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Complexes of 3d transition metal chlorides with di­nitro­benzoic acids (DNBH) and secondary amines have been synthesized in order to model processes of chemisorption of organic salts by metal surfaces. A series of compounds of composition (AmH)2[MCl2(DNB)2] (where M = ZnII, CuII; AmH+ is the cation of piperidine PipH+ = C5H10NH2+ or diethyl­amine DaH+ = C4H10NH2+) have been prepared, the structure of the piperidinium salt of the Zn/3,5-DNB complex anion being authenticated by X-ray crystallography. In the title compound, (C5H12N)2[ZnCl2(C7H3N2O6)2], the Zn atom is four-coordinated. The DNB ligand behaves as a monodentate ligand via an O atom of the carboxyl­ate group, the other carboxyl­ate O atom being hydrogen bonded to one of the ammonium H atoms. The other ammonium H atom of the two cations links to the coordinated chlorides, one within the complex and the other across an inversion center, so forming a dimer.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680400337X/su6076sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680400337X/su6076Isup2.hkl
Contains datablock I

CCDC reference: 236043

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.032
  • wR factor = 0.084
  • Data-to-parameter ratio = 7.6

checkCIF/PLATON results

No syntax errors found



Alert level A REFLT03_ALERT_3_A Reflection count < 85% complete (theta max?) From the CIF: _diffrn_reflns_theta_max 22.54 From the CIF: _diffrn_reflns_theta_full 0.00 From the CIF: _reflns_number_total 3096 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 4197 Completeness (_total/calc) 73.77%
Author Response: This is consequent on the conditions of the reflection intensity measurements as implemented historically in the single counter diffractometer software, whereby using a prescanoption, some reflections were indicated as weak and skipped during data collection.
THETM01_ALERT_3_A  The value of sine(theta_max)/wavelength is less than 0.550
            Calculated sin(theta_max)/wavelength =    0.5394
Author Response: The value of sine(theta_max) was restricted because data beyond 0.54 were weak and did not justify measurement.
PLAT022_ALERT_3_A Ratio Unique / Expected Reflections too Low ....       0.74
Author Response: This was consequent on the overall weakness of the data as dictated by the nature of the specimen.
PLAT023_ALERT_3_A Resolution (too) Low [sin(th)/Lambda < 0.6].....      22.54 Deg.
Author Response: Again, a consequence of a feebly diffracting specimen. Resolution (Lambda/2sin(thmax)=0.545 \%A) been considered as sufficient to resolve atoms of hydrogen from experimental data.
PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............      22.54 Deg.
Author Response: Again, a consequence of a feebly diffracting specimen.
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.74
Author Response: Again, a consequence of a feeble diffracting specimen.

Alert level B REFNR01_ALERT_3_B Ratio of reflections to parameters is < 8 for a centrosymmetric structure sine(theta)/lambda 0.5394 Proportion of unique data used 1.0000 Ratio reflections to parameters 7.6069 PLAT031_ALERT_4_B Refined Extinction Parameter within Range ...... 1.57 Sigma PLAT088_ALERT_3_B Poor Data / Parameter Ratio .................... 7.61 PLAT220_ALERT_2_B Large Non-Solvent O Ueq(max)/Ueq(min) ... 3.88 Ratio PLAT242_ALERT_2_B Check Low U(eq) as Compared to Neighbors .... N3A
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 .... N3B PLAT243_ALERT_4_C High Solvent U(eq) as Compared to Neighbors .... C9A PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... N1A PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 15 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3 C5 H12 N
Alert level G REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values From the CIF: _diffrn_reflns_theta_max 22.54 From the CIF: _reflns_number_total 3096 From the CIF: _diffrn_reflns_limit_ max hkl 8. 11. 16. From the CIF: _diffrn_reflns_limit_ min hkl -8. -11. 0. TEST1: Expected hkl limits for theta max Calculated maximum hkl 10. 11. 16. Calculated minimum hkl -10. -11. -16.
Author Response: This is consequent on the conditions of the reflection intensity measurements as implemented historically in the single counter diffractometer software, whereby using a prescanoption, some reflections were indicated as weak and skipped during data collection.

6 ALERT level A = In general: serious problem 5 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 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 8 ALERT type 3 Indicator that the structure quality may be low 5 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: P3 Diffractometer Control Software (Nicolet, 1985); cell refinement: P3 Diffractometer Control Software; data reduction: PROFIT (Streltsov & Zavodnik, 1989); program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(I) top
Crystal data top
(C5H12N)2[ZnCl2(C7H3N2O6)2]Z = 2
Mr = 730.81F(000) = 752
Triclinic, P1Dx = 1.524 Mg m3
Hall symbol: -P 1Melting point: 190 K
a = 9.786 (3) ÅMo Kα radiation, λ = 0.71069 Å
b = 10.550 (4) ÅCell parameters from 12 reflections
c = 15.603 (5) Åθ = 12.2–14.8°
α = 97.04 (2)°µ = 1.01 mm1
β = 91.47 (2)°T = 293 K
γ = 94.66 (2)°Prism, pale yellow
V = 1592.4 (9) Å30.20 × 0.18 × 0.10 mm
Data collection top
Nicolet P3
diffractometer
3096 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tubeRint = 0.000
Graphite monochromatorθmax = 22.5°, θmin = 2.0°
ω–2θ scansh = 88
Absorption correction: ψ scan
(XEMP; Nicolet, 1985)
k = 1111
Tmin = 0.824, Tmax = 0.906l = 016
3096 measured reflections3 standard reflections every 100 reflections
3096 independent reflections intensity decay: 2.5%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032H-atom parameters constrained
wR(F2) = 0.085 w = 1/[σ2(Fo2) + (0.0475P)2 + 1.2282P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
3096 reflectionsΔρmax = 0.28 e Å3
407 parametersΔρmin = 0.23 e Å3
0 restraintsExtinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0011 (7)
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
xyzUiso*/Ueq
Zn0.19855 (4)0.47824 (4)0.22472 (3)0.04079 (18)
Cl10.00135 (11)0.48581 (10)0.29614 (6)0.0560 (3)
Cl20.17995 (11)0.34105 (9)0.10126 (6)0.0561 (3)
C1A0.5009 (4)0.3674 (3)0.3957 (2)0.0405 (9)
C2A0.5299 (4)0.2766 (4)0.4490 (2)0.0496 (10)
H2A0.47140.20260.44890.059*
C3A0.6461 (4)0.2970 (4)0.5021 (2)0.0521 (10)
N3A0.6767 (6)0.2015 (5)0.5595 (3)0.0824 (12)
O31A0.5895 (6)0.1202 (6)0.5674 (4)0.202 (3)
O32A0.7836 (5)0.2100 (4)0.5970 (3)0.1174 (15)
C4A0.7370 (4)0.4035 (4)0.5041 (2)0.0534 (11)
H4A0.81570.41520.53980.064*
C5A0.7054 (4)0.4921 (4)0.4505 (2)0.0473 (10)
N5A0.7963 (4)0.6121 (4)0.4536 (3)0.0690 (10)
O51A0.8984 (4)0.6234 (4)0.5014 (2)0.0994 (12)
O52A0.7638 (4)0.6907 (3)0.4088 (3)0.0982 (12)
C6A0.5901 (4)0.4761 (3)0.3969 (2)0.0435 (9)
H6A0.57210.53820.36170.052*
C7A0.3716 (4)0.3503 (4)0.3391 (2)0.0475 (10)
O71A0.3501 (3)0.4456 (3)0.30027 (17)0.0580 (7)
O72A0.2983 (3)0.2493 (3)0.3352 (2)0.0757 (9)
N1A0.0135 (4)0.1926 (3)0.3246 (3)0.0753 (11)
H1AA0.01190.27250.32340.090*
H1AB0.10310.19870.34040.090*
C8A0.0676 (5)0.1292 (5)0.3889 (3)0.0863 (17)
H8AA0.04570.17420.44620.104*
H8AB0.16460.13330.37650.104*
C9A0.0384 (8)0.0043 (5)0.3871 (4)0.118 (2)
H9AA0.09630.04420.42750.142*
H9AB0.05630.00750.40610.142*
C10A0.0608 (8)0.0772 (5)0.3016 (4)0.111 (2)
H10A0.15700.08130.28400.133*
H10B0.03570.16410.30300.133*
C11A0.0232 (6)0.0144 (7)0.2400 (4)0.104 (2)
H11A0.00690.06180.18280.125*
H11B0.11930.01630.25600.125*
C12A0.0072 (6)0.1197 (6)0.2370 (3)0.0961 (19)
H12A0.10120.12210.21650.115*
H12B0.05280.15860.19720.115*
C1B0.2877 (4)0.8398 (3)0.1413 (2)0.0389 (9)
C2B0.2491 (4)0.9009 (3)0.0718 (2)0.0460 (9)
H2BA0.17720.86520.03420.055*
C3B0.3191 (5)1.0155 (4)0.0597 (2)0.0530 (10)
N3B0.2848 (6)1.0759 (4)0.0178 (3)0.0862 (14)
O31B0.1788 (7)1.0389 (5)0.0565 (3)0.167 (3)
O32B0.3661 (5)1.1595 (4)0.0380 (2)0.1089 (14)
C4B0.4211 (4)1.0752 (4)0.1156 (3)0.0550 (11)
H4BA0.46541.15380.10720.066*
C5B0.4546 (4)1.0142 (3)0.1841 (3)0.0492 (10)
N5B0.5653 (4)1.0753 (4)0.2460 (3)0.0721 (11)
O51B0.6235 (4)1.1761 (3)0.2317 (3)0.1065 (13)
O52B0.5922 (4)1.0235 (4)0.3076 (3)0.1045 (13)
C6B0.3917 (4)0.8976 (3)0.1983 (2)0.0427 (9)
H6BA0.41850.85820.24540.051*
C7B0.2138 (4)0.7124 (3)0.1545 (2)0.0420 (9)
O71B0.2752 (3)0.6495 (2)0.20483 (17)0.0520 (7)
O72B0.1029 (3)0.6806 (2)0.11521 (18)0.0556 (7)
N1B0.1632 (4)0.5776 (5)0.0970 (2)0.0818 (14)
H1BA0.07430.60140.11110.098*
H1BB0.18300.60720.04680.098*
C8B0.1835 (5)0.4359 (5)0.0842 (3)0.0776 (15)
H8BA0.15380.40250.13610.093*
H8BB0.12850.40250.03710.093*
C9B0.3308 (5)0.3935 (5)0.0639 (3)0.0692 (13)
H9BA0.34370.30080.05940.083*
H9BB0.35730.41890.00860.083*
C10B0.4203 (5)0.4503 (4)0.1319 (3)0.0698 (13)
H10C0.40170.41660.18570.084*
H10D0.51580.42610.11480.084*
C11B0.3962 (5)0.5930 (4)0.1455 (4)0.0751 (14)
H11C0.45000.62640.19320.090*
H11D0.42720.62710.09410.090*
C12B0.2483 (5)0.6375 (4)0.1647 (3)0.0660 (13)
H12C0.23560.73000.16710.079*
H12D0.22010.61460.22040.079*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn0.0377 (3)0.0432 (3)0.0428 (3)0.00016 (18)0.00489 (18)0.01447 (18)
Cl10.0477 (7)0.0720 (7)0.0505 (6)0.0092 (5)0.0057 (4)0.0127 (5)
Cl20.0663 (8)0.0543 (6)0.0476 (6)0.0046 (5)0.0033 (5)0.0064 (4)
C1A0.034 (3)0.053 (2)0.0353 (19)0.0088 (18)0.0003 (16)0.0056 (16)
C2A0.050 (3)0.054 (2)0.046 (2)0.0041 (19)0.0001 (19)0.0113 (18)
C3A0.053 (3)0.065 (3)0.042 (2)0.016 (2)0.004 (2)0.0148 (19)
N3A0.085 (4)0.097 (3)0.071 (3)0.013 (3)0.019 (2)0.036 (2)
O31A0.169 (5)0.212 (6)0.245 (7)0.064 (5)0.099 (5)0.182 (6)
O32A0.115 (4)0.142 (4)0.106 (3)0.038 (3)0.044 (3)0.050 (3)
C4A0.045 (3)0.077 (3)0.038 (2)0.019 (2)0.0059 (18)0.001 (2)
C5A0.038 (3)0.058 (2)0.042 (2)0.0012 (19)0.0050 (18)0.0050 (18)
N5A0.066 (3)0.074 (3)0.060 (2)0.010 (2)0.001 (2)0.006 (2)
O51A0.083 (3)0.119 (3)0.083 (2)0.035 (2)0.028 (2)0.007 (2)
O52A0.094 (3)0.072 (2)0.127 (3)0.018 (2)0.011 (2)0.027 (2)
C6A0.043 (3)0.052 (2)0.0363 (19)0.0104 (19)0.0018 (17)0.0051 (16)
C7A0.039 (3)0.056 (3)0.048 (2)0.006 (2)0.0029 (18)0.0067 (19)
O71A0.0497 (19)0.0705 (18)0.0573 (17)0.0097 (14)0.0145 (13)0.0221 (14)
O72A0.052 (2)0.077 (2)0.099 (2)0.0110 (17)0.0281 (17)0.0283 (18)
N1A0.063 (3)0.050 (2)0.109 (3)0.0103 (18)0.019 (2)0.007 (2)
C8A0.080 (4)0.097 (4)0.067 (3)0.031 (3)0.020 (3)0.030 (3)
C9A0.194 (7)0.080 (4)0.079 (4)0.012 (4)0.023 (4)0.026 (3)
C10A0.163 (7)0.058 (3)0.107 (5)0.009 (4)0.030 (5)0.005 (3)
C11A0.068 (4)0.133 (6)0.098 (4)0.023 (4)0.002 (3)0.052 (4)
C12A0.082 (4)0.147 (6)0.062 (3)0.028 (4)0.008 (3)0.045 (3)
C1B0.034 (3)0.0390 (19)0.044 (2)0.0035 (16)0.0040 (17)0.0064 (16)
C2B0.052 (3)0.042 (2)0.043 (2)0.0043 (18)0.0014 (18)0.0039 (16)
C3B0.068 (3)0.045 (2)0.049 (2)0.013 (2)0.012 (2)0.0143 (18)
N3B0.148 (5)0.058 (3)0.059 (3)0.018 (3)0.012 (3)0.021 (2)
O31B0.255 (7)0.123 (4)0.119 (4)0.047 (4)0.107 (4)0.065 (3)
O32B0.154 (4)0.087 (3)0.105 (3)0.033 (2)0.052 (3)0.062 (2)
C4B0.054 (3)0.038 (2)0.075 (3)0.0004 (19)0.019 (2)0.013 (2)
C5B0.036 (3)0.040 (2)0.069 (3)0.0012 (18)0.0024 (19)0.0015 (19)
N5B0.051 (3)0.052 (2)0.111 (3)0.0107 (19)0.008 (2)0.008 (2)
O51B0.078 (3)0.068 (2)0.168 (4)0.0324 (19)0.029 (2)0.023 (2)
O52B0.089 (3)0.094 (3)0.124 (3)0.026 (2)0.051 (2)0.023 (2)
C6B0.036 (3)0.040 (2)0.053 (2)0.0031 (17)0.0002 (18)0.0097 (17)
C7B0.037 (3)0.039 (2)0.049 (2)0.0001 (18)0.0055 (19)0.0044 (17)
O71B0.0451 (18)0.0438 (14)0.0690 (17)0.0043 (12)0.0103 (13)0.0223 (13)
O72B0.041 (2)0.0545 (16)0.0690 (18)0.0125 (13)0.0102 (15)0.0122 (13)
N1B0.041 (3)0.147 (4)0.053 (2)0.046 (2)0.0148 (18)0.032 (2)
C8B0.047 (4)0.121 (5)0.057 (3)0.007 (3)0.004 (2)0.020 (3)
C9B0.049 (4)0.081 (3)0.073 (3)0.012 (2)0.006 (2)0.002 (2)
C10B0.046 (3)0.067 (3)0.097 (3)0.006 (2)0.019 (3)0.016 (2)
C11B0.050 (4)0.060 (3)0.118 (4)0.009 (2)0.000 (3)0.020 (3)
C12B0.069 (4)0.056 (3)0.073 (3)0.002 (2)0.011 (3)0.014 (2)
Geometric parameters (Å, º) top
Zn—Cl12.255 (1)C7B—O72B1.233 (4)
Zn—Cl22.257 (1)C7B—O71B1.260 (4)
Zn—O71A1.950 (3)N1B—C12B1.474 (6)
Zn—O71B1.963 (2)N1B—C8B1.480 (6)
C1A—C6A1.381 (5)C8B—C9B1.488 (6)
C1A—C2A1.384 (5)C9B—C10B1.493 (6)
C1A—C7A1.510 (5)C10B—C11B1.493 (6)
C2A—C3A1.377 (5)C11B—C12B1.496 (6)
C3A—C4A1.372 (6)C2A—H2A0.93
C3A—N3A1.471 (5)C4A—H4A0.93
N3A—O32A1.177 (5)C6A—H6A0.93
N3A—O31A1.180 (6)N1A—H1AA0.90
C4A—C5A1.376 (5)N1A—H1AB0.90
C5A—C6A1.374 (5)C8A—H8AA0.97
C5A—N5A1.482 (5)C8A—H8AB0.97
N5A—O52A1.204 (5)C9A—H9AA0.97
N5A—O51A1.220 (5)C9A—H9AB0.97
C7A—O72A1.229 (5)C10A—H10A0.97
C7A—O71A1.265 (4)C10A—H10B0.97
N1A—C12A1.484 (6)C11A—H11A0.97
N1A—C8A1.486 (6)C11A—H11B0.97
C8A—C9A1.457 (7)C12A—H12A0.97
C9A—C10A1.458 (8)C12A—H12B0.97
C10A—C11A1.466 (8)C2B—H2BA0.93
C11A—C12A1.475 (8)C4B—H4BA0.93
C1B—C6B1.385 (5)C6B—H6BA0.93
C1B—C2B1.386 (5)N1B—H1BA0.90
C1B—C7B1.513 (5)N1B—H1BB0.90
C2B—C3B1.376 (5)C8B—H8BA0.97
C3B—C4B1.369 (6)C8B—H8BB0.97
C3B—N3B1.477 (5)C9B—H9BA0.97
N3B—O31B1.199 (6)C9B—H9BB0.97
N3B—O32B1.216 (5)C10B—H10C0.97
C4B—C5B1.359 (5)C10B—H10D0.97
C5B—C6B1.376 (5)C11B—H11C0.97
C5B—N5B1.485 (5)C11B—H11D0.97
N5B—O52B1.195 (5)C12B—H12C0.97
N5B—O51B1.213 (5)C12B—H12D0.97
O71A—Zn—O71B95.36 (11)C1A—C6A—H6A120.2
O71A—Zn—Cl1111.18 (9)C12A—N1A—H1AA109.4
O71B—Zn—Cl1111.90 (9)C8A—N1A—H1AA109.4
O71A—Zn—Cl2112.25 (9)C12A—N1A—H1AB109.4
O71B—Zn—Cl2111.61 (9)C8A—N1A—H1AB109.4
Cl1—Zn—Cl2113.26 (5)H1AA—N1A—H1AB108.0
C6A—C1A—C2A119.0 (3)C9A—C8A—H8AA109.4
C6A—C1A—C7A120.3 (3)N1A—C8A—H8AA109.4
C2A—C1A—C7A120.7 (3)C9A—C8A—H8AB109.4
C3A—C2A—C1A119.4 (4)N1A—C8A—H8AB109.4
C4A—C3A—C2A122.9 (4)H8AA—C8A—H8AB108.0
C4A—C3A—N3A117.5 (4)C8A—C9A—H9AA109.0
C2A—C3A—N3A119.6 (4)C10A—C9A—H9AA109.0
O32A—N3A—O31A122.6 (5)C8A—C9A—H9AB109.0
O32A—N3A—C3A120.0 (5)C10A—C9A—H9AB109.0
O31A—N3A—C3A117.4 (5)H9AA—C9A—H9AB107.8
C3A—C4A—C5A116.4 (4)C9A—C10A—H10A109.9
C6A—C5A—C4A122.7 (4)C11A—C10A—H10A109.9
C6A—C5A—N5A118.7 (4)C9A—C10A—H10B109.9
C4A—C5A—N5A118.6 (4)C11A—C10A—H10B109.9
O52A—N5A—O51A125.1 (4)H10A—C10A—H10B108.3
O52A—N5A—C5A117.6 (4)C10A—C11A—H11A109.1
O51A—N5A—C5A117.3 (4)C12A—C11A—H11A109.1
C5A—C6A—C1A119.7 (3)C10A—C11A—H11B109.1
O72A—C7A—O71A126.6 (4)C12A—C11A—H11B109.1
O72A—C7A—C1A119.0 (3)H11A—C11A—H11B107.8
O71A—C7A—C1A114.4 (3)C11A—C12A—H12A109.7
C7A—O71A—Zn131.7 (3)N1A—C12A—H12A109.7
C12A—N1A—C8A111.2 (3)C11A—C12A—H12B109.7
C9A—C8A—N1A111.0 (5)N1A—C12A—H12B109.7
C8A—C9A—C10A112.9 (5)H12A—C12A—H12B108.2
C9A—C10A—C11A109.0 (5)C3B—C2B—H2BA120.6
C10A—C11A—C12A112.4 (5)C1B—C2B—H2BA120.6
C11A—C12A—N1A109.7 (4)C5B—C4B—H4BA121.5
C6B—C1B—C2B119.4 (3)C3B—C4B—H4BA121.5
C6B—C1B—C7B121.1 (3)C5B—C6B—H6BA120.5
C2B—C1B—C7B119.5 (3)C1B—C6B—H6BA120.5
C3B—C2B—C1B118.8 (4)C12B—N1B—H1BA108.9
C4B—C3B—C2B122.8 (4)C8B—N1B—H1BA108.9
C4B—C3B—N3B118.4 (4)C12B—N1B—H1BB108.9
C2B—C3B—N3B118.8 (4)C8B—N1B—H1BB108.9
O31B—N3B—O32B124.5 (5)H1BA—N1B—H1BB107.7
O31B—N3B—C3B117.8 (5)N1B—C8B—H8BA109.6
O32B—N3B—C3B117.8 (5)C9B—C8B—H8BA109.6
C5B—C4B—C3B116.9 (3)N1B—C8B—H8BB109.6
C4B—C5B—C6B123.1 (4)C9B—C8B—H8BB109.6
C4B—C5B—N5B118.6 (4)H8BA—C8B—H8BB108.1
C6B—C5B—N5B118.3 (4)C8B—C9B—H9BA109.3
O52B—N5B—O51B123.3 (4)C10B—C9B—H9BA109.3
O52B—N5B—C5B118.7 (4)C8B—C9B—H9BB109.3
O51B—N5B—C5B118.0 (4)C10B—C9B—H9BB109.3
C5B—C6B—C1B118.9 (3)H9BA—C9B—H9BB108.0
O72B—C7B—O71B127.2 (3)C9B—C10B—H10C109.4
O72B—C7B—C1B117.9 (3)C11B—C10B—H10C109.4
O71B—C7B—C1B114.9 (3)C9B—C10B—H10D109.4
C7B—O71B—Zn120.4 (2)C11B—C10B—H10D109.4
C12B—N1B—C8B113.5 (3)H10C—C10B—H10D108.0
N1B—C8B—C9B110.1 (4)C10B—C11B—H11C109.1
C8B—C9B—C10B111.4 (4)C12B—C11B—H11C109.1
C9B—C10B—C11B111.1 (4)C10B—C11B—H11D109.1
C10B—C11B—C12B112.3 (4)C12B—C11B—H11D109.1
N1B—C12B—C11B110.0 (4)H11C—C11B—H11D107.9
C3A—C2A—H2A120.3N1B—C12B—H12C109.7
C1A—C2A—H2A120.3C11B—C12B—H12C109.7
C3A—C4A—H4A121.8N1B—C12B—H12D109.7
C5A—C4A—H4A121.8C11B—C12B—H12D109.7
C5A—C6A—H6A120.2H12C—C12B—H12D108.2
C6A—C1A—C2A—C3A0.4 (5)C6B—C1B—C2B—C3B2.5 (5)
C7A—C1A—C2A—C3A177.8 (3)C7B—C1B—C2B—C3B178.7 (3)
N3A—C3A—C2A—C1A179.3 (4)N3B—C3B—C2B—C1B175.6 (3)
C4A—C3A—C2A—C1A0.9 (6)C4B—C3B—C2B—C1B3.3 (6)
C2A—C3A—N3A—O31A11.3 (8)C2B—C3B—N3B—O31B16.2 (7)
C2A—C3A—N3A—O32A170.6 (5)C2B—C3B—N3B—O32B163.7 (4)
C4A—C3A—N3A—O31A169.0 (6)C4B—C3B—N3B—O31B164.8 (5)
C4A—C3A—N3A—O32A9.2 (7)C4B—C3B—N3B—O32B15.3 (6)
C5A—C4A—C3A—C2A0.9 (6)C5B—C4B—C3B—C2B1.9 (6)
C5A—C4A—C3A—N3A179.3 (4)C5B—C4B—C3B—N3B177.0 (4)
N5A—C5A—C4A—C3A176.8 (3)N5B—C5B—C4B—C3B179.7 (4)
C6A—C5A—C4A—C3A0.4 (6)C6B—C5B—C4B—C3B0.3 (6)
O51A—N5A—C5A—C4A3.1 (6)O51B—N5B—C5B—C4B1.7 (6)
O51A—N5A—C5A—C6A179.6 (4)O51B—N5B—C5B—C6B177.7 (4)
O52A—N5A—C5A—C4A177.0 (4)O52B—N5B—C5B—C4B177.9 (4)
O52A—N5A—C5A—C6A0.3 (6)O52B—N5B—C5B—C6B2.7 (6)
C5A—C6A—C1A—C2A0.1 (5)C5B—C6B—C1B—C2B0.4 (5)
C5A—C6A—C1A—C7A178.2 (3)C5B—C6B—C1B—C7B179.2 (3)
C4A—C5A—C6A—C1A0.0 (5)C4B—C5B—C6B—C1B1.0 (6)
N5A—C5A—C6A—C1A177.3 (3)N5B—C5B—C6B—C1B179.6 (3)
C2A—C1A—C7A—O71A173.2 (3)C2B—C1B—C7B—O71B163.4 (3)
C2A—C1A—C7A—O72A6.3 (5)C2B—C1B—C7B—O72B15.8 (5)
C6A—C1A—C7A—O71A4.9 (5)C6B—C1B—C7B—O71B17.8 (5)
C6A—C1A—C7A—O72A175.6 (4)C6B—C1B—C7B—O72B163.0 (3)
Cl1—Zn—O71A—C7A64.0 (4)C7B—O71B—Zn—Cl167.3 (3)
Cl2—Zn—O71A—C7A64.1 (4)C7B—O71B—Zn—Cl260.8 (3)
O71B—Zn—O71A—C7A180.0 (3)C7B—O71B—Zn—O71A177.3 (3)
Zn—O71A—C7A—C1A177.0 (2)C1B—C7B—O71B—Zn176.8 (2)
Zn—O71A—C7A—O72A2.5 (6)O72B—C7B—O71B—Zn2.3 (5)
C9A—C8A—N1A—C12A53.8 (6)C12B—N1B—C8B—C9B56.5 (5)
N1A—C8A—C9A—C10A55.6 (7)C10B—C9B—C8B—N1B55.3 (5)
C8A—C9A—C10A—C11A56.7 (8)C11B—C10B—C9B—C8B54.9 (6)
C9A—C10A—C11A—C12A57.7 (7)C12B—C11B—C10B—C9B54.1 (6)
C8A—N1A—C12A—C11A54.3 (6)C11B—C12B—N1B—C8B55.1 (5)
N1A—C12A—C11A—C10A57.2 (6)C10B—C11B—C12B—N1B53.4 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1AB···O72A0.901.952.799 (5)157
N1A—H1AA···Cl10.902.333.189 (4)159
N1B—H1BA···O72B0.901.862.734 (4)163
N1B—H1BB···Cl2i0.902.443.313 (4)164
Symmetry code: (i) x, y+1, z.
 

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