Di­chloro­bis­[1-(2-ethoxy­ethyl)-1H-benz­imidazole-κN³]­cobalt(II)

The title compound, [CoCl₂(C₁₁H₁₄N₂O)₂], was synthesized from 1-(2-ethoxy­ethyl)­benz­imidazole and cobalt dichloride in ethanol. The Co^II atom is coordinated in a distorted tetrahedral environment by two Cl atoms and two N atoms. The crystal structure is stabilized by intermolecular C—H...Cl and C—H...O interactions.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.030
• wR factor = 0.073
• Data-to-parameter ratio = 20.6

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT220_ALERT_2_A Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       4.80 Ratio
PLAT222_ALERT_3_A Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       5.68 Ratio

Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.64 mm
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C21    -   C22    ...       1.42 Ang.
PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su ..       0.00

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           28.31
           From the CIF: _reflns_number_total               5762
           Count of symmetry unique reflns         3074
           Completeness (_total/calc)            187.44%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2688
           Fraction of Friedel pairs measured     0.874
           Are heavy atom types Z>Si present          yes

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Dichlorobis[1-(2-ethoxyethyl)-1H-benzimidazole-κN³]cobalt(II)

Crystal data

[CoCl2(C11H14N2O)2]	F(000) = 1060
Mr = 510.31	Dx = 1.413 Mg m^−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 5762 reflections
a = 17.5842 (17) Å	θ = 1.6–28.4°
b = 7.6235 (8) Å	µ = 0.96 mm^−1
c = 17.8892 (13) Å	T = 150 K
V = 2398.1 (4) Å^3	Prism, violet
Z = 4	0.64 × 0.50 × 0.41 mm

Data collection

Stoe IPDS II diffractometer	5762 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	5101 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.031
Detector resolution: 6.67 pixels mm^-1	θmax = 28.3°, θmin = 2.3°
ω scans	h = −23→23
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −10→10
Tmin = 0.577, Tmax = 0.693	l = −23→22
15539 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.030	H-atom parameters constrained
wR(F^2) = 0.073	w = 1/[σ^2(Fo^2) + (0.0489P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.98	(Δ/σ)max = 0.001
5762 reflections	Δρmax = 0.50 e Å^−3
280 parameters	Δρmin = −0.32 e Å^−3
1 restraint	Absolute structure: Flack (1983), with how many Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.000 (1)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > 2σ(F²) is used only for calculating -R-factor-obs 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	0.43647 (1)	0.13445 (3)	0.99175 (2)	0.0221 (1)
Cl1	0.52384 (3)	0.29074 (7)	1.05419 (3)	0.0294 (1)
Cl2	0.41752 (3)	−0.14960 (7)	1.02076 (4)	0.0351 (2)
O1	0.30541 (10)	0.0041 (2)	0.70782 (10)	0.0323 (5)
O2	0.25378 (14)	0.5134 (3)	1.20599 (12)	0.0515 (7)
N1	0.45752 (11)	0.1537 (2)	0.88137 (11)	0.0259 (5)
N2	0.45672 (11)	0.0868 (3)	0.76074 (11)	0.0273 (5)
N3	0.33842 (9)	0.2607 (2)	1.01024 (10)	0.0257 (5)
N4	0.25644 (10)	0.4643 (2)	1.04593 (12)	0.0281 (5)
C1	0.44138 (13)	0.0342 (3)	0.83076 (13)	0.0270 (6)
C2	0.48519 (13)	0.2969 (3)	0.84154 (12)	0.0253 (6)
C3	0.51056 (15)	0.4610 (3)	0.86561 (14)	0.0326 (7)
C4	0.53533 (17)	0.5767 (3)	0.81145 (15)	0.0385 (8)
C5	0.53532 (16)	0.5326 (3)	0.73497 (15)	0.0359 (8)
C6	0.50993 (14)	0.3725 (3)	0.71034 (14)	0.0324 (7)
C7	0.48500 (12)	0.2557 (3)	0.76531 (13)	0.0263 (6)
C8	0.43941 (15)	−0.0083 (3)	0.69226 (14)	0.0340 (7)
C9	0.36518 (14)	0.0502 (3)	0.65847 (13)	0.0324 (7)
C10	0.23301 (14)	0.0545 (3)	0.67792 (15)	0.0353 (7)
C11	0.17177 (17)	−0.0089 (4)	0.7295 (2)	0.0501 (10)
C12	0.32948 (12)	0.4122 (3)	1.04334 (13)	0.0261 (6)
C13	0.26592 (10)	0.2065 (3)	0.98884 (14)	0.0244 (5)
C14	0.24169 (13)	0.0546 (3)	0.95324 (13)	0.0307 (7)
C15	0.16422 (14)	0.0370 (3)	0.94086 (14)	0.0329 (7)
C16	0.11307 (14)	0.1664 (3)	0.96345 (15)	0.0339 (7)
C17	0.13585 (12)	0.3169 (3)	0.99857 (15)	0.0313 (6)
C18	0.21374 (12)	0.3344 (3)	1.01154 (12)	0.0259 (6)
C19	0.22826 (15)	0.6201 (3)	1.08385 (17)	0.0378 (8)
C20	0.19570 (15)	0.5781 (4)	1.16058 (19)	0.0440 (9)
C21	0.2321 (3)	0.4574 (6)	1.2803 (2)	0.0707 (14)
C22	0.2174 (5)	0.5930 (7)	1.3331 (3)	0.117 (3)
H1	0.42140	−0.07550	0.84230	0.0320*
H3	0.51080	0.49120	0.91600	0.0390*
H4	0.55250	0.68690	0.82590	0.0460*
H5	0.55290	0.61390	0.70030	0.0430*
H6	0.50940	0.34330	0.65990	0.0390*
H8A	0.43690	−0.13280	0.70300	0.0410*
H8B	0.48000	0.01020	0.65640	0.0410*
H9A	0.36570	0.17620	0.65080	0.0390*
H9B	0.35770	−0.00620	0.61040	0.0390*
H10A	0.22620	0.00340	0.62870	0.0420*
H10B	0.23040	0.18110	0.67320	0.0420*
H11A	0.12300	0.02360	0.70990	0.0750*
H11B	0.17850	0.04330	0.77790	0.0750*
H11C	0.17460	−0.13430	0.73390	0.0750*
H12	0.36950	0.47720	1.06310	0.0310*
H14	0.27590	−0.03150	0.93830	0.0370*
H15	0.14600	−0.06300	0.91710	0.0390*
H16	0.06150	0.14970	0.95430	0.0410*
H17	0.10130	0.40280	1.01300	0.0380*
H19A	0.18910	0.67440	1.05350	0.0450*
H19B	0.26950	0.70370	1.08930	0.0450*
H20A	0.17420	0.68320	1.18270	0.0530*
H20B	0.15560	0.49130	1.15600	0.0530*
H21A	0.18680	0.38540	1.27610	0.0850*
H21B	0.27230	0.38360	1.29990	0.0850*
H22A	0.20430	0.54170	1.38040	0.1760*
H22B	0.17600	0.66420	1.31580	0.1760*
H22C	0.26200	0.66430	1.33890	0.1760*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.0199 (1)	0.0253 (1)	0.0211 (1)	−0.0004 (1)	0.0013 (1)	0.0011 (1)
Cl1	0.0283 (2)	0.0343 (3)	0.0256 (2)	−0.0066 (2)	−0.0049 (2)	0.0032 (2)
Cl2	0.0312 (3)	0.0274 (3)	0.0468 (3)	−0.0012 (2)	0.0050 (2)	0.0084 (2)
O1	0.0375 (9)	0.0339 (9)	0.0255 (9)	−0.0002 (7)	−0.0013 (7)	0.0025 (7)
O2	0.0601 (13)	0.0547 (13)	0.0396 (11)	0.0020 (10)	0.0091 (10)	−0.0080 (9)
N1	0.0281 (9)	0.0281 (9)	0.0214 (9)	−0.0022 (7)	0.0015 (7)	−0.0003 (7)
N2	0.0310 (9)	0.0272 (9)	0.0238 (10)	−0.0024 (7)	0.0020 (8)	−0.0054 (7)
N3	0.0204 (8)	0.0290 (8)	0.0276 (11)	0.0017 (6)	−0.0004 (7)	0.0003 (7)
N4	0.0249 (8)	0.0259 (9)	0.0335 (10)	0.0032 (7)	0.0015 (8)	0.0011 (8)
C1	0.0304 (10)	0.0258 (10)	0.0249 (11)	−0.0036 (8)	0.0033 (9)	−0.0021 (8)
C2	0.0277 (10)	0.0282 (10)	0.0200 (10)	−0.0018 (8)	−0.0001 (8)	−0.0013 (9)
C3	0.0406 (13)	0.0341 (12)	0.0230 (12)	−0.0066 (10)	−0.0020 (10)	−0.0012 (9)
C4	0.0516 (15)	0.0350 (13)	0.0289 (13)	−0.0135 (11)	−0.0045 (12)	0.0010 (10)
C5	0.0450 (14)	0.0359 (13)	0.0269 (12)	−0.0097 (11)	−0.0003 (11)	0.0056 (10)
C6	0.0357 (12)	0.0395 (13)	0.0219 (11)	−0.0028 (10)	0.0006 (9)	0.0025 (10)
C7	0.0254 (10)	0.0299 (11)	0.0236 (11)	−0.0002 (8)	0.0008 (9)	−0.0018 (8)
C8	0.0407 (13)	0.0366 (13)	0.0248 (12)	−0.0039 (10)	0.0014 (10)	−0.0085 (9)
C9	0.0447 (13)	0.0304 (11)	0.0222 (11)	−0.0059 (10)	−0.0001 (10)	−0.0018 (9)
C10	0.0406 (13)	0.0310 (11)	0.0344 (13)	0.0018 (10)	−0.0080 (11)	−0.0028 (10)
C11	0.0420 (16)	0.063 (2)	0.0453 (17)	−0.0029 (13)	−0.0034 (13)	0.0025 (14)
C12	0.0210 (9)	0.0268 (10)	0.0304 (12)	−0.0022 (7)	−0.0007 (8)	0.0011 (8)
C13	0.0208 (8)	0.0308 (9)	0.0217 (9)	0.0004 (7)	0.0018 (10)	0.0032 (10)
C14	0.0257 (11)	0.0374 (12)	0.0291 (13)	0.0000 (9)	−0.0001 (9)	−0.0029 (10)
C15	0.0309 (12)	0.0396 (12)	0.0281 (12)	−0.0073 (10)	−0.0040 (10)	−0.0013 (10)
C16	0.0247 (10)	0.0437 (13)	0.0334 (12)	−0.0024 (9)	−0.0049 (9)	0.0081 (10)
C17	0.0233 (9)	0.0394 (11)	0.0313 (12)	0.0063 (8)	0.0006 (10)	0.0073 (11)
C18	0.0243 (9)	0.0276 (10)	0.0259 (12)	0.0014 (8)	−0.0006 (8)	0.0053 (7)
C19	0.0340 (12)	0.0242 (11)	0.0551 (16)	0.0060 (9)	0.0026 (11)	−0.0012 (11)
C20	0.0383 (13)	0.0314 (13)	0.0624 (19)	−0.0006 (10)	0.0173 (13)	−0.0144 (12)
C21	0.092 (3)	0.068 (2)	0.052 (2)	−0.012 (2)	0.011 (2)	−0.0042 (17)
C22	0.214 (8)	0.085 (4)	0.053 (3)	0.014 (4)	0.030 (4)	−0.004 (2)

Geometric parameters (Å, º)

Co1—Cl1	2.2423 (6)	C17—C18	1.396 (3)
Co1—Cl2	2.2516 (6)	C19—C20	1.521 (4)
Co1—N1	2.014 (2)	C21—C22	1.424 (7)
Co1—N3	2.0021 (16)	C1—H1	0.9303
O1—C9	1.417 (3)	C3—H3	0.9304
O1—C10	1.433 (3)	C4—H4	0.9294
O2—C20	1.395 (4)	C5—H5	0.9297
O2—C21	1.447 (4)	C6—H6	0.9294
N1—C1	1.315 (3)	C8—H8A	0.9694
N1—C2	1.392 (3)	C8—H8B	0.9700
N2—C1	1.343 (3)	C9—H9A	0.9704
N2—C7	1.383 (3)	C9—H9B	0.9704
N2—C8	1.456 (3)	C10—H10A	0.9703
N3—C12	1.307 (3)	C10—H10B	0.9699
N3—C13	1.394 (2)	C11—H11A	0.9590
N4—C12	1.345 (3)	C11—H11B	0.9602
N4—C18	1.387 (3)	C11—H11C	0.9605
N4—C19	1.455 (3)	C12—H12	0.9304
C2—C3	1.396 (3)	C14—H14	0.9296
C2—C7	1.399 (3)	C15—H15	0.9298
C3—C4	1.381 (4)	C16—H16	0.9302
C4—C5	1.409 (4)	C17—H17	0.9298
C5—C6	1.372 (3)	C19—H19A	0.9697
C6—C7	1.397 (3)	C19—H19B	0.9703
C8—C9	1.506 (4)	C20—H20A	0.9703
C10—C11	1.498 (4)	C20—H20B	0.9705
C13—C14	1.389 (3)	C21—H21A	0.9703
C13—C18	1.399 (3)	C21—H21B	0.9691
C14—C15	1.387 (3)	C22—H22A	0.9602
C15—C16	1.395 (3)	C22—H22B	0.9594
C16—C17	1.368 (3)	C22—H22C	0.9598
Co1···C16^i	3.894 (2)	C18···H20B	3.0256
Co1···H3	3.3078	C19···H17	3.0553
Co1···H14	3.2383	C20···H22B	2.8742
Co1···H16^i	3.1583	C21···H10B^vii	2.9227
Cl1···N1	3.466 (2)	C22···H20A	2.8790
Cl1···N3	3.3617 (17)	H1···H8A	2.5446
Cl1···C3	3.622 (3)	H3···Co1	3.3078
Cl1···C12	3.546 (2)	H3···Cl1	2.9154
Cl1···C8^ii	3.340 (3)	H3···C17^iii	3.0261
Cl2···C16^i	3.591 (3)	H3···H17^iii	2.4893
Cl2···N1	3.4726 (19)	H4···C16^iii	2.9052
Cl2···N3	3.4284 (17)	H5···Cl1^xiii	3.0301
Cl1···H8A^ii	3.0022	H6···C8	3.0057
Cl1···H8B^ii	2.9345	H6···H8B	2.5922
Cl1···H3	2.9154	H8A···H1	2.5446
Cl1···H19A^iii	2.9181	H8A···Cl1^viii	3.0022
Cl1···H12	3.0678	H8A···H20A^vi	2.4323
Cl1···H5^iv	3.0301	H8B···C6	2.9727
Cl1···H17^iii	2.8029	H8B···H6	2.5922
Cl2···H14	3.0312	H8B···Cl1^viii	2.9345
Cl2···H19B^v	3.0869	H9A···C7	2.9941
Cl2···H12^v	3.0629	H9A···H10B	2.4129
Cl2···H16^i	2.7970	H9A···C17^ix	2.9270
O1···N2	2.894 (3)	H9A···H20B^ix	2.4330
O1···C1	3.257 (3)	H9B···H10A	2.3365
O1···C20^vi	3.356 (3)	H9B···C15^ix	3.0750
O2···N4	2.888 (3)	H9B···C16^ix	2.9843
O2···C12	3.291 (3)	H10A···H9B	2.3365
O1···H20A^vi	2.5130	H10A···C13^ix	2.9456
O2···H10B^vii	2.6152	H10A···H19B^vi	2.3922
N1···Cl1	3.466 (2)	H10B···H9A	2.4129
N1···Cl2	3.4726 (19)	H10B···O2^ix	2.6152
N1···N3	3.220 (3)	H10B···C12^ix	3.0999
N2···O1	2.894 (3)	H10B···C21^ix	2.9227
N3···Cl1	3.3617 (17)	H11B···C15	2.9264
N3···Cl2	3.4284 (17)	H12···Cl1	3.0678
N3···N1	3.220 (3)	H12···Cl2^xiv	3.0629
N4···O2	2.888 (3)	H12···H19B	2.5086
C1···O1	3.257 (3)	H14···Co1	3.2383
C3···Cl1	3.622 (3)	H14···Cl2	3.0312
C8···Cl1^viii	3.340 (3)	H16···Co1^x	3.1583
C9···C17^ix	3.510 (3)	H16···Cl2^x	2.7970
C10···C13^ix	3.576 (4)	H17···C19	3.0553
C12···O2	3.291 (3)	H17···Cl1^xii	2.8029
C13···C10^vii	3.576 (4)	H17···H3^xii	2.4893
C16···Cl2^x	3.591 (3)	H19A···C17	3.0447
C16···Co1^x	3.894 (2)	H19A···Cl1^xii	2.9181
C17···C9^vii	3.510 (3)	H19B···Cl2^xiv	3.0869
C20···O1^xi	3.356 (3)	H19B···H12	2.5086
C6···H8B	2.9727	H19B···H10A^xi	2.3922
C7···H9A	2.9941	H20A···C22	2.8790
C8···H6	3.0057	H20A···H22B	2.3857
C8···H20A^vi	3.0905	H20A···O1^xi	2.5130
C9···H20A^vi	2.9147	H20A···C8^xi	3.0905
C12···H10B^vii	3.0999	H20A···C9^xi	2.9147
C13···H10A^vii	2.9456	H20A···H8A^xi	2.4323
C15···H9B^vii	3.0750	H20B···C18	3.0256
C15···H11B	2.9264	H20B···H21A	2.3598
C16···H9B^vii	2.9843	H20B···H9A^vii	2.4330
C16···H4^xii	2.9052	H21A···H20B	2.3598
C17···H9A^vii	2.9270	H22B···C20	2.8742
C17···H3^xii	3.0261	H22B···H20A	2.3857
C17···H19A	3.0447
Cl1—Co1—Cl2	119.84 (2)	C6—C5—H5	119.14
Cl1—Co1—N1	108.89 (5)	C5—C6—H6	121.87
Cl1—Co1—N3	104.61 (5)	C7—C6—H6	121.84
Cl2—Co1—N1	108.86 (5)	N2—C8—H8A	109.29
Cl2—Co1—N3	107.27 (5)	N2—C8—H8B	109.29
N1—Co1—N3	106.57 (7)	C9—C8—H8A	109.27
C9—O1—C10	111.09 (18)	C9—C8—H8B	109.22
C20—O2—C21	116.5 (3)	H8A—C8—H8B	107.88
Co1—N1—C1	125.78 (15)	O1—C9—H9A	109.92
Co1—N1—C2	128.56 (14)	O1—C9—H9B	109.98
C1—N1—C2	105.45 (19)	C8—C9—H9A	109.98
C1—N2—C7	107.2 (2)	C8—C9—H9B	110.00
C1—N2—C8	126.5 (2)	H9A—C9—H9B	108.34
C7—N2—C8	126.1 (2)	O1—C10—H10A	109.92
Co1—N3—C12	127.09 (14)	O1—C10—H10B	109.95
Co1—N3—C13	126.85 (14)	C11—C10—H10A	109.92
C12—N3—C13	106.04 (17)	C11—C10—H10B	109.91
C12—N4—C18	106.91 (17)	H10A—C10—H10B	108.34
C12—N4—C19	125.62 (19)	C10—C11—H11A	109.52
C18—N4—C19	127.26 (19)	C10—C11—H11B	109.45
N1—C1—N2	113.1 (2)	C10—C11—H11C	109.53
N1—C2—C3	131.1 (2)	H11A—C11—H11B	109.44
N1—C2—C7	108.79 (19)	H11A—C11—H11C	109.48
C3—C2—C7	120.2 (2)	H11B—C11—H11C	109.40
C2—C3—C4	117.2 (2)	N3—C12—H12	123.48
C3—C4—C5	121.9 (2)	N4—C12—H12	123.49
C4—C5—C6	121.6 (2)	C13—C14—H14	121.48
C5—C6—C7	116.3 (2)	C15—C14—H14	121.43
N2—C7—C2	105.5 (2)	C14—C15—H15	119.40
N2—C7—C6	131.7 (2)	C16—C15—H15	119.35
C2—C7—C6	122.8 (2)	C15—C16—H16	118.74
N2—C8—C9	111.8 (2)	C17—C16—H16	118.75
O1—C9—C8	108.63 (19)	C16—C17—H17	121.79
O1—C10—C11	108.8 (2)	C18—C17—H17	121.85
N3—C12—N4	113.03 (19)	N4—C19—H19A	109.23
N3—C13—C14	130.84 (19)	N4—C19—H19B	109.18
N3—C13—C18	108.27 (19)	C20—C19—H19A	109.13
C14—C13—C18	120.87 (18)	C20—C19—H19B	109.20
C13—C14—C15	117.1 (2)	H19A—C19—H19B	107.85
C14—C15—C16	121.3 (2)	O2—C20—H20A	109.86
C15—C16—C17	122.5 (2)	O2—C20—H20B	109.88
C16—C17—C18	116.4 (2)	C19—C20—H20A	109.93
N4—C18—C13	105.75 (18)	C19—C20—H20B	109.92
N4—C18—C17	132.3 (2)	H20A—C20—H20B	108.32
C13—C18—C17	121.9 (2)	O2—C21—H21A	108.18
N4—C19—C20	112.2 (2)	O2—C21—H21B	108.15
O2—C20—C19	108.9 (2)	C22—C21—H21A	108.24
O2—C21—C22	116.3 (4)	C22—C21—H21B	108.29
N1—C1—H1	123.46	H21A—C21—H21B	107.36
N2—C1—H1	123.46	C21—C22—H22A	109.42
C2—C3—H3	121.46	C21—C22—H22B	109.54
C4—C3—H3	121.36	C21—C22—H22C	109.54
C3—C4—H4	119.00	H22A—C22—H22B	109.43
C5—C4—H4	119.07	H22A—C22—H22C	109.35
C4—C5—H5	119.26	H22B—C22—H22C	109.54
Cl1—Co1—N1—C1	150.71 (18)	Co1—N3—C13—C14	2.8 (4)
Cl2—Co1—N1—C1	18.5 (2)	Co1—N3—C12—N4	178.71 (15)
N3—Co1—N1—C1	−96.95 (19)	C12—N4—C18—C13	−0.4 (2)
Cl1—Co1—N1—C2	−35.4 (2)	C18—N4—C19—C20	75.7 (3)
Cl2—Co1—N1—C2	−167.65 (17)	C19—N4—C12—N3	175.2 (2)
N3—Co1—N1—C2	77.0 (2)	C19—N4—C18—C13	−175.3 (2)
Cl1—Co1—N3—C12	7.77 (19)	C18—N4—C12—N3	0.2 (3)
Cl2—Co1—N3—C12	136.05 (18)	C19—N4—C18—C17	4.6 (4)
N1—Co1—N3—C12	−107.48 (19)	C12—N4—C19—C20	−98.3 (3)
Cl1—Co1—N3—C13	−173.82 (17)	C12—N4—C18—C17	179.5 (3)
Cl2—Co1—N3—C13	−45.54 (19)	C7—C2—C3—C4	−0.5 (4)
N1—Co1—N3—C13	70.93 (19)	N1—C2—C3—C4	179.7 (2)
C10—O1—C9—C8	−179.15 (18)	N1—C2—C7—N2	0.2 (2)
C9—O1—C10—C11	175.9 (2)	C3—C2—C7—N2	−179.7 (2)
C21—O2—C20—C19	−176.8 (3)	N1—C2—C7—C6	−179.7 (2)
C20—O2—C21—C22	−75.5 (6)	C3—C2—C7—C6	0.4 (4)
Co1—N1—C2—C7	−175.23 (15)	C2—C3—C4—C5	0.0 (4)
C1—N1—C2—C3	179.5 (3)	C3—C4—C5—C6	0.6 (4)
C2—N1—C1—N2	0.4 (3)	C4—C5—C6—C7	−0.7 (4)
C1—N1—C2—C7	−0.4 (2)	C5—C6—C7—N2	−179.7 (2)
Co1—N1—C1—N2	175.50 (15)	C5—C6—C7—C2	0.2 (4)
Co1—N1—C2—C3	4.6 (4)	N2—C8—C9—O1	−65.5 (2)
C1—N2—C7—C6	180.0 (2)	N3—C13—C18—C17	−179.5 (2)
C8—N2—C7—C2	174.2 (2)	C14—C13—C18—N4	178.8 (2)
C1—N2—C7—C2	0.1 (2)	C18—C13—C14—C15	0.6 (3)
C7—N2—C1—N1	−0.4 (3)	C14—C13—C18—C17	−1.0 (4)
C8—N2—C1—N1	−174.4 (2)	N3—C13—C14—C15	178.6 (2)
C7—N2—C8—C9	−77.8 (3)	N3—C13—C18—N4	0.4 (3)
C1—N2—C8—C9	95.2 (3)	C13—C14—C15—C16	−0.2 (4)
C8—N2—C7—C6	−6.0 (4)	C14—C15—C16—C17	0.2 (4)
C12—N3—C13—C18	−0.3 (3)	C15—C16—C17—C18	−0.6 (4)
Co1—N3—C13—C18	−178.95 (15)	C16—C17—C18—N4	−178.8 (2)
C13—N3—C12—N4	0.0 (3)	C16—C17—C18—C13	1.0 (4)
C12—N3—C13—C14	−178.5 (3)	N4—C19—C20—O2	63.7 (3)

Symmetry codes: (i) x+1/2, −y, z; (ii) −x+1, −y, z+1/2; (iii) x+1/2, −y+1, z; (iv) −x+1, −y+1, z+1/2; (v) x, y−1, z; (vi) −x+1/2, y−1, z−1/2; (vii) −x+1/2, y, z+1/2; (viii) −x+1, −y, z−1/2; (ix) −x+1/2, y, z−1/2; (x) x−1/2, −y, z; (xi) −x+1/2, y+1, z+1/2; (xii) x−1/2, −y+1, z; (xiii) −x+1, −y+1, z−1/2; (xiv) x, y+1, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···Cl2^x	0.93	2.80	3.591 (3)	144
C17—H17···Cl1^xii	0.93	2.80	3.717 (2)	168
C20—H20A···O1^xi	0.97	2.51	3.356 (3)	145

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