{2-[2-(1H-1,3-Benzimidazol-2-yl)ethyl­imino­meth­yl]-2,4-dibromo­phenolato}(1,10-phenanthroline)copper(II) tetra­fluoro­borate

Qiu, X.-H.; Zhao, J.; Tong, X.-L.

doi:10.1107/S1600536806009883

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{2-[2-(1H-1,3-Benzimidazol-2-yl)ethyliminomethyl]-2,4-dibromophenolato}(1,10-phenanthroline)copper(II) tetrafluoroborate

X.-H. Qiu, J. Zhao and X.-L. Tong

In the title compound, [Cu(C₁₈H₁₂Br₂N₃O)(C₁₀H₈N₂)]BF₄, the Cu atom is pentacoordinated by three atoms, viz. N, N and O of the tridentate 2-[2-(1H-1,3-benzimidazol-2-yl)ethyliminomethyl]-2,4-dibromophenolate ligand and two N atoms of the 1,10-phenanthroline ligand. The Cu coordination geometry is highly distorted trigonal bipyramidal, with Cu—O and Cu—N bond lengths of 1.916 (3) and 1.954 (4)–2.212 (4) Å, respectively. The axial positions are occupied by two N atoms which form an N—Cu—N angle of 170.29 (16)°.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806009883/cv2011sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806009883/cv2011Isup2.hkl Contains datablock I

CCDC reference: 605028

checkCIF report

Key indicators

Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.008 Å
Disorder in solvent or counterion
R factor = 0.047
wR factor = 0.119
Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         B1
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      44.00 Perc.
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br1    ..  F4      ..       3.27 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br2    ..  F4'     ..       3.21 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          6
            N4  -CU1 -N1  -C7     65.50  1.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         10
            N4  -CU1 -N1  -C8   -118.50  0.90   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         22
            N1  -CU1 -N4  -C17  -118.80  0.90   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         26
            N1  -CU1 -N4  -C28    61.30  1.00   1.555   1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      25.40 Deg.
              F2'  -B1   -F2      1.555   1.555   1.555

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

   2 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
   1 ALERT type 3 Indicator that the structure quality may be low
   7 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

{2-[2-(1H-1,3-Benzimidazol-2-yl)ethyliminomethyl]-2,4-dibromophenolato}(1,10- phenanthroline)copper(II) tetrafluoroborate top

Crystal data top

[Cu(C₁₈H₁₂Br₂N₃O)(C₁₀H₈N₂)]BF₄	F(000) = 2968
M_r = 752.66	D_x = 1.789 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 25.568 (3) Å	Cell parameters from 4857 reflections
b = 15.730 (2) Å	θ = 2.4–26.5°
c = 16.664 (2) Å	µ = 3.70 mm⁻¹
β = 123.520 (2)°	T = 294 K
V = 5587.5 (12) Å³	Block, green
Z = 8	0.24 × 0.22 × 0.20 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	5882 independent reflections
Radiation source: fine-focus sealed tube	3801 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
φ and ω scans	θ_max = 26.7°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −32→31
T_min = 0.427, T_max = 0.477	k = −15→19
15693 measured reflections	l = −18→21

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0425P)² + 19.5623P] where P = (F_o² + 2F_c²)/3
5882 reflections	(Δ/σ)_max = 0.002
417 parameters	Δρ_max = 0.88 e Å⁻³
86 restraints	Δρ_min = −0.62 e Å⁻³

Special details top

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

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

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cu1	0.10403 (3)	0.67162 (4)	0.52121 (4)	0.04659 (17)
Br1	0.23374 (3)	0.65030 (4)	0.86750 (4)	0.0677 (2)
Br2	0.09597 (3)	0.91474 (4)	0.89474 (5)	0.0823 (2)
O1	0.14897 (14)	0.68687 (19)	0.6578 (2)	0.0456 (8)
N1	0.05974 (17)	0.7794 (2)	0.4971 (3)	0.0447 (9)
N2	0.13553 (17)	0.7097 (2)	0.4302 (3)	0.0438 (9)
N3	0.15116 (19)	0.7998 (3)	0.3429 (3)	0.0548 (11)
H3A	0.1472	0.8445	0.3102	0.048 (14)*
N4	0.13924 (16)	0.5528 (2)	0.5509 (3)	0.0435 (9)
N5	0.01907 (17)	0.5953 (2)	0.4245 (3)	0.0458 (9)
C1	0.13723 (19)	0.7397 (3)	0.7054 (3)	0.0385 (10)
C2	0.1700 (2)	0.7338 (3)	0.8066 (3)	0.0415 (10)
C3	0.1585 (2)	0.7854 (3)	0.8615 (3)	0.0493 (12)
H3	0.1813	0.7792	0.9280	0.059*
C4	0.1122 (2)	0.8473 (3)	0.8159 (4)	0.0542 (13)
C5	0.0806 (2)	0.8593 (3)	0.7188 (4)	0.0509 (12)
H5	0.0512	0.9028	0.6899	0.061*
C6	0.0920 (2)	0.8064 (3)	0.6622 (3)	0.0413 (10)
C7	0.0581 (2)	0.8241 (3)	0.5602 (3)	0.0459 (11)
H7	0.0327	0.8722	0.5382	0.055*
C8	0.0289 (2)	0.8149 (3)	0.3996 (3)	0.0558 (13)
H8A	0.0003	0.8598	0.3911	0.067*
H8B	0.0049	0.7709	0.3524	0.067*
C9	0.0780 (2)	0.8500 (3)	0.3846 (4)	0.0551 (13)
H9A	0.0569	0.8791	0.3230	0.066*
H9B	0.1029	0.8918	0.4342	0.066*
C10	0.1210 (2)	0.7850 (3)	0.3864 (3)	0.0462 (11)
C11	0.1897 (2)	0.7313 (3)	0.3594 (3)	0.0488 (12)
C12	0.2312 (3)	0.7160 (4)	0.3321 (4)	0.0654 (15)
H12	0.2365	0.7543	0.2947	0.079*
C13	0.2639 (2)	0.6412 (4)	0.3636 (4)	0.0638 (15)
H13	0.2931	0.6293	0.3484	0.077*
C14	0.2551 (2)	0.5827 (4)	0.4169 (4)	0.0586 (14)
H14	0.2779	0.5324	0.4361	0.070*
C15	0.2127 (2)	0.5981 (3)	0.4423 (4)	0.0549 (13)
H15	0.2064	0.5583	0.4774	0.066*
C16	0.1797 (2)	0.6747 (3)	0.4140 (3)	0.0444 (11)
C17	0.1974 (2)	0.5318 (3)	0.6213 (3)	0.0534 (13)
H17	0.2241	0.5740	0.6629	0.064*
C18	0.2196 (3)	0.4490 (4)	0.6346 (4)	0.0645 (15)
H18	0.2609	0.4368	0.6838	0.077*
C19	0.1812 (3)	0.3858 (4)	0.5759 (5)	0.0708 (16)
H19	0.1961	0.3305	0.5839	0.085*
C20	0.1188 (3)	0.4051 (3)	0.5030 (4)	0.0552 (13)
C21	0.0733 (3)	0.3429 (4)	0.4393 (5)	0.0772 (18)
H21	0.0854	0.2863	0.4441	0.093*
C22	0.0140 (3)	0.3651 (4)	0.3734 (5)	0.0758 (18)
H22	−0.0139	0.3238	0.3318	0.091*
C23	−0.0078 (3)	0.4503 (3)	0.3651 (4)	0.0576 (13)
C24	−0.0711 (3)	0.4759 (4)	0.3034 (4)	0.0711 (17)
H24	−0.1015	0.4370	0.2614	0.085*
C25	−0.0871 (3)	0.5576 (4)	0.3059 (4)	0.0699 (17)
H25	−0.1287	0.5747	0.2668	0.084*
C26	−0.0414 (2)	0.6155 (4)	0.3669 (4)	0.0564 (13)
H26	−0.0534	0.6711	0.3677	0.068*
C27	0.0351 (2)	0.5135 (3)	0.4242 (3)	0.0438 (11)
C28	0.0995 (2)	0.4899 (3)	0.4932 (3)	0.0432 (11)
B1	0.1166 (2)	0.0710 (3)	0.6418 (4)	0.0575 (16)
F1	0.1245 (4)	0.0580 (3)	0.7288 (4)	0.109 (3)	0.751 (9)
F2	0.1169 (4)	0.1564 (3)	0.6279 (6)	0.094 (2)	0.751 (9)
F3	0.0635 (2)	0.0363 (3)	0.5715 (5)	0.123 (3)	0.751 (9)
F4	0.1658 (3)	0.0328 (5)	0.6455 (6)	0.128 (3)	0.751 (9)
F1'	0.1728 (6)	0.0813 (12)	0.7247 (11)	0.137 (9)	0.249 (9)
F2'	0.0955 (9)	0.1432 (8)	0.5904 (13)	0.094 (8)	0.249 (9)
F3'	0.0752 (8)	0.0470 (10)	0.6661 (15)	0.102 (7)	0.249 (9)
F4'	0.1186 (9)	0.0072 (8)	0.5893 (11)	0.095 (6)	0.249 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0457 (3)	0.0442 (3)	0.0331 (3)	0.0139 (3)	0.0113 (3)	0.0015 (2)
Br1	0.0618 (4)	0.0643 (4)	0.0403 (3)	0.0188 (3)	0.0051 (2)	−0.0009 (2)
Br2	0.1006 (5)	0.0759 (4)	0.0750 (4)	0.0081 (3)	0.0515 (4)	−0.0234 (3)
O1	0.0393 (17)	0.0478 (18)	0.0340 (16)	0.0121 (14)	0.0104 (14)	−0.0046 (14)
N1	0.041 (2)	0.045 (2)	0.038 (2)	0.0157 (17)	0.0152 (18)	0.0054 (17)
N2	0.044 (2)	0.044 (2)	0.036 (2)	0.0020 (17)	0.0172 (18)	−0.0011 (16)
N3	0.060 (3)	0.047 (2)	0.053 (3)	−0.006 (2)	0.029 (2)	0.004 (2)
N4	0.037 (2)	0.049 (2)	0.034 (2)	0.0105 (17)	0.0125 (17)	0.0017 (17)
N5	0.036 (2)	0.050 (2)	0.041 (2)	0.0005 (17)	0.0144 (18)	0.0031 (17)
C1	0.031 (2)	0.036 (2)	0.039 (2)	−0.0026 (18)	0.013 (2)	−0.0016 (19)
C2	0.035 (2)	0.037 (2)	0.038 (2)	−0.0022 (19)	0.011 (2)	−0.0034 (19)
C3	0.057 (3)	0.045 (3)	0.042 (3)	−0.009 (2)	0.024 (2)	−0.008 (2)
C4	0.059 (3)	0.048 (3)	0.058 (3)	−0.005 (2)	0.034 (3)	−0.015 (2)
C5	0.048 (3)	0.043 (3)	0.053 (3)	0.005 (2)	0.022 (3)	−0.003 (2)
C6	0.037 (2)	0.036 (2)	0.041 (3)	−0.0023 (18)	0.016 (2)	−0.0055 (19)
C7	0.036 (2)	0.037 (2)	0.052 (3)	0.0112 (19)	0.017 (2)	0.004 (2)
C8	0.048 (3)	0.059 (3)	0.042 (3)	0.017 (2)	0.013 (2)	0.008 (2)
C9	0.058 (3)	0.046 (3)	0.043 (3)	0.011 (2)	0.017 (2)	0.008 (2)
C10	0.042 (3)	0.047 (3)	0.036 (2)	−0.003 (2)	0.013 (2)	−0.001 (2)
C11	0.041 (3)	0.054 (3)	0.043 (3)	−0.012 (2)	0.018 (2)	−0.010 (2)
C12	0.061 (4)	0.074 (4)	0.068 (4)	−0.018 (3)	0.039 (3)	−0.009 (3)
C13	0.047 (3)	0.077 (4)	0.069 (4)	−0.014 (3)	0.033 (3)	−0.020 (3)
C14	0.042 (3)	0.063 (3)	0.060 (3)	0.001 (2)	0.021 (3)	−0.014 (3)
C15	0.055 (3)	0.054 (3)	0.054 (3)	0.005 (2)	0.029 (3)	−0.002 (2)
C16	0.038 (2)	0.048 (3)	0.036 (2)	−0.008 (2)	0.013 (2)	−0.011 (2)
C17	0.046 (3)	0.054 (3)	0.043 (3)	0.009 (2)	0.013 (2)	0.000 (2)
C18	0.060 (3)	0.064 (4)	0.056 (3)	0.028 (3)	0.024 (3)	0.016 (3)
C19	0.082 (4)	0.047 (3)	0.087 (4)	0.023 (3)	0.049 (4)	0.007 (3)
C20	0.062 (3)	0.045 (3)	0.065 (3)	0.005 (2)	0.039 (3)	−0.001 (2)
C21	0.093 (5)	0.046 (3)	0.107 (5)	−0.004 (3)	0.064 (5)	−0.017 (3)
C22	0.079 (4)	0.062 (4)	0.092 (5)	−0.028 (3)	0.051 (4)	−0.029 (3)
C23	0.058 (3)	0.063 (3)	0.056 (3)	−0.020 (3)	0.034 (3)	−0.010 (3)
C24	0.053 (4)	0.087 (5)	0.061 (4)	−0.033 (3)	0.024 (3)	−0.012 (3)
C25	0.038 (3)	0.094 (5)	0.055 (3)	−0.010 (3)	0.011 (3)	0.014 (3)
C26	0.041 (3)	0.065 (3)	0.049 (3)	0.003 (2)	0.017 (2)	0.014 (2)
C27	0.038 (3)	0.054 (3)	0.039 (3)	−0.006 (2)	0.022 (2)	−0.003 (2)
C28	0.048 (3)	0.041 (3)	0.042 (3)	−0.002 (2)	0.026 (2)	−0.003 (2)
B1	0.046 (4)	0.067 (4)	0.057 (4)	0.006 (3)	0.027 (3)	−0.005 (3)
F1	0.201 (7)	0.068 (3)	0.083 (4)	−0.016 (4)	0.094 (4)	−0.014 (3)
F2	0.120 (5)	0.068 (3)	0.097 (5)	−0.013 (3)	0.062 (4)	−0.001 (3)
F3	0.074 (4)	0.083 (4)	0.118 (5)	−0.006 (3)	−0.006 (3)	−0.010 (3)
F4	0.094 (4)	0.149 (5)	0.162 (6)	0.049 (4)	0.084 (4)	0.022 (4)
F1'	0.109 (11)	0.131 (11)	0.136 (12)	0.012 (8)	0.044 (8)	−0.023 (8)
F2'	0.097 (11)	0.103 (11)	0.082 (11)	0.020 (8)	0.049 (8)	0.020 (7)
F3'	0.105 (9)	0.092 (9)	0.132 (11)	0.028 (7)	0.081 (8)	0.036 (8)
F4'	0.119 (11)	0.091 (9)	0.086 (9)	0.007 (7)	0.064 (8)	−0.015 (7)

Geometric parameters (Å, º) top

Cu1—O1	1.916 (3)	C12—C13	1.369 (8)
Cu1—N1	1.954 (4)	C12—H12	0.9300
Cu1—N4	2.014 (4)	C13—C14	1.381 (8)
Cu1—N2	2.158 (4)	C13—H13	0.9300
Cu1—N5	2.212 (4)	C14—C15	1.384 (7)
Br1—C2	1.894 (4)	C14—H14	0.9300
Br2—C4	1.904 (5)	C15—C16	1.395 (7)
O1—C1	1.293 (5)	C15—H15	0.9300
N1—C7	1.284 (6)	C17—C18	1.389 (7)
N1—C8	1.470 (6)	C17—H17	0.9300
N2—C10	1.332 (6)	C18—C19	1.359 (8)
N2—C16	1.410 (6)	C18—H18	0.9300
N3—C10	1.340 (6)	C19—C20	1.405 (8)
N3—C11	1.381 (6)	C19—H19	0.9300
N3—H3A	0.8600	C20—C28	1.400 (6)
N4—C17	1.330 (6)	C20—C21	1.440 (8)
N4—C28	1.363 (6)	C21—C22	1.338 (8)
N5—C26	1.331 (6)	C21—H21	0.9300
N5—C27	1.351 (6)	C22—C23	1.428 (8)
C1—C2	1.413 (6)	C22—H22	0.9300
C1—C6	1.428 (6)	C23—C27	1.403 (6)
C2—C3	1.369 (6)	C23—C24	1.415 (8)
C3—C4	1.391 (7)	C24—C25	1.357 (9)
C3—H3	0.9300	C24—H24	0.9300
C4—C5	1.365 (7)	C25—C26	1.384 (8)
C5—C6	1.403 (6)	C25—H25	0.9300
C5—H5	0.9300	C26—H26	0.9300
C6—C7	1.446 (6)	C27—C28	1.443 (6)
C7—H7	0.9300	B1—F3	1.326 (6)
C8—C9	1.513 (7)	B1—F1'	1.343 (9)
C8—H8A	0.9700	B1—F2'	1.343 (9)
C8—H8B	0.9700	B1—F4'	1.351 (9)
C9—C10	1.489 (7)	B1—F2	1.363 (7)
C9—H9A	0.9700	B1—F4	1.364 (6)
C9—H9B	0.9700	B1—F1	1.364 (6)
C11—C12	1.388 (7)	B1—F3'	1.378 (9)
C11—C16	1.392 (7)

O1—Cu1—N1	91.99 (14)	C13—C14—H14	119.5
O1—Cu1—N4	86.03 (13)	C15—C14—H14	119.5
N1—Cu1—N4	170.29 (16)	C14—C15—C16	118.4 (5)
O1—Cu1—N2	126.07 (14)	C14—C15—H15	120.8
N1—Cu1—N2	90.77 (15)	C16—C15—H15	120.8
N4—Cu1—N2	98.08 (15)	C11—C16—C15	118.6 (5)
O1—Cu1—N5	129.58 (14)	C11—C16—N2	109.3 (4)
N1—Cu1—N5	95.57 (15)	C15—C16—N2	132.1 (5)
N4—Cu1—N5	78.52 (14)	N4—C17—C18	122.3 (5)
N2—Cu1—N5	103.64 (14)	N4—C17—H17	118.9
C1—O1—Cu1	128.2 (3)	C18—C17—H17	118.9
C7—N1—C8	117.3 (4)	C19—C18—C17	120.0 (5)
C7—N1—Cu1	125.7 (3)	C19—C18—H18	120.0
C8—N1—Cu1	116.9 (3)	C17—C18—H18	120.0
C10—N2—C16	104.7 (4)	C18—C19—C20	119.3 (5)
C10—N2—Cu1	122.1 (3)	C18—C19—H19	120.3
C16—N2—Cu1	132.5 (3)	C20—C19—H19	120.3
C10—N3—C11	108.4 (4)	C28—C20—C19	117.7 (5)
C10—N3—H3A	125.8	C28—C20—C21	118.2 (5)
C11—N3—H3A	125.8	C19—C20—C21	124.1 (5)
C17—N4—C28	118.5 (4)	C22—C21—C20	121.0 (5)
C17—N4—Cu1	125.3 (3)	C22—C21—H21	119.5
C28—N4—Cu1	116.3 (3)	C20—C21—H21	119.5
C26—N5—C27	117.3 (4)	C21—C22—C23	122.0 (5)
C26—N5—Cu1	132.7 (4)	C21—C22—H22	119.0
C27—N5—Cu1	110.0 (3)	C23—C22—H22	119.0
O1—C1—C2	120.3 (4)	C27—C23—C24	116.5 (5)
O1—C1—C6	124.2 (4)	C27—C23—C22	119.0 (5)
C2—C1—C6	115.6 (4)	C24—C23—C22	124.5 (5)
C3—C2—C1	123.6 (4)	C25—C24—C23	119.3 (5)
C3—C2—Br1	119.4 (4)	C25—C24—H24	120.3
C1—C2—Br1	116.9 (3)	C23—C24—H24	120.3
C2—C3—C4	118.8 (5)	C24—C25—C26	120.0 (5)
C2—C3—H3	120.6	C24—C25—H25	120.0
C4—C3—H3	120.6	C26—C25—H25	120.0
C5—C4—C3	120.8 (5)	N5—C26—C25	123.1 (5)
C5—C4—Br2	121.9 (4)	N5—C26—H26	118.5
C3—C4—Br2	117.3 (4)	C25—C26—H26	118.5
C4—C5—C6	120.5 (4)	N5—C27—C23	123.8 (4)
C4—C5—H5	119.7	N5—C27—C28	117.2 (4)
C6—C5—H5	119.7	C23—C27—C28	118.9 (5)
C5—C6—C1	120.5 (4)	N4—C28—C20	122.2 (4)
C5—C6—C7	117.7 (4)	N4—C28—C27	117.0 (4)
C1—C6—C7	121.8 (4)	C20—C28—C27	120.7 (4)
N1—C7—C6	126.0 (4)	F3—B1—F1'	161.7 (9)
N1—C7—H7	117.0	F3—B1—F2'	85.9 (9)
C6—C7—H7	117.0	F1'—B1—F2'	112.3 (10)
N1—C8—C9	109.5 (4)	F3—B1—F4'	60.5 (8)
N1—C8—H8A	109.8	F1'—B1—F4'	110.8 (9)
C9—C8—H8A	109.8	F2'—B1—F4'	111.2 (9)
N1—C8—H8B	109.8	F3—B1—F2	110.7 (5)
C9—C8—H8B	109.8	F1'—B1—F2	87.3 (9)
H8A—C8—H8B	108.2	F2'—B1—F2	25.4 (9)
C10—C9—C8	114.6 (4)	F4'—B1—F2	128.1 (8)
C10—C9—H9A	108.6	F3—B1—F4	109.1 (5)
C8—C9—H9A	108.6	F1'—B1—F4	64.7 (8)
C10—C9—H9B	108.6	F2'—B1—F4	116.0 (10)
C8—C9—H9B	108.6	F4'—B1—F4	48.5 (7)
H9A—C9—H9B	107.6	F2—B1—F4	110.6 (6)
N2—C10—N3	112.4 (4)	F3—B1—F1	110.8 (6)
N2—C10—C9	127.1 (5)	F1'—B1—F1	58.6 (9)
N3—C10—C9	120.5 (4)	F2'—B1—F1	125.2 (9)
N3—C11—C12	131.3 (5)	F4'—B1—F1	122.7 (8)
N3—C11—C16	105.2 (4)	F2—B1—F1	108.5 (5)
C12—C11—C16	123.5 (5)	F4—B1—F1	107.1 (5)
C13—C12—C11	116.1 (5)	F3—B1—F3'	64.4 (9)
C13—C12—H12	122.0	F1'—B1—F3'	106.8 (9)
C11—C12—H12	122.0	F2'—B1—F3'	108.3 (9)
C12—C13—C14	122.4 (5)	F4'—B1—F3'	107.2 (9)
C12—C13—H13	118.8	F2—B1—F3'	113.3 (8)
C14—C13—H13	118.8	F4—B1—F3'	134.8 (8)
C13—C14—C15	120.9 (5)	F1—B1—F3'	48.3 (8)

N1—Cu1—O1—C1	15.1 (4)	Cu1—N2—C10—N3	172.6 (3)
N4—Cu1—O1—C1	−155.4 (4)	C16—N2—C10—C9	−177.4 (4)
N2—Cu1—O1—C1	107.5 (4)	Cu1—N2—C10—C9	−5.9 (6)
N5—Cu1—O1—C1	−83.8 (4)	C11—N3—C10—N2	−1.3 (5)
O1—Cu1—N1—C7	−12.6 (4)	C11—N3—C10—C9	177.3 (4)
N4—Cu1—N1—C7	65.5 (10)	C8—C9—C10—N2	−24.8 (7)
N2—Cu1—N1—C7	−138.7 (4)	C8—C9—C10—N3	156.8 (4)
N5—Cu1—N1—C7	117.5 (4)	C10—N3—C11—C12	−178.5 (5)
O1—Cu1—N1—C8	163.5 (3)	C10—N3—C11—C16	0.9 (5)
N4—Cu1—N1—C8	−118.5 (9)	N3—C11—C12—C13	178.2 (5)
N2—Cu1—N1—C8	37.4 (3)	C16—C11—C12—C13	−1.2 (7)
N5—Cu1—N1—C8	−66.4 (4)	C11—C12—C13—C14	1.8 (8)
O1—Cu1—N2—C10	−92.4 (4)	C12—C13—C14—C15	−0.8 (8)
N1—Cu1—N2—C10	0.6 (3)	C13—C14—C15—C16	−1.0 (7)
N4—Cu1—N2—C10	176.6 (3)	N3—C11—C16—C15	180.0 (4)
N5—Cu1—N2—C10	96.5 (3)	C12—C11—C16—C15	−0.5 (7)
O1—Cu1—N2—C16	76.4 (4)	N3—C11—C16—N2	−0.2 (5)
N1—Cu1—N2—C16	169.5 (4)	C12—C11—C16—N2	179.3 (4)
N4—Cu1—N2—C16	−14.5 (4)	C14—C15—C16—C11	1.6 (7)
N5—Cu1—N2—C16	−94.6 (4)	C14—C15—C16—N2	−178.1 (5)
O1—Cu1—N4—C17	−40.3 (4)	C10—N2—C16—C11	−0.5 (5)
N1—Cu1—N4—C17	−118.8 (9)	Cu1—N2—C16—C11	−170.7 (3)
N2—Cu1—N4—C17	85.6 (4)	C10—N2—C16—C15	179.3 (5)
N5—Cu1—N4—C17	−172.1 (4)	Cu1—N2—C16—C15	9.0 (7)
O1—Cu1—N4—C28	139.9 (3)	C28—N4—C17—C18	3.3 (7)
N1—Cu1—N4—C28	61.3 (10)	Cu1—N4—C17—C18	−176.6 (4)
N2—Cu1—N4—C28	−94.2 (3)	N4—C17—C18—C19	−1.3 (9)
N5—Cu1—N4—C28	8.1 (3)	C17—C18—C19—C20	−1.0 (9)
O1—Cu1—N5—C26	99.2 (5)	C18—C19—C20—C28	1.3 (8)
N1—Cu1—N5—C26	1.9 (5)	C18—C19—C20—C21	−177.4 (6)
N4—Cu1—N5—C26	174.1 (5)	C28—C20—C21—C22	−1.0 (9)
N2—Cu1—N5—C26	−90.2 (5)	C19—C20—C21—C22	177.8 (6)
O1—Cu1—N5—C27	−83.8 (3)	C20—C21—C22—C23	−2.3 (10)
N1—Cu1—N5—C27	179.0 (3)	C21—C22—C23—C27	3.6 (9)
N4—Cu1—N5—C27	−8.8 (3)	C21—C22—C23—C24	−173.6 (6)
N2—Cu1—N5—C27	86.8 (3)	C27—C23—C24—C25	−1.5 (8)
Cu1—O1—C1—C2	170.8 (3)	C22—C23—C24—C25	175.7 (6)
Cu1—O1—C1—C6	−9.2 (6)	C23—C24—C25—C26	1.5 (9)
O1—C1—C2—C3	−177.5 (4)	C27—N5—C26—C25	−2.0 (7)
C6—C1—C2—C3	2.4 (6)	Cu1—N5—C26—C25	174.9 (4)
O1—C1—C2—Br1	3.4 (6)	C24—C25—C26—N5	0.3 (9)
C6—C1—C2—Br1	−176.6 (3)	C26—N5—C27—C23	2.0 (7)
C1—C2—C3—C4	0.0 (7)	Cu1—N5—C27—C23	−175.6 (4)
Br1—C2—C3—C4	179.0 (4)	C26—N5—C27—C28	−174.2 (4)
C2—C3—C4—C5	−2.9 (7)	Cu1—N5—C27—C28	8.3 (5)
C2—C3—C4—Br2	177.8 (3)	C24—C23—C27—N5	−0.3 (7)
C3—C4—C5—C6	3.2 (8)	C22—C23—C27—N5	−177.7 (5)
Br2—C4—C5—C6	−177.5 (4)	C24—C23—C27—C28	175.8 (4)
C4—C5—C6—C1	−0.6 (7)	C22—C23—C27—C28	−1.6 (7)
C4—C5—C6—C7	−178.3 (4)	C17—N4—C28—C20	−2.9 (7)
O1—C1—C6—C5	177.8 (4)	Cu1—N4—C28—C20	176.9 (4)
C2—C1—C6—C5	−2.1 (6)	C17—N4—C28—C27	173.8 (4)
O1—C1—C6—C7	−4.5 (7)	Cu1—N4—C28—C27	−6.4 (5)
C2—C1—C6—C7	175.5 (4)	C19—C20—C28—N4	0.7 (7)
C8—N1—C7—C6	−171.5 (4)	C21—C20—C28—N4	179.5 (5)
Cu1—N1—C7—C6	4.5 (7)	C19—C20—C28—C27	−175.9 (5)
C5—C6—C7—N1	−175.5 (5)	C21—C20—C28—C27	2.9 (7)
C1—C6—C7—N1	6.8 (7)	N5—C27—C28—N4	−2.0 (6)
C7—N1—C8—C9	103.0 (5)	C23—C27—C28—N4	−178.4 (4)
Cu1—N1—C8—C9	−73.4 (5)	N5—C27—C28—C20	174.8 (4)
N1—C8—C9—C10	65.1 (5)	C23—C27—C28—C20	−1.6 (7)
C16—N2—C10—N3	1.1 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···F1′ⁱ	0.86	2.20	2.98 (2)	151
N3—H3A···F1ⁱ	0.86	1.91	2.766 (6)	171

Symmetry code: (i) x, −y+1, z−1/2.

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