(1H-Benzotriazole-κN³)­tri­chloro­cobalt(III)–1H-benzotriazole–water (1/1/1)

The title compound, the new phase [CoCl₃(BTA)]·BTA·H₂O (BTA is benzotriazole, C₆H₅N₃), has been synthesized and characterized by X-ray single-crystal diffraction methods. In the monomeric complex, the Co³⁺ ion is four-coordinated by three Cl⁻ anions and one N atom of the BTA, forming a distorted tetrahedral coordination. There are also uncoordinated BTA mol­ecules in the crystal structure, lying between the parallel ring planes of the coordinated BTA ligands and involved in π–π interactions. The asymmetric unit, which is the entire unit cell in space group P1, contains two molecules each of the complex, uncoordinated BTA and water.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.029
• wR factor = 0.064
• Data-to-parameter ratio = 11.6

checkCIF/PLATON results

No syntax errors found





Alert level A
PLAT052_ALERT_1_A (Proper) Absorption Correction Method Missing ..          ?
PLAT057_ALERT_3_A Correction for Absorption Required   RT(exp) ...       1.33

Alert level B
PLAT420_ALERT_2_B D-H Without Acceptor       O1W    -   H1A    ...          ?

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        Co1
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        Co2
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT417_ALERT_2_C Short Inter D-H..H-D       H1A    ..  H2A     ..       2.11 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1A    ..  CL4     ..       2.89 Ang.

Alert level G
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           27.50
           From the CIF: _reflns_number_total               4846
           Count of symmetry unique reflns         3926
           Completeness (_total/calc)            123.43%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       920
           Fraction of Friedel pairs measured     0.234
           Are heavy atom types Z>Si present          yes

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

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

---

Computing details

Data collection: XSCANS (Bruker, 1997); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXL97.

(1H-Benzotriazole-κN³)trichlorocobalt(III)–1H-benzotriazole–water (1/1/1)

Crystal data

[CoCl3(C6H5N3)]·C6H5N3·H2O	Z = 2
Mr = 421.56	F(000) = 424
Triclinic, P1	Dx = 1.636 Mg m^−3
Hall symbol: P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.8760 (8) Å	Cell parameters from 28 reflections
b = 7.8033 (12) Å	θ = 5.3–12.6°
c = 16.657 (3) Å	µ = 1.48 mm^−1
α = 95.450 (13)°	T = 293 K
β = 95.962 (8)°	Prism, blue
γ = 103.989 (9)°	0.4 × 0.4 × 0.2 mm
V = 855.8 (2) Å^3

Data collection

Bruker P4 diffractometer	4528 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.078
Graphite monochromator	θmax = 27.5°, θmin = 2.5°
ω scans	h = −8→1
Absorption correction: ψ scan (North et al., 1968)	k = −9→10
Tmin = 0.611, Tmax = 0.744	l = −21→21
4906 measured reflections	3 standard reflections every 100 reflections
4846 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.029	w = 1/[σ^2(Fo^2) + (0.001P)^2 + 0.65P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.065	(Δ/σ)max = 0.001
S = 1.02	Δρmax = 0.31 e Å^−3
4846 reflections	Δρmin = −0.27 e Å^−3
416 parameters	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
3 restraints	Extinction coefficient: 0.0215 (4)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 920 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.016 (14)

Special details

Experimental. Hydrogen atoms of benzotriazoles were generated theoretically. Hydrogen atoms of waters were found on difference Fourier map and moved to have standard O—H distanse. All hydrogen atoms were rided on their parent atoms in the final refinement.

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
Co1	0.44477 (8)	0.01444 (6)	0.90021 (3)	0.04761 (14)
Co2	0.55519 (8)	0.48552 (6)	0.39976 (3)	0.04994 (15)
Cl1	0.2006 (2)	−0.24248 (15)	0.89017 (7)	0.0725 (4)
Cl2	0.3426 (2)	0.22287 (16)	0.97694 (6)	0.0726 (4)
Cl3	0.7531 (3)	−0.0145 (3)	0.93712 (9)	0.0988 (5)
Cl4	0.6619 (3)	0.24195 (16)	0.42135 (7)	0.0762 (4)
Cl5	0.7827 (3)	0.72395 (17)	0.46861 (9)	0.0987 (6)
Cl6	0.2407 (3)	0.4751 (3)	0.43038 (9)	0.0914 (5)
N1	0.4455 (5)	0.0917 (4)	0.78737 (18)	0.0447 (7)
N2	0.3859 (6)	−0.0320 (4)	0.72391 (19)	0.0502 (8)
N3	0.3929 (6)	0.0507 (5)	0.6576 (2)	0.0503 (8)
H3A	0.3610	−0.0027	0.6087	0.060*
N4	0.5288 (6)	0.5119 (4)	0.27986 (18)	0.0457 (7)
N5	0.4785 (6)	0.3693 (4)	0.22465 (19)	0.0526 (9)
N6	0.4664 (6)	0.4286 (5)	0.15252 (19)	0.0554 (9)
H6A	0.4353	0.3600	0.1070	0.066*
N7	0.9893 (6)	0.4709 (5)	0.5897 (2)	0.0562 (9)
N8	1.0597 (7)	0.6211 (5)	0.6382 (2)	0.0619 (10)
N9	1.0799 (6)	0.5722 (5)	0.7112 (2)	0.0544 (9)
H9B	1.1236	0.6464	0.7546	0.065*
N10	0.0518 (7)	0.8804 (5)	0.0750 (2)	0.0627 (11)
H10B	0.0444	0.9015	0.0252	0.075*
N11	0.0965 (8)	1.0068 (5)	0.1375 (2)	0.0690 (11)
N12	0.0897 (7)	0.9206 (5)	0.2022 (2)	0.0592 (9)
C1	0.4912 (6)	0.2565 (5)	0.7613 (2)	0.0447 (8)
C2	0.4569 (6)	0.2308 (6)	0.6769 (2)	0.0458 (8)
C3	0.4845 (8)	0.3729 (7)	0.6308 (3)	0.0593 (11)
H3B	0.4608	0.3550	0.5743	0.071*
C4	0.5477 (8)	0.5389 (6)	0.6727 (3)	0.0680 (13)
H4A	0.5677	0.6368	0.6440	0.082*
C5	0.5837 (8)	0.5672 (6)	0.7579 (4)	0.0687 (13)
H5A	0.6269	0.6832	0.7839	0.082*
C6	0.5571 (7)	0.4292 (6)	0.8038 (3)	0.0568 (11)
H6B	0.5813	0.4485	0.8603	0.068*
C7	0.5483 (6)	0.6623 (5)	0.2421 (2)	0.0417 (8)
C8	0.5086 (7)	0.6086 (6)	0.1584 (2)	0.0459 (9)
C9	0.5173 (8)	0.7324 (7)	0.1020 (3)	0.0588 (11)
H9A	0.4934	0.6973	0.0462	0.071*
C10	0.5624 (8)	0.9050 (7)	0.1336 (3)	0.0646 (13)
H10A	0.5690	0.9910	0.0983	0.078*
C11	0.6003 (8)	0.9608 (6)	0.2188 (3)	0.0615 (12)
H11A	0.6297	1.0816	0.2375	0.074*
C12	0.5946 (7)	0.8420 (5)	0.2735 (2)	0.0516 (10)
H12A	0.6202	0.8784	0.3292	0.062*
C13	0.9661 (7)	0.3245 (5)	0.6304 (2)	0.0472 (9)
C14	1.0247 (6)	0.3921 (6)	0.7116 (2)	0.0449 (9)
C15	1.0187 (7)	0.2826 (7)	0.7731 (3)	0.0592 (11)
H15A	1.0547	0.3283	0.8278	0.071*
C16	0.9558 (8)	0.1017 (7)	0.7478 (3)	0.0681 (13)
H16A	0.9502	0.0225	0.7864	0.082*
C17	0.9004 (8)	0.0351 (6)	0.6652 (4)	0.0706 (14)
H17A	0.8598	−0.0876	0.6511	0.085*
C18	0.9029 (8)	0.1401 (6)	0.6051 (3)	0.0616 (12)
H18A	0.8654	0.0935	0.5506	0.074*
C19	0.0184 (8)	0.7133 (6)	0.0973 (3)	0.0545 (10)
C20	0.0444 (7)	0.7418 (6)	0.1816 (3)	0.0523 (10)
C21	0.0244 (8)	0.5962 (8)	0.2273 (3)	0.0677 (14)
H21A	0.0419	0.6126	0.2839	0.081*
C22	−0.0214 (10)	0.4330 (8)	0.1850 (4)	0.0813 (17)
H22A	−0.0349	0.3343	0.2131	0.098*
C23	−0.0492 (9)	0.4073 (7)	0.0996 (4)	0.0812 (16)
H23A	−0.0823	0.2916	0.0731	0.097*
C24	−0.0300 (9)	0.5433 (7)	0.0545 (3)	0.0691 (13)
H24A	−0.0479	0.5247	−0.0021	0.083*
O1W	0.1158 (10)	0.0547 (7)	0.3551 (3)	0.131 (2)
H1A	0.2435	0.0852	0.3561	0.157*
H1B	0.0696	0.1455	0.3636	0.157*
O2W	0.3207 (10)	0.9007 (6)	0.5000 (2)	0.128 (2)
H2A	0.2569	0.9538	0.4610	0.153*
H2B	0.3107	0.7942	0.4797	0.153*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.0536 (3)	0.0558 (3)	0.0346 (2)	0.0166 (3)	0.0029 (2)	0.0073 (2)
Co2	0.0641 (4)	0.0512 (3)	0.0350 (2)	0.0166 (3)	0.0036 (3)	0.0062 (2)
Cl1	0.0985 (10)	0.0597 (6)	0.0480 (5)	−0.0031 (7)	0.0181 (6)	0.0019 (4)
Cl2	0.1043 (11)	0.0711 (7)	0.0431 (5)	0.0295 (7)	0.0097 (6)	−0.0076 (5)
Cl3	0.0707 (9)	0.1849 (16)	0.0602 (7)	0.0598 (10)	0.0066 (6)	0.0426 (8)
Cl4	0.1122 (12)	0.0628 (6)	0.0582 (6)	0.0369 (7)	−0.0034 (7)	0.0079 (5)
Cl5	0.1390 (16)	0.0623 (7)	0.0703 (8)	0.0033 (9)	−0.0369 (10)	−0.0011 (6)
Cl6	0.0859 (11)	0.1386 (13)	0.0676 (7)	0.0487 (10)	0.0315 (7)	0.0260 (8)
N1	0.0507 (19)	0.0479 (16)	0.0385 (14)	0.0178 (16)	0.0040 (14)	0.0078 (12)
N2	0.061 (2)	0.0512 (17)	0.0400 (15)	0.0181 (17)	0.0034 (16)	0.0050 (13)
N3	0.058 (2)	0.0562 (19)	0.0380 (15)	0.0176 (18)	0.0061 (16)	0.0041 (14)
N4	0.057 (2)	0.0449 (16)	0.0359 (14)	0.0148 (16)	0.0041 (14)	0.0038 (12)
N5	0.070 (2)	0.0473 (17)	0.0399 (15)	0.0193 (18)	0.0015 (17)	0.0003 (13)
N6	0.071 (3)	0.0605 (19)	0.0358 (15)	0.025 (2)	0.0016 (17)	−0.0011 (14)
N7	0.064 (2)	0.060 (2)	0.0430 (17)	0.0146 (19)	0.0013 (17)	0.0081 (15)
N8	0.069 (3)	0.0536 (19)	0.062 (2)	0.014 (2)	−0.001 (2)	0.0128 (17)
N9	0.058 (2)	0.0545 (19)	0.0478 (18)	0.0169 (18)	−0.0025 (17)	−0.0032 (14)
N10	0.074 (3)	0.069 (2)	0.0492 (19)	0.025 (2)	0.003 (2)	0.0157 (17)
N11	0.082 (3)	0.064 (2)	0.065 (2)	0.027 (2)	0.003 (2)	0.0133 (19)
N12	0.060 (2)	0.065 (2)	0.055 (2)	0.019 (2)	0.0042 (19)	0.0085 (17)
C1	0.043 (2)	0.051 (2)	0.0441 (18)	0.0166 (18)	0.0065 (17)	0.0089 (15)
C2	0.044 (2)	0.054 (2)	0.0439 (18)	0.0180 (18)	0.0095 (17)	0.0114 (16)
C3	0.060 (3)	0.073 (3)	0.055 (2)	0.025 (3)	0.019 (2)	0.028 (2)
C4	0.068 (3)	0.063 (3)	0.088 (4)	0.025 (3)	0.031 (3)	0.039 (3)
C5	0.065 (3)	0.048 (2)	0.095 (4)	0.014 (2)	0.021 (3)	0.009 (2)
C6	0.058 (3)	0.056 (2)	0.054 (2)	0.011 (2)	0.008 (2)	−0.0005 (18)
C7	0.044 (2)	0.0475 (19)	0.0374 (17)	0.0164 (17)	0.0060 (16)	0.0088 (14)
C8	0.048 (2)	0.057 (2)	0.0379 (17)	0.021 (2)	0.0090 (17)	0.0069 (15)
C9	0.063 (3)	0.079 (3)	0.044 (2)	0.028 (3)	0.010 (2)	0.022 (2)
C10	0.066 (3)	0.075 (3)	0.065 (3)	0.028 (3)	0.016 (3)	0.035 (2)
C11	0.069 (3)	0.051 (2)	0.068 (3)	0.019 (2)	0.010 (2)	0.016 (2)
C12	0.062 (3)	0.046 (2)	0.048 (2)	0.017 (2)	0.009 (2)	0.0052 (16)
C13	0.044 (2)	0.051 (2)	0.0466 (19)	0.0128 (18)	0.0036 (17)	0.0062 (16)
C14	0.042 (2)	0.054 (2)	0.0411 (18)	0.0165 (18)	0.0053 (16)	0.0055 (15)
C15	0.060 (3)	0.080 (3)	0.046 (2)	0.028 (3)	0.011 (2)	0.021 (2)
C16	0.057 (3)	0.074 (3)	0.086 (3)	0.024 (3)	0.021 (3)	0.040 (3)
C17	0.058 (3)	0.048 (2)	0.104 (4)	0.012 (2)	0.005 (3)	0.010 (2)
C18	0.058 (3)	0.051 (2)	0.071 (3)	0.014 (2)	−0.001 (2)	−0.004 (2)
C19	0.054 (3)	0.066 (3)	0.048 (2)	0.022 (2)	0.008 (2)	0.0107 (18)
C20	0.046 (2)	0.058 (2)	0.054 (2)	0.015 (2)	0.0037 (19)	0.0101 (18)
C21	0.055 (3)	0.088 (4)	0.069 (3)	0.024 (3)	0.014 (3)	0.033 (3)
C22	0.072 (4)	0.067 (3)	0.114 (5)	0.020 (3)	0.021 (4)	0.037 (3)
C23	0.070 (4)	0.056 (3)	0.115 (5)	0.012 (3)	0.016 (4)	0.003 (3)
C24	0.071 (3)	0.069 (3)	0.066 (3)	0.018 (3)	0.011 (3)	−0.002 (2)
O1W	0.167 (6)	0.129 (4)	0.077 (3)	0.018 (4)	0.007 (3)	−0.021 (3)
O2W	0.201 (7)	0.113 (3)	0.063 (2)	0.043 (4)	0.013 (3)	−0.015 (2)

Geometric parameters (Å, º)

Co1—N1	2.028 (3)	C5—H5A	0.9300
Co1—Cl3	2.2162 (16)	C6—H6B	0.9300
Co1—Cl2	2.2620 (13)	C7—C8	1.396 (5)
Co1—Cl1	2.2622 (14)	C7—C12	1.397 (5)
Co2—N4	2.021 (3)	C8—C9	1.405 (6)
Co2—Cl4	2.2427 (13)	C9—C10	1.348 (7)
Co2—Cl5	2.2448 (15)	C9—H9A	0.9300
Co2—Cl6	2.2569 (18)	C10—C11	1.422 (7)
N1—N2	1.320 (4)	C10—H10A	0.9300
N1—C1	1.370 (5)	C11—C12	1.357 (6)
N2—N3	1.331 (4)	C11—H11A	0.9300
N3—C2	1.363 (5)	C12—H12A	0.9300
N3—H3A	0.8600	C13—C14	1.386 (5)
N4—N5	1.326 (4)	C13—C18	1.408 (6)
N4—C7	1.368 (4)	C14—C15	1.392 (6)
N5—N6	1.330 (4)	C15—C16	1.383 (7)
N6—C8	1.356 (5)	C15—H15A	0.9300
N6—H6A	0.8600	C16—C17	1.403 (8)
N7—N8	1.314 (5)	C16—H16A	0.9300
N7—C13	1.368 (5)	C17—C18	1.351 (7)
N8—N9	1.312 (5)	C17—H17A	0.9300
N9—C14	1.365 (5)	C18—H18A	0.9300
N9—H9B	0.8600	C19—C20	1.386 (6)
N10—N11	1.321 (5)	C19—C24	1.391 (7)
N10—C19	1.363 (6)	C20—C21	1.414 (6)
N10—H10B	0.8600	C21—C22	1.345 (8)
N11—N12	1.322 (5)	C21—H21A	0.9300
N12—C20	1.356 (6)	C22—C23	1.403 (8)
C1—C2	1.388 (5)	C22—H22A	0.9300
C1—C6	1.407 (6)	C23—C24	1.347 (8)
C2—C3	1.395 (6)	C23—H23A	0.9300
C3—C4	1.359 (7)	C24—H24A	0.9300
C3—H3B	0.9300	O1W—H1A	0.8500
C4—C5	1.401 (7)	O1W—H1B	0.8500
C4—H4A	0.9300	O2W—H2A	0.9299
C5—C6	1.367 (6)	O2W—H2B	0.8500
N1—Co1—Cl3	106.18 (11)	N4—C7—C12	131.3 (3)
N1—Co1—Cl2	105.75 (10)	C8—C7—C12	121.2 (3)
Cl3—Co1—Cl2	116.64 (7)	N6—C8—C7	103.6 (3)
N1—Co1—Cl1	106.87 (10)	N6—C8—C9	134.7 (4)
Cl3—Co1—Cl1	113.72 (8)	C7—C8—C9	121.7 (4)
Cl2—Co1—Cl1	106.99 (6)	C10—C9—C8	116.0 (4)
N4—Co2—Cl4	110.29 (10)	C10—C9—H9A	122.0
N4—Co2—Cl5	109.45 (10)	C8—C9—H9A	122.0
Cl4—Co2—Cl5	108.41 (6)	C9—C10—C11	122.6 (4)
N4—Co2—Cl6	102.70 (12)	C9—C10—H10A	118.7
Cl4—Co2—Cl6	114.39 (7)	C11—C10—H10A	118.7
Cl5—Co2—Cl6	111.44 (8)	C12—C11—C10	121.5 (4)
N2—N1—C1	109.6 (3)	C12—C11—H11A	119.2
N2—N1—Co1	118.4 (2)	C10—C11—H11A	119.2
C1—N1—Co1	132.0 (3)	C11—C12—C7	116.8 (4)
N1—N2—N3	107.3 (3)	C11—C12—H12A	121.6
N2—N3—C2	111.5 (3)	C7—C12—H12A	121.6
N2—N3—H3A	124.3	N7—C13—C14	105.0 (4)
C2—N3—H3A	124.3	N7—C13—C18	133.4 (4)
N5—N4—C7	109.8 (3)	C14—C13—C18	121.7 (4)
N5—N4—Co2	120.4 (2)	N9—C14—C13	104.2 (3)
C7—N4—Co2	129.8 (2)	N9—C14—C15	133.5 (4)
N4—N5—N6	106.4 (3)	C13—C14—C15	122.2 (4)
N5—N6—C8	112.8 (3)	C16—C15—C14	115.7 (4)
N5—N6—H6A	123.6	C16—C15—H15A	122.1
C8—N6—H6A	123.6	C14—C15—H15A	122.1
N8—N7—C13	112.8 (3)	C15—C16—C17	121.4 (4)
N9—N8—N7	104.4 (3)	C15—C16—H16A	119.3
N8—N9—C14	113.5 (3)	C17—C16—H16A	119.3
N8—N9—H9B	123.2	C18—C17—C16	123.4 (5)
C14—N9—H9B	123.2	C18—C17—H17A	118.3
N11—N10—C19	113.3 (4)	C16—C17—H17A	118.3
N11—N10—H10B	123.4	C17—C18—C13	115.5 (5)
C19—N10—H10B	123.4	C17—C18—H18A	122.2
N10—N11—N12	104.6 (4)	C13—C18—H18A	122.2
N11—N12—C20	112.0 (4)	N10—C19—C20	103.8 (4)
N1—C1—C2	107.3 (3)	N10—C19—C24	134.0 (4)
N1—C1—C6	132.0 (4)	C20—C19—C24	122.2 (4)
C2—C1—C6	120.7 (4)	N12—C20—C19	106.2 (4)
N3—C2—C1	104.4 (3)	N12—C20—C21	133.4 (4)
N3—C2—C3	133.5 (4)	C19—C20—C21	120.4 (5)
C1—C2—C3	122.0 (4)	C22—C21—C20	116.7 (5)
C4—C3—C2	116.6 (4)	C22—C21—H21A	121.7
C4—C3—H3B	121.7	C20—C21—H21A	121.7
C2—C3—H3B	121.7	C21—C22—C23	122.0 (5)
C3—C4—C5	122.1 (4)	C21—C22—H22A	119.0
C3—C4—H4A	118.9	C23—C22—H22A	119.0
C5—C4—H4A	118.9	C24—C23—C22	122.6 (5)
C6—C5—C4	121.9 (4)	C24—C23—H23A	118.7
C6—C5—H5A	119.0	C22—C23—H23A	118.7
C4—C5—H5A	119.0	C23—C24—C19	116.2 (5)
C5—C6—C1	116.7 (4)	C23—C24—H24A	121.9
C5—C6—H6B	121.7	C19—C24—H24A	121.9
C1—C6—H6B	121.7	H1A—O1W—H1B	110.8
N4—C7—C8	107.5 (3)	H2A—O2W—H2B	107.3

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O2W^i	0.86	1.86	2.716 (5)	173
N6—H6A···Cl2^ii	0.86	2.28	3.128 (3)	170
N9—H9B···Cl1^iii	0.86	2.30	3.123 (4)	160
N10—H10B···Cl3^iv	0.86	2.61	3.218 (4)	129
O1W—H1A···Cl4	0.85	2.89	3.692 (7)	158
O1W—H1B···Cl6	0.85	2.64	3.272 (5)	132
O2W—H2A···O1W^v	0.93	2.22	3.148 (7)	172
O2W—H2B···Cl6	0.85	2.46	3.306 (5)	172

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