Dibromo­{2,4-dichloro-6-[2-(diethyl­amino)ethyl­imino­meth­yl]phenolato}zinc(II)

In the title mononuclear zinc(II) complex, [ZnBr₂(C₁₃H₁₈Cl₂N₂O)], there are two independent complex mol­ecules in the asymmetric unit. Each Zn^II atom is four-coordinated by the imine N and phenolate O atoms of the Schiff base ligand, and by two Br atoms, forming a tetra­hedral geometry. In the crystal structure, the mol­ecules are linked through inter­molecular N—H...O and C—H...Br hydrogen bonds, forming a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.018 Å
• R factor = 0.066
• wR factor = 0.130
• Data-to-parameter ratio = 19.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        C12
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for         N2
PLAT341_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ...         18

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.06 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.77 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.74 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.44 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C9
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C10

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           27.50
           From the CIF: _reflns_number_total               7708
           Count of symmetry unique reflns         4105
           Completeness (_total/calc)            187.77%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      3603
           Fraction of Friedel pairs measured     0.878
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   3 ALERT level B = Potentially serious problem
   6 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
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Dibromo{2,4-dichloro-6-[2-(diethylamino)ethyliminomethyl]phenolato}zinc(II)

Crystal data

[ZnBr2(C13H18Cl2N2O)]	F(000) = 1008
Mr = 514.38	Dx = 1.912 Mg m^−3
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yc	Cell parameters from 2723 reflections
a = 7.687 (1) Å	θ = 2.3–25.1°
b = 19.102 (3) Å	µ = 6.14 mm^−1
c = 13.841 (2) Å	T = 298 K
β = 118.452 (3)°	Needle, light yellow
V = 1786.9 (4) Å^3	0.12 × 0.07 × 0.06 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	7708 independent reflections
Radiation source: fine-focus sealed tube	4594 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.075
ω scans	θmax = 27.5°, θmin = 1.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −9→9
Tmin = 0.515, Tmax = 0.695	k = −23→24
15186 measured reflections	l = −17→17

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)] = 0.066	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.130	w = 1/[σ^2(Fo^2)]
S = 0.94	(Δ/σ)max < 0.001
7708 reflections	Δρmax = 0.67 e Å^−3
389 parameters	Δρmin = −0.55 e Å^−3
4 restraints	Absolute structure: Flack (1983), 3653 Friedel pairs.
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.007 (13)

Special details

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
Zn1	−0.12680 (17)	0.39542 (7)	0.24197 (10)	0.0369 (3)
Zn2	0.09222 (17)	0.10895 (7)	0.82759 (10)	0.0383 (3)
Br1	−0.18874 (16)	0.29897 (6)	0.11886 (10)	0.0452 (3)
Br2	−0.29188 (19)	0.49459 (7)	0.13601 (11)	0.0584 (4)
Br3	0.10760 (16)	0.01440 (6)	0.94171 (9)	0.0480 (3)
Br4	−0.06958 (19)	0.20750 (7)	0.85011 (12)	0.0591 (4)
Cl1	−0.3263 (4)	0.31079 (17)	0.4985 (3)	0.0529 (9)
Cl2	0.4171 (5)	0.33573 (19)	0.8258 (3)	0.0692 (10)
Cl3	−0.3381 (4)	0.11551 (16)	0.4518 (3)	0.0571 (9)
Cl4	0.2253 (5)	0.23369 (16)	0.3827 (2)	0.0510 (8)
O1	−0.1720 (10)	0.3693 (4)	0.3616 (6)	0.045 (2)
O2	−0.0168 (10)	0.0856 (4)	0.6706 (6)	0.0383 (19)
N1	0.1607 (11)	0.4198 (4)	0.3328 (7)	0.029 (2)
N2	0.2025 (13)	0.3814 (5)	0.1227 (8)	0.043 (2)
N3	0.3650 (12)	0.1289 (4)	0.8474 (7)	0.034 (2)
N4	0.8008 (13)	0.0545 (5)	1.1022 (7)	0.036 (2)
C1	0.1666 (16)	0.3795 (6)	0.5009 (9)	0.041 (3)
C2	−0.0337 (16)	0.3637 (6)	0.4651 (9)	0.036 (3)
C3	−0.0790 (15)	0.3365 (5)	0.5449 (9)	0.035 (3)
C4	0.0501 (18)	0.3275 (6)	0.6509 (10)	0.044 (3)
H4	0.0087	0.3094	0.6990	0.053*
C5	0.2477 (16)	0.3456 (5)	0.6887 (9)	0.040 (3)
C6	0.3043 (16)	0.3712 (5)	0.6169 (9)	0.036 (3)
H6	0.4359	0.3840	0.6428	0.043*
C7	0.2491 (16)	0.4114 (5)	0.4388 (10)	0.038 (3)
H7	0.3784	0.4277	0.4778	0.045*
C8	0.2743 (17)	0.4571 (6)	0.2893 (10)	0.050 (3)
H8A	0.1924	0.4942	0.2414	0.060*
H8B	0.3875	0.4789	0.3501	0.060*
C9	0.344 (2)	0.4142 (8)	0.2290 (11)	0.072 (4)
H9A	0.4219	0.3767	0.2777	0.086*
H9B	0.4342	0.4427	0.2151	0.086*
C10	0.291 (2)	0.3269 (7)	0.0795 (14)	0.084 (5)
H10A	0.4058	0.3460	0.0769	0.101*
H10B	0.1948	0.3129	0.0058	0.101*
C11	0.353 (2)	0.2622 (7)	0.1585 (13)	0.079 (5)
H11A	0.4537	0.2759	0.2302	0.118*
H11B	0.4030	0.2259	0.1304	0.118*
H11C	0.2398	0.2451	0.1633	0.118*
C12	0.115 (3)	0.4387 (9)	0.0368 (14)	0.106 (6)
H12A	0.0727	0.4767	0.0672	0.127*
H12B	0.2190	0.4568	0.0228	0.127*
C13	−0.055 (3)	0.4179 (9)	−0.0700 (12)	0.108 (7)
H13A	−0.0113	0.3844	−0.1056	0.161*
H13B	−0.1062	0.4585	−0.1160	0.161*
H13C	−0.1562	0.3975	−0.0574	0.161*
C14	0.2400 (16)	0.1493 (5)	0.6516 (9)	0.036 (3)
C15	0.0379 (15)	0.1248 (5)	0.6090 (9)	0.036 (3)
C16	−0.0951 (15)	0.1392 (5)	0.5018 (10)	0.040 (3)
C17	−0.0448 (17)	0.1754 (5)	0.4317 (9)	0.040 (3)
H17	−0.1405	0.1872	0.3610	0.048*
C18	0.1553 (16)	0.1936 (5)	0.4706 (9)	0.034 (3)
C19	0.2912 (17)	0.1833 (5)	0.5790 (9)	0.037 (3)
H19	0.4201	0.1993	0.6048	0.045*
C20	0.3897 (15)	0.1463 (5)	0.7657 (9)	0.039 (3)
H20	0.5176	0.1584	0.7812	0.047*
C21	0.5452 (15)	0.1322 (5)	0.9568 (8)	0.034 (3)
H21A	0.5104	0.1483	1.0119	0.041*
H21B	0.6397	0.1649	0.9544	0.041*
C22	0.6348 (16)	0.0603 (5)	0.9859 (8)	0.034 (3)
H22A	0.6849	0.0477	0.9358	0.041*
H22B	0.5322	0.0270	0.9756	0.041*
C23	0.9649 (16)	0.1040 (6)	1.1228 (9)	0.044 (3)
H23A	0.9362	0.1490	1.1444	0.053*
H23B	0.9713	0.1106	1.0551	0.053*
C24	1.1612 (16)	0.0790 (6)	1.2100 (9)	0.053 (3)
H24A	1.1571	0.0736	1.2778	0.080*
H24B	1.2612	0.1126	1.2197	0.080*
H24C	1.1918	0.0348	1.1886	0.080*
C25	0.7357 (19)	0.0595 (6)	1.1861 (9)	0.049 (3)
H25A	0.6606	0.1025	1.1738	0.058*
H25B	0.8521	0.0632	1.2575	0.058*
C26	0.611 (2)	−0.0008 (9)	1.1893 (13)	0.094 (6)
H26A	0.4803	0.0023	1.1275	0.141*
H26B	0.6016	0.0014	1.2561	0.141*
H26C	0.6704	−0.0443	1.1865	0.141*
H2	0.109 (14)	0.357 (6)	0.130 (11)	0.080*
H4A	0.834 (18)	0.012 (3)	1.088 (11)	0.080*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0265 (7)	0.0448 (8)	0.0354 (8)	−0.0015 (6)	0.0113 (6)	0.0015 (7)
Zn2	0.0367 (8)	0.0421 (8)	0.0344 (8)	−0.0055 (6)	0.0155 (6)	−0.0022 (6)
Br1	0.0375 (6)	0.0428 (7)	0.0492 (7)	−0.0048 (6)	0.0157 (6)	−0.0078 (6)
Br2	0.0516 (8)	0.0532 (8)	0.0646 (9)	0.0154 (7)	0.0230 (7)	0.0178 (7)
Br3	0.0508 (8)	0.0538 (8)	0.0346 (7)	−0.0105 (6)	0.0164 (6)	0.0038 (6)
Br4	0.0584 (8)	0.0504 (8)	0.0782 (10)	0.0000 (7)	0.0404 (8)	−0.0068 (7)
Cl1	0.0397 (18)	0.068 (2)	0.054 (2)	−0.0071 (16)	0.0248 (16)	0.0050 (17)
Cl2	0.063 (2)	0.089 (3)	0.0340 (18)	−0.014 (2)	0.0055 (17)	0.0095 (18)
Cl3	0.0313 (17)	0.054 (2)	0.057 (2)	−0.0087 (15)	−0.0031 (15)	0.0100 (17)
Cl4	0.0621 (19)	0.0555 (19)	0.0370 (17)	−0.0030 (16)	0.0249 (15)	0.0083 (15)
O1	0.032 (4)	0.060 (5)	0.034 (5)	−0.006 (4)	0.009 (4)	0.008 (4)
O2	0.037 (4)	0.043 (5)	0.032 (4)	−0.012 (4)	0.014 (4)	0.005 (4)
N1	0.024 (5)	0.035 (5)	0.027 (5)	0.003 (4)	0.011 (4)	0.001 (4)
N2	0.034 (5)	0.046 (6)	0.042 (6)	−0.004 (5)	0.012 (5)	0.013 (5)
N3	0.039 (5)	0.026 (5)	0.031 (5)	0.006 (4)	0.013 (4)	0.005 (4)
N4	0.033 (5)	0.047 (6)	0.024 (5)	0.002 (5)	0.012 (4)	−0.006 (5)
C1	0.034 (7)	0.036 (7)	0.040 (7)	0.005 (5)	0.006 (6)	0.003 (6)
C2	0.038 (7)	0.042 (7)	0.032 (7)	−0.005 (5)	0.018 (6)	−0.007 (5)
C3	0.027 (6)	0.033 (6)	0.050 (8)	0.003 (5)	0.023 (6)	−0.005 (5)
C4	0.053 (8)	0.050 (8)	0.034 (7)	0.003 (6)	0.024 (6)	−0.003 (6)
C5	0.040 (7)	0.039 (7)	0.030 (6)	−0.007 (5)	0.006 (5)	0.011 (5)
C6	0.031 (6)	0.041 (6)	0.024 (6)	−0.010 (5)	0.003 (5)	−0.004 (5)
C7	0.031 (6)	0.033 (7)	0.052 (8)	0.004 (5)	0.022 (6)	−0.001 (6)
C8	0.043 (8)	0.050 (8)	0.046 (8)	−0.007 (6)	0.013 (6)	0.000 (6)
C9	0.059 (9)	0.109 (12)	0.047 (9)	−0.032 (9)	0.026 (8)	−0.009 (9)
C10	0.088 (12)	0.075 (11)	0.120 (15)	−0.014 (9)	0.074 (12)	−0.017 (10)
C11	0.081 (11)	0.067 (10)	0.104 (13)	0.010 (9)	0.056 (10)	0.011 (9)
C12	0.108 (14)	0.114 (15)	0.104 (15)	−0.003 (12)	0.057 (13)	0.045 (12)
C13	0.103 (14)	0.129 (16)	0.035 (9)	−0.035 (12)	−0.012 (9)	0.015 (10)
C14	0.038 (7)	0.042 (7)	0.030 (6)	0.003 (5)	0.017 (5)	−0.002 (5)
C15	0.031 (6)	0.028 (6)	0.037 (7)	0.007 (5)	0.005 (5)	−0.011 (5)
C16	0.033 (6)	0.028 (6)	0.061 (8)	0.003 (5)	0.024 (6)	0.003 (6)
C17	0.044 (7)	0.032 (6)	0.031 (7)	0.001 (5)	0.008 (6)	0.001 (5)
C18	0.038 (6)	0.033 (6)	0.030 (6)	0.001 (5)	0.016 (5)	0.006 (5)
C19	0.035 (6)	0.033 (6)	0.043 (7)	−0.001 (5)	0.019 (6)	−0.003 (5)
C20	0.029 (6)	0.041 (7)	0.040 (7)	0.002 (5)	0.010 (6)	0.007 (5)
C21	0.027 (6)	0.036 (6)	0.033 (6)	−0.002 (5)	0.009 (5)	−0.004 (5)
C22	0.039 (6)	0.031 (6)	0.034 (7)	0.003 (5)	0.018 (5)	−0.003 (5)
C23	0.045 (7)	0.048 (8)	0.035 (7)	−0.012 (6)	0.015 (6)	−0.002 (6)
C24	0.044 (8)	0.059 (9)	0.042 (8)	−0.004 (6)	0.009 (6)	−0.003 (7)
C25	0.064 (8)	0.061 (9)	0.022 (6)	0.013 (7)	0.021 (6)	0.008 (6)
C26	0.054 (9)	0.149 (16)	0.088 (12)	0.039 (10)	0.042 (9)	0.049 (11)

Geometric parameters (Å, º)

Zn1—O1	1.913 (7)	C9—H9B	0.9700
Zn1—N1	2.009 (8)	C10—C11	1.567 (19)
Zn1—Br2	2.3616 (18)	C10—H10A	0.9700
Zn1—Br1	2.3982 (17)	C10—H10B	0.9700
Zn2—O2	1.972 (7)	C11—H11A	0.9600
Zn2—N3	2.017 (8)	C11—H11B	0.9600
Zn2—Br4	2.3575 (18)	C11—H11C	0.9600
Zn2—Br3	2.3649 (17)	C12—C13	1.49 (2)
Cl1—C3	1.762 (10)	C12—H12A	0.9700
Cl2—C5	1.725 (11)	C12—H12B	0.9700
Cl3—C16	1.715 (11)	C13—H13A	0.9600
Cl4—C18	1.726 (10)	C13—H13B	0.9600
O1—C2	1.321 (12)	C13—H13C	0.9600
O2—C15	1.343 (12)	C14—C19	1.401 (14)
N1—C7	1.300 (13)	C14—C20	1.445 (14)
N1—C8	1.460 (13)	C14—C15	1.451 (14)
N2—C9	1.489 (15)	C15—C16	1.370 (15)
N2—C10	1.514 (16)	C16—C17	1.387 (15)
N2—C12	1.517 (17)	C17—C18	1.410 (14)
N2—H2	0.90 (12)	C17—H17	0.9300
N3—C20	1.278 (12)	C18—C19	1.374 (14)
N3—C21	1.489 (12)	C19—H19	0.9300
N4—C25	1.469 (13)	C20—H20	0.9300
N4—C23	1.491 (13)	C21—C22	1.503 (13)
N4—C22	1.508 (13)	C21—H21A	0.9700
N4—H4A	0.90 (9)	C21—H21B	0.9700
C1—C2	1.407 (14)	C22—H22A	0.9700
C1—C7	1.426 (15)	C22—H22B	0.9700
C1—C6	1.450 (14)	C23—C24	1.492 (15)
C2—C3	1.406 (14)	C23—H23A	0.9700
C3—C4	1.334 (15)	C23—H23B	0.9700
C4—C5	1.394 (15)	C24—H24A	0.9600
C4—H4	0.9300	C24—H24B	0.9600
C5—C6	1.353 (14)	C24—H24C	0.9600
C6—H6	0.9300	C25—C26	1.516 (18)
C7—H7	0.9300	C25—H25A	0.9700
C8—C9	1.442 (16)	C25—H25B	0.9700
C8—H8A	0.9700	C26—H26A	0.9600
C8—H8B	0.9700	C26—H26B	0.9600
C9—H9A	0.9700	C26—H26C	0.9600
O1—Zn1—N1	96.8 (3)	H11A—C11—H11B	109.5
O1—Zn1—Br2	118.8 (2)	C10—C11—H11C	109.5
N1—Zn1—Br2	107.9 (2)	H11A—C11—H11C	109.5
O1—Zn1—Br1	111.0 (2)	H11B—C11—H11C	109.5
N1—Zn1—Br1	114.2 (2)	C13—C12—N2	116.0 (14)
Br2—Zn1—Br1	107.99 (7)	C13—C12—H12A	108.3
O2—Zn2—N3	93.5 (3)	N2—C12—H12A	108.3
O2—Zn2—Br4	110.6 (2)	C13—C12—H12B	108.3
N3—Zn2—Br4	114.3 (2)	N2—C12—H12B	108.3
O2—Zn2—Br3	115.1 (2)	H12A—C12—H12B	107.4
N3—Zn2—Br3	109.6 (2)	C12—C13—H13A	109.5
Br4—Zn2—Br3	112.53 (7)	C12—C13—H13B	109.5
C2—O1—Zn1	125.2 (7)	H13A—C13—H13B	109.5
C15—O2—Zn2	118.4 (6)	C12—C13—H13C	109.5
C7—N1—C8	115.6 (9)	H13A—C13—H13C	109.5
C7—N1—Zn1	120.4 (7)	H13B—C13—H13C	109.5
C8—N1—Zn1	123.4 (7)	C19—C14—C20	116.9 (10)
C9—N2—C10	115.2 (11)	C19—C14—C15	118.0 (10)
C9—N2—C12	108.3 (11)	C20—C14—C15	124.9 (10)
C10—N2—C12	107.5 (11)	O2—C15—C16	120.1 (10)
C9—N2—H2	111 (9)	O2—C15—C14	121.3 (9)
C10—N2—H2	103 (8)	C16—C15—C14	118.5 (11)
C12—N2—H2	112 (8)	C15—C16—C17	123.0 (10)
C20—N3—C21	115.5 (9)	C15—C16—Cl3	119.4 (9)
C20—N3—Zn2	120.8 (7)	C17—C16—Cl3	117.5 (9)
C21—N3—Zn2	123.3 (7)	C16—C17—C18	118.2 (10)
C25—N4—C23	112.5 (9)	C16—C17—H17	120.9
C25—N4—C22	113.9 (9)	C18—C17—H17	120.9
C23—N4—C22	111.5 (8)	C19—C18—C17	120.3 (10)
C25—N4—H4A	118 (9)	C19—C18—Cl4	120.2 (9)
C23—N4—H4A	108 (8)	C17—C18—Cl4	119.4 (8)
C22—N4—H4A	91 (9)	C18—C19—C14	121.5 (11)
C2—C1—C7	127.3 (10)	C18—C19—H19	119.3
C2—C1—C6	117.8 (11)	C14—C19—H19	119.3
C7—C1—C6	114.5 (10)	N3—C20—C14	126.9 (10)
O1—C2—C3	120.7 (10)	N3—C20—H20	116.5
O1—C2—C1	123.0 (10)	C14—C20—H20	116.5
C3—C2—C1	116.2 (10)	N3—C21—C22	108.6 (8)
C4—C3—C2	125.3 (10)	N3—C21—H21A	110.0
C4—C3—Cl1	118.3 (9)	C22—C21—H21A	110.0
C2—C3—Cl1	116.4 (9)	N3—C21—H21B	110.0
C3—C4—C5	119.2 (11)	C22—C21—H21B	110.0
C3—C4—H4	120.4	H21A—C21—H21B	108.4
C5—C4—H4	120.4	C21—C22—N4	113.5 (8)
C6—C5—C4	119.2 (10)	C21—C22—H22A	108.9
C6—C5—Cl2	120.6 (9)	N4—C22—H22A	108.9
C4—C5—Cl2	120.2 (9)	C21—C22—H22B	108.9
C5—C6—C1	122.1 (10)	N4—C22—H22B	108.9
C5—C6—H6	118.9	H22A—C22—H22B	107.7
C1—C6—H6	118.9	N4—C23—C24	113.0 (9)
N1—C7—C1	126.2 (10)	N4—C23—H23A	109.0
N1—C7—H7	116.9	C24—C23—H23A	109.0
C1—C7—H7	116.9	N4—C23—H23B	109.0
C9—C8—N1	114.9 (10)	C24—C23—H23B	109.0
C9—C8—H8A	108.5	H23A—C23—H23B	107.8
N1—C8—H8A	108.5	C23—C24—H24A	109.5
C9—C8—H8B	108.5	C23—C24—H24B	109.5
N1—C8—H8B	108.5	H24A—C24—H24B	109.5
H8A—C8—H8B	107.5	C23—C24—H24C	109.5
C8—C9—N2	120.9 (11)	H24A—C24—H24C	109.5
C8—C9—H9A	107.1	H24B—C24—H24C	109.5
N2—C9—H9A	107.1	N4—C25—C26	115.7 (11)
C8—C9—H9B	107.1	N4—C25—H25A	108.4
N2—C9—H9B	107.1	C26—C25—H25A	108.4
H9A—C9—H9B	106.8	N4—C25—H25B	108.4
N2—C10—C11	108.1 (11)	C26—C25—H25B	108.4
N2—C10—H10A	110.1	H25A—C25—H25B	107.4
C11—C10—H10A	110.1	C25—C26—H26A	109.5
N2—C10—H10B	110.1	C25—C26—H26B	109.5
C11—C10—H10B	110.1	H26A—C26—H26B	109.5
H10A—C10—H10B	108.4	C25—C26—H26C	109.5
C10—C11—H11A	109.5	H26A—C26—H26C	109.5
C10—C11—H11B	109.5	H26B—C26—H26C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O2^i	0.90 (9)	2.20 (8)	2.960 (11)	142 (11)
N2—H2···Br1	0.90 (12)	2.48 (13)	3.373 (9)	170 (11)
C7—H7···Br2^ii	0.93	2.85	3.735 (8)	159
C23—H23B···Br3^iii	0.97	2.92	3.611 (8)	129
C25—H25B···Br3^i	0.97	2.79	3.613 (8)	143
C26—H26A···Br3	0.96	2.80	3.764 (17)	177

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