Bis­[2-(cyclo­propyl­imino­methyl)­phenolato]­zinc(II)

The title compound, [Zn(C₁₀H₁₀NO)₂], contains an enantiomeric pair of mol­ecules in the asymmetric unit of the non-centrosymmetric space group C2. In this mononuclear compound, each Zn^II atom is coordinated by two N atoms and two O atoms from two Schiff bases in a slightly distorted tetrahedral geometry.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.019 Å
• R factor = 0.055
• wR factor = 0.159
• Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT341_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ...         19

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.70 Ratio
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....         O2
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....         C5
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....         C6
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....        C10
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....        C20
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....        C25

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           25.03
           From the CIF: _reflns_number_total               6279
           Count of symmetry unique reflns         3501
           Completeness (_total/calc)            179.35%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2778
           Fraction of Friedel pairs measured     0.793
           Are heavy atom types Z>Si present          yes

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   7 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
   7 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Bis{2-[(cyclopropylimino)methyl]phenolato}zinc(II)

Crystal data

[Zn(C10H10NO)2]	F(000) = 1600
Mr = 385.75	Dx = 1.376 Mg m^−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 2380 reflections
a = 26.99 (2) Å	θ = 2.3–19.0°
b = 9.862 (9) Å	µ = 1.33 mm^−1
c = 19.276 (17) Å	T = 293 K
β = 133.473 (10)°	Block, colorless
V = 3723 (6) Å^3	0.32 × 0.27 × 0.19 mm
Z = 8

Data collection

Siemens SMART CCD area-detector diffractometer	6279 independent reflections
Radiation source: fine-focus sealed tube	3750 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.056
φ and ω scans	θmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −32→30
Tmin = 0.675, Tmax = 0.786	k = −11→11
9558 measured reflections	l = −15→22

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)] = 0.055	H-atom parameters constrained
wR(F^2) = 0.159	w = 1/[σ^2(Fo^2) + (0.0889P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.88	(Δ/σ)max < 0.001
6279 reflections	Δρmax = 0.69 e Å^−3
451 parameters	Δρmin = −0.36 e Å^−3
1 restraint	Absolute structure: Flack (1983); 786 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (2)

Special details

Experimental. C, H and N elemental analyses were performed on a Perkin-Elmer elemental analyser. The IR spectra were recorded in the 4000–600 cm^-1 region using a Smart OMNI-Sampler spectrophotometer.

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	0.15137 (5)	0.74189 (8)	0.98021 (6)	0.0584 (3)
Zn2	0.83165 (5)	0.47991 (9)	0.67704 (7)	0.0607 (3)
N1	0.2510 (3)	0.7810 (6)	1.0852 (4)	0.0532 (16)
N2	0.1161 (3)	0.5510 (7)	0.9488 (5)	0.0576 (17)
N3	0.8326 (3)	0.6709 (6)	0.7136 (4)	0.0564 (17)
N4	0.8339 (4)	0.4403 (7)	0.5771 (5)	0.0655 (19)
O1	0.1211 (3)	0.8579 (6)	1.0229 (4)	0.0700 (16)
O2	0.1191 (3)	0.7851 (6)	0.8588 (5)	0.0798 (18)
O3	0.7464 (3)	0.4314 (6)	0.6348 (5)	0.0784 (18)
O4	0.9065 (3)	0.3672 (6)	0.7734 (4)	0.0734 (16)
C1	0.0849 (4)	0.5024 (9)	0.8641 (6)	0.065 (2)
H1	0.0684	0.4143	0.8527	0.078*
C2	0.0724 (4)	0.5664 (9)	0.7863 (6)	0.060 (2)
C3	0.0897 (5)	0.7039 (9)	0.7868 (7)	0.068 (3)
C4	0.0754 (6)	0.7463 (15)	0.7058 (7)	0.110 (4)
H4	0.0872	0.8344	0.7047	0.133*
C5	0.0458 (8)	0.6677 (19)	0.6294 (10)	0.146 (6)
H5	0.0389	0.7008	0.5782	0.175*
C6	0.0255 (7)	0.5386 (19)	0.6264 (9)	0.143 (6)
H6	0.0020	0.4860	0.5716	0.172*
C7	0.0404 (4)	0.4876 (13)	0.7059 (6)	0.090 (3)
H7	0.0286	0.3986	0.7052	0.108*
C8	0.1229 (5)	0.4678 (10)	1.0164 (6)	0.076 (3)
H8	0.1080	0.3734	0.9969	0.091*
C9	0.1823 (7)	0.4890 (14)	1.1204 (7)	0.104 (3)
H9A	0.2033	0.4095	1.1612	0.125*
H9B	0.2137	0.5618	1.1394	0.125*
C10	0.1140 (8)	0.5260 (13)	1.0778 (9)	0.111 (4)
H10A	0.1032	0.6217	1.0707	0.133*
H10B	0.0928	0.4695	1.0925	0.133*
C11	0.2704 (4)	0.8753 (8)	1.1459 (6)	0.060 (2)
H11	0.3172	0.8905	1.1926	0.072*
C12	0.2300 (4)	0.9603 (8)	1.1518 (5)	0.0539 (19)
C13	0.1587 (5)	0.9462 (8)	1.0925 (6)	0.058 (2)
C14	0.1275 (6)	1.0319 (10)	1.1118 (7)	0.084 (3)
H14	0.0811	1.0229	1.0762	0.101*
C15	0.1652 (8)	1.1295 (11)	1.1831 (9)	0.095 (4)
H15	0.1430	1.1888	1.1917	0.114*
C16	0.2339 (7)	1.1402 (10)	1.2406 (8)	0.090 (3)
H16	0.2588	1.2027	1.2903	0.108*
C17	0.2659 (5)	1.0586 (8)	1.2247 (6)	0.069 (2)
H17	0.3127	1.0680	1.2630	0.083*
C18	0.3019 (4)	0.7143 (9)	1.0942 (7)	0.073 (3)
H18	0.3493	0.7348	1.1524	0.088*
C19	0.2898 (6)	0.6849 (12)	1.0083 (9)	0.097 (3)
H19A	0.2465	0.7132	0.9469	0.117*
H19B	0.3284	0.6908	1.0142	0.117*
C20	0.2889 (5)	0.5733 (12)	1.0576 (9)	0.101 (4)
H20A	0.3270	0.5105	1.0940	0.122*
H20B	0.2451	0.5329	1.0266	0.122*
C21	0.7802 (4)	0.7168 (8)	0.6968 (5)	0.057 (2)
H21	0.7842	0.8053	0.7167	0.069*
C22	0.7173 (4)	0.6509 (9)	0.6520 (6)	0.060 (2)
C23	0.7048 (4)	0.5124 (10)	0.6259 (6)	0.070 (3)
C24	0.6408 (5)	0.4618 (14)	0.5887 (8)	0.106 (4)
H24	0.6290	0.3727	0.5669	0.127*
C25	0.5964 (6)	0.5382 (19)	0.5836 (11)	0.131 (5)
H25	0.5570	0.4985	0.5631	0.157*
C26	0.6089 (6)	0.6728 (19)	0.6083 (9)	0.116 (4)
H26	0.5776	0.7261	0.6020	0.139*
C27	0.6702 (5)	0.7270 (13)	0.6433 (6)	0.084 (3)
H27	0.6798	0.8177	0.6614	0.101*
C28	0.8916 (4)	0.7568 (10)	0.7599 (6)	0.078 (3)
H28	0.8858	0.8517	0.7682	0.094*
C29	0.9351 (6)	0.7351 (12)	0.7411 (9)	0.099 (3)
H29A	0.9241	0.6600	0.7000	0.119*
H29B	0.9537	0.8144	0.7360	0.119*
C30	0.9597 (5)	0.7038 (13)	0.8332 (9)	0.104 (4)
H30A	0.9645	0.6089	0.8501	0.124*
H30B	0.9941	0.7632	0.8861	0.124*
C31	0.8725 (4)	0.3456 (9)	0.5902 (6)	0.069 (2)
H31	0.8693	0.3288	0.5397	0.083*
C32	0.9209 (4)	0.2616 (8)	0.6754 (6)	0.061 (2)
C33	0.9344 (4)	0.2772 (7)	0.7580 (6)	0.058 (2)
C34	0.9846 (5)	0.1869 (10)	0.8358 (7)	0.079 (3)
H34	0.9961	0.1931	0.8935	0.094*
C35	1.0159 (5)	0.0904 (11)	0.8239 (11)	0.101 (4)
H35	1.0473	0.0310	0.8739	0.121*
C36	1.0021 (6)	0.0798 (12)	0.7412 (11)	0.104 (4)
H36	1.0252	0.0182	0.7355	0.125*
C37	0.9540 (5)	0.1617 (9)	0.6690 (8)	0.081 (3)
H37	0.9420	0.1513	0.6110	0.097*
C38	0.7906 (5)	0.5095 (9)	0.4856 (7)	0.085 (3)
H38	0.7985	0.4872	0.4444	0.103*
C39	0.7694 (7)	0.6470 (13)	0.4794 (8)	0.106 (4)
H39A	0.7654	0.7086	0.4365	0.127*
H39B	0.7851	0.6884	0.5373	0.127*
C40	0.7193 (6)	0.5366 (12)	0.4365 (7)	0.108 (4)
H40A	0.7045	0.5096	0.4683	0.130*
H40B	0.6847	0.5298	0.3674	0.130*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0673 (6)	0.0426 (5)	0.0560 (6)	−0.0015 (5)	0.0388 (5)	−0.0034 (5)
Zn2	0.0673 (6)	0.0407 (5)	0.0649 (6)	0.0018 (5)	0.0419 (5)	0.0022 (5)
N1	0.064 (4)	0.035 (4)	0.057 (4)	−0.001 (3)	0.040 (4)	−0.008 (3)
N2	0.062 (4)	0.050 (4)	0.059 (5)	−0.005 (3)	0.041 (4)	−0.002 (3)
N3	0.060 (4)	0.047 (4)	0.052 (4)	−0.009 (3)	0.034 (4)	−0.008 (3)
N4	0.079 (5)	0.042 (4)	0.075 (5)	0.007 (3)	0.053 (4)	0.006 (3)
O1	0.072 (4)	0.052 (4)	0.078 (4)	0.008 (3)	0.048 (4)	−0.008 (3)
O2	0.111 (5)	0.056 (4)	0.070 (4)	−0.014 (3)	0.061 (4)	−0.004 (3)
O3	0.072 (4)	0.052 (4)	0.095 (5)	−0.004 (3)	0.051 (4)	−0.007 (3)
O4	0.074 (4)	0.057 (4)	0.069 (4)	0.012 (3)	0.041 (3)	0.018 (3)
C1	0.054 (5)	0.058 (6)	0.071 (6)	−0.016 (4)	0.039 (5)	−0.022 (5)
C2	0.058 (5)	0.068 (6)	0.044 (5)	−0.008 (4)	0.031 (4)	−0.005 (4)
C3	0.080 (6)	0.068 (7)	0.064 (6)	−0.003 (5)	0.053 (5)	0.005 (5)
C4	0.140 (10)	0.108 (9)	0.064 (7)	−0.006 (9)	0.063 (7)	0.009 (8)
C5	0.183 (15)	0.152 (15)	0.068 (9)	−0.029 (12)	0.073 (10)	0.006 (9)
C6	0.156 (12)	0.176 (18)	0.052 (8)	−0.057 (11)	0.055 (8)	−0.035 (8)
C7	0.078 (6)	0.104 (8)	0.057 (6)	−0.034 (7)	0.035 (5)	−0.029 (6)
C8	0.097 (7)	0.050 (5)	0.076 (6)	−0.012 (5)	0.058 (6)	0.004 (5)
C9	0.129 (9)	0.087 (8)	0.069 (7)	−0.005 (8)	0.058 (7)	0.021 (7)
C10	0.178 (13)	0.103 (10)	0.102 (9)	−0.014 (9)	0.116 (10)	−0.002 (7)
C11	0.064 (5)	0.061 (5)	0.057 (5)	−0.001 (4)	0.043 (5)	0.006 (4)
C12	0.078 (5)	0.039 (4)	0.051 (5)	0.005 (4)	0.047 (4)	0.001 (4)
C13	0.080 (6)	0.043 (5)	0.062 (6)	0.007 (4)	0.053 (5)	0.010 (4)
C14	0.108 (8)	0.076 (7)	0.086 (7)	0.022 (6)	0.074 (7)	0.006 (5)
C15	0.155 (12)	0.057 (6)	0.103 (9)	0.018 (7)	0.100 (10)	0.003 (6)
C16	0.141 (11)	0.056 (6)	0.074 (8)	−0.002 (7)	0.075 (8)	−0.011 (5)
C17	0.084 (6)	0.045 (5)	0.071 (6)	−0.002 (4)	0.051 (6)	−0.008 (4)
C18	0.061 (5)	0.068 (6)	0.087 (6)	−0.009 (4)	0.049 (5)	−0.024 (5)
C19	0.104 (8)	0.101 (9)	0.115 (9)	0.010 (6)	0.086 (8)	−0.014 (7)
C20	0.092 (8)	0.071 (7)	0.131 (11)	0.008 (6)	0.073 (8)	−0.012 (7)
C21	0.059 (5)	0.053 (5)	0.045 (4)	0.006 (4)	0.030 (4)	−0.006 (4)
C22	0.048 (5)	0.067 (6)	0.056 (5)	0.009 (4)	0.032 (4)	0.002 (4)
C23	0.065 (6)	0.066 (7)	0.052 (5)	−0.008 (5)	0.030 (5)	0.004 (4)
C24	0.061 (6)	0.103 (9)	0.117 (9)	−0.012 (7)	0.047 (6)	0.004 (8)
C25	0.068 (7)	0.143 (15)	0.151 (13)	0.005 (8)	0.064 (9)	0.015 (10)
C26	0.074 (8)	0.149 (14)	0.102 (9)	0.033 (8)	0.051 (7)	0.019 (9)
C27	0.069 (6)	0.094 (7)	0.071 (6)	0.003 (6)	0.041 (5)	−0.009 (6)
C28	0.070 (6)	0.052 (6)	0.090 (7)	−0.021 (5)	0.046 (6)	−0.019 (5)
C29	0.119 (8)	0.072 (7)	0.159 (11)	−0.034 (7)	0.116 (9)	−0.025 (8)
C30	0.059 (6)	0.095 (9)	0.122 (10)	−0.012 (6)	0.049 (7)	−0.011 (7)
C31	0.081 (6)	0.050 (5)	0.070 (6)	−0.005 (5)	0.049 (5)	−0.007 (4)
C32	0.063 (5)	0.039 (5)	0.070 (6)	−0.003 (4)	0.041 (5)	0.004 (4)
C33	0.046 (4)	0.037 (5)	0.056 (6)	−0.006 (3)	0.022 (4)	0.002 (4)
C34	0.067 (6)	0.068 (7)	0.074 (7)	−0.009 (5)	0.038 (5)	0.011 (5)
C35	0.056 (6)	0.048 (6)	0.146 (12)	0.003 (5)	0.049 (8)	0.010 (7)
C36	0.088 (8)	0.063 (7)	0.137 (12)	0.009 (6)	0.067 (9)	−0.002 (8)
C37	0.087 (7)	0.050 (6)	0.089 (7)	0.006 (5)	0.054 (6)	0.004 (5)
C38	0.111 (8)	0.060 (7)	0.070 (6)	0.027 (6)	0.056 (6)	0.013 (5)
C39	0.147 (11)	0.080 (8)	0.064 (7)	0.039 (8)	0.062 (8)	0.029 (6)
C40	0.118 (10)	0.089 (9)	0.053 (6)	0.025 (7)	0.034 (7)	0.018 (6)

Geometric parameters (Å, º)

Zn1—O1	1.892 (6)	C16—H16	0.93
Zn1—O2	1.901 (7)	C17—H17	0.93
Zn1—N1	1.996 (6)	C18—C19	1.478 (13)
Zn1—N2	2.006 (7)	C18—C20	1.488 (13)
Zn2—O3	1.899 (6)	C18—H18	0.98
Zn2—O4	1.898 (6)	C19—C20	1.465 (15)
Zn2—N3	2.005 (7)	C19—H19A	0.97
Zn2—N4	2.006 (7)	C19—H19B	0.97
N1—C11	1.290 (10)	C20—H20A	0.97
N1—C18	1.424 (10)	C20—H20B	0.97
N2—C1	1.308 (10)	C21—C22	1.428 (11)
N2—C8	1.442 (11)	C21—H21	0.93
N3—C21	1.296 (9)	C22—C27	1.383 (12)
N3—C28	1.447 (10)	C22—C23	1.414 (12)
N4—C31	1.288 (10)	C23—C24	1.430 (12)
N4—C38	1.451 (11)	C24—C25	1.361 (17)
O1—C13	1.310 (10)	C24—H24	0.93
O2—C3	1.296 (10)	C25—C26	1.372 (18)
O3—C23	1.289 (10)	C25—H25	0.93
O4—C33	1.322 (10)	C26—C27	1.393 (16)
C1—C2	1.439 (12)	C26—H26	0.93
C1—H1	0.93	C27—H27	0.93
C2—C7	1.382 (12)	C28—C30	1.440 (13)
C2—C3	1.432 (12)	C28—C29	1.463 (13)
C3—C4	1.391 (13)	C28—H28	0.98
C4—C5	1.337 (18)	C29—C30	1.436 (15)
C4—H4	0.93	C29—H29A	0.97
C5—C6	1.372 (19)	C29—H29B	0.97
C5—H5	0.93	C30—H30A	0.97
C6—C7	1.383 (16)	C30—H30B	0.97
C6—H6	0.93	C31—C32	1.462 (11)
C7—H7	0.93	C31—H31	0.93
C8—C10	1.475 (14)	C32—C33	1.376 (12)
C8—C9	1.486 (13)	C32—C37	1.393 (12)
C8—H8	0.98	C33—C34	1.443 (12)
C9—C10	1.456 (16)	C34—C35	1.391 (14)
C9—H9A	0.97	C34—H34	0.93
C9—H9B	0.97	C35—C36	1.368 (16)
C10—H10A	0.97	C35—H35	0.93
C10—H10B	0.97	C36—C37	1.338 (14)
C11—C12	1.442 (10)	C36—H36	0.93
C11—H11	0.93	C37—H37	0.93
C12—C17	1.407 (11)	C38—C39	1.444 (14)
C12—C13	1.414 (11)	C38—C40	1.471 (15)
C13—C14	1.411 (12)	C38—H38	0.98
C14—C15	1.388 (15)	C39—C40	1.469 (16)
C14—H14	0.93	C39—H39A	0.97
C15—C16	1.361 (15)	C39—H39B	0.97
C15—H15	0.93	C40—H40A	0.97
C16—C17	1.360 (13)	C40—H40B	0.97
O1—Zn1—O2	115.5 (3)	C19—C18—H18	115.7
O1—Zn1—N1	97.2 (3)	C20—C18—H18	115.7
O2—Zn1—N1	111.2 (3)	C20—C19—C18	60.7 (7)
O1—Zn1—N2	116.2 (3)	C20—C19—H19A	117.7
O2—Zn1—N2	96.8 (3)	C18—C19—H19A	117.7
N1—Zn1—N2	121.0 (3)	C20—C19—H19B	117.7
O3—Zn2—O4	115.6 (3)	C18—C19—H19B	117.7
O3—Zn2—N3	96.1 (3)	H19A—C19—H19B	114.8
O4—Zn2—N3	117.3 (3)	C19—C20—C18	60.1 (7)
O3—Zn2—N4	111.5 (3)	C19—C20—H20A	117.8
O4—Zn2—N4	96.4 (3)	C18—C20—H20A	117.8
N3—Zn2—N4	121.2 (3)	C19—C20—H20B	117.8
C11—N1—C18	117.8 (7)	C18—C20—H20B	117.8
C11—N1—Zn1	118.9 (6)	H20A—C20—H20B	114.9
C18—N1—Zn1	123.2 (5)	N3—C21—C22	129.2 (8)
C1—N2—C8	119.4 (8)	N3—C21—H21	115.4
C1—N2—Zn1	119.0 (6)	C22—C21—H21	115.4
C8—N2—Zn1	121.5 (6)	C27—C22—C23	120.5 (9)
C21—N3—C28	119.9 (7)	C27—C22—C21	116.0 (9)
C21—N3—Zn2	119.5 (5)	C23—C22—C21	123.2 (8)
C28—N3—Zn2	120.6 (6)	O3—C23—C22	125.4 (8)
C31—N4—C38	116.5 (8)	O3—C23—C24	119.5 (9)
C31—N4—Zn2	120.5 (6)	C22—C23—C24	115.1 (10)
C38—N4—Zn2	122.9 (6)	C25—C24—C23	122.9 (13)
C13—O1—Zn1	125.8 (5)	C25—C24—H24	118.6
C3—O2—Zn1	127.1 (5)	C23—C24—H24	118.6
C23—O3—Zn2	126.0 (5)	C24—C25—C26	121.2 (13)
C33—O4—Zn2	124.1 (5)	C24—C25—H25	119.4
N2—C1—C2	128.9 (8)	C26—C25—H25	119.4
N2—C1—H1	115.5	C25—C26—C27	117.8 (12)
C2—C1—H1	115.5	C25—C26—H26	121.1
C7—C2—C3	119.4 (9)	C27—C26—H26	121.1
C7—C2—C1	116.1 (9)	C22—C27—C26	122.4 (12)
C3—C2—C1	124.5 (8)	C22—C27—H27	118.8
O2—C3—C4	120.6 (10)	C26—C27—H27	118.8
O2—C3—C2	123.3 (8)	C30—C28—N3	120.9 (9)
C4—C3—C2	116.1 (10)	C30—C28—C29	59.3 (7)
C5—C4—C3	123.8 (14)	N3—C28—C29	119.4 (8)
C5—C4—H4	118.1	C30—C28—H28	115.3
C3—C4—H4	118.1	N3—C28—H28	115.3
C4—C5—C6	120.3 (13)	C29—C28—H28	115.3
C4—C5—H5	119.9	C30—C29—C28	59.6 (7)
C6—C5—H5	119.9	C30—C29—H29A	117.8
C5—C6—C7	119.2 (12)	C28—C29—H29A	117.8
C5—C6—H6	120.4	C30—C29—H29B	117.8
C7—C6—H6	120.4	C28—C29—H29B	117.8
C2—C7—C6	121.2 (12)	H29A—C29—H29B	115.0
C2—C7—H7	119.4	C28—C30—C29	61.1 (7)
C6—C7—H7	119.4	C28—C30—H30A	117.7
N2—C8—C10	120.9 (9)	C29—C30—H30A	117.7
N2—C8—C9	119.1 (8)	C28—C30—H30B	117.7
C10—C8—C9	58.9 (8)	C29—C30—H30B	117.7
N2—C8—H8	115.4	H30A—C30—H30B	114.8
C10—C8—H8	115.4	N4—C31—C32	127.4 (9)
C9—C8—H8	115.4	N4—C31—H31	116.3
C10—C9—C8	60.2 (7)	C32—C31—H31	116.3
C10—C9—H9A	117.8	C33—C32—C37	120.5 (8)
C8—C9—H9A	117.8	C33—C32—C31	123.9 (8)
C10—C9—H9B	117.8	C37—C32—C31	115.6 (9)
C8—C9—H9B	117.8	O4—C33—C32	126.6 (7)
H9A—C9—H9B	114.9	O4—C33—C34	117.1 (9)
C9—C10—C8	60.9 (7)	C32—C33—C34	116.3 (9)
C9—C10—H10A	117.7	C35—C34—C33	119.7 (10)
C8—C10—H10A	117.7	C35—C34—H34	120.2
C9—C10—H10B	117.7	C33—C34—H34	120.2
C8—C10—H10B	117.7	C36—C35—C34	122.2 (11)
H10A—C10—H10B	114.8	C36—C35—H35	118.9
N1—C11—C12	129.3 (8)	C34—C35—H35	118.9
N1—C11—H11	115.4	C37—C36—C35	117.3 (12)
C12—C11—H11	115.4	C37—C36—H36	121.3
C17—C12—C13	119.6 (7)	C35—C36—H36	121.3
C17—C12—C11	116.2 (8)	C36—C37—C32	123.8 (11)
C13—C12—C11	124.2 (7)	C36—C37—H37	118.1
O1—C13—C14	119.1 (8)	C32—C37—H37	118.1
O1—C13—C12	123.9 (7)	C39—C38—N4	119.0 (9)
C14—C13—C12	117.0 (8)	C39—C38—C40	60.5 (7)
C15—C14—C13	120.9 (10)	N4—C38—C40	118.1 (9)
C15—C14—H14	119.6	C39—C38—H38	115.9
C13—C14—H14	119.6	N4—C38—H38	115.9
C16—C15—C14	121.3 (10)	C40—C38—H38	115.9
C16—C15—H15	119.4	C38—C39—C40	60.7 (8)
C14—C15—H15	119.4	C38—C39—H39A	117.7
C15—C16—C17	119.4 (10)	C40—C39—H39A	117.7
C15—C16—H16	120.3	C38—C39—H39B	117.7
C17—C16—H16	120.3	C40—C39—H39B	117.7
C16—C17—C12	121.6 (9)	H39A—C39—H39B	114.8
C16—C17—H17	119.2	C38—C40—C39	58.8 (7)
C12—C17—H17	119.2	C38—C40—H40A	117.9
N1—C18—C19	120.2 (8)	C39—C40—H40A	117.9
N1—C18—C20	118.7 (8)	C38—C40—H40B	117.9
C19—C18—C20	59.2 (7)	C39—C40—H40B	117.9
N1—C18—H18	115.7	H40A—C40—H40B	115.0
O1—Zn1—N1—C11	−6.6 (6)	Zn1—O1—C13—C12	−5.2 (11)
O2—Zn1—N1—C11	114.4 (6)	C17—C12—C13—O1	179.9 (7)
N2—Zn1—N1—C11	−133.2 (6)	C11—C12—C13—O1	−3.1 (12)
O1—Zn1—N1—C18	176.4 (6)	C17—C12—C13—C14	−1.1 (11)
O2—Zn1—N1—C18	−62.6 (7)	C11—C12—C13—C14	175.8 (7)
N2—Zn1—N1—C18	49.9 (7)	O1—C13—C14—C15	−178.1 (9)
O1—Zn1—N2—C1	125.0 (6)	C12—C13—C14—C15	2.9 (13)
O2—Zn1—N2—C1	2.1 (6)	C13—C14—C15—C16	−4.2 (16)
N1—Zn1—N2—C1	−117.7 (6)	C14—C15—C16—C17	3.6 (17)
O1—Zn1—N2—C8	−53.4 (7)	C15—C16—C17—C12	−1.8 (15)
O2—Zn1—N2—C8	−176.2 (6)	C13—C12—C17—C16	0.6 (13)
N1—Zn1—N2—C8	64.0 (7)	C11—C12—C17—C16	−176.6 (8)
O3—Zn2—N3—C21	−4.2 (6)	C11—N1—C18—C19	−137.2 (9)
O4—Zn2—N3—C21	−127.1 (6)	Zn1—N1—C18—C19	39.8 (11)
N4—Zn2—N3—C21	115.6 (6)	C11—N1—C18—C20	153.7 (9)
O3—Zn2—N3—C28	174.7 (6)	Zn1—N1—C18—C20	−29.3 (12)
O4—Zn2—N3—C28	51.8 (7)	N1—C18—C19—C20	−107.5 (10)
N4—Zn2—N3—C28	−65.5 (7)	N1—C18—C20—C19	109.9 (10)
O3—Zn2—N4—C31	−111.5 (7)	C28—N3—C21—C22	179.6 (8)
O4—Zn2—N4—C31	9.3 (7)	Zn2—N3—C21—C22	−1.5 (11)
N3—Zn2—N4—C31	136.6 (6)	N3—C21—C22—C27	−179.5 (8)
O3—Zn2—N4—C38	65.1 (7)	N3—C21—C22—C23	6.6 (14)
O4—Zn2—N4—C38	−174.1 (7)	Zn2—O3—C23—C22	−4.2 (13)
N3—Zn2—N4—C38	−46.8 (8)	Zn2—O3—C23—C24	177.0 (7)
O2—Zn1—O1—C13	−108.8 (6)	C27—C22—C23—O3	−177.1 (8)
N1—Zn1—O1—C13	8.9 (7)	C21—C22—C23—O3	−3.5 (14)
N2—Zn1—O1—C13	138.8 (6)	C27—C22—C23—C24	1.7 (13)
O1—Zn1—O2—C3	−128.7 (7)	C21—C22—C23—C24	175.4 (8)
N1—Zn1—O2—C3	121.7 (7)	O3—C23—C24—C25	175.1 (11)
N2—Zn1—O2—C3	−5.4 (8)	C22—C23—C24—C25	−3.8 (16)
O4—Zn2—O3—C23	131.3 (7)	C23—C24—C25—C26	5 (2)
N3—Zn2—O3—C23	7.0 (7)	C24—C25—C26—C27	−3 (2)
N4—Zn2—O3—C23	−120.0 (7)	C23—C22—C27—C26	−0.5 (14)
O3—Zn2—O4—C33	105.6 (6)	C21—C22—C27—C26	−174.6 (9)
N3—Zn2—O4—C33	−142.0 (6)	C25—C26—C27—C22	1.2 (18)
N4—Zn2—O4—C33	−11.9 (6)	C21—N3—C28—C30	138.0 (10)
C8—N2—C1—C2	−179.9 (8)	Zn2—N3—C28—C30	−40.9 (12)
Zn1—N2—C1—C2	1.7 (12)	C21—N3—C28—C29	−152.2 (9)
N2—C1—C2—C7	177.3 (8)	Zn2—N3—C28—C29	28.9 (12)
N2—C1—C2—C3	−3.9 (14)	N3—C28—C29—C30	−110.5 (11)
Zn1—O2—C3—C4	−173.0 (8)	N3—C28—C30—C29	108.1 (11)
Zn1—O2—C3—C2	4.7 (13)	C38—N4—C31—C32	179.6 (8)
C7—C2—C3—O2	179.2 (9)	Zn2—N4—C31—C32	−3.6 (12)
C1—C2—C3—O2	0.4 (14)	N4—C31—C32—C33	−3.2 (14)
C7—C2—C3—C4	−3.1 (13)	N4—C31—C32—C37	177.0 (8)
C1—C2—C3—C4	178.2 (9)	Zn2—O4—C33—C32	9.0 (11)
O2—C3—C4—C5	179.5 (13)	Zn2—O4—C33—C34	−171.8 (5)
C2—C3—C4—C5	1.7 (18)	C37—C32—C33—O4	−179.8 (8)
C3—C4—C5—C6	2 (3)	C31—C32—C33—O4	0.4 (13)
C4—C5—C6—C7	−5 (3)	C37—C32—C33—C34	1.0 (11)
C3—C2—C7—C6	0.8 (16)	C31—C32—C33—C34	−178.8 (7)
C1—C2—C7—C6	179.6 (11)	O4—C33—C34—C35	−179.8 (8)
C5—C6—C7—C2	3 (2)	C32—C33—C34—C35	−0.4 (12)
C1—N2—C8—C10	−139.7 (10)	C33—C34—C35—C36	1.8 (15)
Zn1—N2—C8—C10	38.6 (12)	C34—C35—C36—C37	−3.6 (18)
C1—N2—C8—C9	151.1 (10)	C35—C36—C37—C32	4.2 (17)
Zn1—N2—C8—C9	−30.5 (12)	C33—C32—C37—C36	−3.0 (15)
N2—C8—C9—C10	110.6 (11)	C31—C32—C37—C36	176.8 (10)
N2—C8—C10—C9	−107.5 (11)	C31—N4—C38—C39	−153.6 (10)
C18—N1—C11—C12	178.3 (8)	Zn2—N4—C38—C39	29.7 (14)
Zn1—N1—C11—C12	1.2 (11)	C31—N4—C38—C40	136.4 (9)
N1—C11—C12—C17	−177.7 (8)	Zn2—N4—C38—C40	−40.4 (11)
N1—C11—C12—C13	5.2 (13)	N4—C38—C39—C40	−107.8 (12)
Zn1—O1—C13—C14	175.8 (6)	N4—C38—C40—C39	109.2 (10)