−0.003 (3)	0.002 (4)
C14A	0.033 (4)	0.038 (5)	0.038 (5)	−0.002 (3)	−0.007 (3)	−0.001 (3)
C13A	0.023 (8)	0.019 (4)	0.049 (9)	−0.007 (4)	−0.005 (4)	−0.009 (4)
Cl1A	0.115 (3)	0.0295 (14)	0.074 (3)	0.0142 (16)	−0.005 (3)	0.0107 (16)
C18B	0.029 (4)	0.018 (3)	0.047 (4)	−0.002 (3)	−0.008 (3)	−0.006 (3)
C17B	0.037 (3)	0.024 (3)	0.048 (4)	−0.005 (3)	−0.008 (3)	−0.005 (3)
C16B	0.040 (4)	0.014 (3)	0.053 (6)	0.000 (2)	−0.007 (4)	−0.005 (3)
C15B	0.039 (3)	0.031 (3)	0.048 (4)	0.003 (2)	−0.013 (3)	0.004 (3)
C14B	0.031 (3)	0.025 (3)	0.046 (4)	−0.003 (2)	−0.013 (3)	0.001 (2)
C13B	0.024 (6)	0.016 (4)	0.042 (5)	0.001 (3)	−0.013 (3)	−0.004 (3)
Cl1B	0.0604 (11)	0.0223 (7)	0.0653 (19)	−0.0027 (6)	−0.0091 (9)	0.0113 (8)
Cl2	0.0481 (4)	0.0235 (3)	0.0752 (5)	0.0052 (2)	−0.0126 (3)	0.0058 (3)
S1	0.0384 (4)	0.0613 (4)	0.0678 (5)	0.0131 (3)	−0.0132 (3)	−0.0363 (4)
N2	0.0263 (9)	0.0207 (8)	0.0393 (10)	−0.0031 (7)	−0.0069 (7)	−0.0070 (7)
N3	0.0290 (9)	0.0224 (9)	0.0394 (10)	0.0001 (7)	−0.0034 (8)	−0.0057 (7)
N1	0.0252 (9)	0.0184 (8)	0.0431 (10)	−0.0006 (7)	−0.0067 (8)	−0.0031 (7)
N4	0.0503 (13)	0.0236 (10)	0.0462 (12)	0.0039 (9)	0.0054 (10)	0.0014 (9)
O3	0.0357 (10)	0.1022 (18)	0.0671 (14)	−0.0191 (11)	−0.0201 (10)	0.0176 (12)
C12	0.0248 (10)	0.0239 (10)	0.0415 (12)	−0.0022 (8)	−0.0092 (9)	−0.0079 (9)
C5	0.0251 (10)	0.0220 (10)	0.0405 (12)	−0.0027 (8)	−0.0076 (9)	−0.0087 (8)
C6	0.0252 (10)	0.0197 (10)	0.0375 (11)	−0.0044 (8)	−0.0084 (9)	−0.0042 (8)
N5	0.0307 (11)	0.0562 (13)	0.0497 (13)	0.0104 (9)	−0.0025 (9)	−0.0041 (10)
C7	0.0279 (10)	0.0178 (9)	0.0386 (12)	−0.0017 (8)	−0.0086 (9)	−0.0039 (8)
C19	0.0338 (11)	0.0202 (10)	0.0373 (11)	0.0015 (8)	−0.0086 (9)	−0.0079 (8)
C10	0.0298 (11)	0.0185 (10)	0.0434 (12)	−0.0026 (8)	−0.0081 (9)	−0.0012 (8)
C11	0.0233 (10)	0.0188 (10)	0.0420 (12)	−0.0027 (7)	−0.0085 (9)	−0.0067 (8)
O1	0.0619 (14)	0.148 (3)	0.0534 (13)	0.0458 (15)	−0.0226 (11)	−0.0456 (15)
C9	0.0288 (11)	0.0234 (10)	0.0396 (12)	−0.0042 (8)	−0.0041 (9)	−0.0028 (9)
C8	0.0275 (10)	0.0193 (10)	0.0378 (11)	−0.0012 (8)	−0.0087 (9)	−0.0063 (8)
C24	0.0318 (11)	0.0222 (10)	0.0443 (13)	0.0032 (8)	−0.0112 (10)	−0.0080 (9)
C34	0.0278 (11)	0.0258 (11)	0.0429 (13)	−0.0010 (8)	−0.0032 (9)	−0.0020 (9)
C29	0.0368 (12)	0.0327 (12)	0.0378 (12)	−0.0055 (9)	−0.0083 (10)	0.0038 (9)
C3	0.0288 (11)	0.0347 (12)	0.0421 (13)	−0.0031 (9)	−0.0056 (9)	−0.0143 (10)
C4	0.0303 (11)	0.0257 (11)	0.0416 (12)	−0.0042 (8)	−0.0073 (9)	−0.0082 (9)
C2	0.0283 (11)	0.0304 (11)	0.0496 (14)	0.0030 (9)	−0.0107 (10)	−0.0176 (10)
C23	0.0349 (12)	0.0223 (10)	0.0467 (13)	−0.0008 (9)	−0.0094 (10)	−0.0065 (9)
C1	0.0299 (11)	0.0233 (10)	0.0496 (14)	0.0020 (8)	−0.0119 (10)	−0.0103 (9)
C20	0.0310 (11)	0.0285 (11)	0.0460 (13)	−0.0001 (9)	−0.0092 (10)	−0.0062 (9)
C21	0.0346 (12)	0.0303 (12)	0.0519 (14)	0.0082 (9)	−0.0119 (11)	−0.0052 (10)
C22	0.0413 (13)	0.0195 (10)	0.0478 (13)	0.0026 (9)	−0.0120 (10)	−0.0020 (9)
O2	0.0756 (17)	0.0711 (17)	0.198 (3)	0.0021 (13)	−0.0245 (19)	−0.089 (2)
C28	0.0274 (12)	0.0492 (15)	0.0492 (15)	−0.0066 (10)	−0.0085 (10)	0.0158 (12)
C33	0.0284 (12)	0.0461 (14)	0.0587 (16)	0.0022 (10)	−0.0007 (11)	0.0015 (12)
C30	0.076 (2)	0.077 (2)	0.0471 (17)	−0.0017 (17)	−0.0204 (15)	−0.0176 (15)
C32	0.0560 (19)	0.085 (2)	0.0505 (17)	0.0292 (17)	0.0128 (15)	−0.0016 (16)
C31	0.097 (3)	0.108 (3)	0.0452 (18)	0.031 (2)	−0.0077 (19)	−0.0297 (19)
N6	0.065 (4)	0.084 (5)	0.054 (4)	−0.025 (3)	−0.019 (3)	0.001 (3)
C36	0.070 (5)	0.059 (4)	0.046 (4)	−0.023 (3)	−0.019 (4)	0.000 (3)
C35	0.088 (6)	0.053 (4)	0.052 (4)	−0.015 (4)	−0.003 (4)	−0.009 (3)
C38	0.045 (3)	0.058 (4)	0.051 (4)	−0.010 (3)	−0.002 (3)	−0.014 (3)
N7	0.053 (4)	0.117 (6)	0.083 (5)	−0.016 (4)	0.000 (3)	−0.037 (4)
C37	0.052 (6)	0.090 (9)	0.025 (3)	0.008 (6)	−0.006 (3)	−0.013 (4)
N7A	0.079 (5)	0.109 (7)	0.131 (7)	0.014 (4)	−0.051 (5)	−0.056 (5)
C38A	0.069 (5)	0.106 (8)	0.084 (6)	0.017 (5)	−0.039 (4)	−0.044 (5)
C37A	0.165 (19)	0.165 (19)	0.19 (2)	0.123 (15)	−0.080 (14)	−0.099 (15)
C25A	0.091 (8)	0.019 (5)	0.037 (4)	0.006 (4)	0.018 (4)	0.005 (4)
C27A	0.080 (4)	0.056 (3)	0.045 (3)	−0.012 (3)	−0.007 (3)	0.010 (2)
C26A	0.188 (9)	0.055 (4)	0.058 (4)	−0.064 (5)	−0.031 (5)	0.020 (3)
C25B	0.042 (4)	0.019 (5)	0.062 (8)	−0.008 (3)	0.001 (4)	−0.013 (4)
C26B	0.086 (6)	0.042 (4)	0.050 (4)	0.010 (4)	0.029 (4)	0.009 (3)
C27B	0.090 (6)	0.034 (3)	0.059 (4)	−0.006 (3)	−0.026 (4)	0.010 (3)

Geometric parameters (Å, º) top

C18A—C17A	1.42 (3)	C34—C33	1.378 (3)
C18A—C13A	1.44 (3)	C34—C29	1.378 (3)
C18A—H18A	0.9500	C29—C30	1.376 (4)
C17A—C16A	1.36 (2)	C29—C28	1.508 (4)
C17A—H17A	0.9500	C3—C4	1.374 (3)
C16A—C15A	1.335 (19)	C3—C2	1.404 (3)
C16A—Cl1A	1.786 (19)	C3—H3A	0.9500
C15A—C14A	1.397 (13)	C4—H4A	0.9500
C15A—H15A	0.9500	C2—C1	1.372 (3)
C14A—C13A	1.35 (2)	C2—H2	0.9500
C14A—H14A	0.9500	C23—C22	1.389 (3)
C13A—N1	1.470 (12)	C23—H23	0.9500
C18B—C13B	1.34 (2)	C1—H1	0.9500
C18B—C17B	1.366 (19)	C20—C21	1.390 (3)
C18B—H18B	0.9500	C20—H20	0.9500
C17B—C16B	1.397 (12)	C21—C22	1.381 (4)
C17B—H17B	0.9500	C21—H21	0.9500
C16B—C15B	1.387 (11)	C33—C32	1.385 (5)
C16B—Cl1B	1.725 (12)	C33—H33	0.9500
C15B—C14B	1.381 (8)	C30—C31	1.375 (5)
C15B—H15B	0.9500	C30—H30	0.9500
C14B—C13B	1.400 (15)	C32—C31	1.384 (6)
C14B—H14B	0.9500	C32—H32	0.9500
C13B—N1	1.459 (8)	C31—H31	0.9500
Cl2—C22	1.746 (2)	N6—C36	1.160 (10)
S1—O1	1.433 (3)	C36—C35	1.486 (11)
S1—O2	1.441 (3)	C35—H35A	0.9800
S1—N5	1.599 (2)	C35—H35B	0.9800
S1—C34	1.755 (2)	C35—H35C	0.9800
N2—C6	1.319 (3)	C38—N7	1.169 (9)
N2—C5	1.368 (3)	C38—C37	1.495 (13)
N3—C8	1.380 (3)	C37—H37A	0.9800
N3—C19	1.412 (3)	C37—H37B	0.9800
N3—H3	0.87 (3)	C37—H37C	0.9800
N1—C11	1.370 (3)	N7A—C38A	1.174 (13)
N1—C12	1.385 (3)	C38A—C37A	1.14 (3)
N4—C9	1.321 (3)	C37A—H37D	0.9800
N4—C25B	1.48 (2)	C37A—H37E	0.9800
N4—C25A	1.494 (14)	C37A—H37F	0.9800
N4—H4N	0.85 (3)	C25A—C26A	1.404 (16)
O3—C28	1.230 (3)	C25A—C27A	1.525 (15)
C12—C1	1.406 (3)	C25A—H25A	1.0000
C12—C5	1.414 (3)	C27A—H27A	0.9800
C5—C4	1.408 (3)	C27A—H27B	0.9800
C6—C7	1.420 (3)	C27A—H27C	0.9800
C6—C11	1.458 (3)	C26A—H26A	0.9800
N5—C28	1.339 (4)	C26A—H26B	0.9800
C7—C8	1.357 (3)	C26A—H26C	0.9800
C7—H7	0.9500	C25B—C27B	1.46 (2)
C19—C24	1.388 (3)	C25B—C26B	1.55 (2)
C19—C20	1.398 (3)	C25B—H25B	1.0000
C10—C11	1.371 (3)	C26B—H26D	0.9800
C10—C9	1.403 (3)	C26B—H26E	0.9800
C10—H10	0.9500	C26B—H26F	0.9800
C9—C8	1.469 (3)	C27B—H27D	0.9800
C24—C23	1.385 (3)	C27B—H27E	0.9800
C24—H24	0.9500	C27B—H27F	0.9800

C17A—C18A—C13A	118.3 (19)	C2—C3—H3A	120.2
C17A—C18A—H18A	120.9	C3—C4—C5	120.7 (2)
C13A—C18A—H18A	120.9	C3—C4—H4A	119.7
C16A—C17A—C18A	117.4 (18)	C5—C4—H4A	119.7
C16A—C17A—H17A	121.3	C1—C2—C3	121.4 (2)
C18A—C17A—H17A	121.3	C1—C2—H2	119.3
C15A—C16A—C17A	125.0 (16)	C3—C2—H2	119.3
C15A—C16A—Cl1A	118.2 (12)	C24—C23—C22	119.3 (2)
C17A—C16A—Cl1A	116.8 (13)	C24—C23—H23	120.4
C16A—C15A—C14A	118.5 (11)	C22—C23—H23	120.4
C16A—C15A—H15A	120.8	C2—C1—C12	119.5 (2)
C14A—C15A—H15A	120.8	C2—C1—H1	120.3
C13A—C14A—C15A	120.6 (11)	C12—C1—H1	120.3
C13A—C14A—H14A	119.7	C21—C20—C19	119.7 (2)
C15A—C14A—H14A	119.7	C21—C20—H20	120.2
C14A—C13A—C18A	120.0 (15)	C19—C20—H20	120.2
C14A—C13A—N1	126.1 (15)	C22—C21—C20	119.6 (2)
C18A—C13A—N1	113.7 (17)	C22—C21—H21	120.2
C13B—C18B—C17B	119.0 (10)	C20—C21—H21	120.2
C13B—C18B—H18B	120.5	C21—C22—C23	121.2 (2)
C17B—C18B—H18B	120.5	C21—C22—Cl2	120.24 (18)
C18B—C17B—C16B	120.0 (10)	C23—C22—Cl2	118.55 (18)
C18B—C17B—H17B	120.0	O3—C28—N5	122.3 (3)
C16B—C17B—H17B	120.0	O3—C28—C29	124.4 (3)
C15B—C16B—C17B	120.4 (10)	N5—C28—C29	113.2 (2)
C15B—C16B—Cl1B	119.7 (8)	C34—C33—C32	116.0 (3)
C17B—C16B—Cl1B	120.0 (8)	C34—C33—H33	122.0
C14B—C15B—C16B	119.6 (7)	C32—C33—H33	122.0
C14B—C15B—H15B	120.2	C31—C30—C29	118.0 (3)
C16B—C15B—H15B	120.2	C31—C30—H30	121.0
C15B—C14B—C13B	117.8 (7)	C29—C30—H30	121.0
C15B—C14B—H14B	121.1	C31—C32—C33	121.6 (3)
C13B—C14B—H14B	121.1	C31—C32—H32	119.2
C18B—C13B—C14B	123.3 (9)	C33—C32—H32	119.2
C18B—C13B—N1	121.2 (12)	C30—C31—C32	121.2 (3)
C14B—C13B—N1	115.5 (11)	C30—C31—H31	119.4
O1—S1—O2	116.2 (2)	C32—C31—H31	119.4
O1—S1—N5	110.38 (15)	N6—C36—C35	178.2 (8)
O2—S1—N5	110.66 (15)	C36—C35—H35A	109.5
O1—S1—C34	110.34 (12)	C36—C35—H35B	109.5
O2—S1—C34	110.14 (16)	H35A—C35—H35B	109.5
N5—S1—C34	97.59 (11)	C36—C35—H35C	109.5
C6—N2—C5	118.30 (18)	H35A—C35—H35C	109.5
C8—N3—C19	123.59 (19)	H35B—C35—H35C	109.5
C8—N3—H3	117.2 (18)	N7—C38—C37	173.9 (8)
C19—N3—H3	114.9 (18)	C38—C37—H37A	109.5
C11—N1—C12	121.68 (18)	C38—C37—H37B	109.5
C11—N1—C13B	119.4 (13)	H37A—C37—H37B	109.5
C12—N1—C13B	118.6 (13)	C38—C37—H37C	109.5
C11—N1—C13A	117.0 (19)	H37A—C37—H37C	109.5
C12—N1—C13A	121.0 (19)	H37B—C37—H37C	109.5
C9—N4—C25B	129.2 (8)	C37A—C38A—N7A	175.6 (15)
C9—N4—C25A	122.8 (7)	C38A—C37A—H37D	109.5
C9—N4—H4N	117 (2)	C38A—C37A—H37E	109.5
C25B—N4—H4N	113 (2)	H37D—C37A—H37E	109.5
C25A—N4—H4N	120 (2)	C38A—C37A—H37F	109.5
N1—C12—C1	122.4 (2)	H37D—C37A—H37F	109.5
N1—C12—C5	117.74 (18)	H37E—C37A—H37F	109.5
C1—C12—C5	119.9 (2)	C26A—C25A—N4	112.6 (12)
N2—C5—C4	118.52 (19)	C26A—C25A—C27A	117.5 (11)
N2—C5—C12	122.5 (2)	N4—C25A—C27A	102.1 (9)
C4—C5—C12	119.01 (19)	C26A—C25A—H25A	108.1
N2—C6—C7	119.01 (19)	N4—C25A—H25A	108.1
N2—C6—C11	123.14 (18)	C27A—C25A—H25A	108.1
C7—C6—C11	117.80 (19)	C25A—C27A—H27A	109.5
C28—N5—S1	111.61 (17)	C25A—C27A—H27B	109.5
C8—C7—C6	122.18 (19)	H27A—C27A—H27B	109.5
C8—C7—H7	118.9	C25A—C27A—H27C	109.5
C6—C7—H7	118.9	H27A—C27A—H27C	109.5
C24—C19—C20	120.1 (2)	H27B—C27A—H27C	109.5
C24—C19—N3	120.59 (19)	C25A—C26A—H26A	109.5
C20—C19—N3	119.3 (2)	C25A—C26A—H26B	109.5
C11—C10—C9	120.8 (2)	H26A—C26A—H26B	109.5
C11—C10—H10	119.6	C25A—C26A—H26C	109.5
C9—C10—H10	119.6	H26A—C26A—H26C	109.5
N1—C11—C10	122.86 (19)	H26B—C26A—H26C	109.5
N1—C11—C6	116.57 (19)	C27B—C25B—N4	116.3 (10)
C10—C11—C6	120.56 (18)	C27B—C25B—C26B	112.9 (13)
N4—C9—C10	122.2 (2)	N4—C25B—C26B	110.3 (14)
N4—C9—C8	118.53 (19)	C27B—C25B—H25B	105.5
C10—C9—C8	119.2 (2)	N4—C25B—H25B	105.5
C7—C8—N3	123.86 (19)	C26B—C25B—H25B	105.5
C7—C8—C9	119.16 (18)	C25B—C26B—H26D	109.5
N3—C8—C9	116.97 (19)	C25B—C26B—H26E	109.5
C23—C24—C19	120.2 (2)	H26D—C26B—H26E	109.5
C23—C24—H24	119.9	C25B—C26B—H26F	109.5
C19—C24—H24	119.9	H26D—C26B—H26F	109.5
C33—C34—C29	123.0 (2)	H26E—C26B—H26F	109.5
C33—C34—S1	130.2 (2)	C25B—C27B—H27D	109.5
C29—C34—S1	106.79 (17)	C25B—C27B—H27E	109.5
C30—C29—C34	120.2 (3)	H27D—C27B—H27E	109.5
C30—C29—C28	129.0 (3)	C25B—C27B—H27F	109.5
C34—C29—C28	110.8 (2)	H27D—C27B—H27F	109.5
C4—C3—C2	119.5 (2)	H27E—C27B—H27F	109.5
C4—C3—H3A	120.2

C13A—C18A—C17A—C16A	0 (4)	C7—C6—C11—C10	2.0 (3)
C18A—C17A—C16A—C15A	−3 (3)	C25B—N4—C9—C10	−6.2 (7)
C18A—C17A—C16A—Cl1A	178.2 (18)	C25A—N4—C9—C10	8.1 (8)
C17A—C16A—C15A—C14A	2 (3)	C25B—N4—C9—C8	172.4 (7)
Cl1A—C16A—C15A—C14A	−179.5 (10)	C25A—N4—C9—C8	−173.3 (7)
C16A—C15A—C14A—C13A	3 (3)	C11—C10—C9—N4	172.9 (2)
C15A—C14A—C13A—C18A	−6 (5)	C11—C10—C9—C8	−5.7 (3)
C15A—C14A—C13A—N1	−180 (3)	C6—C7—C8—N3	178.19 (19)
C17A—C18A—C13A—C14A	5 (5)	C6—C7—C8—C9	−2.5 (3)
C17A—C18A—C13A—N1	179 (2)	C19—N3—C8—C7	12.9 (3)
C13B—C18B—C17B—C16B	2 (3)	C19—N3—C8—C9	−166.40 (19)
C18B—C17B—C16B—C15B	−1.2 (19)	N4—C9—C8—C7	−172.5 (2)
C18B—C17B—C16B—Cl1B	178.8 (12)	C10—C9—C8—C7	6.2 (3)
C17B—C16B—C15B—C14B	0.1 (14)	N4—C9—C8—N3	6.8 (3)
Cl1B—C16B—C15B—C14B	−179.8 (6)	C10—C9—C8—N3	−174.51 (19)
C16B—C15B—C14B—C13B	−0.3 (18)	C20—C19—C24—C23	1.3 (3)
C17B—C18B—C13B—C14B	−3 (4)	N3—C19—C24—C23	177.7 (2)
C17B—C18B—C13B—N1	178.3 (18)	O1—S1—C34—C33	64.9 (3)
C15B—C14B—C13B—C18B	2 (3)	O2—S1—C34—C33	−64.6 (3)
C15B—C14B—C13B—N1	−179.3 (14)	N5—S1—C34—C33	−180.0 (2)
C18B—C13B—N1—C11	−74 (3)	O1—S1—C34—C29	−115.3 (2)
C14B—C13B—N1—C11	107 (2)	O2—S1—C34—C29	115.1 (2)
C18B—C13B—N1—C12	99 (3)	N5—S1—C34—C29	−0.23 (18)
C14B—C13B—N1—C12	−80 (2)	C33—C34—C29—C30	−0.5 (4)
C14A—C13A—N1—C11	79 (4)	S1—C34—C29—C30	179.7 (2)
C18A—C13A—N1—C11	−95 (3)	C33—C34—C29—C28	178.9 (2)
C14A—C13A—N1—C12	−95 (4)	S1—C34—C29—C28	−0.9 (2)
C18A—C13A—N1—C12	91 (3)	C2—C3—C4—C5	−1.2 (3)
C11—N1—C12—C1	−176.96 (19)	N2—C5—C4—C3	−178.39 (19)
C13B—N1—C12—C1	9.9 (7)	C12—C5—C4—C3	2.0 (3)
C13A—N1—C12—C1	−3.3 (11)	C4—C3—C2—C1	−0.6 (3)
C11—N1—C12—C5	2.8 (3)	C19—C24—C23—C22	−1.5 (4)
C13B—N1—C12—C5	−170.3 (7)	C3—C2—C1—C12	1.6 (3)
C13A—N1—C12—C5	176.5 (10)	N1—C12—C1—C2	179.0 (2)
C6—N2—C5—C4	178.28 (19)	C5—C12—C1—C2	−0.8 (3)
C6—N2—C5—C12	−2.1 (3)	C24—C19—C20—C21	−0.3 (3)
N1—C12—C5—N2	−0.4 (3)	N3—C19—C20—C21	−176.7 (2)
C1—C12—C5—N2	179.42 (19)	C19—C20—C21—C22	−0.6 (4)
N1—C12—C5—C4	179.24 (19)	C20—C21—C22—C23	0.5 (4)
C1—C12—C5—C4	−1.0 (3)	C20—C21—C22—Cl2	179.66 (19)
C5—N2—C6—C7	179.51 (18)	C24—C23—C22—C21	0.6 (4)
C5—N2—C6—C11	2.3 (3)	C24—C23—C22—Cl2	−178.62 (18)
O1—S1—N5—C28	116.5 (2)	S1—N5—C28—O3	176.9 (2)
O2—S1—N5—C28	−113.5 (2)	S1—N5—C28—C29	−2.2 (3)
C34—S1—N5—C28	1.4 (2)	C30—C29—C28—O3	2.2 (4)
N2—C6—C7—C8	−178.87 (19)	C34—C29—C28—O3	−177.1 (2)
C11—C6—C7—C8	−1.5 (3)	C30—C29—C28—N5	−178.7 (3)
C8—N3—C19—C24	48.1 (3)	C34—C29—C28—N5	2.0 (3)
C8—N3—C19—C20	−135.5 (2)	C29—C34—C33—C32	1.2 (4)
C12—N1—C11—C10	178.2 (2)	S1—C34—C33—C32	−179.1 (2)
C13B—N1—C11—C10	−8.8 (7)	C34—C29—C30—C31	−0.6 (5)
C13A—N1—C11—C10	4.2 (10)	C28—C29—C30—C31	−179.9 (3)
C12—N1—C11—C6	−2.7 (3)	C34—C33—C32—C31	−0.7 (5)
C13B—N1—C11—C6	170.4 (7)	C29—C30—C31—C32	1.1 (6)
C13A—N1—C11—C6	−176.6 (10)	C33—C32—C31—C30	−0.4 (6)
C9—C10—C11—N1	−179.16 (19)	C9—N4—C25A—C26A	88.5 (12)
C9—C10—C11—C6	1.7 (3)	C9—N4—C25A—C27A	−144.6 (7)
N2—C6—C11—N1	0.1 (3)	C9—N4—C25B—C27B	−69.2 (14)
C7—C6—C11—N1	−177.22 (18)	C9—N4—C25B—C26B	160.6 (6)
N2—C6—C11—C10	179.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C33—H33···O3ⁱ	0.95	2.45	3.283 (3)	146
C24—H24···O1ⁱⁱ	0.95	2.42	3.314 (3)	157
N3—H3···N5ⁱⁱⁱ	0.87 (3)	2.03 (3)	2.893 (3)	170 (3)

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

1,1,3-trioxo-2,3-dihydro-1,2-benzothiazol-2-ide; N-[(2E)-10-(4-chlorophenyl)-3-[(4-chlorophenyl)amino] -2,10-dihydrophenazin-2-ylidene]propan-2-aminium (lb0587_CFZ-SACC_LAG_MeCN_dried) top

Crystal data top

C₃₄H₂₇Cl₂N₅O₃S	Z = 2
M_r = 656.56	F(000) = 680
Triclinic, P1	D_x = 1.378 Mg m⁻³
a = 8.2115 (7) Å	Cu Kα radiation, λ = 1.54184 Å
b = 13.5327 (12) Å	Cell parameters from 1561 reflections
c = 14.325 (3) Å	θ = 3.3–52.9°
α = 89.04 (1)°	µ = 2.82 mm⁻¹
β = 88.864 (10)°	T = 295 K
γ = 83.781 (7)°	Plate, metallic dark red
V = 1582.0 (3) Å³	0.54 × 0.29 × 0.05 mm

Data collection top

Xcalibur Ruby Gemini ultra diffractometer	3783 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance Ultra (Cu) X-ray Source	2265 reflections with I > 2σ(I)
Detector resolution: 10.3712 pixels mm^-1	R_int = 0.038
ω scans	θ_max = 54.2°, θ_min = 3.1°
Absorption correction: multi-scan CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −8→8
T_min = 0.549, T_max = 1.000	k = −14→14
7488 measured reflections	l = −15→15

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: dual
R[F² > 2σ(F²)] = 0.064	Hydrogen site location: mixed
wR(F²) = 0.190	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.0788P)² + 0.959P] where P = (F_o² + 2F_c²)/3
3783 reflections	(Δ/σ)_max = 0.001
525 parameters	Δρ_max = 0.23 e Å⁻³
483 restraints	Δρ_min = −0.22 e Å⁻³

Special details top

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cl1	−0.2923 (3)	0.96020 (11)	0.17761 (14)	0.1148 (8)
Cl2	0.2546 (2)	−0.16057 (13)	0.45445 (18)	0.1325 (9)
N1	−0.2004 (5)	0.5741 (3)	0.3774 (4)	0.0639 (13)
N2	−0.1568 (5)	0.4065 (3)	0.4940 (4)	0.0649 (13)
N4	0.1854 (7)	0.4043 (4)	0.1625 (4)	0.0743 (16)
H4	0.257 (10)	0.362 (6)	0.152 (6)	0.13 (3)*
C1	−0.3858 (7)	0.6581 (4)	0.4937 (5)	0.0743 (17)
H1	−0.399649	0.715725	0.457152	0.089*
C2	−0.4656 (7)	0.6538 (4)	0.5760 (5)	0.0742 (17)
H2	−0.535646	0.708528	0.595355	0.089*
C3	−0.4458 (7)	0.5683 (4)	0.6336 (5)	0.0749 (17)
H3A	−0.502537	0.566300	0.690306	0.090*
C4	−0.3418 (7)	0.4880 (4)	0.6050 (4)	0.0700 (16)
H4A	−0.326619	0.431816	0.643367	0.084*
C5	−0.2586 (7)	0.4892 (4)	0.5198 (4)	0.0630 (15)
C6	−0.0822 (6)	0.4082 (4)	0.4121 (5)	0.0616 (15)
C7	0.0247 (7)	0.3233 (4)	0.3854 (4)	0.0636 (16)
H7	0.036083	0.268255	0.425432	0.076*
C8	0.1104 (7)	0.3200 (4)	0.3038 (4)	0.0630 (15)
C9	0.0979 (7)	0.4073 (4)	0.2409 (5)	0.0645 (16)
C10	−0.0097 (7)	0.4908 (4)	0.2660 (4)	0.0680 (16)
H10	−0.021300	0.545838	0.226074	0.082*
C11	−0.0975 (7)	0.4926 (4)	0.3480 (4)	0.0620 (15)
C12	−0.2805 (6)	0.5752 (4)	0.4623 (4)	0.0634 (15)
C13	−0.2138 (7)	0.6643 (4)	0.3203 (4)	0.0679 (16)
C14	−0.1029 (8)	0.7307 (4)	0.3308 (5)	0.090 (2)
H14	−0.013321	0.715739	0.369216	0.108*
C15	−0.1255 (10)	0.8216 (4)	0.2830 (5)	0.095 (2)
H15	−0.049763	0.867416	0.288455	0.114*
C16	−0.2593 (9)	0.8430 (4)	0.2283 (5)	0.083 (2)
C17	−0.3643 (9)	0.7737 (5)	0.2140 (5)	0.096 (2)
H17	−0.450597	0.787317	0.173022	0.116*
C18	−0.3425 (8)	0.6837 (4)	0.2601 (5)	0.086 (2)
H18	−0.414054	0.636118	0.250860	0.104*
C19	0.2194 (7)	0.1435 (4)	0.3205 (4)	0.0728 (17)
C20	0.3726 (7)	0.0911 (4)	0.3348 (5)	0.084 (2)
H20	0.467485	0.118719	0.317006	0.101*
C21	0.3820 (8)	−0.0027 (5)	0.3759 (5)	0.100 (2)
H21	0.483761	−0.038350	0.385372	0.120*
C22	0.2419 (8)	−0.0433 (4)	0.4027 (5)	0.088 (2)
C23	0.0904 (7)	0.0086 (4)	0.3883 (5)	0.0800 (19)
H23	−0.004189	−0.018734	0.407378	0.096*
C24	0.0791 (7)	0.1007 (4)	0.3458 (4)	0.0772 (18)
H24	−0.023337	0.134556	0.334001	0.093*
C25	0.1866 (7)	0.4829 (5)	0.0912 (5)	0.0797 (18)
H25	0.073661	0.512890	0.082721	0.096*
C26	0.2483 (9)	0.4372 (5)	0.0003 (5)	0.108 (2)
H26A	0.180346	0.387223	−0.016709	0.162*
H26B	0.359055	0.407539	0.007267	0.162*
H26C	0.244878	0.487843	−0.047598	0.162*
C27	0.2894 (9)	0.5641 (5)	0.1210 (6)	0.113 (3)
H27A	0.401039	0.536275	0.128374	0.170*
H27B	0.247211	0.591198	0.179259	0.170*
H27C	0.284398	0.615841	0.074175	0.170*
N3	0.2125 (6)	0.2377 (3)	0.2749 (4)	0.0718 (14)
H3	0.316 (8)	0.249 (4)	0.233 (4)	0.10 (2)*
S1	0.6765 (18)	0.2865 (12)	0.1857 (14)	0.073 (3)	0.50 (4)
O1	0.732 (3)	0.2359 (18)	0.2713 (15)	0.102 (6)	0.50 (4)
O2	0.691 (3)	0.3920 (13)	0.179 (2)	0.094 (6)	0.50 (4)
O3	0.361 (2)	0.184 (3)	0.052 (3)	0.099 (6)	0.50 (4)
N5	0.492 (2)	0.263 (2)	0.1608 (19)	0.061 (4)	0.50 (4)
C28	0.487 (2)	0.210 (3)	0.085 (2)	0.069 (5)	0.50 (4)
C29	0.654 (3)	0.181 (2)	0.041 (2)	0.061 (4)	0.50 (4)
C30	0.697 (3)	0.123 (2)	−0.036 (2)	0.072 (5)	0.50 (4)
H30	0.619307	0.093209	−0.068231	0.086*	0.50 (4)
C31	0.861 (4)	0.111 (3)	−0.063 (2)	0.092 (7)	0.50 (4)
H31	0.894143	0.071508	−0.113450	0.110*	0.50 (4)
C32	0.976 (3)	0.158 (3)	−0.016 (2)	0.087 (7)	0.50 (4)
H32	1.084466	0.150460	−0.037673	0.104*	0.50 (4)
C33	0.936 (2)	0.214 (3)	0.060 (2)	0.079 (6)	0.50 (4)
H33	1.014062	0.244590	0.092201	0.095*	0.50 (4)
C34	0.772 (2)	0.225 (2)	0.0885 (17)	0.064 (4)	0.50 (4)
S1A	0.6572 (19)	0.2720 (10)	0.1633 (12)	0.061 (3)	0.50 (4)
O1A	0.699 (3)	0.2341 (17)	0.2567 (13)	0.087 (5)	0.50 (4)
O2A	0.675 (3)	0.3774 (10)	0.1486 (19)	0.080 (5)	0.50 (4)
O3A	0.358 (2)	0.158 (3)	0.028 (2)	0.089 (5)	0.50 (4)
N5A	0.476 (2)	0.248 (2)	0.1365 (19)	0.063 (4)	0.50 (4)
C28A	0.480 (2)	0.186 (2)	0.064 (2)	0.061 (4)	0.50 (4)
C29A	0.650 (2)	0.157 (3)	0.024 (2)	0.062 (4)	0.50 (4)
C30A	0.702 (4)	0.094 (3)	−0.048 (2)	0.079 (6)	0.50 (4)
H30A	0.628825	0.061293	−0.081237	0.095*	0.50 (4)
C31A	0.868 (4)	0.081 (3)	−0.068 (2)	0.087 (6)	0.50 (4)
H31A	0.905520	0.040953	−0.118165	0.104*	0.50 (4)
C32A	0.980 (3)	0.125 (3)	−0.017 (2)	0.088 (6)	0.50 (4)
H32A	1.090549	0.115527	−0.034011	0.106*	0.50 (4)
C33A	0.932 (3)	0.183 (2)	0.058 (2)	0.076 (6)	0.50 (4)
H33A	1.007678	0.209755	0.095216	0.091*	0.50 (4)
C34A	0.764 (2)	0.200 (2)	0.0765 (16)	0.061 (4)	0.50 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1469 (16)	0.0543 (10)	0.1322 (16)	0.0285 (10)	0.0319 (13)	0.0227 (10)
Cl2	0.1178 (15)	0.0653 (11)	0.206 (2)	0.0156 (10)	0.0146 (15)	0.0463 (13)
N1	0.060 (3)	0.043 (3)	0.086 (4)	0.005 (2)	0.001 (3)	0.003 (2)
N2	0.063 (3)	0.044 (3)	0.086 (4)	0.003 (2)	0.002 (3)	0.002 (2)
N4	0.072 (3)	0.062 (3)	0.083 (4)	0.010 (3)	0.014 (3)	0.013 (3)
C1	0.071 (4)	0.051 (4)	0.099 (5)	0.006 (3)	0.001 (4)	−0.004 (3)
C2	0.065 (4)	0.055 (4)	0.100 (5)	0.007 (3)	0.000 (4)	−0.009 (4)
C3	0.065 (4)	0.062 (4)	0.096 (5)	−0.003 (3)	0.010 (3)	−0.012 (4)
C4	0.073 (4)	0.052 (3)	0.083 (5)	−0.001 (3)	0.002 (4)	0.004 (3)
C5	0.063 (3)	0.046 (3)	0.080 (4)	−0.003 (3)	0.000 (3)	−0.005 (3)
C6	0.057 (3)	0.045 (3)	0.082 (4)	−0.001 (3)	−0.003 (3)	0.002 (3)
C7	0.066 (3)	0.038 (3)	0.085 (5)	0.001 (3)	0.003 (3)	0.007 (3)
C8	0.060 (3)	0.040 (3)	0.087 (5)	0.000 (3)	−0.004 (3)	0.002 (3)
C9	0.059 (3)	0.044 (3)	0.090 (5)	−0.001 (3)	−0.003 (3)	0.002 (3)
C10	0.070 (4)	0.048 (3)	0.083 (5)	0.004 (3)	−0.001 (4)	0.010 (3)
C11	0.060 (3)	0.040 (3)	0.085 (4)	0.003 (3)	−0.007 (3)	0.004 (3)
C12	0.059 (3)	0.045 (3)	0.086 (5)	−0.002 (3)	−0.002 (3)	−0.002 (3)
C13	0.071 (4)	0.039 (3)	0.091 (5)	0.007 (3)	−0.002 (4)	0.002 (3)
C14	0.095 (5)	0.061 (4)	0.116 (6)	−0.009 (4)	−0.017 (4)	0.007 (4)
C15	0.124 (6)	0.045 (4)	0.117 (6)	−0.013 (4)	0.003 (5)	0.003 (4)
C16	0.093 (5)	0.049 (4)	0.099 (5)	0.018 (4)	0.015 (4)	0.014 (4)
C17	0.086 (5)	0.076 (5)	0.122 (6)	0.008 (4)	−0.015 (4)	0.025 (4)
C18	0.083 (4)	0.058 (4)	0.117 (6)	−0.006 (3)	−0.018 (4)	0.011 (4)
C19	0.069 (4)	0.045 (3)	0.101 (5)	0.009 (3)	0.007 (4)	0.003 (3)
C20	0.071 (4)	0.056 (4)	0.121 (6)	0.010 (3)	0.008 (4)	0.004 (4)
C21	0.074 (4)	0.063 (4)	0.156 (7)	0.017 (3)	0.007 (4)	0.020 (4)
C22	0.084 (5)	0.040 (3)	0.136 (6)	0.005 (3)	0.009 (4)	0.012 (4)
C23	0.074 (4)	0.049 (4)	0.114 (5)	0.002 (3)	0.006 (4)	0.003 (4)
C24	0.065 (4)	0.048 (4)	0.116 (5)	0.008 (3)	0.000 (4)	−0.001 (3)
C25	0.071 (4)	0.077 (4)	0.087 (5)	0.003 (3)	0.009 (4)	0.017 (4)
C26	0.105 (5)	0.106 (6)	0.104 (6)	0.018 (4)	0.024 (5)	0.019 (5)
C27	0.117 (6)	0.084 (5)	0.138 (7)	−0.019 (4)	0.002 (5)	0.020 (5)
N3	0.067 (3)	0.047 (3)	0.098 (4)	0.007 (2)	0.012 (3)	0.006 (3)
S1	0.060 (4)	0.074 (5)	0.086 (6)	−0.008 (3)	0.001 (3)	−0.033 (4)
O1	0.088 (10)	0.117 (11)	0.093 (8)	0.037 (9)	−0.031 (7)	−0.026 (8)
O2	0.112 (9)	0.068 (7)	0.107 (14)	−0.031 (7)	0.013 (9)	−0.050 (7)
O3	0.073 (6)	0.095 (16)	0.132 (17)	−0.010 (8)	−0.022 (9)	−0.063 (9)
N5	0.055 (6)	0.058 (9)	0.071 (11)	−0.004 (5)	−0.010 (6)	−0.028 (7)
C28	0.062 (6)	0.058 (16)	0.089 (14)	−0.004 (8)	−0.007 (7)	−0.029 (9)
C29	0.073 (6)	0.031 (12)	0.078 (11)	0.007 (7)	−0.002 (7)	−0.011 (6)
C30	0.075 (7)	0.038 (14)	0.098 (11)	0.017 (8)	−0.014 (8)	−0.021 (8)
C31	0.089 (9)	0.057 (17)	0.126 (11)	0.015 (10)	0.015 (8)	−0.033 (10)
C32	0.065 (8)	0.070 (18)	0.123 (11)	0.009 (9)	0.019 (7)	−0.015 (12)
C33	0.064 (6)	0.051 (16)	0.121 (10)	0.000 (7)	0.014 (7)	−0.018 (10)
C34	0.065 (6)	0.041 (11)	0.087 (8)	−0.011 (7)	0.014 (6)	−0.014 (7)
S1A	0.074 (4)	0.043 (4)	0.067 (5)	−0.007 (3)	−0.008 (3)	−0.011 (3)
O1A	0.090 (11)	0.110 (10)	0.060 (8)	−0.013 (8)	−0.007 (7)	0.026 (8)
O2A	0.117 (9)	0.024 (7)	0.101 (14)	−0.014 (5)	−0.002 (9)	−0.022 (6)
O3A	0.070 (6)	0.090 (15)	0.111 (14)	−0.014 (7)	0.001 (7)	−0.059 (8)
N5A	0.070 (6)	0.053 (10)	0.066 (12)	−0.003 (6)	−0.003 (6)	−0.025 (7)
C28A	0.065 (6)	0.036 (11)	0.082 (12)	−0.001 (7)	−0.005 (7)	−0.022 (7)
C29A	0.070 (6)	0.039 (14)	0.076 (11)	0.005 (7)	0.006 (7)	−0.015 (7)
C30A	0.093 (7)	0.046 (16)	0.096 (10)	0.006 (9)	0.005 (8)	−0.028 (8)
C31A	0.095 (8)	0.057 (16)	0.100 (10)	0.026 (10)	0.019 (7)	−0.020 (9)
C32A	0.081 (8)	0.059 (16)	0.119 (11)	0.018 (9)	0.013 (8)	−0.008 (10)
C33A	0.071 (6)	0.049 (15)	0.109 (10)	−0.012 (8)	0.010 (7)	−0.005 (9)
C34A	0.067 (6)	0.031 (10)	0.083 (9)	0.003 (7)	0.003 (7)	−0.010 (6)

Geometric parameters (Å, º) top

Cl1—C16	1.730 (6)	C23—C24	1.373 (7)
Cl2—C22	1.733 (6)	C23—H23	0.9300
N1—C12	1.371 (7)	C24—H24	0.9300
N1—C11	1.381 (6)	C25—C26	1.506 (8)
N1—C13	1.453 (7)	C25—C27	1.528 (9)
N2—C6	1.313 (7)	C25—H25	0.9800
N2—C5	1.374 (6)	C26—H26A	0.9600
N4—C9	1.320 (7)	C26—H26B	0.9600
N4—C25	1.462 (7)	C26—H26C	0.9600
N4—H4	0.79 (7)	C27—H27A	0.9600
C1—C2	1.341 (8)	C27—H27B	0.9600
C1—C12	1.414 (7)	C27—H27C	0.9600
C1—H1	0.9300	N3—H3	1.05 (7)
C2—C3	1.407 (8)	S1—O2	1.446 (11)
C2—H2	0.9300	S1—O1	1.451 (11)
C3—C4	1.370 (7)	S1—N5	1.629 (11)
C3—H3A	0.9300	S1—C34	1.759 (11)
C4—C5	1.387 (8)	O3—C28	1.232 (13)
C4—H4A	0.9300	N5—C28	1.321 (14)
C5—C12	1.412 (7)	C28—C29	1.515 (14)
C6—C7	1.420 (7)	C29—C30	1.378 (13)
C6—C11	1.451 (7)	C29—C34	1.387 (13)
C7—C8	1.352 (7)	C30—C31	1.386 (14)
C7—H7	0.9300	C30—H30	0.9300
C8—N3	1.383 (6)	C31—C32	1.379 (15)
C8—C9	1.469 (7)	C31—H31	0.9300
C9—C10	1.404 (7)	C32—C33	1.363 (14)
C10—C11	1.364 (7)	C32—H32	0.9300
C10—H10	0.9300	C33—C34	1.388 (13)
C13—C14	1.359 (8)	C33—H33	0.9300
C13—C18	1.377 (8)	S1A—O1A	1.459 (11)
C14—C15	1.394 (8)	S1A—O2A	1.460 (10)
C14—H14	0.9300	S1A—N5A	1.617 (11)
C15—C16	1.365 (9)	S1A—C34A	1.752 (11)
C15—H15	0.9300	O3A—C28A	1.234 (13)
C16—C17	1.362 (9)	N5A—C28A	1.342 (13)
C17—C18	1.373 (8)	C28A—C29A	1.512 (13)
C17—H17	0.9300	C29A—C30A	1.383 (13)
C18—H18	0.9300	C29A—C34A	1.395 (13)
C19—C24	1.384 (8)	C30A—C31A	1.378 (14)
C19—C20	1.392 (8)	C30A—H30A	0.9300
C19—N3	1.420 (7)	C31A—C32A	1.380 (15)
C20—C21	1.385 (8)	C31A—H31A	0.9300
C20—H20	0.9300	C32A—C33A	1.371 (14)
C21—C22	1.373 (9)	C32A—H32A	0.9300
C21—H21	0.9300	C33A—C34A	1.395 (13)
C22—C23	1.379 (8)	C33A—H33A	0.9300

C12—N1—C11	121.9 (5)	C19—C24—H24	119.9
C12—N1—C13	118.8 (4)	N4—C25—C26	108.9 (5)
C11—N1—C13	119.1 (5)	N4—C25—C27	111.3 (6)
C6—N2—C5	118.0 (5)	C26—C25—C27	111.7 (6)
C9—N4—C25	127.0 (5)	N4—C25—H25	108.3
C9—N4—H4	122 (6)	C26—C25—H25	108.3
C25—N4—H4	110 (6)	C27—C25—H25	108.3
C2—C1—C12	120.2 (6)	C25—C26—H26A	109.5
C2—C1—H1	119.9	C25—C26—H26B	109.5
C12—C1—H1	119.9	H26A—C26—H26B	109.5
C1—C2—C3	121.4 (5)	C25—C26—H26C	109.5
C1—C2—H2	119.3	H26A—C26—H26C	109.5
C3—C2—H2	119.3	H26B—C26—H26C	109.5
C4—C3—C2	119.1 (6)	C25—C27—H27A	109.5
C4—C3—H3A	120.5	C25—C27—H27B	109.5
C2—C3—H3A	120.5	H27A—C27—H27B	109.5
C3—C4—C5	121.2 (6)	C25—C27—H27C	109.5
C3—C4—H4A	119.4	H27A—C27—H27C	109.5
C5—C4—H4A	119.4	H27B—C27—H27C	109.5
N2—C5—C4	118.9 (5)	C8—N3—C19	123.4 (5)
N2—C5—C12	121.9 (5)	C8—N3—H3	118 (3)
C4—C5—C12	119.2 (5)	C19—N3—H3	115 (3)
N2—C6—C7	118.3 (5)	O2—S1—O1	117.1 (12)
N2—C6—C11	124.2 (5)	O2—S1—N5	110.7 (11)
C7—C6—C11	117.5 (6)	O1—S1—N5	111.2 (11)
C8—C7—C6	122.1 (5)	O2—S1—C34	110.2 (10)
C8—C7—H7	118.9	O1—S1—C34	110.1 (11)
C6—C7—H7	118.9	N5—S1—C34	95.5 (7)
C7—C8—N3	123.5 (5)	C28—N5—S1	113.0 (10)
C7—C8—C9	119.8 (5)	O3—C28—N5	124.8 (14)
N3—C8—C9	116.7 (6)	O3—C28—C29	121.9 (15)
N4—C9—C10	122.2 (5)	N5—C28—C29	113.3 (11)
N4—C9—C8	119.4 (5)	C30—C29—C34	120.6 (11)
C10—C9—C8	118.4 (6)	C30—C29—C28	129.6 (13)
C11—C10—C9	121.3 (5)	C34—C29—C28	109.8 (10)
C11—C10—H10	119.4	C29—C30—C31	117.4 (13)
C9—C10—H10	119.4	C29—C30—H30	121.3
C10—C11—N1	123.5 (5)	C31—C30—H30	121.3
C10—C11—C6	120.9 (5)	C32—C31—C30	121.3 (14)
N1—C11—C6	115.6 (5)	C32—C31—H31	119.3
N1—C12—C5	118.4 (5)	C30—C31—H31	119.3
N1—C12—C1	122.7 (5)	C33—C32—C31	121.8 (14)
C5—C12—C1	118.9 (6)	C33—C32—H32	119.1
C14—C13—C18	121.0 (5)	C31—C32—H32	119.1
C14—C13—N1	119.0 (5)	C32—C33—C34	117.1 (14)
C18—C13—N1	119.9 (5)	C32—C33—H33	121.4
C13—C14—C15	119.0 (6)	C34—C33—H33	121.4
C13—C14—H14	120.5	C29—C34—C33	121.7 (12)
C15—C14—H14	120.5	C29—C34—S1	108.2 (9)
C16—C15—C14	119.7 (7)	C33—C34—S1	130.0 (12)
C16—C15—H15	120.1	O1A—S1A—O2A	114.5 (11)
C14—C15—H15	120.1	O1A—S1A—N5A	110.7 (10)
C17—C16—C15	120.7 (6)	O2A—S1A—N5A	110.9 (10)
C17—C16—Cl1	120.8 (6)	O1A—S1A—C34A	111.7 (11)
C15—C16—Cl1	118.5 (6)	O2A—S1A—C34A	110.8 (9)
C16—C17—C18	119.8 (7)	N5A—S1A—C34A	96.8 (7)
C16—C17—H17	120.1	C28A—N5A—S1A	111.7 (10)
C18—C17—H17	120.1	O3A—C28A—N5A	124.7 (13)
C17—C18—C13	119.5 (6)	O3A—C28A—C29A	121.3 (13)
C17—C18—H18	120.2	N5A—C28A—C29A	113.8 (12)
C13—C18—H18	120.2	C30A—C29A—C34A	119.9 (12)
C24—C19—C20	119.8 (5)	C30A—C29A—C28A	130.5 (13)
C24—C19—N3	121.8 (5)	C34A—C29A—C28A	109.5 (11)
C20—C19—N3	118.3 (6)	C31A—C30A—C29A	117.6 (14)
C21—C20—C19	119.3 (6)	C31A—C30A—H30A	121.2
C21—C20—H20	120.4	C29A—C30A—H30A	121.2
C19—C20—H20	120.4	C30A—C31A—C32A	122.1 (14)
C22—C21—C20	120.4 (6)	C30A—C31A—H31A	119.0
C22—C21—H21	119.8	C32A—C31A—H31A	119.0
C20—C21—H21	119.8	C33A—C32A—C31A	121.4 (14)
C21—C22—C23	120.2 (5)	C33A—C32A—H32A	119.3
C21—C22—Cl2	120.2 (5)	C31A—C32A—H32A	119.3
C23—C22—Cl2	119.6 (5)	C32A—C33A—C34A	116.7 (14)
C24—C23—C22	120.0 (6)	C32A—C33A—H33A	121.6
C24—C23—H23	120.0	C34A—C33A—H33A	121.6
C22—C23—H23	120.0	C29A—C34A—C33A	122.1 (12)
C23—C24—C19	120.3 (5)	C29A—C34A—S1A	108.1 (9)
C23—C24—H24	119.9	C33A—C34A—S1A	129.8 (12)

C12—C1—C2—C3	0.9 (9)	C22—C23—C24—C19	−2.5 (10)
C1—C2—C3—C4	0.4 (9)	C20—C19—C24—C23	2.6 (10)
C2—C3—C4—C5	−1.2 (9)	N3—C19—C24—C23	178.8 (6)
C6—N2—C5—C4	178.4 (5)	C9—N4—C25—C26	−158.4 (6)
C6—N2—C5—C12	−1.8 (8)	C9—N4—C25—C27	78.1 (8)
C3—C4—C5—N2	−179.4 (5)	C7—C8—N3—C19	9.9 (9)
C3—C4—C5—C12	0.8 (8)	C9—C8—N3—C19	−170.4 (5)
C5—N2—C6—C7	179.3 (5)	C24—C19—N3—C8	46.8 (9)
C5—N2—C6—C11	1.4 (8)	C20—C19—N3—C8	−137.0 (6)
N2—C6—C7—C8	−177.8 (5)	O2—S1—N5—C28	115 (2)
C11—C6—C7—C8	0.2 (8)	O1—S1—N5—C28	−113 (3)
C6—C7—C8—N3	−178.5 (5)	C34—S1—N5—C28	1 (3)
C6—C7—C8—C9	1.8 (8)	S1—N5—C28—O3	−179 (3)
C25—N4—C9—C10	0.0 (10)	S1—N5—C28—C29	2 (4)
C25—N4—C9—C8	178.9 (6)	O3—C28—C29—C30	−1 (5)
C7—C8—C9—N4	178.2 (6)	N5—C28—C29—C30	177 (4)
N3—C8—C9—N4	−1.5 (8)	O3—C28—C29—C34	176 (4)
C7—C8—C9—C10	−2.8 (8)	N5—C28—C29—C34	−5 (4)
N3—C8—C9—C10	177.4 (5)	C34—C29—C30—C31	0 (4)
N4—C9—C10—C11	−179.2 (6)	C28—C29—C30—C31	177 (3)
C8—C9—C10—C11	1.9 (8)	C29—C30—C31—C32	−2 (4)
C9—C10—C11—N1	177.6 (5)	C30—C31—C32—C33	2 (4)
C9—C10—C11—C6	0.1 (9)	C31—C32—C33—C34	−1 (4)
C12—N1—C11—C10	−176.7 (5)	C30—C29—C34—C33	1 (4)
C13—N1—C11—C10	−1.8 (8)	C28—C29—C34—C33	−177 (3)
C12—N1—C11—C6	0.9 (7)	C30—C29—C34—S1	−177 (3)
C13—N1—C11—C6	175.8 (5)	C28—C29—C34—S1	6 (3)
N2—C6—C11—C10	176.7 (5)	C32—C33—C34—C29	0 (4)
C7—C6—C11—C10	−1.2 (8)	C32—C33—C34—S1	177 (2)
N2—C6—C11—N1	−1.0 (8)	O2—S1—C34—C29	−119 (2)
C7—C6—C11—N1	−178.9 (5)	O1—S1—C34—C29	111 (2)
C11—N1—C12—C5	−1.3 (8)	N5—S1—C34—C29	−4 (2)
C13—N1—C12—C5	−176.2 (5)	O2—S1—C34—C33	64 (3)
C11—N1—C12—C1	179.8 (5)	O1—S1—C34—C33	−66 (3)
C13—N1—C12—C1	4.9 (8)	N5—S1—C34—C33	179 (3)
N2—C5—C12—N1	1.7 (8)	O1A—S1A—N5A—C28A	−116 (2)
C4—C5—C12—N1	−178.5 (5)	O2A—S1A—N5A—C28A	116 (2)
N2—C5—C12—C1	−179.3 (5)	C34A—S1A—N5A—C28A	0 (2)
C4—C5—C12—C1	0.5 (8)	S1A—N5A—C28A—O3A	−178 (3)
C2—C1—C12—N1	177.6 (6)	S1A—N5A—C28A—C29A	−2 (3)
C2—C1—C12—C5	−1.3 (8)	O3A—C28A—C29A—C30A	−5 (5)
C12—N1—C13—C14	89.7 (7)	N5A—C28A—C29A—C30A	178 (4)
C11—N1—C13—C14	−85.3 (7)	O3A—C28A—C29A—C34A	179 (3)
C12—N1—C13—C18	−87.0 (7)	N5A—C28A—C29A—C34A	2 (4)
C11—N1—C13—C18	98.0 (6)	C34A—C29A—C30A—C31A	−4 (4)
C18—C13—C14—C15	3.2 (10)	C28A—C29A—C30A—C31A	−179 (3)
N1—C13—C14—C15	−173.5 (6)	C29A—C30A—C31A—C32A	3 (4)
C13—C14—C15—C16	1.2 (10)	C30A—C31A—C32A—C33A	1 (4)
C14—C15—C16—C17	−5.1 (11)	C31A—C32A—C33A—C34A	−4 (4)
C14—C15—C16—Cl1	174.9 (5)	C30A—C29A—C34A—C33A	1 (4)
C15—C16—C17—C18	4.6 (11)	C28A—C29A—C34A—C33A	177 (3)
Cl1—C16—C17—C18	−175.3 (5)	C30A—C29A—C34A—S1A	−178 (3)
C16—C17—C18—C13	−0.3 (10)	C28A—C29A—C34A—S1A	−2 (3)
C14—C13—C18—C17	−3.7 (10)	C32A—C33A—C34A—C29A	3 (4)
N1—C13—C18—C17	173.0 (6)	C32A—C33A—C34A—S1A	−178 (2)
C24—C19—C20—C21	−1.2 (10)	O1A—S1A—C34A—C29A	116 (2)
N3—C19—C20—C21	−177.5 (6)	O2A—S1A—C34A—C29A	−115 (2)
C19—C20—C21—C22	−0.4 (11)	N5A—S1A—C34A—C29A	1 (2)
C20—C21—C22—C23	0.5 (12)	O1A—S1A—C34A—C33A	−62 (3)
C20—C21—C22—Cl2	−179.8 (6)	O2A—S1A—C34A—C33A	67 (3)
C21—C22—C23—C24	0.9 (11)	N5A—S1A—C34A—C33A	−178 (3)
Cl2—C22—C23—C24	−178.8 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···N5	0.79 (7)	2.22 (8)	2.99 (2)	163 (8)
N4—H4···N5A	0.79 (7)	2.25 (8)	3.04 (2)	174 (8)
C24—H24···O1ⁱ	0.93	2.48	3.40 (2)	168
C26—H26C···O2ⁱⁱ	0.96	2.55	3.49 (2)	166
C26—H26C···O2Aⁱⁱ	0.96	2.45	3.370 (18)	161
N3—H3···N5	1.05 (7)	1.78 (7)	2.84 (2)	178 (5)
N3—H3···N5A	1.05 (7)	1.88 (7)	2.92 (2)	165 (5)

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

N-[10-(4-chlorophenyl)-3-[(4-chlorophenyl)amino] -2,10-dihydrophenazin-2-ylidene]propan-2-aminium methanol 2,4-dihydroxybenzoate (lb0214_CLZ-24DHBA) top

Crystal data top

C₂₇H₂₃Cl₂N₄⁺·C₇H₅O₄⁻·CH₄O	Z = 2
M_r = 659.54	F(000) = 688
Triclinic, P1	D_x = 1.358 Mg m⁻³
a = 9.4861 (4) Å	Cu Kα radiation, λ = 1.54184 Å
b = 12.5322 (5) Å	Cell parameters from 8225 reflections
c = 15.3641 (5) Å	θ = 3.0–67.0°
α = 98.415 (3)°	µ = 2.22 mm⁻¹
β = 103.379 (3)°	T = 295 K
γ = 110.450 (4)°	Plate, metallic dark red
V = 1612.41 (12) Å³	0.49 × 0.12 × 0.06 mm

Data collection top

Xcalibur Ruby Gemini ultra diffractometer	5692 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance Ultra (Cu) X-ray Source	4965 reflections with I > 2σ(I)
Detector resolution: 10.3712 pixels mm^-1	R_int = 0.021
ω scans	θ_max = 67.0°, θ_min = 3.1°
Absorption correction: gaussian CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −10→11
T_min = 0.539, T_max = 0.991	k = −14→13
15458 measured reflections	l = −18→18

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: dual
R[F² > 2σ(F²)] = 0.037	Hydrogen site location: mixed
wR(F²) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.064P)² + 0.2274P] where P = (F_o² + 2F_c²)/3
5692 reflections	(Δ/σ)_max = 0.002
555 parameters	Δρ_max = 0.24 e Å⁻³
66 restraints	Δρ_min = −0.32 e Å⁻³

Special details top

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cl1	0.92778 (7)	0.64690 (5)	1.08028 (3)	0.08218 (18)
Cl2	0.42975 (7)	0.25241 (5)	−0.01186 (3)	0.08626 (19)
N1	0.80881 (14)	0.52714 (10)	0.37170 (8)	0.0405 (3)
N2	1.00055 (14)	0.65504 (10)	0.55080 (8)	0.0445 (3)
N4	0.43568 (14)	0.29295 (10)	0.50511 (9)	0.0459 (3)
N3	0.62938 (16)	0.42285 (11)	0.68051 (8)	0.0489 (3)
C6	0.86292 (16)	0.56847 (11)	0.53666 (9)	0.0399 (3)
C11	0.75643 (16)	0.50049 (11)	0.44487 (9)	0.0387 (3)
C9	0.56945 (16)	0.38265 (11)	0.51290 (9)	0.0407 (3)
C8	0.67605 (16)	0.45195 (11)	0.60654 (9)	0.0408 (3)
C13	0.71374 (16)	0.45841 (12)	0.27813 (9)	0.0422 (3)
C7	0.81622 (17)	0.53962 (12)	0.61393 (9)	0.0429 (3)
H7	0.884238	0.582415	0.672638	0.052*
C12	0.95332 (16)	0.61812 (12)	0.38469 (9)	0.0408 (3)
C14	0.64032 (17)	0.50957 (13)	0.21917 (10)	0.0469 (3)
H14	0.648524	0.585737	0.239635	0.056*
C19	0.71067 (17)	0.48042 (13)	0.77468 (10)	0.0458 (3)
C5	1.04507 (17)	0.68274 (12)	0.47617 (10)	0.0428 (3)
C10	0.61242 (16)	0.41237 (12)	0.43546 (9)	0.0422 (3)
H10	0.542748	0.372060	0.376658	0.051*
C1	1.01126 (18)	0.64547 (14)	0.31100 (10)	0.0484 (3)
H1	0.953983	0.600969	0.250864	0.058*
C24	0.78060 (19)	0.60214 (13)	0.80789 (10)	0.0509 (4)
H24	0.781350	0.649648	0.766675	0.061*
C18	0.7033 (2)	0.34564 (14)	0.24968 (11)	0.0524 (4)
H18	0.754710	0.313048	0.290148	0.063*
C20	0.7081 (2)	0.41092 (14)	0.83753 (11)	0.0530 (4)
H20	0.660565	0.329458	0.816225	0.064*
C15	0.55427 (18)	0.44575 (15)	0.12910 (11)	0.0537 (4)
H15	0.505144	0.479035	0.088101	0.064*
C4	1.18961 (18)	0.77851 (14)	0.49095 (11)	0.0521 (4)
H4	1.249615	0.823192	0.550681	0.063*
C2	1.15274 (19)	0.73815 (14)	0.32829 (11)	0.0528 (4)
H2	1.190395	0.756419	0.279274	0.063*
C16	0.54218 (19)	0.33319 (15)	0.10096 (11)	0.0558 (4)
C3	1.24169 (19)	0.80584 (14)	0.41809 (12)	0.0552 (4)
H3	1.336321	0.869475	0.428220	0.066*
C25	0.32132 (18)	0.20930 (13)	0.41840 (11)	0.0510 (3)
H25	0.292871	0.253720	0.374869	0.061*
C21	0.7753 (2)	0.46162 (16)	0.93132 (11)	0.0591 (4)
H21	0.773179	0.414730	0.973056	0.071*
C22	0.8452 (2)	0.58181 (16)	0.96217 (10)	0.0559 (4)
C17	0.6151 (2)	0.28162 (15)	0.16008 (11)	0.0597 (4)
H17	0.604941	0.204881	0.139826	0.072*
C23	0.8489 (2)	0.65304 (14)	0.90151 (11)	0.0556 (4)
H23	0.896850	0.734418	0.923422	0.067*
C27	0.1743 (2)	0.13729 (16)	0.44088 (14)	0.0672 (5)
H27A	0.198898	0.088269	0.479234	0.101*
H27B	0.092802	0.088933	0.384642	0.101*
H27C	0.138323	0.189207	0.472965	0.101*
C26	0.3899 (2)	0.13041 (16)	0.37480 (15)	0.0704 (5)
H26A	0.480622	0.177625	0.359681	0.106*
H26B	0.311824	0.075790	0.319589	0.106*
H26C	0.420588	0.087949	0.417556	0.106*
C28A	0.3578 (11)	0.1478 (10)	0.6875 (7)	0.070 (4)	0.632 (6)
O1A	0.3539 (18)	0.2399 (9)	0.6657 (7)	0.067 (2)	0.632 (6)
O2A	0.4533 (14)	0.1034 (10)	0.6683 (10)	0.085 (2)	0.632 (6)
C34A	0.1363 (13)	0.1257 (8)	0.7532 (8)	0.048 (2)	0.632 (6)
H34A	0.135193	0.193619	0.736008	0.057*	0.632 (6)
C29A	0.2461 (14)	0.0839 (9)	0.7342 (10)	0.043 (3)	0.632 (6)
C30A	0.2368 (17)	−0.0234 (9)	0.7544 (11)	0.053 (2)	0.632 (6)
O3A	0.3403 (13)	−0.0703 (9)	0.7363 (8)	0.0704 (15)	0.632 (6)
H3OA	0.410 (5)	−0.019 (3)	0.704 (5)	0.106*	0.632 (6)
C33A	0.0282 (11)	0.0715 (7)	0.7964 (6)	0.0518 (16)	0.632 (6)
H33A	−0.037936	0.105349	0.812741	0.062*	0.632 (6)
C31A	0.1240 (11)	−0.0823 (8)	0.7933 (8)	0.062 (2)	0.632 (6)
H31A	0.117285	−0.154325	0.805059	0.074*	0.632 (6)
C32A	0.0217 (14)	−0.0348 (8)	0.8147 (8)	0.0604 (18)	0.632 (6)
O4A	−0.0945 (9)	−0.1010 (8)	0.8473 (6)	0.0910 (18)	0.632 (6)
H4OA	−0.136155	−0.059926	0.867831	0.098 (15)*	0.632 (6)
C35A	0.302 (2)	0.9240 (15)	0.0614 (13)	0.187 (7)	0.632 (6)
H35A	0.225923	0.847255	0.056713	0.224*	0.632 (6)
H35B	0.403930	0.921390	0.068755	0.224*	0.632 (6)
H35C	0.271236	0.948527	0.006253	0.224*	0.632 (6)
O5A	0.3087 (4)	1.0002 (3)	0.1342 (3)	0.1140 (15)	0.632 (6)
H5OA	0.398751	1.029525	0.170189	0.171*	0.632 (6)
C28B	0.3707 (16)	0.1417 (11)	0.6888 (9)	0.048 (4)	0.368 (6)
O1B	0.364 (3)	0.2324 (14)	0.6664 (14)	0.071 (4)	0.368 (6)
O2B	0.474 (2)	0.1010 (16)	0.6845 (18)	0.096 (6)	0.368 (6)
C34B	0.154 (2)	0.1260 (13)	0.7577 (16)	0.065 (6)	0.368 (6)
H34B	0.158153	0.197994	0.746758	0.078*	0.368 (6)
C29B	0.256 (3)	0.0801 (18)	0.735 (2)	0.056 (6)	0.368 (6)
C30B	0.266 (3)	−0.0172 (18)	0.765 (2)	0.059 (5)	0.368 (6)
O3B	0.376 (2)	−0.0558 (19)	0.7494 (16)	0.094 (6)	0.368 (6)
H3OB	0.445 (12)	−0.001 (8)	0.719 (9)	0.141*	0.368 (6)
C33B	0.045 (3)	0.0648 (17)	0.7968 (16)	0.083 (6)	0.368 (6)
H33B	−0.034319	0.089174	0.804819	0.099*	0.368 (6)
C31B	0.165 (2)	−0.0732 (16)	0.8099 (15)	0.076 (5)	0.368 (6)
H31B	0.172229	−0.137879	0.830571	0.091*	0.368 (6)
C32B	0.054 (3)	−0.0329 (17)	0.8241 (17)	0.088 (7)	0.368 (6)
O4B	−0.0386 (18)	−0.0842 (15)	0.8755 (12)	0.117 (5)	0.368 (6)
H4OB	0.010197	−0.056396	0.930586	0.30 (11)*	0.368 (6)
C35B	0.291 (2)	0.9229 (19)	0.0590 (17)	0.123 (6)	0.368 (6)
H35D	0.248996	0.851786	0.010883	0.148*	0.368 (6)
H35E	0.312159	0.904921	0.118059	0.148*	0.368 (6)
H35F	0.387500	0.976280	0.052943	0.148*	0.368 (6)
O5B	0.1889 (11)	0.9714 (9)	0.0523 (6)	0.153 (4)	0.368 (6)
H5OB	0.218144	1.025765	0.098031	0.230*	0.368 (6)
H4N	0.417 (2)	0.2781 (15)	0.5548 (13)	0.051 (4)*
H3N	0.549 (3)	0.355 (2)	0.6725 (15)	0.074 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0994 (4)	0.1009 (4)	0.0376 (2)	0.0387 (3)	0.0120 (2)	0.0095 (2)
Cl2	0.0885 (4)	0.0909 (4)	0.0471 (2)	0.0230 (3)	−0.0042 (2)	−0.0049 (2)
N1	0.0442 (6)	0.0417 (6)	0.0360 (6)	0.0160 (5)	0.0130 (5)	0.0121 (5)
N2	0.0438 (6)	0.0457 (6)	0.0397 (6)	0.0126 (5)	0.0136 (5)	0.0102 (5)
N4	0.0466 (7)	0.0423 (6)	0.0434 (7)	0.0102 (5)	0.0153 (5)	0.0113 (5)
N3	0.0546 (7)	0.0456 (6)	0.0405 (6)	0.0095 (6)	0.0194 (5)	0.0118 (5)
C6	0.0424 (7)	0.0401 (7)	0.0374 (7)	0.0158 (6)	0.0131 (5)	0.0105 (5)
C11	0.0434 (7)	0.0396 (6)	0.0357 (7)	0.0179 (6)	0.0130 (5)	0.0120 (5)
C9	0.0431 (7)	0.0372 (6)	0.0418 (7)	0.0153 (6)	0.0139 (6)	0.0102 (5)
C8	0.0476 (7)	0.0401 (7)	0.0379 (7)	0.0179 (6)	0.0168 (6)	0.0123 (5)
C13	0.0437 (7)	0.0466 (7)	0.0353 (7)	0.0157 (6)	0.0134 (6)	0.0112 (6)
C7	0.0456 (7)	0.0442 (7)	0.0350 (7)	0.0138 (6)	0.0119 (6)	0.0090 (5)
C12	0.0427 (7)	0.0429 (7)	0.0423 (7)	0.0197 (6)	0.0154 (6)	0.0163 (6)
C14	0.0472 (8)	0.0498 (8)	0.0451 (8)	0.0200 (6)	0.0132 (6)	0.0150 (6)
C19	0.0512 (8)	0.0494 (8)	0.0391 (7)	0.0171 (6)	0.0209 (6)	0.0139 (6)
C5	0.0439 (7)	0.0443 (7)	0.0428 (7)	0.0177 (6)	0.0158 (6)	0.0141 (6)
C10	0.0438 (7)	0.0413 (7)	0.0366 (7)	0.0131 (6)	0.0101 (5)	0.0090 (5)
C1	0.0515 (8)	0.0587 (8)	0.0425 (7)	0.0249 (7)	0.0183 (6)	0.0212 (6)
C24	0.0619 (9)	0.0487 (8)	0.0413 (8)	0.0162 (7)	0.0210 (7)	0.0157 (6)
C18	0.0651 (9)	0.0506 (8)	0.0432 (8)	0.0266 (7)	0.0131 (7)	0.0132 (6)
C20	0.0669 (10)	0.0505 (8)	0.0489 (8)	0.0241 (7)	0.0259 (7)	0.0183 (7)
C15	0.0514 (8)	0.0649 (9)	0.0435 (8)	0.0233 (7)	0.0094 (6)	0.0181 (7)
C4	0.0468 (8)	0.0503 (8)	0.0520 (8)	0.0112 (6)	0.0149 (7)	0.0125 (7)
C2	0.0541 (8)	0.0616 (9)	0.0563 (9)	0.0253 (7)	0.0279 (7)	0.0302 (7)
C16	0.0530 (9)	0.0637 (9)	0.0395 (8)	0.0169 (7)	0.0082 (6)	0.0054 (7)
C3	0.0477 (8)	0.0536 (8)	0.0651 (10)	0.0139 (7)	0.0227 (7)	0.0239 (7)
C25	0.0458 (8)	0.0459 (8)	0.0516 (8)	0.0123 (6)	0.0091 (6)	0.0083 (6)
C21	0.0770 (11)	0.0691 (10)	0.0460 (8)	0.0362 (9)	0.0264 (8)	0.0270 (8)
C22	0.0610 (9)	0.0697 (10)	0.0379 (8)	0.0269 (8)	0.0159 (7)	0.0123 (7)
C17	0.0726 (11)	0.0513 (8)	0.0493 (9)	0.0239 (8)	0.0138 (8)	0.0053 (7)
C23	0.0620 (9)	0.0529 (8)	0.0454 (8)	0.0140 (7)	0.0200 (7)	0.0092 (7)
C27	0.0489 (9)	0.0612 (10)	0.0745 (12)	0.0075 (7)	0.0160 (8)	0.0076 (9)
C26	0.0597 (10)	0.0553 (9)	0.0778 (12)	0.0129 (8)	0.0173 (9)	−0.0062 (8)
C28A	0.056 (4)	0.068 (5)	0.071 (5)	0.018 (3)	0.014 (3)	−0.008 (3)
O1A	0.078 (4)	0.052 (3)	0.065 (4)	0.009 (3)	0.038 (3)	0.014 (2)
O2A	0.080 (4)	0.092 (4)	0.105 (3)	0.039 (3)	0.059 (4)	0.030 (2)
C34A	0.050 (3)	0.043 (4)	0.056 (4)	0.020 (3)	0.023 (2)	0.012 (3)
C29A	0.054 (5)	0.032 (4)	0.043 (4)	0.013 (4)	0.017 (4)	0.010 (3)
C30A	0.059 (5)	0.052 (3)	0.048 (3)	0.028 (3)	0.011 (4)	0.0072 (19)
O3A	0.078 (4)	0.068 (2)	0.084 (3)	0.047 (3)	0.029 (4)	0.023 (2)
C33A	0.062 (3)	0.038 (3)	0.062 (3)	0.017 (2)	0.034 (2)	0.018 (2)
C31A	0.078 (4)	0.047 (2)	0.069 (4)	0.025 (2)	0.024 (3)	0.031 (2)
C32A	0.072 (3)	0.053 (3)	0.066 (3)	0.023 (2)	0.036 (2)	0.022 (2)
O4A	0.101 (4)	0.076 (3)	0.122 (5)	0.030 (3)	0.071 (3)	0.054 (3)
C35A	0.147 (11)	0.181 (13)	0.154 (12)	0.019 (9)	0.027 (8)	−0.040 (9)
O5A	0.081 (2)	0.146 (3)	0.102 (3)	0.0398 (19)	0.0326 (18)	0.001 (2)
C28B	0.052 (6)	0.034 (5)	0.053 (6)	−0.001 (4)	0.035 (5)	0.017 (4)
O1B	0.079 (7)	0.043 (5)	0.097 (9)	0.013 (5)	0.044 (5)	0.034 (5)
O2B	0.061 (4)	0.072 (5)	0.159 (15)	0.019 (4)	0.053 (6)	0.031 (6)
C34B	0.076 (10)	0.032 (7)	0.071 (8)	0.002 (5)	0.019 (6)	0.024 (5)
C29B	0.039 (7)	0.062 (13)	0.055 (10)	0.009 (7)	0.014 (6)	0.005 (8)
C30B	0.057 (8)	0.058 (6)	0.056 (7)	0.017 (4)	0.008 (6)	0.024 (6)
O3B	0.076 (8)	0.102 (8)	0.109 (8)	0.048 (6)	0.015 (5)	0.028 (6)
C33B	0.077 (7)	0.082 (10)	0.102 (10)	0.037 (6)	0.048 (7)	0.010 (7)
C31B	0.105 (11)	0.079 (7)	0.068 (8)	0.053 (8)	0.035 (9)	0.038 (6)
C32B	0.122 (14)	0.067 (7)	0.095 (10)	0.026 (7)	0.068 (11)	0.052 (7)
O4B	0.149 (11)	0.102 (6)	0.129 (10)	0.034 (8)	0.098 (10)	0.065 (7)
C35B	0.092 (9)	0.153 (15)	0.130 (14)	0.041 (9)	0.061 (10)	0.029 (11)
O5B	0.172 (8)	0.206 (9)	0.147 (7)	0.111 (7)	0.093 (7)	0.075 (6)

Geometric parameters (Å, º) top

Cl1—C22	1.7419 (16)	C22—C23	1.380 (2)
Cl2—C16	1.7446 (16)	C17—H17	0.9300
N1—C11	1.3692 (17)	C23—H23	0.9300
N1—C12	1.3905 (18)	C27—H27A	0.9600
N1—C13	1.4549 (17)	C27—H27B	0.9600
N2—C6	1.3185 (18)	C27—H27C	0.9600
N2—C5	1.3607 (18)	C26—H26A	0.9600
N4—C9	1.3349 (18)	C26—H26B	0.9600
N4—C25	1.4759 (19)	C26—H26C	0.9600
N4—H4N	0.853 (19)	C28A—O1A	1.259 (8)
N3—C8	1.3645 (18)	C28A—O2A	1.282 (9)
N3—C19	1.4135 (19)	C28A—C29A	1.486 (8)
N3—H3N	0.89 (2)	C34A—C33A	1.384 (7)
C6—C7	1.4119 (19)	C34A—C29A	1.387 (8)
C6—C11	1.4569 (19)	C34A—H34A	0.9300
C11—C10	1.3836 (19)	C29A—C30A	1.401 (7)
C9—C10	1.4031 (19)	C30A—O3A	1.366 (7)
C9—C8	1.4812 (19)	C30A—C31A	1.385 (8)
C8—C7	1.364 (2)	O3A—H3OA	1.02 (4)
C13—C18	1.378 (2)	C33A—C32A	1.383 (7)
C13—C14	1.381 (2)	C33A—H33A	0.9300
C7—H7	0.9300	C31A—C32A	1.378 (8)
C12—C1	1.404 (2)	C31A—H31A	0.9300
C12—C5	1.413 (2)	C32A—O4A	1.377 (8)
C14—C15	1.385 (2)	O4A—H4OA	0.8200
C14—H14	0.9300	C35A—O5A	1.334 (13)
C19—C20	1.391 (2)	C35A—H35A	0.9600
C19—C24	1.391 (2)	C35A—H35B	0.9600
C5—C4	1.414 (2)	C35A—H35C	0.9600
C10—H10	0.9300	O5A—H5OA	0.8200
C1—C2	1.370 (2)	C28B—O1B	1.251 (12)
C1—H1	0.9300	C28B—O2B	1.264 (12)
C24—C23	1.381 (2)	C28B—C29B	1.483 (11)
C24—H24	0.9300	C34B—C33B	1.373 (13)
C18—C17	1.383 (2)	C34B—C29B	1.376 (12)
C18—H18	0.9300	C34B—H34B	0.9300
C20—C21	1.382 (2)	C29B—C30B	1.390 (12)
C20—H20	0.9300	C30B—O3B	1.343 (12)
C15—C16	1.369 (2)	C30B—C31B	1.366 (12)
C15—H15	0.9300	O3B—H3OB	1.02 (4)
C4—C3	1.365 (2)	C33B—C32B	1.375 (13)
C4—H4	0.9300	C33B—H33B	0.9300
C2—C3	1.398 (2)	C31B—C32B	1.363 (13)
C2—H2	0.9300	C31B—H31B	0.9300
C16—C17	1.384 (2)	C32B—O4B	1.374 (12)
C3—H3	0.9300	O4B—H4OB	0.8200
C25—C26	1.519 (2)	C35B—O5B	1.306 (15)
C25—C27	1.521 (2)	C35B—H35D	0.9600
C25—H25	0.9800	C35B—H35E	0.9600
C21—C22	1.371 (3)	C35B—H35F	0.9600
C21—H21	0.9300	O5B—H5OB	0.8200

C11—N1—C12	121.36 (11)	C21—C22—Cl1	119.77 (12)
C11—N1—C13	119.95 (11)	C23—C22—Cl1	118.90 (13)
C12—N1—C13	118.68 (11)	C18—C17—C16	119.16 (15)
C6—N2—C5	118.51 (12)	C18—C17—H17	120.4
C9—N4—C25	126.25 (13)	C16—C17—H17	120.4
C9—N4—H4N	117.7 (12)	C22—C23—C24	119.26 (15)
C25—N4—H4N	115.8 (12)	C22—C23—H23	120.4
C8—N3—C19	126.69 (13)	C24—C23—H23	120.4
C8—N3—H3N	119.7 (14)	C25—C27—H27A	109.5
C19—N3—H3N	112.9 (14)	C25—C27—H27B	109.5
N2—C6—C7	118.67 (12)	H27A—C27—H27B	109.5
N2—C6—C11	123.14 (12)	C25—C27—H27C	109.5
C7—C6—C11	118.19 (12)	H27A—C27—H27C	109.5
N1—C11—C10	123.55 (12)	H27B—C27—H27C	109.5
N1—C11—C6	116.59 (12)	C25—C26—H26A	109.5
C10—C11—C6	119.84 (12)	C25—C26—H26B	109.5
N4—C9—C10	122.11 (13)	H26A—C26—H26B	109.5
N4—C9—C8	118.62 (12)	C25—C26—H26C	109.5
C10—C9—C8	119.27 (12)	H26A—C26—H26C	109.5
C7—C8—N3	123.81 (13)	H26B—C26—H26C	109.5
C7—C8—C9	118.22 (12)	O1A—C28A—O2A	122.2 (10)
N3—C8—C9	117.96 (12)	O1A—C28A—C29A	120.3 (9)
C18—C13—C14	121.71 (13)	O2A—C28A—C29A	117.4 (8)
C18—C13—N1	119.37 (12)	C33A—C34A—C29A	123.3 (7)
C14—C13—N1	118.89 (12)	C33A—C34A—H34A	118.4
C8—C7—C6	123.11 (13)	C29A—C34A—H34A	118.4
C8—C7—H7	118.4	C34A—C29A—C30A	117.0 (6)
C6—C7—H7	118.4	C34A—C29A—C28A	119.7 (7)
N1—C12—C1	122.45 (13)	C30A—C29A—C28A	123.2 (7)
N1—C12—C5	117.86 (12)	O3A—C30A—C31A	119.5 (7)
C1—C12—C5	119.67 (13)	O3A—C30A—C29A	119.9 (7)
C13—C14—C15	119.00 (14)	C31A—C30A—C29A	120.5 (6)
C13—C14—H14	120.5	C30A—O3A—H3OA	109.5
C15—C14—H14	120.5	C32A—C33A—C34A	117.9 (8)
C20—C19—C24	118.84 (14)	C32A—C33A—H33A	121.0
C20—C19—N3	117.54 (13)	C34A—C33A—H33A	121.0
C24—C19—N3	123.38 (13)	C32A—C31A—C30A	120.4 (6)
N2—C5—C12	122.38 (12)	C32A—C31A—H31A	119.8
N2—C5—C4	118.69 (13)	C30A—C31A—H31A	119.8
C12—C5—C4	118.92 (13)	O4A—C32A—C31A	117.7 (7)
C11—C10—C9	121.27 (13)	O4A—C32A—C33A	121.5 (7)
C11—C10—H10	119.4	C31A—C32A—C33A	120.7 (7)
C9—C10—H10	119.4	C32A—O4A—H4OA	109.5
C2—C1—C12	119.53 (14)	O5A—C35A—H35A	109.5
C2—C1—H1	120.2	O5A—C35A—H35B	109.5
C12—C1—H1	120.2	H35A—C35A—H35B	109.5
C23—C24—C19	120.58 (14)	O5A—C35A—H35C	109.5
C23—C24—H24	119.7	H35A—C35A—H35C	109.5
C19—C24—H24	119.7	H35B—C35A—H35C	109.5
C13—C18—C17	119.05 (14)	C35A—O5A—H5OA	109.5
C13—C18—H18	120.5	O1B—C28B—O2B	127.0 (14)
C17—C18—H18	120.5	O1B—C28B—C29B	118.1 (13)
C21—C20—C19	120.71 (15)	O2B—C28B—C29B	114.5 (11)
C21—C20—H20	119.6	C33B—C34B—C29B	119.5 (12)
C19—C20—H20	119.6	C33B—C34B—H34B	120.3
C16—C15—C14	119.40 (14)	C29B—C34B—H34B	120.3
C16—C15—H15	120.3	C34B—C29B—C30B	119.5 (11)
C14—C15—H15	120.3	C34B—C29B—C28B	120.7 (11)
C3—C4—C5	120.43 (15)	C30B—C29B—C28B	119.3 (11)
C3—C4—H4	119.8	O3B—C30B—C31B	120.2 (14)
C5—C4—H4	119.8	O3B—C30B—C29B	119.4 (13)
C1—C2—C3	121.35 (14)	C31B—C30B—C29B	120.4 (12)
C1—C2—H2	119.3	C30B—O3B—H3OB	109.5
C3—C2—H2	119.3	C34B—C33B—C32B	119.3 (13)
C15—C16—C17	121.66 (14)	C34B—C33B—H33B	120.4
C15—C16—Cl2	119.02 (12)	C32B—C33B—H33B	120.4
C17—C16—Cl2	119.31 (13)	C32B—C31B—C30B	119.0 (13)
C4—C3—C2	119.99 (14)	C32B—C31B—H31B	120.5
C4—C3—H3	120.0	C30B—C31B—H31B	120.5
C2—C3—H3	120.0	C31B—C32B—O4B	118.5 (13)
N4—C25—C26	111.55 (13)	C31B—C32B—C33B	121.6 (12)
N4—C25—C27	107.63 (14)	O4B—C32B—C33B	119.6 (14)
C26—C25—C27	111.05 (14)	C32B—O4B—H4OB	109.5
N4—C25—H25	108.8	O5B—C35B—H35D	109.5
C26—C25—H25	108.8	O5B—C35B—H35E	109.5
C27—C25—H25	108.8	H35D—C35B—H35E	109.5
C22—C21—C20	119.29 (14)	O5B—C35B—H35F	109.5
C22—C21—H21	120.4	H35D—C35B—H35F	109.5
C20—C21—H21	120.4	H35E—C35B—H35F	109.5
C21—C22—C23	121.32 (15)	C35B—O5B—H5OB	109.5

C5—N2—C6—C7	−179.89 (12)	N2—C5—C4—C3	177.12 (14)
C5—N2—C6—C11	0.4 (2)	C12—C5—C4—C3	−1.9 (2)
C12—N1—C11—C10	178.75 (12)	C12—C1—C2—C3	0.5 (2)
C13—N1—C11—C10	−2.25 (19)	C14—C15—C16—C17	−0.6 (3)
C12—N1—C11—C6	−2.82 (18)	C14—C15—C16—Cl2	178.54 (12)
C13—N1—C11—C6	176.18 (11)	C5—C4—C3—C2	−0.7 (2)
N2—C6—C11—N1	2.78 (19)	C1—C2—C3—C4	1.4 (2)
C7—C6—C11—N1	−176.97 (12)	C9—N4—C25—C26	68.3 (2)
N2—C6—C11—C10	−178.73 (13)	C9—N4—C25—C27	−169.69 (14)
C7—C6—C11—C10	1.53 (19)	C19—C20—C21—C22	0.0 (3)
C25—N4—C9—C10	4.1 (2)	C20—C21—C22—C23	0.4 (3)
C25—N4—C9—C8	−175.31 (12)	C20—C21—C22—Cl1	179.05 (13)
C19—N3—C8—C7	3.7 (2)	C13—C18—C17—C16	1.1 (3)
C19—N3—C8—C9	−177.49 (13)	C15—C16—C17—C18	−0.4 (3)
N4—C9—C8—C7	176.72 (13)	Cl2—C16—C17—C18	−179.56 (14)
C10—C9—C8—C7	−2.73 (19)	C21—C22—C23—C24	0.1 (3)
N4—C9—C8—N3	−2.12 (19)	Cl1—C22—C23—C24	−178.59 (13)
C10—C9—C8—N3	178.43 (13)	C19—C24—C23—C22	−0.9 (2)
C11—N1—C13—C18	−72.77 (17)	C33A—C34A—C29A—C30A	5 (2)
C12—N1—C13—C18	106.25 (15)	C33A—C34A—C29A—C28A	180.0 (11)
C11—N1—C13—C14	109.26 (15)	O1A—C28A—C29A—C34A	0 (2)
C12—N1—C13—C14	−71.71 (17)	O2A—C28A—C29A—C34A	−177.5 (13)
N3—C8—C7—C6	179.85 (13)	O1A—C28A—C29A—C30A	175.4 (15)
C9—C8—C7—C6	1.1 (2)	O2A—C28A—C29A—C30A	−3 (2)
N2—C6—C7—C8	179.75 (13)	C34A—C29A—C30A—O3A	179.2 (13)
C11—C6—C7—C8	−0.5 (2)	C28A—C29A—C30A—O3A	4 (2)
C11—N1—C12—C1	178.53 (12)	C34A—C29A—C30A—C31A	−1 (2)
C13—N1—C12—C1	−0.48 (19)	C28A—C29A—C30A—C31A	−176.2 (13)
C11—N1—C12—C5	−0.05 (18)	C29A—C34A—C33A—C32A	−5.4 (18)
C13—N1—C12—C5	−179.06 (11)	O3A—C30A—C31A—C32A	178.0 (13)
C18—C13—C14—C15	−0.1 (2)	C29A—C30A—C31A—C32A	−2 (2)
N1—C13—C14—C15	177.78 (13)	C30A—C31A—C32A—O4A	175.7 (12)
C8—N3—C19—C20	−142.18 (15)	C30A—C31A—C32A—C33A	1 (2)
C8—N3—C19—C24	43.5 (2)	C34A—C33A—C32A—O4A	−172.2 (11)
C6—N2—C5—C12	−3.5 (2)	C34A—C33A—C32A—C31A	2.4 (18)
C6—N2—C5—C4	177.50 (13)	C33B—C34B—C29B—C30B	−10 (4)
N1—C12—C5—N2	3.4 (2)	C33B—C34B—C29B—C28B	177 (2)
C1—C12—C5—N2	−175.19 (13)	O1B—C28B—C29B—C34B	−4 (4)
N1—C12—C5—C4	−177.61 (12)	O2B—C28B—C29B—C34B	169 (2)
C1—C12—C5—C4	3.8 (2)	O1B—C28B—C29B—C30B	−177 (3)
N1—C11—C10—C9	175.10 (12)	O2B—C28B—C29B—C30B	−3 (4)
C6—C11—C10—C9	−3.3 (2)	C34B—C29B—C30B—O3B	−174 (3)
N4—C9—C10—C11	−175.55 (13)	C28B—C29B—C30B—O3B	−2 (4)
C8—C9—C10—C11	3.9 (2)	C34B—C29B—C30B—C31B	6 (5)
N1—C12—C1—C2	178.35 (13)	C28B—C29B—C30B—C31B	178 (2)
C5—C12—C1—C2	−3.1 (2)	C29B—C34B—C33B—C32B	9 (4)
C20—C19—C24—C23	1.2 (2)	O3B—C30B—C31B—C32B	−179 (3)
N3—C19—C24—C23	175.50 (15)	C29B—C30B—C31B—C32B	1 (4)
C14—C13—C18—C17	−0.9 (2)	C30B—C31B—C32B—O4B	−175 (2)
N1—C13—C18—C17	−178.79 (14)	C30B—C31B—C32B—C33B	−2 (4)
C24—C19—C20—C21	−0.8 (2)	C34B—C33B—C32B—C31B	−3 (4)
N3—C19—C20—C21	−175.36 (15)	C34B—C33B—C32B—O4B	170 (2)
C13—C14—C15—C16	0.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O1Aⁱ	0.93	2.45	3.346 (11)	161
C14—H14···O1Bⁱ	0.93	2.57	3.467 (19)	162
C23—H23···O4Aⁱⁱ	0.93	2.50	3.207 (8)	133
C23—H23···O4Bⁱⁱ	0.93	2.41	3.204 (16)	143
O3A—H3OA···O2A	1.02	1.66	2.556 (15)	145
O4A—H4OA···O5Aⁱⁱⁱ	0.82	2.02	2.786 (10)	155
O5A—H5OA···O3Aⁱ	0.82	2.39	3.192 (12)	167
O3B—H3OB···O2B	1.02	1.42	2.33 (3)	146
O4B—H4OB···O5B^iv	0.82	2.10	2.86 (2)	155
O5B—H5OB···O4Bⁱⁱⁱ	0.82	2.17	2.64 (2)	116
N4—H4N···O1A	0.853 (19)	2.00 (2)	2.852 (10)	174.9 (17)
N4—H4N···O1B	0.853 (19)	2.00 (3)	2.854 (18)	176.2 (18)
N3—H3N···O1A	0.89 (2)	1.88 (3)	2.743 (13)	164 (2)
N3—H3N···O1B	0.89 (2)	1.86 (3)	2.73 (2)	169 (2)

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

N-[(2E)-10-(4-chlorophenyl)-3-[(4-chlorophenyl)amino] -2,10-dihydrophenazin-2-ylidene]propan-2-aminium benzene-1,4-dicarboxylic acid benzene-1,4-dicarboxylate (lb0221_clz-trpta_100k_remo_sq) top

Crystal data top

C₂₇H₂₃Cl₂N₄⁺·0.5C₈H₄O₄²⁻·0.5C₈H₆O₄	Z = 2
M_r = 639.51	F(000) = 664
Triclinic, P1	D_x = 1.123 Mg m⁻³
a = 11.7990 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.0736 (4) Å	Cell parameters from 9616 reflections
c = 14.6803 (5) Å	θ = 2.2–32.2°
α = 72.472 (3)°	µ = 0.21 mm⁻¹
β = 80.688 (3)°	T = 100 K
γ = 72.030 (3)°	Polygon, metallic dark red
V = 1891.44 (12) Å³	0.57 × 0.39 × 0.26 mm

Data collection top

Xcalibur Ruby Gemini ultra diffractometer	11543 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	9100 reflections with I > 2σ(I)
Detector resolution: 10.3712 pixels mm^-1	R_int = 0.022
ω scans	θ_max = 30.5°, θ_min = 2.2°
Absorption correction: analytical CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −16→14
T_min = 0.917, T_max = 0.960	k = −17→11
20823 measured reflections	l = −20→20

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: dual
R[F² > 2σ(F²)] = 0.044	Hydrogen site location: mixed
wR(F²) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0519P)² + 0.3325P] where P = (F_o² + 2F_c²)/3
11543 reflections	(Δ/σ)_max = 0.002
420 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Special details top

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

	x	y	z	U_iso*/U_eq
Cl1	−0.02201 (3)	0.69984 (4)	0.31761 (3)	0.03712 (10)
N1	0.42663 (8)	0.83916 (9)	0.17739 (7)	0.0171 (2)
O2	0.93349 (10)	0.32936 (9)	0.42744 (7)	0.0345 (2)
C12	0.41613 (10)	0.96169 (11)	0.14635 (8)	0.0177 (2)
N2	0.63176 (9)	0.91784 (9)	0.11198 (7)	0.0185 (2)
O1	0.91588 (7)	0.27322 (8)	0.30078 (6)	0.02007 (18)
Cl2	1.35123 (3)	0.55850 (3)	0.00749 (3)	0.03562 (10)
C1	0.30515 (10)	1.04931 (11)	0.14859 (9)	0.0208 (2)
H1	0.233955	1.025325	0.171479	0.025*
C2	0.30093 (11)	1.16933 (12)	0.11746 (9)	0.0234 (3)
H2	0.225922	1.228185	0.118495	0.028*
O1A	1.00383 (8)	0.15272 (8)	0.17821 (6)	0.02108 (18)
N3	0.87829 (9)	0.51148 (10)	0.19133 (8)	0.0193 (2)
C3	0.40467 (12)	1.20757 (12)	0.08405 (9)	0.0246 (3)
H3A	0.399521	1.291346	0.062445	0.030*
O2A	0.82117 (8)	0.12706 (10)	0.19268 (7)	0.0286 (2)
N4	0.67811 (9)	0.43347 (10)	0.26532 (8)	0.0208 (2)
C4	0.51363 (11)	1.12331 (11)	0.08275 (9)	0.0221 (2)
H4A	0.584011	1.149090	0.060939	0.027*
C5	0.52190 (10)	0.99841 (11)	0.11362 (8)	0.0181 (2)
C6	0.63911 (10)	0.80160 (11)	0.14428 (8)	0.0171 (2)
C7	0.75338 (10)	0.71651 (11)	0.14707 (9)	0.0181 (2)
H7	0.821628	0.744957	0.121491	0.022*
C8	0.76886 (10)	0.59540 (11)	0.18511 (8)	0.0171 (2)
C10	0.54887 (10)	0.63300 (11)	0.21616 (9)	0.0196 (2)
H10	0.480083	0.604120	0.236262	0.024*
C14	0.28656 (11)	0.77378 (12)	0.30997 (9)	0.0214 (2)
H14	0.335456	0.778084	0.353537	0.026*
C9	0.66279 (10)	0.55057 (11)	0.22351 (8)	0.0180 (2)
C13	0.31933 (10)	0.79988 (11)	0.21268 (9)	0.0175 (2)
C11	0.53534 (10)	0.75560 (11)	0.18009 (8)	0.0174 (2)
C15	0.18117 (11)	0.74119 (13)	0.34301 (9)	0.0244 (3)
H15	0.157191	0.722034	0.409542	0.029*
C17	0.14503 (11)	0.76204 (12)	0.18002 (9)	0.0221 (3)
H17	0.096326	0.757713	0.136321	0.027*
C16	0.11141 (10)	0.73710 (12)	0.27699 (10)	0.0231 (3)
C19	0.98759 (10)	0.53085 (11)	0.14638 (9)	0.0181 (2)
C18	0.25080 (11)	0.79346 (11)	0.14735 (9)	0.0205 (2)
H18	0.275915	0.810354	0.080994	0.025*
C20	1.08905 (11)	0.47015 (12)	0.19764 (9)	0.0214 (2)
H20	1.081257	0.423520	0.262039	0.026*
C21	1.20093 (11)	0.47784 (12)	0.15475 (10)	0.0249 (3)
H21	1.269973	0.436789	0.189493	0.030*
C22	1.21119 (10)	0.54574 (12)	0.06101 (10)	0.0234 (3)
C23	1.11233 (11)	0.60587 (11)	0.00873 (9)	0.0213 (2)
H23	1.120964	0.651686	−0.055833	0.026*
C24	1.00038 (11)	0.59846 (11)	0.05176 (9)	0.0198 (2)
H24	0.931801	0.639781	0.016497	0.024*
C25	0.58235 (11)	0.37606 (12)	0.31139 (10)	0.0261 (3)
H25	0.517188	0.434256	0.339923	0.031*
C26	0.53154 (14)	0.34265 (15)	0.23785 (12)	0.0385 (4)
H26A	0.498922	0.415734	0.187652	0.058*
H26B	0.467882	0.304633	0.269222	0.058*
H26C	0.595057	0.286019	0.209238	0.058*
C27	0.63342 (13)	0.26535 (14)	0.39069 (12)	0.0376 (4)
H27A	0.696242	0.207131	0.363096	0.056*
H27B	0.569822	0.228217	0.424034	0.056*
H27C	0.667233	0.289142	0.436192	0.056*
C28	0.93859 (11)	0.25054 (11)	0.38822 (9)	0.0198 (2)
C29	0.97130 (10)	0.12017 (11)	0.44509 (8)	0.0179 (2)
C30	1.03100 (11)	0.08628 (11)	0.52799 (9)	0.0195 (2)
H30	1.052091	0.145265	0.547257	0.023*
C31	0.94024 (10)	0.03319 (11)	0.41749 (8)	0.0191 (2)
H31	0.899274	0.055737	0.361227	0.023*
C32	0.92162 (11)	0.11484 (11)	0.15402 (9)	0.0196 (2)
C33	0.96372 (10)	0.05587 (11)	0.07404 (8)	0.0178 (2)
C34	0.89503 (10)	−0.00961 (11)	0.05655 (8)	0.0188 (2)
H34	0.823201	−0.015822	0.095099	0.023*
C35	1.06901 (10)	0.06579 (11)	0.01685 (8)	0.0187 (2)
H35	1.115769	0.110999	0.028368	0.022*
H4	0.7470 (15)	0.3852 (15)	0.2674 (11)	0.028 (4)*
H3	0.8849 (14)	0.4451 (16)	0.2369 (12)	0.035 (5)*
H3B	0.9696 (17)	0.1893 (19)	0.2259 (14)	0.053 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.02217 (17)	0.0564 (3)	0.0442 (2)	−0.02169 (16)	0.01047 (13)	−0.02555 (19)
N1	0.0133 (4)	0.0143 (5)	0.0208 (5)	−0.0028 (4)	−0.0003 (3)	−0.0022 (4)
O2	0.0625 (7)	0.0159 (5)	0.0247 (5)	−0.0089 (5)	−0.0074 (5)	−0.0047 (4)
C12	0.0172 (5)	0.0141 (6)	0.0198 (5)	−0.0032 (4)	−0.0013 (4)	−0.0028 (4)
N2	0.0164 (5)	0.0146 (5)	0.0222 (5)	−0.0034 (4)	−0.0002 (4)	−0.0031 (4)
O1	0.0225 (4)	0.0146 (4)	0.0188 (4)	−0.0020 (3)	−0.0026 (3)	−0.0010 (3)
Cl2	0.01732 (15)	0.02804 (19)	0.0491 (2)	−0.00443 (12)	0.01013 (13)	−0.00075 (15)
C1	0.0159 (5)	0.0178 (6)	0.0255 (6)	−0.0014 (4)	−0.0019 (4)	−0.0045 (5)
C2	0.0198 (6)	0.0175 (6)	0.0286 (7)	0.0007 (5)	−0.0023 (5)	−0.0055 (5)
O1A	0.0200 (4)	0.0226 (5)	0.0220 (4)	−0.0059 (3)	−0.0007 (3)	−0.0085 (4)
N3	0.0136 (5)	0.0144 (5)	0.0237 (5)	−0.0021 (4)	−0.0003 (4)	0.0014 (4)
C3	0.0264 (6)	0.0147 (6)	0.0290 (7)	−0.0026 (5)	−0.0024 (5)	−0.0034 (5)
O2A	0.0203 (5)	0.0371 (6)	0.0320 (5)	−0.0089 (4)	0.0048 (4)	−0.0168 (4)
N4	0.0140 (5)	0.0144 (5)	0.0282 (6)	−0.0024 (4)	−0.0002 (4)	0.0007 (4)
C4	0.0226 (6)	0.0159 (6)	0.0263 (6)	−0.0066 (5)	0.0012 (5)	−0.0037 (5)
C5	0.0170 (5)	0.0149 (6)	0.0201 (6)	−0.0029 (4)	−0.0014 (4)	−0.0030 (4)
C6	0.0159 (5)	0.0150 (5)	0.0186 (5)	−0.0039 (4)	−0.0013 (4)	−0.0023 (4)
C7	0.0139 (5)	0.0160 (6)	0.0225 (6)	−0.0048 (4)	0.0007 (4)	−0.0029 (5)
C8	0.0137 (5)	0.0152 (6)	0.0196 (5)	−0.0033 (4)	−0.0012 (4)	−0.0014 (4)
C10	0.0141 (5)	0.0156 (6)	0.0264 (6)	−0.0042 (4)	0.0005 (4)	−0.0026 (5)
C14	0.0168 (6)	0.0236 (6)	0.0233 (6)	−0.0054 (5)	−0.0012 (4)	−0.0057 (5)
C9	0.0161 (5)	0.0150 (6)	0.0205 (6)	−0.0039 (4)	−0.0012 (4)	−0.0020 (4)
C13	0.0127 (5)	0.0136 (5)	0.0235 (6)	−0.0023 (4)	−0.0005 (4)	−0.0026 (4)
C11	0.0135 (5)	0.0167 (6)	0.0198 (5)	−0.0027 (4)	−0.0014 (4)	−0.0031 (4)
C15	0.0204 (6)	0.0279 (7)	0.0244 (6)	−0.0082 (5)	0.0031 (5)	−0.0074 (5)
C17	0.0167 (6)	0.0215 (6)	0.0287 (6)	−0.0029 (5)	−0.0041 (4)	−0.0086 (5)
C16	0.0136 (5)	0.0244 (7)	0.0322 (7)	−0.0060 (5)	0.0031 (4)	−0.0107 (5)
C19	0.0144 (5)	0.0137 (5)	0.0248 (6)	−0.0031 (4)	0.0006 (4)	−0.0052 (5)
C18	0.0186 (6)	0.0181 (6)	0.0220 (6)	−0.0025 (4)	−0.0010 (4)	−0.0043 (5)
C20	0.0180 (6)	0.0168 (6)	0.0243 (6)	−0.0027 (4)	−0.0009 (4)	−0.0004 (5)
C21	0.0148 (6)	0.0186 (6)	0.0338 (7)	−0.0005 (4)	−0.0021 (5)	−0.0005 (5)
C22	0.0147 (5)	0.0166 (6)	0.0335 (7)	−0.0028 (4)	0.0056 (5)	−0.0047 (5)
C23	0.0230 (6)	0.0144 (6)	0.0226 (6)	−0.0036 (4)	0.0032 (4)	−0.0036 (5)
C24	0.0186 (6)	0.0156 (6)	0.0230 (6)	−0.0029 (4)	−0.0014 (4)	−0.0038 (5)
C25	0.0165 (6)	0.0171 (6)	0.0358 (7)	−0.0049 (5)	0.0015 (5)	0.0040 (5)
C26	0.0304 (8)	0.0351 (9)	0.0499 (10)	−0.0179 (6)	−0.0063 (6)	−0.0006 (7)
C27	0.0273 (7)	0.0270 (8)	0.0441 (9)	−0.0089 (6)	−0.0021 (6)	0.0123 (6)
C28	0.0214 (6)	0.0159 (6)	0.0193 (6)	−0.0038 (4)	−0.0007 (4)	−0.0023 (5)
C29	0.0179 (5)	0.0147 (6)	0.0180 (5)	−0.0034 (4)	0.0004 (4)	−0.0021 (4)
C30	0.0215 (6)	0.0176 (6)	0.0199 (6)	−0.0065 (4)	−0.0014 (4)	−0.0045 (5)
C31	0.0190 (6)	0.0177 (6)	0.0184 (5)	−0.0037 (4)	−0.0027 (4)	−0.0024 (5)
C32	0.0185 (6)	0.0170 (6)	0.0211 (6)	−0.0029 (4)	−0.0022 (4)	−0.0034 (5)
C33	0.0168 (5)	0.0154 (6)	0.0182 (5)	−0.0026 (4)	−0.0025 (4)	−0.0016 (4)
C34	0.0150 (5)	0.0191 (6)	0.0205 (6)	−0.0054 (4)	0.0001 (4)	−0.0026 (5)
C35	0.0186 (6)	0.0161 (6)	0.0209 (6)	−0.0064 (4)	−0.0027 (4)	−0.0020 (4)

Geometric parameters (Å, º) top

Cl1—C16	1.7343 (13)	C13—C18	1.3835 (17)
N1—C11	1.3633 (14)	C15—C16	1.3896 (18)
N1—C12	1.3823 (15)	C15—H15	0.9500
N1—C13	1.4514 (15)	C17—C16	1.3811 (18)
O2—C28	1.2346 (16)	C17—C18	1.3857 (17)
C12—C1	1.4097 (16)	C17—H17	0.9500
C12—C5	1.4155 (17)	C19—C24	1.3942 (17)
N2—C6	1.3189 (16)	C19—C20	1.3980 (16)
N2—C5	1.3613 (14)	C18—H18	0.9500
O1—C28	1.2841 (14)	C20—C21	1.3852 (17)
Cl2—C22	1.7422 (13)	C20—H20	0.9500
C1—C2	1.3694 (18)	C21—C22	1.3815 (19)
C1—H1	0.9500	C21—H21	0.9500
C2—C3	1.4035 (19)	C22—C23	1.3813 (18)
C2—H2	0.9500	C23—C24	1.3859 (17)
O1A—C32	1.3263 (15)	C23—H23	0.9500
O1A—H3B	0.91 (2)	C24—H24	0.9500
N3—C8	1.3701 (14)	C25—C27	1.5157 (18)
N3—C19	1.4040 (15)	C25—C26	1.519 (2)
N3—H3	0.866 (18)	C25—H25	1.0000
C3—C4	1.3728 (17)	C26—H26A	0.9800
C3—H3A	0.9500	C26—H26B	0.9800
O2A—C32	1.2138 (15)	C26—H26C	0.9800
N4—C9	1.3281 (16)	C27—H27A	0.9800
N4—C25	1.4725 (16)	C27—H27B	0.9800
N4—H4	0.841 (16)	C27—H27C	0.9800
C4—C5	1.4145 (17)	C28—C29	1.5037 (17)
C4—H4A	0.9500	C29—C31	1.3940 (17)
C6—C7	1.4187 (16)	C29—C30	1.3943 (16)
C6—C11	1.4558 (16)	C30—C31ⁱ	1.3882 (17)
C7—C8	1.3637 (17)	C30—H30	0.9500
C7—H7	0.9500	C31—H31	0.9500
C8—C9	1.4775 (16)	C32—C33	1.4929 (17)
C10—C11	1.3806 (17)	C33—C34	1.3903 (17)
C10—C9	1.4021 (16)	C33—C35	1.3987 (16)
C10—H10	0.9500	C34—C35ⁱⁱ	1.3842 (17)
C14—C13	1.3835 (17)	C34—H34	0.9500
C14—C15	1.3886 (17)	C35—H35	0.9500
C14—H14	0.9500

C11—N1—C12	121.51 (10)	C24—C19—N3	123.19 (10)
C11—N1—C13	119.76 (10)	C20—C19—N3	117.25 (11)
C12—N1—C13	118.64 (9)	C13—C18—C17	119.10 (11)
N1—C12—C1	122.24 (11)	C13—C18—H18	120.5
N1—C12—C5	117.90 (10)	C17—C18—H18	120.5
C1—C12—C5	119.85 (11)	C21—C20—C19	120.17 (12)
C6—N2—C5	118.23 (10)	C21—C20—H20	119.9
C2—C1—C12	119.37 (12)	C19—C20—H20	119.9
C2—C1—H1	120.3	C22—C21—C20	119.40 (11)
C12—C1—H1	120.3	C22—C21—H21	120.3
C1—C2—C3	121.64 (11)	C20—C21—H21	120.3
C1—C2—H2	119.2	C23—C22—C21	121.48 (11)
C3—C2—H2	119.2	C23—C22—Cl2	118.88 (10)
C32—O1A—H3B	107.5 (13)	C21—C22—Cl2	119.63 (10)
C8—N3—C19	126.60 (10)	C22—C23—C24	119.10 (11)
C8—N3—H3	117.3 (11)	C22—C23—H23	120.4
C19—N3—H3	114.5 (11)	C24—C23—H23	120.4
C4—C3—C2	119.68 (12)	C23—C24—C19	120.53 (11)
C4—C3—H3A	120.2	C23—C24—H24	119.7
C2—C3—H3A	120.2	C19—C24—H24	119.7
C9—N4—C25	125.53 (10)	N4—C25—C27	108.49 (11)
C9—N4—H4	120.3 (12)	N4—C25—C26	110.14 (11)
C25—N4—H4	114.1 (12)	C27—C25—C26	111.17 (13)
C3—C4—C5	120.51 (12)	N4—C25—H25	109.0
C3—C4—H4A	119.7	C27—C25—H25	109.0
C5—C4—H4A	119.7	C26—C25—H25	109.0
N2—C5—C4	118.64 (11)	C25—C26—H26A	109.5
N2—C5—C12	122.41 (11)	C25—C26—H26B	109.5
C4—C5—C12	118.95 (11)	H26A—C26—H26B	109.5
N2—C6—C7	118.99 (11)	C25—C26—H26C	109.5
N2—C6—C11	123.15 (10)	H26A—C26—H26C	109.5
C7—C6—C11	117.84 (11)	H26B—C26—H26C	109.5
C8—C7—C6	122.43 (11)	C25—C27—H27A	109.5
C8—C7—H7	118.8	C25—C27—H27B	109.5
C6—C7—H7	118.8	H27A—C27—H27B	109.5
C7—C8—N3	123.74 (11)	C25—C27—H27C	109.5
C7—C8—C9	118.97 (10)	H27A—C27—H27C	109.5
N3—C8—C9	117.28 (11)	H27B—C27—H27C	109.5
C11—C10—C9	120.87 (11)	O2—C28—O1	123.67 (12)
C11—C10—H10	119.6	O2—C28—C29	119.13 (11)
C9—C10—H10	119.6	O1—C28—C29	117.19 (11)
C13—C14—C15	119.03 (11)	C31—C29—C30	119.49 (11)
C13—C14—H14	120.5	C31—C29—C28	120.99 (11)
C15—C14—H14	120.5	C30—C29—C28	119.50 (11)
N4—C9—C10	121.80 (11)	C31ⁱ—C30—C29	120.34 (12)
N4—C9—C8	119.05 (10)	C31ⁱ—C30—H30	119.8
C10—C9—C8	119.14 (11)	C29—C30—H30	119.8
C18—C13—C14	121.99 (11)	C30ⁱ—C31—C29	120.17 (11)
C18—C13—N1	118.75 (11)	C30ⁱ—C31—H31	119.9
C14—C13—N1	119.22 (11)	C29—C31—H31	119.9
N1—C11—C10	122.67 (11)	O2A—C32—O1A	123.51 (12)
N1—C11—C6	116.74 (11)	O2A—C32—C33	122.74 (12)
C10—C11—C6	120.58 (10)	O1A—C32—C33	113.74 (10)
C14—C15—C16	118.81 (12)	C34—C33—C35	119.92 (11)
C14—C15—H15	120.6	C34—C33—C32	118.38 (11)
C16—C15—H15	120.6	C35—C33—C32	121.70 (11)
C16—C17—C18	119.07 (12)	C35ⁱⁱ—C34—C33	120.20 (11)
C16—C17—H17	120.5	C35ⁱⁱ—C34—H34	119.9
C18—C17—H17	120.5	C33—C34—H34	119.9
C17—C16—C15	121.98 (12)	C34ⁱⁱ—C35—C33	119.89 (11)
C17—C16—Cl1	119.02 (10)	C34ⁱⁱ—C35—H35	120.1
C15—C16—Cl1	119.00 (10)	C33—C35—H35	120.1
C24—C19—C20	119.32 (11)

C11—N1—C12—C1	−176.05 (11)	C9—C10—C11—C6	3.16 (18)
C13—N1—C12—C1	0.52 (17)	N2—C6—C11—N1	1.23 (17)
C11—N1—C12—C5	2.43 (17)	C7—C6—C11—N1	179.48 (10)
C13—N1—C12—C5	179.00 (10)	N2—C6—C11—C10	−177.72 (12)
N1—C12—C1—C2	179.51 (11)	C7—C6—C11—C10	0.52 (17)
C5—C12—C1—C2	1.06 (18)	C13—C14—C15—C16	−0.66 (19)
C12—C1—C2—C3	−0.58 (19)	C18—C17—C16—C15	−0.8 (2)
C1—C2—C3—C4	−0.4 (2)	C18—C17—C16—Cl1	179.11 (10)
C2—C3—C4—C5	0.82 (19)	C14—C15—C16—C17	1.3 (2)
C6—N2—C5—C4	177.48 (11)	C14—C15—C16—Cl1	−178.53 (10)
C6—N2—C5—C12	−1.59 (17)	C8—N3—C19—C24	−42.48 (19)
C3—C4—C5—N2	−179.43 (11)	C8—N3—C19—C20	143.09 (13)
C3—C4—C5—C12	−0.33 (18)	C14—C13—C18—C17	1.18 (18)
N1—C12—C5—N2	−0.07 (17)	N1—C13—C18—C17	−176.72 (11)
C1—C12—C5—N2	178.45 (11)	C16—C17—C18—C13	−0.49 (18)
N1—C12—C5—C4	−179.13 (11)	C24—C19—C20—C21	0.3 (2)
C1—C12—C5—C4	−0.62 (17)	N3—C19—C20—C21	174.99 (12)
C5—N2—C6—C7	−177.23 (10)	C19—C20—C21—C22	−0.1 (2)
C5—N2—C6—C11	1.00 (17)	C20—C21—C22—C23	−0.3 (2)
N2—C6—C7—C8	175.72 (12)	C20—C21—C22—Cl2	178.59 (11)
C11—C6—C7—C8	−2.60 (18)	C21—C22—C23—C24	0.5 (2)
C6—C7—C8—N3	−178.02 (11)	Cl2—C22—C23—C24	−178.41 (10)
C6—C7—C8—C9	1.01 (18)	C22—C23—C24—C19	−0.27 (19)
C19—N3—C8—C7	−12.0 (2)	C20—C19—C24—C23	−0.13 (19)
C19—N3—C8—C9	168.99 (11)	N3—C19—C24—C23	−174.46 (12)
C25—N4—C9—C10	−2.4 (2)	C9—N4—C25—C27	−150.77 (14)
C25—N4—C9—C8	176.60 (12)	C9—N4—C25—C26	87.34 (16)
C11—C10—C9—N4	174.24 (12)	O2—C28—C29—C31	158.11 (12)
C11—C10—C9—C8	−4.75 (18)	O1—C28—C29—C31	−21.02 (17)
C7—C8—C9—N4	−176.34 (12)	O2—C28—C29—C30	−20.29 (18)
N3—C8—C9—N4	2.75 (17)	O1—C28—C29—C30	160.58 (11)
C7—C8—C9—C10	2.68 (17)	C31—C29—C30—C31ⁱ	0.25 (19)
N3—C8—C9—C10	−178.23 (11)	C28—C29—C30—C31ⁱ	178.67 (11)
C15—C14—C13—C18	−0.59 (19)	C30—C29—C31—C30ⁱ	−0.25 (19)
C15—C14—C13—N1	177.29 (11)	C28—C29—C31—C30ⁱ	−178.65 (11)
C11—N1—C13—C18	−99.59 (13)	O2A—C32—C33—C34	−13.81 (18)
C12—N1—C13—C18	83.78 (14)	O1A—C32—C33—C34	166.46 (11)
C11—N1—C13—C14	82.46 (14)	O2A—C32—C33—C35	165.77 (12)
C12—N1—C13—C14	−94.17 (14)	O1A—C32—C33—C35	−13.96 (16)
C12—N1—C11—C10	175.98 (11)	C35—C33—C34—C35ⁱⁱ	0.48 (19)
C13—N1—C11—C10	−0.55 (17)	C32—C33—C34—C35ⁱⁱ	−179.93 (11)
C12—N1—C11—C6	−2.95 (16)	C34—C33—C35—C34ⁱⁱ	−0.48 (19)
C13—N1—C11—C6	−179.48 (10)	C32—C33—C35—C34ⁱⁱ	179.94 (11)
C9—C10—C11—N1	−175.73 (11)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O2ⁱⁱⁱ	0.95	2.44	3.3792 (17)	171
N4—H4···O1	0.841 (16)	2.071 (16)	2.8985 (13)	167.7 (15)
N3—H3···O1	0.866 (18)	1.947 (18)	2.7772 (14)	160.1 (16)
O1A—H3B···O1	0.91 (2)	1.64 (2)	2.5442 (13)	171 (2)

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

N-[(2E)-10-(4-chlorophenyl)-3-[(4-chlorophenyl)amino] -2,10-dihydrophenazin-2-ylidene]propan-2-aminium benzene-1,4-dicarboxylic acid benzene-1,4-dicarboxylate (lb0329_CLZ-TRPTA_reMo) top

Crystal data top

C₂₇H₂₃Cl₂N₄⁺·0.5C₈H₄O₄²⁻·0.5C₈H₆O₄	Z = 2
M_r = 639.51	F(000) = 664
Triclinic, P1	D_x = 1.360 Mg m⁻³
a = 10.4028 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.8454 (3) Å	Cell parameters from 5839 reflections
c = 15.4229 (5) Å	θ = 2.5–32.4°
α = 71.183 (3)°	µ = 0.25 mm⁻¹
β = 73.984 (3)°	T = 295 K
γ = 76.148 (2)°	Prism, metallic dark red
V = 1561.33 (9) Å³	0.72 × 0.48 × 0.41 mm

Data collection top

Xcalibur Ruby Gemini ultra diffractometer	5704 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	4554 reflections with I > 2σ(I)
Detector resolution: 10.3712 pixels mm^-1	R_int = 0.018
ω scans	θ_max = 25.4°, θ_min = 2.5°
Absorption correction: analytical CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R. C. Clark & J. S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −12→11
T_min = 0.886, T_max = 0.921	k = −13→13
13059 measured reflections	l = −18→15

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: dual
R[F² > 2σ(F²)] = 0.040	Hydrogen site location: mixed
wR(F²) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.054P)² + 0.249P] where P = (F_o² + 2F_c²)/3
5704 reflections	(Δ/σ)_max < 0.001
420 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Special details top

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

	x	y	z	U_iso*/U_eq
Cl2	0.39753 (6)	−0.16703 (5)	0.95873 (4)	0.07025 (18)
Cl1	0.23504 (6)	1.15410 (5)	0.16479 (4)	0.0799 (2)
O2	0.28392 (14)	0.54295 (13)	0.83562 (10)	0.0627 (4)
O1B	0.11614 (15)	0.69607 (14)	0.93073 (10)	0.0639 (4)
O1	0.49787 (15)	0.51905 (14)	0.75952 (10)	0.0673 (4)
N1	0.17527 (13)	0.59934 (13)	0.36530 (9)	0.0402 (3)
O2B	0.14146 (16)	0.86002 (15)	0.79915 (10)	0.0730 (4)
N4	0.37932 (15)	0.62506 (15)	0.60028 (10)	0.0452 (3)
N2	0.13470 (14)	0.34376 (14)	0.47124 (9)	0.0442 (3)
N3	0.33146 (19)	0.37532 (16)	0.70677 (11)	0.0592 (5)
C29	0.45548 (18)	0.51297 (16)	0.91956 (12)	0.0468 (4)
C11	0.21962 (16)	0.54535 (16)	0.44716 (11)	0.0392 (4)
C5	0.09563 (16)	0.39971 (17)	0.38734 (11)	0.0421 (4)
C13	0.18856 (16)	0.73544 (16)	0.31428 (11)	0.0405 (4)
C12	0.11452 (16)	0.52797 (17)	0.33236 (11)	0.0417 (4)
C6	0.19508 (16)	0.41300 (16)	0.49977 (11)	0.0397 (4)
C29B	0.04861 (16)	0.91308 (17)	0.94426 (12)	0.0448 (4)
C9	0.32155 (16)	0.55837 (16)	0.56698 (11)	0.0411 (4)
C28B	0.10638 (18)	0.82179 (19)	0.88364 (14)	0.0507 (4)
C15	0.30967 (18)	0.89154 (18)	0.19341 (12)	0.0501 (4)
H15	0.381476	0.911439	0.142524	0.060*
C14	0.29640 (17)	0.76187 (17)	0.23982 (12)	0.0452 (4)
H14	0.359316	0.693379	0.221090	0.054*
C7	0.23582 (17)	0.35815 (17)	0.58644 (11)	0.0457 (4)
H7	0.221092	0.272984	0.620853	0.055*
C28	0.4093 (2)	0.52717 (16)	0.83193 (14)	0.0528 (5)
C10	0.28306 (17)	0.61318 (16)	0.48020 (11)	0.0425 (4)
H10	0.300778	0.696942	0.444351	0.051*
C31	0.36919 (19)	0.48584 (18)	1.00677 (13)	0.0522 (5)
H31	0.280803	0.475950	1.011888	0.063*
C8	0.29561 (17)	0.42432 (17)	0.62180 (11)	0.0445 (4)
C21	0.32937 (18)	0.09801 (18)	0.92005 (13)	0.0530 (5)
H21	0.310044	0.085678	0.984567	0.064*
C18	0.09338 (17)	0.83489 (18)	0.34331 (12)	0.0481 (4)
H18	0.020818	0.814795	0.393556	0.058*
C16	0.21598 (18)	0.99167 (17)	0.22279 (12)	0.0488 (4)
C25	0.40036 (18)	0.76238 (17)	0.55565 (12)	0.0480 (4)
H25	0.441020	0.772207	0.488906	0.058*
C20	0.31243 (19)	0.22383 (18)	0.86026 (12)	0.0516 (4)
H20	0.281686	0.295948	0.884987	0.062*
C17	0.10715 (18)	0.96458 (18)	0.29687 (13)	0.0533 (5)
H17	0.043752	1.033019	0.315293	0.064*
C22	0.37485 (17)	−0.00880 (17)	0.88395 (13)	0.0490 (4)
C4	0.03202 (18)	0.32686 (19)	0.35552 (13)	0.0506 (4)
H4A	0.018621	0.241819	0.391230	0.061*
C19	0.34055 (18)	0.24422 (17)	0.76396 (12)	0.0482 (4)
C1	0.07091 (18)	0.58094 (19)	0.24744 (12)	0.0511 (4)
H1	0.083759	0.665665	0.210633	0.061*
C30	0.58695 (19)	0.52680 (18)	0.91332 (13)	0.0522 (5)
H30	0.646204	0.544698	0.855025	0.063*
C3	−0.01021 (19)	0.3796 (2)	0.27285 (13)	0.0550 (5)
H3A	−0.051925	0.330510	0.252429	0.066*
C2	0.00924 (19)	0.5067 (2)	0.21928 (13)	0.0566 (5)
H2	−0.020192	0.542051	0.163199	0.068*
C30B	0.0220 (2)	1.04692 (19)	0.90400 (13)	0.0572 (5)
H34	0.036702	1.079580	0.839052	0.069*
C32	−0.0262 (2)	1.13326 (19)	0.95919 (13)	0.0564 (5)
H35	−0.043774	1.223561	0.931024	0.068*
C23	0.4027 (2)	0.00880 (19)	0.78864 (14)	0.0561 (5)
H23	0.432384	−0.063843	0.764443	0.067*
C24	0.3862 (2)	0.13476 (19)	0.72907 (13)	0.0559 (5)
H24	0.406099	0.146447	0.664611	0.067*
C26	0.2680 (2)	0.85861 (19)	0.56416 (16)	0.0660 (5)
H26A	0.206996	0.838045	0.536099	0.099*
H26B	0.285334	0.946984	0.532543	0.099*
H26C	0.227995	0.851673	0.629217	0.099*
C27	0.4985 (2)	0.7927 (2)	0.59984 (17)	0.0716 (6)
H27A	0.457964	0.788221	0.664522	0.107*
H27B	0.519009	0.879794	0.567179	0.107*
H27C	0.580454	0.729337	0.595766	0.107*
H4	0.4107 (18)	0.5879 (19)	0.6504 (14)	0.060 (6)*
H3	0.337 (2)	0.429 (2)	0.7340 (17)	0.085 (8)*
H3B	0.169 (3)	0.641 (3)	0.892 (2)	0.117 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl2	0.0840 (4)	0.0429 (3)	0.0718 (4)	−0.0043 (2)	−0.0233 (3)	0.0012 (2)
Cl1	0.0986 (4)	0.0429 (3)	0.0806 (4)	−0.0127 (3)	−0.0012 (3)	−0.0081 (3)
O2	0.0771 (9)	0.0589 (8)	0.0727 (9)	0.0159 (7)	−0.0507 (7)	−0.0361 (7)
O1B	0.0854 (10)	0.0479 (8)	0.0609 (9)	0.0057 (7)	−0.0273 (7)	−0.0205 (7)
O1	0.0893 (10)	0.0713 (10)	0.0494 (8)	0.0136 (7)	−0.0378 (8)	−0.0278 (7)
N1	0.0517 (8)	0.0409 (8)	0.0317 (7)	−0.0047 (6)	−0.0177 (6)	−0.0096 (6)
O2B	0.1005 (11)	0.0678 (10)	0.0480 (9)	0.0030 (8)	−0.0176 (7)	−0.0234 (7)
N4	0.0603 (9)	0.0457 (8)	0.0373 (8)	−0.0084 (7)	−0.0222 (7)	−0.0121 (7)
N2	0.0567 (8)	0.0438 (8)	0.0379 (8)	−0.0082 (6)	−0.0187 (6)	−0.0119 (6)
N3	0.1023 (13)	0.0436 (9)	0.0449 (9)	−0.0174 (8)	−0.0429 (9)	−0.0033 (7)
C29	0.0669 (11)	0.0350 (9)	0.0471 (10)	0.0071 (8)	−0.0335 (9)	−0.0163 (8)
C11	0.0475 (9)	0.0413 (9)	0.0308 (8)	−0.0036 (7)	−0.0145 (7)	−0.0102 (7)
C5	0.0476 (9)	0.0471 (10)	0.0372 (9)	−0.0040 (7)	−0.0151 (7)	−0.0166 (8)
C13	0.0514 (9)	0.0410 (9)	0.0319 (8)	−0.0055 (7)	−0.0189 (7)	−0.0069 (7)
C12	0.0453 (9)	0.0482 (10)	0.0365 (9)	−0.0024 (7)	−0.0149 (7)	−0.0171 (8)
C6	0.0489 (9)	0.0405 (9)	0.0333 (8)	−0.0054 (7)	−0.0141 (7)	−0.0118 (7)
C29B	0.0473 (9)	0.0466 (10)	0.0435 (10)	0.0000 (7)	−0.0193 (7)	−0.0139 (8)
C9	0.0503 (9)	0.0423 (9)	0.0353 (9)	−0.0047 (7)	−0.0158 (7)	−0.0136 (7)
C28B	0.0538 (10)	0.0524 (11)	0.0509 (11)	0.0022 (8)	−0.0247 (8)	−0.0175 (9)
C15	0.0509 (10)	0.0511 (11)	0.0439 (10)	−0.0092 (8)	−0.0060 (8)	−0.0101 (8)
C14	0.0484 (9)	0.0439 (10)	0.0421 (9)	0.0012 (7)	−0.0128 (7)	−0.0140 (8)
C7	0.0644 (11)	0.0394 (9)	0.0364 (9)	−0.0097 (8)	−0.0209 (8)	−0.0054 (7)
C28	0.0808 (14)	0.0335 (9)	0.0563 (12)	0.0119 (8)	−0.0437 (11)	−0.0200 (8)
C10	0.0580 (10)	0.0388 (9)	0.0345 (9)	−0.0098 (7)	−0.0181 (7)	−0.0071 (7)
C31	0.0608 (11)	0.0476 (10)	0.0571 (12)	0.0006 (8)	−0.0336 (9)	−0.0159 (9)
C8	0.0617 (10)	0.0415 (9)	0.0348 (9)	−0.0053 (8)	−0.0221 (8)	−0.0091 (7)
C21	0.0638 (11)	0.0516 (11)	0.0398 (10)	−0.0047 (9)	−0.0166 (8)	−0.0062 (8)
C18	0.0505 (10)	0.0511 (11)	0.0390 (9)	−0.0042 (8)	−0.0069 (7)	−0.0130 (8)
C16	0.0570 (10)	0.0401 (10)	0.0473 (10)	−0.0044 (8)	−0.0152 (8)	−0.0087 (8)
C25	0.0612 (11)	0.0491 (10)	0.0387 (9)	−0.0162 (8)	−0.0116 (8)	−0.0129 (8)
C20	0.0690 (11)	0.0435 (10)	0.0453 (10)	−0.0018 (8)	−0.0235 (9)	−0.0122 (8)
C17	0.0571 (11)	0.0464 (11)	0.0512 (11)	0.0031 (8)	−0.0102 (8)	−0.0163 (9)
C22	0.0536 (10)	0.0406 (10)	0.0509 (11)	−0.0054 (8)	−0.0190 (8)	−0.0053 (8)
C4	0.0605 (11)	0.0502 (11)	0.0501 (10)	−0.0093 (8)	−0.0199 (8)	−0.0188 (9)
C19	0.0627 (11)	0.0455 (10)	0.0424 (10)	−0.0098 (8)	−0.0271 (8)	−0.0063 (8)
C1	0.0638 (11)	0.0550 (11)	0.0397 (10)	−0.0077 (9)	−0.0237 (8)	−0.0109 (8)
C30	0.0664 (12)	0.0492 (11)	0.0447 (10)	0.0016 (8)	−0.0252 (9)	−0.0149 (8)
C3	0.0618 (11)	0.0649 (13)	0.0532 (11)	−0.0081 (9)	−0.0252 (9)	−0.0272 (10)
C2	0.0672 (12)	0.0675 (13)	0.0439 (10)	−0.0044 (9)	−0.0288 (9)	−0.0180 (9)
C30B	0.0803 (13)	0.0522 (11)	0.0365 (10)	−0.0023 (9)	−0.0191 (9)	−0.0095 (9)
C32	0.0803 (13)	0.0412 (10)	0.0462 (11)	0.0018 (9)	−0.0241 (9)	−0.0100 (8)
C23	0.0692 (12)	0.0485 (11)	0.0560 (12)	−0.0038 (9)	−0.0222 (9)	−0.0188 (9)
C24	0.0752 (12)	0.0572 (12)	0.0401 (10)	−0.0095 (9)	−0.0220 (9)	−0.0129 (9)
C26	0.0755 (13)	0.0483 (12)	0.0762 (14)	−0.0085 (10)	−0.0210 (11)	−0.0169 (10)
C27	0.0830 (14)	0.0698 (14)	0.0798 (15)	−0.0256 (11)	−0.0331 (12)	−0.0220 (12)

Geometric parameters (Å, º) top

Cl2—C22	1.7350 (17)	C7—H7	0.9300
Cl1—C16	1.7308 (18)	C10—H10	0.9300
O2—C28	1.261 (2)	C31—C30ⁱⁱ	1.385 (2)
O1B—C28B	1.316 (2)	C31—H31	0.9300
O1B—H3B	0.95 (3)	C21—C22	1.373 (3)
O1—C28	1.249 (2)	C21—C20	1.381 (2)
N1—C11	1.3656 (19)	C21—H21	0.9300
N1—C12	1.386 (2)	C18—C17	1.379 (2)
N1—C13	1.451 (2)	C18—H18	0.9300
O2B—C28B	1.210 (2)	C16—C17	1.379 (2)
N4—C9	1.329 (2)	C25—C26	1.517 (3)
N4—C25	1.467 (2)	C25—C27	1.518 (2)
N4—H4	0.86 (2)	C25—H25	0.9800
N2—C6	1.320 (2)	C20—C19	1.386 (2)
N2—C5	1.369 (2)	C20—H20	0.9300
N3—C8	1.365 (2)	C17—H17	0.9300
N3—C19	1.408 (2)	C22—C23	1.375 (3)
N3—H3	0.85 (2)	C4—C3	1.365 (2)
C29—C31	1.381 (3)	C4—H4A	0.9300
C29—C30	1.385 (3)	C19—C24	1.388 (3)
C29—C28	1.507 (2)	C1—C2	1.369 (2)
C11—C10	1.377 (2)	C1—H1	0.9300
C11—C6	1.447 (2)	C30—H30	0.9300
C5—C12	1.404 (2)	C3—C2	1.389 (3)
C5—C4	1.408 (2)	C3—H3A	0.9300
C13—C14	1.375 (2)	C2—H2	0.9300
C13—C18	1.378 (2)	C30B—C32	1.381 (3)
C12—C1	1.403 (2)	C30B—H34	0.9300
C6—C7	1.414 (2)	C32—H35	0.9300
C29B—C30B	1.375 (2)	C23—C24	1.380 (3)
C29B—C32ⁱ	1.381 (2)	C23—H23	0.9300
C29B—C28B	1.489 (2)	C24—H24	0.9300
C9—C10	1.405 (2)	C26—H26A	0.9600
C9—C8	1.473 (2)	C26—H26B	0.9600
C15—C14	1.378 (2)	C26—H26C	0.9600
C15—C16	1.379 (2)	C27—H27A	0.9600
C15—H15	0.9300	C27—H27B	0.9600
C14—H14	0.9300	C27—H27C	0.9600
C7—C8	1.361 (2)

C28B—O1B—H3B	111.5 (18)	C13—C18—H18	120.4
C11—N1—C12	121.20 (14)	C17—C18—H18	120.4
C11—N1—C13	118.73 (13)	C15—C16—C17	121.18 (17)
C12—N1—C13	120.03 (12)	C15—C16—Cl1	119.20 (14)
C9—N4—C25	124.72 (14)	C17—C16—Cl1	119.61 (14)
C9—N4—H4	120.9 (13)	N4—C25—C26	111.82 (15)
C25—N4—H4	114.3 (13)	N4—C25—C27	109.06 (15)
C6—N2—C5	118.12 (14)	C26—C25—C27	110.44 (16)
C8—N3—C19	127.90 (16)	N4—C25—H25	108.5
C8—N3—H3	118.2 (16)	C26—C25—H25	108.5
C19—N3—H3	113.1 (16)	C27—C25—H25	108.5
C31—C29—C30	118.90 (16)	C21—C20—C19	120.98 (17)
C31—C29—C28	121.25 (17)	C21—C20—H20	119.5
C30—C29—C28	119.84 (18)	C19—C20—H20	119.5
N1—C11—C10	122.27 (15)	C18—C17—C16	119.27 (16)
N1—C11—C6	117.12 (14)	C18—C17—H17	120.4
C10—C11—C6	120.60 (14)	C16—C17—H17	120.4
N2—C5—C12	122.53 (14)	C21—C22—C23	120.36 (17)
N2—C5—C4	118.86 (16)	C21—C22—Cl2	119.95 (14)
C12—C5—C4	118.60 (15)	C23—C22—Cl2	119.68 (14)
C14—C13—C18	121.84 (16)	C3—C4—C5	120.78 (18)
C14—C13—N1	119.45 (14)	C3—C4—H4A	119.6
C18—C13—N1	118.69 (15)	C5—C4—H4A	119.6
N1—C12—C1	121.95 (16)	C20—C19—C24	118.24 (16)
N1—C12—C5	117.97 (14)	C20—C19—N3	117.98 (16)
C1—C12—C5	120.07 (15)	C24—C19—N3	123.57 (16)
N2—C6—C7	119.41 (15)	C2—C1—C12	119.37 (18)
N2—C6—C11	123.00 (14)	C2—C1—H1	120.3
C7—C6—C11	117.57 (14)	C12—C1—H1	120.3
C30B—C29B—C32ⁱ	118.75 (17)	C31ⁱⁱ—C30—C29	120.49 (18)
C30B—C29B—C28B	119.87 (16)	C31ⁱⁱ—C30—H30	119.8
C32ⁱ—C29B—C28B	121.32 (16)	C29—C30—H30	119.8
N4—C9—C10	121.46 (16)	C4—C3—C2	119.88 (17)
N4—C9—C8	119.93 (14)	C4—C3—H3A	120.1
C10—C9—C8	118.61 (14)	C2—C3—H3A	120.1
O2B—C28B—O1B	123.41 (18)	C1—C2—C3	121.30 (16)
O2B—C28B—C29B	122.98 (18)	C1—C2—H2	119.4
O1B—C28B—C29B	113.61 (16)	C3—C2—H2	119.4
C14—C15—C16	119.68 (16)	C29B—C30B—C32	120.56 (17)
C14—C15—H15	120.2	C29B—C30B—H34	119.7
C16—C15—H15	120.2	C32—C30B—H34	119.7
C13—C14—C15	118.88 (16)	C29Bⁱ—C32—C30B	120.68 (17)
C13—C14—H14	120.6	C29Bⁱ—C32—H35	119.7
C15—C14—H14	120.6	C30B—C32—H35	119.7
C8—C7—C6	122.99 (16)	C22—C23—C24	119.70 (17)
C8—C7—H7	118.5	C22—C23—H23	120.2
C6—C7—H7	118.5	C24—C23—H23	120.2
O1—C28—O2	123.17 (16)	C23—C24—C19	120.95 (17)
O1—C28—C29	118.01 (17)	C23—C24—H24	119.5
O2—C28—C29	118.79 (18)	C19—C24—H24	119.5
C11—C10—C9	121.32 (15)	C25—C26—H26A	109.5
C11—C10—H10	119.3	C25—C26—H26B	109.5
C9—C10—H10	119.3	H26A—C26—H26B	109.5
C29—C31—C30ⁱⁱ	120.61 (17)	C25—C26—H26C	109.5
C29—C31—H31	119.7	H26A—C26—H26C	109.5
C30ⁱⁱ—C31—H31	119.7	H26B—C26—H26C	109.5
C7—C8—N3	124.07 (16)	C25—C27—H27A	109.5
C7—C8—C9	118.88 (14)	C25—C27—H27B	109.5
N3—C8—C9	117.04 (14)	H27A—C27—H27B	109.5
C22—C21—C20	119.77 (17)	C25—C27—H27C	109.5
C22—C21—H21	120.1	H27A—C27—H27C	109.5
C20—C21—H21	120.1	H27B—C27—H27C	109.5
C13—C18—C17	119.14 (16)

C12—N1—C11—C10	178.47 (15)	C30—C29—C31—C30ⁱⁱ	0.3 (3)
C13—N1—C11—C10	−3.6 (2)	C28—C29—C31—C30ⁱⁱ	−179.93 (15)
C12—N1—C11—C6	−2.6 (2)	C6—C7—C8—N3	177.59 (17)
C13—N1—C11—C6	175.29 (13)	C6—C7—C8—C9	−1.1 (3)
C6—N2—C5—C12	−1.5 (2)	C19—N3—C8—C7	13.9 (3)
C6—N2—C5—C4	179.52 (15)	C19—N3—C8—C9	−167.39 (17)
C11—N1—C13—C14	98.18 (18)	N4—C9—C8—C7	179.73 (16)
C12—N1—C13—C14	−83.88 (19)	C10—C9—C8—C7	0.2 (2)
C11—N1—C13—C18	−80.62 (19)	N4—C9—C8—N3	1.0 (2)
C12—N1—C13—C18	97.32 (18)	C10—C9—C8—N3	−178.53 (16)
C11—N1—C12—C1	−178.66 (15)	C14—C13—C18—C17	−0.5 (3)
C13—N1—C12—C1	3.5 (2)	N1—C13—C18—C17	178.27 (14)
C11—N1—C12—C5	2.1 (2)	C14—C15—C16—C17	−1.3 (3)
C13—N1—C12—C5	−175.76 (14)	C14—C15—C16—Cl1	179.20 (13)
N2—C5—C12—N1	0.0 (2)	C9—N4—C25—C26	71.4 (2)
C4—C5—C12—N1	178.97 (15)	C9—N4—C25—C27	−166.14 (17)
N2—C5—C12—C1	−179.20 (16)	C22—C21—C20—C19	0.1 (3)
C4—C5—C12—C1	−0.3 (2)	C13—C18—C17—C16	−0.2 (3)
C5—N2—C6—C7	179.60 (15)	C15—C16—C17—C18	1.2 (3)
C5—N2—C6—C11	1.0 (2)	Cl1—C16—C17—C18	−179.38 (14)
N1—C11—C6—N2	1.1 (2)	C20—C21—C22—C23	−0.5 (3)
C10—C11—C6—N2	179.99 (16)	C20—C21—C22—Cl2	179.52 (13)
N1—C11—C6—C7	−177.58 (15)	N2—C5—C4—C3	179.11 (16)
C10—C11—C6—C7	1.3 (2)	C12—C5—C4—C3	0.1 (3)
C25—N4—C9—C10	4.5 (3)	C21—C20—C19—C24	0.0 (3)
C25—N4—C9—C8	−174.99 (15)	C21—C20—C19—N3	−175.03 (16)
C30B—C29B—C28B—O2B	5.7 (3)	C8—N3—C19—C20	−148.7 (2)
C32ⁱ—C29B—C28B—O2B	−171.44 (19)	C8—N3—C19—C24	36.6 (3)
C30B—C29B—C28B—O1B	−174.57 (16)	N1—C12—C1—C2	−178.79 (16)
C32ⁱ—C29B—C28B—O1B	8.2 (2)	C5—C12—C1—C2	0.4 (3)
C18—C13—C14—C15	0.3 (3)	C31—C29—C30—C31ⁱⁱ	−0.3 (3)
N1—C13—C14—C15	−178.43 (14)	C28—C29—C30—C31ⁱⁱ	179.93 (15)
C16—C15—C14—C13	0.6 (3)	C5—C4—C3—C2	−0.1 (3)
N2—C6—C7—C8	−178.37 (16)	C12—C1—C2—C3	−0.4 (3)
C11—C6—C7—C8	0.3 (3)	C4—C3—C2—C1	0.3 (3)
C31—C29—C28—O1	−162.65 (17)	C32ⁱ—C29B—C30B—C32	0.0 (3)
C30—C29—C28—O1	17.1 (2)	C28B—C29B—C30B—C32	−177.29 (17)
C31—C29—C28—O2	15.4 (2)	C29B—C30B—C32—C29Bⁱ	0.0 (3)
C30—C29—C28—O2	−164.78 (16)	C21—C22—C23—C24	0.8 (3)
N1—C11—C10—C9	176.65 (15)	Cl2—C22—C23—C24	−179.19 (14)
C6—C11—C10—C9	−2.2 (3)	C22—C23—C24—C19	−0.7 (3)
N4—C9—C10—C11	−178.07 (15)	C20—C19—C24—C23	0.3 (3)
C8—C9—C10—C11	1.4 (2)	N3—C19—C24—C23	175.06 (17)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O1ⁱⁱⁱ	0.93	2.40	3.276 (2)	157
C20—H20···O2	0.93	2.54	3.307 (2)	140
C26—H26C···O2B	0.96	2.55	3.502 (3)	172
N4—H4···O1	0.86 (2)	1.98 (2)	2.8363 (19)	172.9 (18)
N3—H3···O2	0.85 (2)	2.17 (2)	2.976 (2)	159 (2)
N3—H3···O1	0.85 (2)	2.30 (2)	2.996 (2)	140 (2)
O1B—H3B···O2	0.95 (3)	1.66 (3)	2.5936 (19)	170 (3)

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

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Format		BIBTeX
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		Plain Text