Aqua­bis[N-(5,7-dibromo­quinolin-8-yl)-4-methyl­benzene­sulfonamidato-κ²N,N′]zinc(II)

The mol­ecule of the title compound, [Zn(C₁₆H₁₁Br₂N₂O₂S)₂(H₂O)], occupies a special position on a twofold axis. Zinc is square-pyramidal coordinated by the N atoms of the quinoline and the sulfonamide groups and one water mol­ecule. The water mol­ecule has one weak inter­molecular hydrogen bond to a sulfonyl O atom.

Key indicators

• Single-crystal X-ray study
• T = 299 K
• Mean [sigma](C-C) = 0.012 Å
• Disorder in main residue
• R factor = 0.047
• wR factor = 0.123
• Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        C16
PLAT420_ALERT_2_B D-H Without Acceptor       O3     -   H3O    ...          ?

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C7
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for       C14'
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Zn1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C14
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C16'
PLAT301_ALERT_3_C Main Residue  Disorder .........................      14.00 Perc.
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         12
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C10    -   C11    ...       1.35 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C11    -   C12    ...       1.38 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3O    ..  O2      ..       2.66 Ang.
PLAT731_ALERT_1_C Bond    Calc     0.84(6), Rep     0.84(2) ......       3.00 su-Rat
              O3   -H3O     1.555   1.555
PLAT732_ALERT_1_C Angle   Calc      126(5), Rep      125(2) ......       2.50 su-Rat
              ZN1  -O3   -H3O     1.555   1.555   1.555
PLAT733_ALERT_1_C Torsion Calc    36.7(10), Rep     36.7(4) ......       2.50 su-Rat
              C9  -N2  -ZN1 -N2     1.555   1.555   1.555   6.555
PLAT735_ALERT_1_C D-H     Calc     0.84(6), Rep     0.84(2) ......       3.00 su-Rat
              O3   -H3O     1.555   1.555

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           26.34
           From the CIF: _reflns_number_total               3491
           Count of symmetry unique reflns         2006
           Completeness (_total/calc)            174.03%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1485
           Fraction of Friedel pairs measured     0.740
           Are heavy atom types Z>Si present        yes

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

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   9 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
   2 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis RED (Oxford Diffraction, 2004); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Aquabis[N-(5,7-dibromoquinolin-8-yl)-4-methylbenzenesulfonamidato- κ²N,N']zinc(II)

Crystal data

[Zn(C16H11Br2N2O2S)2(H2O)]	Dx = 1.865 Mg m^−3
Mr = 993.68	Mo Kα radiation, λ = 0.71073 Å
Trigonal, P3221	Cell parameters from 1552 reflections
Hall symbol: P 32 2"	θ = 1.5–21.4°
a = 15.8969 (9) Å	µ = 5.37 mm^−1
c = 12.1289 (9) Å	T = 299 K
V = 2654.5 (3) Å^3	Prism, light green
Z = 3	0.28 × 0.10 × 0.10 mm
F(000) = 1458

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	3491 independent reflections
Radiation source: fine-focus sealed tube	2807 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
Rotation method data acquisition using φ scans	θmax = 26.3°, θmin = 4.2°
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2004)	h = −19→19
Tmin = 0.272, Tmax = 0.583	k = −19→19
20412 measured reflections	l = −14→14

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)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.123	w = 1/[σ^2(Fo^2) + (0.0676P)^2 + 0.0141P] where P = (Fo^2 + 2Fc^2)/3
S = 1.13	(Δ/σ)max = 0.049
3491 reflections	Δρmax = 0.55 e Å^−3
259 parameters	Δρmin = −0.45 e Å^−3
15 restraints	Absolute structure: Flack (1983), 1485 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.004 (14)

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	Occ. (<1)
C1	0.3241 (4)	0.0888 (4)	0.0077 (4)	0.0598 (13)
C2	0.4002 (5)	0.1049 (5)	−0.0580 (6)	0.0753 (17)
C3	0.4817 (5)	0.1968 (5)	−0.0741 (7)	0.085 (2)
H3	0.5313	0.2046	−0.1211	0.102*
C4	0.4873 (6)	0.2734 (5)	−0.0212 (6)	0.0817 (19)
C5	0.4147 (6)	0.2654 (5)	0.0503 (5)	0.0762 (18)
C6	0.4146 (8)	0.3425 (6)	0.1040 (6)	0.095 (3)
H6	0.4673	0.4051	0.0963	0.115*
C7	0.3384 (10)	0.3268 (7)	0.1670 (8)	0.115 (3)
H7	0.3380	0.3781	0.2035	0.138*
C8	0.2594 (8)	0.2319 (7)	0.1768 (6)	0.096 (3)
H8	0.2060	0.2220	0.2184	0.116*
C9	0.3317 (5)	0.1711 (5)	0.0630 (5)	0.0657 (15)
C10	0.1668 (5)	−0.1560 (5)	−0.1141 (5)	0.080 (2)
C11	0.1918 (6)	−0.2061 (5)	−0.0440 (6)	0.088 (2)
H11	0.2122	−0.1816	0.0267	0.106*
C12	0.1885 (6)	−0.2920 (5)	−0.0723 (7)	0.093 (2)
H12	0.1956	−0.3309	−0.0201	0.112*
C13	0.1734 (15)	−0.3176 (12)	−0.1869 (14)	0.110 (10)	0.50
C14	0.1668 (10)	−0.2520 (11)	−0.2630 (12)	0.086 (5)	0.50
H14	0.1631	−0.2658	−0.3380	0.103*	0.50
C15	0.1656 (11)	−0.1688 (12)	−0.2300 (8)	0.082 (4)	0.50
H15	0.1641	−0.1251	−0.2799	0.099*	0.50
C16	0.163 (2)	−0.4049 (16)	−0.239 (3)	0.145 (12)	0.50
H161	0.1177	−0.4612	−0.1987	0.174*	0.50
H162	0.2253	−0.4017	−0.2404	0.174*	0.50
H163	0.1405	−0.4091	−0.3136	0.174*	0.50
C13'	0.1369 (13)	−0.3501 (11)	−0.1581 (14)	0.116 (10)	0.50
C14'	0.0938 (16)	−0.3078 (13)	−0.2152 (16)	0.122 (7)	0.50
H14'	0.0577	−0.3400	−0.2773	0.146*	0.50
C15'	0.0999 (11)	−0.2229 (12)	−0.1879 (13)	0.101 (5)	0.50
H15'	0.0562	−0.2078	−0.2208	0.122*	0.50
C16'	0.138 (2)	−0.4418 (13)	−0.1753 (19)	0.113 (8)	0.50
H164	0.1464	−0.4655	−0.1057	0.135*	0.50
H165	0.1908	−0.4300	−0.2234	0.135*	0.50
H166	0.0778	−0.4893	−0.2080	0.135*	0.50
N1	0.2374 (3)	−0.0008 (3)	0.0260 (4)	0.0581 (11)
N2	0.2576 (4)	0.1567 (4)	0.1300 (4)	0.0704 (14)
O1	0.1922 (4)	0.0129 (4)	−0.1698 (4)	0.0910 (14)
O2	0.0673 (3)	−0.0867 (3)	−0.0337 (4)	0.0708 (11)
O3	0.0377 (4)	0.0000	0.1667	0.107 (3)
H3O	−0.008 (4)	−0.030 (5)	0.122 (5)	0.128*
S1	0.16513 (12)	−0.05013 (12)	−0.07607 (12)	0.0641 (4)
Zn1	0.16254 (5)	0.0000	0.1667	0.0609 (3)
Br1	0.40264 (6)	0.00076 (6)	−0.13287 (9)	0.1075 (3)
Br2	0.60013 (8)	0.39734 (6)	−0.04589 (9)	0.1213 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.061 (3)	0.066 (4)	0.060 (3)	0.037 (3)	−0.004 (3)	−0.005 (3)
C2	0.072 (4)	0.062 (4)	0.093 (4)	0.034 (3)	0.013 (3)	−0.005 (3)
C3	0.075 (4)	0.069 (4)	0.109 (5)	0.034 (3)	0.020 (4)	0.010 (4)
C4	0.087 (5)	0.064 (4)	0.082 (5)	0.029 (4)	0.004 (4)	0.011 (3)
C5	0.112 (6)	0.066 (4)	0.062 (4)	0.052 (4)	−0.005 (4)	0.000 (3)
C6	0.134 (8)	0.068 (4)	0.076 (5)	0.044 (5)	−0.002 (5)	−0.008 (4)
C7	0.205 (12)	0.072 (5)	0.086 (6)	0.083 (7)	−0.009 (7)	−0.018 (4)
C8	0.160 (8)	0.115 (7)	0.060 (4)	0.103 (7)	0.003 (4)	−0.006 (4)
C9	0.075 (4)	0.074 (4)	0.066 (4)	0.050 (4)	−0.004 (3)	−0.006 (3)
C10	0.070 (4)	0.105 (5)	0.079 (4)	0.056 (4)	−0.012 (3)	−0.040 (4)
C11	0.102 (5)	0.079 (5)	0.087 (5)	0.048 (4)	0.009 (4)	−0.011 (4)
C12	0.099 (6)	0.065 (4)	0.113 (6)	0.040 (4)	0.025 (5)	−0.006 (4)
C13	0.047 (13)	0.080 (12)	0.21 (3)	0.033 (12)	−0.047 (13)	−0.084 (16)
C14	0.054 (8)	0.123 (13)	0.094 (11)	0.054 (9)	−0.024 (7)	−0.064 (10)
C15	0.064 (9)	0.100 (11)	0.098 (11)	0.052 (8)	−0.040 (8)	−0.047 (9)
C16	0.17 (2)	0.085 (15)	0.18 (3)	0.062 (17)	0.02 (2)	−0.060 (16)
C13'	0.053 (15)	0.112 (17)	0.17 (2)	0.029 (13)	−0.016 (13)	−0.047 (15)
C14'	0.132 (19)	0.097 (14)	0.111 (15)	0.039 (14)	−0.065 (15)	−0.037 (11)
C15'	0.065 (9)	0.105 (13)	0.115 (13)	0.029 (9)	−0.047 (10)	−0.034 (11)
C16'	0.15 (2)	0.074 (12)	0.114 (17)	0.060 (14)	−0.023 (15)	−0.021 (11)
N1	0.058 (3)	0.067 (3)	0.053 (2)	0.035 (2)	−0.005 (2)	−0.005 (2)
N2	0.097 (4)	0.079 (3)	0.056 (3)	0.060 (3)	−0.007 (3)	−0.010 (2)
O1	0.090 (3)	0.130 (5)	0.068 (3)	0.066 (3)	−0.005 (2)	0.006 (3)
O2	0.055 (2)	0.096 (3)	0.072 (2)	0.047 (2)	−0.0075 (19)	−0.015 (2)
O3	0.086 (3)	0.161 (9)	0.098 (6)	0.080 (4)	−0.009 (3)	−0.018 (5)
S1	0.0642 (9)	0.0831 (10)	0.0583 (8)	0.0468 (8)	−0.0078 (7)	−0.0117 (8)
Zn1	0.0535 (4)	0.0810 (7)	0.0574 (5)	0.0405 (3)	−0.0045 (2)	−0.0090 (5)
Br1	0.0804 (5)	0.0766 (5)	0.1603 (8)	0.0353 (4)	0.0472 (5)	−0.0133 (5)
Br2	0.1170 (7)	0.0661 (5)	0.1418 (8)	0.0165 (5)	0.0044 (6)	0.0196 (5)

Geometric parameters (Å, º)

C1—C2	1.363 (8)	C12—H12	0.9300
C1—N1	1.419 (7)	C13—C14	1.436 (17)
C1—C9	1.420 (8)	C13—C16	1.461 (16)
C2—C3	1.399 (9)	C14—C15	1.391 (16)
C2—Br1	1.906 (6)	C14—H14	0.9300
C3—C4	1.339 (10)	C15—H15	0.9300
C3—H3	0.9300	C16—H161	0.9600
C4—C5	1.398 (10)	C16—H162	0.9600
C4—Br2	1.912 (7)	C16—H163	0.9600
C5—C6	1.389 (10)	C13'—C14'	1.364 (9)
C5—C9	1.426 (9)	C13'—C16'	1.484 (17)
C6—C7	1.347 (14)	C14'—C15'	1.346 (18)
C6—H6	0.9300	C14'—H14'	0.9300
C7—C8	1.404 (14)	C15'—H15'	0.9300
C7—H7	0.9300	C16'—H164	0.9600
C8—N2	1.311 (9)	C16'—H165	0.9600
C8—H8	0.9300	C16'—H166	0.9600
C9—N2	1.354 (8)	N1—S1	1.602 (5)
C10—C11	1.353 (7)	N1—Zn1	2.084 (4)
C10—C15'	1.390 (13)	N2—Zn1	2.219 (6)
C10—C15	1.420 (8)	O1—S1	1.432 (5)
C10—S1	1.759 (6)	O2—S1	1.454 (4)
C11—C12	1.383 (7)	O3—Zn1	1.984 (7)
C11—H11	0.9300	O3—H3O	0.84 (2)
C12—C13'	1.360 (9)	Zn1—N1^i	2.084 (4)
C12—C13	1.434 (16)	Zn1—N2^i	2.219 (6)
C2—C1—N1	127.3 (5)	C15—C14—C13	123.1 (11)
C2—C1—C9	116.3 (6)	C15—C14—H14	118.4
N1—C1—C9	116.4 (5)	C13—C14—H14	118.4
C1—C2—C3	123.3 (6)	C14—C15—C10	114.5 (12)
C1—C2—Br1	121.2 (5)	C14—C15—H15	122.7
C3—C2—Br1	115.5 (5)	C10—C15—H15	122.7
C4—C3—C2	119.3 (7)	C12—C13'—C14'	109.6 (12)
C4—C3—H3	120.4	C12—C13'—C16'	118.4 (15)
C2—C3—H3	120.4	C14'—C13'—C16'	132.0 (15)
C3—C4—C5	122.5 (7)	C15'—C14'—C13'	124.6 (15)
C3—C4—Br2	117.7 (6)	C15'—C14'—H14'	117.7
C5—C4—Br2	119.8 (6)	C13'—C14'—H14'	117.7
C6—C5—C4	125.1 (7)	C14'—C15'—C10	124.6 (14)
C6—C5—C9	118.0 (7)	C14'—C15'—H15'	117.7
C4—C5—C9	116.8 (6)	C10—C15'—H15'	117.7
C7—C6—C5	120.0 (8)	C13'—C16'—H164	109.5
C7—C6—H6	120.0	C13'—C16'—H165	109.5
C5—C6—H6	120.0	H164—C16'—H165	109.5
C6—C7—C8	119.1 (7)	C13'—C16'—H166	109.5
C6—C7—H7	120.5	H164—C16'—H166	109.5
C8—C7—H7	120.5	H165—C16'—H166	109.5
N2—C8—C7	122.9 (8)	C1—N1—S1	118.0 (4)
N2—C8—H8	118.6	C1—N1—Zn1	113.1 (3)
C7—C8—H8	118.6	S1—N1—Zn1	111.4 (2)
N2—C9—C1	117.5 (6)	C8—N2—C9	119.1 (7)
N2—C9—C5	120.8 (6)	C8—N2—Zn1	129.0 (6)
C1—C9—C5	121.7 (6)	C9—N2—Zn1	110.9 (4)
C11—C10—C15'	107.0 (10)	Zn1—O3—H3O	125 (2)
C11—C10—C15	121.7 (8)	O1—S1—O2	116.6 (3)
C15'—C10—C15	45.7 (8)	O1—S1—N1	112.3 (3)
C11—C10—S1	123.2 (5)	O2—S1—N1	106.5 (2)
C15'—C10—S1	121.9 (8)	O1—S1—C10	108.6 (3)
C15—C10—S1	113.0 (7)	O2—S1—C10	103.6 (3)
C10—C11—C12	123.2 (7)	N1—S1—C10	108.7 (3)
C10—C11—H11	118.4	O3—Zn1—N1^i	125.03 (12)
C12—C11—H11	118.4	O3—Zn1—N1	125.02 (12)
C13'—C12—C11	124.9 (10)	N1^i—Zn1—N1	109.9 (2)
C11—C12—C13	116.1 (9)	O3—Zn1—N2	96.87 (14)
C13'—C12—H12	107.6	N1^i—Zn1—N2	95.19 (18)
C11—C12—H12	122.0	N1—Zn1—N2	76.83 (19)
C13—C12—H12	122.0	O3—Zn1—N2^i	96.87 (14)
C12—C13—C14	118.7 (9)	N1^i—Zn1—N2^i	76.83 (19)
C12—C13—C16	128.0 (19)	N1—Zn1—N2^i	95.19 (18)
C14—C13—C16	113.4 (18)	N2—Zn1—N2^i	166.3 (3)
N1—C1—C2—C3	177.6 (6)	C13'—C14'—C15'—C10	15 (4)
C9—C1—C2—C3	−1.5 (10)	C11—C10—C15'—C14'	−26 (2)
N1—C1—C2—Br1	−3.4 (9)	C15—C10—C15'—C14'	92 (2)
C9—C1—C2—Br1	177.5 (4)	S1—C10—C15'—C14'	−175.9 (16)
C1—C2—C3—C4	1.5 (12)	C2—C1—N1—S1	−65.4 (7)
Br1—C2—C3—C4	−177.6 (6)	C9—C1—N1—S1	113.7 (5)
C2—C3—C4—C5	0.1 (12)	C2—C1—N1—Zn1	162.1 (5)
C2—C3—C4—Br2	179.9 (6)	C9—C1—N1—Zn1	−18.8 (6)
C3—C4—C5—C6	−177.3 (8)	C7—C8—N2—C9	−4.6 (11)
Br2—C4—C5—C6	3.0 (10)	C7—C8—N2—Zn1	162.5 (6)
C3—C4—C5—C9	−1.5 (10)	C1—C9—N2—C8	−175.7 (6)
Br2—C4—C5—C9	178.7 (5)	C5—C9—N2—C8	5.2 (9)
C4—C5—C6—C7	176.7 (8)	C1—C9—N2—Zn1	14.9 (6)
C9—C5—C6—C7	1.0 (11)	C5—C9—N2—Zn1	−164.2 (5)
C5—C6—C7—C8	−0.4 (13)	C1—N1—S1—O1	−9.4 (5)
C6—C7—C8—N2	2.2 (13)	Zn1—N1—S1—O1	123.9 (3)
C2—C1—C9—N2	−179.1 (5)	C1—N1—S1—O2	−138.1 (4)
N1—C1—C9—N2	1.7 (7)	Zn1—N1—S1—O2	−4.9 (3)
C2—C1—C9—C5	0.0 (9)	C1—N1—S1—C10	110.8 (4)
N1—C1—C9—C5	−179.2 (5)	Zn1—N1—S1—C10	−115.9 (3)
C6—C5—C9—N2	−3.4 (9)	C11—C10—S1—O1	146.6 (6)
C4—C5—C9—N2	−179.5 (6)	C15'—C10—S1—O1	−68.3 (11)
C6—C5—C9—C1	177.5 (6)	C15—C10—S1—O1	−17.3 (8)
C4—C5—C9—C1	1.4 (9)	C11—C10—S1—O2	−88.9 (7)
C15'—C10—C11—C12	27.2 (13)	C15'—C10—S1—O2	56.2 (10)
C15—C10—C11—C12	−20.8 (14)	C15—C10—S1—O2	107.2 (8)
S1—C10—C11—C12	176.7 (7)	C11—C10—S1—N1	24.1 (7)
C10—C11—C12—C13'	−18.9 (18)	C15'—C10—S1—N1	169.2 (10)
C10—C11—C12—C13	10.7 (16)	C15—C10—S1—N1	−139.7 (8)
C13'—C12—C13—C14	119 (3)	C1—N1—Zn1—O3	108.9 (3)
C11—C12—C13—C14	2 (2)	S1—N1—Zn1—O3	−26.7 (3)
C13'—C12—C13—C16	−61 (3)	C1—N1—Zn1—N1^i	−71.1 (3)
C11—C12—C13—C16	−178 (2)	S1—N1—Zn1—N1^i	153.3 (3)
C12—C13—C14—C15	−6 (3)	C1—N1—Zn1—N2	19.7 (3)
C16—C13—C14—C15	174 (2)	S1—N1—Zn1—N2	−115.9 (3)
C13—C14—C15—C10	−3 (2)	C1—N1—Zn1—N2^i	−148.9 (4)
C11—C10—C15—C14	15.9 (17)	S1—N1—Zn1—N2^i	75.4 (3)
C15'—C10—C15—C14	−67.2 (15)	C8—N2—Zn1—O3	48.7 (6)
S1—C10—C15—C14	−179.9 (10)	C9—N2—Zn1—O3	−143.3 (4)
C11—C12—C13'—C14'	3 (3)	C8—N2—Zn1—N1^i	−77.6 (6)
C13—C12—C13'—C14'	−75 (2)	C9—N2—Zn1—N1^i	90.4 (4)
C11—C12—C13'—C16'	−177.9 (12)	C8—N2—Zn1—N1	173.1 (6)
C13—C12—C13'—C16'	103 (2)	C9—N2—Zn1—N1	−18.9 (4)
C12—C13'—C14'—C15'	−2 (4)	C8—N2—Zn1—N2^i	−131.3 (6)
C16'—C13'—C14'—C15'	179.9 (4)	C9—N2—Zn1—N2^i	36.7 (4)

Symmetry code: (i) x−y, −y, −z+1/3.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O2^ii	0.84 (2)	2.66 (7)	3.126 (7)	117 (5)

Symmetry code: (ii) y, x, −z.