Bis(1,10-phenanthroline-κ²N,N′)(2-phenethyl­malonato-κ²O,O′)zinc(II) octa­hydrate

The title compound, [Zn(C₁₁H₁₁O₄)(C₁₂H₈N₂)]·8H₂O, was synthesized by the reaction of 1,10-phenanthroline (phen) and 2-phenethyl­malonic acid (H₂pmal) with Zn(NO₃)₂. Two mol­ecules of phen and one H₂pmal are chelated to the Zn^II ion in a bidentate manner in a distorted octa­hedral geometry. The structure is stabilized by extensive C—H...O intra- and inter­molecular inter­actions, forming a three-dimensional network. In addition, π–π and C—H...π inter­actions are also present in the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.040
• wR factor = 0.090
• Data-to-parameter ratio = 12.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT417_ALERT_2_B Short Inter D-H..H-D       H8B    ..  H9B     ..       2.08 Ang.

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.70 Ratio
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          5
            N3  -ZN1 -O1  -C1     89.90  0.60   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         31
            O1  -ZN1 -N3  -C24  -170.90  0.50   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         36
            O1  -ZN1 -N3  -C35     6.40  0.70   1.555   1.555   1.555   1.555

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

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

Bis(1,10-phenanthroline-κ²N,N')(phenethylmalonate-κ²O,O')zinc(II) octahydrate

Crystal data

[Zn(C11H11O4)(C12H8N2)]·8H2O	Z = 2
Mr = 776.10	F(000) = 812
Triclinic, P1	Dx = 1.426 Mg m^−3
a = 10.493 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.144 (3) Å	Cell parameters from 3140 reflections
c = 14.214 (3) Å	θ = 2.5–25.0°
α = 76.395 (4)°	µ = 0.75 mm^−1
β = 83.852 (4)°	T = 294 K
γ = 71.694 (4)°	Block, colourless
V = 1807.8 (7) Å^3	0.24 × 0.22 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer	6343 independent reflections
Radiation source: fine-focus sealed tube	4663 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
φ and ω scans	θmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −8→12
Tmin = 0.831, Tmax = 0.877	k = −15→13
9290 measured reflections	l = −15→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0311P)^2 + 0.4083P] where P = (Fo^2 + 2Fc^2)/3
6343 reflections	(Δ/σ)max = 0.001
517 parameters	Δρmax = 0.26 e Å^−3
24 restraints	Δρmin = −0.41 e Å^−3

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	0.79734 (3)	0.82591 (3)	0.74476 (2)	0.03081 (11)
O1	0.73488 (18)	0.71028 (15)	0.70181 (12)	0.0340 (4)
O2	0.5691 (2)	0.63508 (18)	0.73630 (15)	0.0512 (6)
O3	0.71529 (19)	0.78877 (15)	0.88250 (13)	0.0374 (5)
O4	0.5835 (2)	0.70673 (19)	0.98276 (16)	0.0583 (6)
N1	0.6145 (2)	0.95847 (18)	0.70335 (16)	0.0343 (5)
N2	0.8393 (2)	0.89342 (18)	0.59301 (16)	0.0341 (5)
N3	0.8871 (2)	0.93180 (18)	0.79661 (16)	0.0351 (6)
N4	1.0026 (2)	0.72488 (18)	0.77147 (16)	0.0335 (5)
C1	0.6668 (3)	0.6548 (2)	0.75976 (19)	0.0312 (6)
C2	0.7120 (3)	0.6125 (2)	0.86400 (18)	0.0300 (6)
H2	0.8105	0.5888	0.8616	0.036*
C3	0.6657 (3)	0.7096 (2)	0.91472 (19)	0.0327 (6)
C4	0.6672 (3)	0.5151 (2)	0.9185 (2)	0.0412 (7)
H4A	0.5699	0.5380	0.9246	0.049*
H4B	0.7013	0.4931	0.9833	0.049*
C5	0.7125 (3)	0.4158 (2)	0.8718 (2)	0.0514 (9)
H5A	0.6892	0.3551	0.9158	0.062*
H5B	0.6633	0.4329	0.8132	0.062*
C6	0.8616 (3)	0.3796 (2)	0.8464 (2)	0.0443 (8)
C7	0.9067 (4)	0.3775 (3)	0.7526 (3)	0.0630 (10)
H7	0.8449	0.3993	0.7040	0.076*
C8	1.0431 (5)	0.3432 (3)	0.7290 (3)	0.0813 (13)
H8	1.0720	0.3417	0.6650	0.098*
C9	1.1341 (5)	0.3121 (3)	0.7990 (4)	0.0809 (13)
H9	1.2254	0.2890	0.7830	0.097*
C10	1.0918 (4)	0.3145 (3)	0.8930 (3)	0.0773 (12)
H10	1.1542	0.2938	0.9411	0.093*
C11	0.9561 (4)	0.3479 (3)	0.9162 (3)	0.0615 (10)
H11	0.9278	0.3491	0.9804	0.074*
C12	0.5036 (3)	0.9872 (2)	0.7571 (2)	0.0413 (7)
H12	0.5013	0.9489	0.8209	0.050*
C13	0.3906 (3)	1.0720 (3)	0.7227 (3)	0.0502 (8)
H13	0.3150	1.0903	0.7631	0.060*
C14	0.3915 (3)	1.1280 (2)	0.6293 (3)	0.0499 (8)
H14	0.3162	1.1846	0.6053	0.060*
C15	0.5062 (3)	1.1002 (2)	0.5694 (2)	0.0406 (7)
C16	0.5150 (4)	1.1522 (3)	0.4703 (3)	0.0515 (9)
H16	0.4417	1.2086	0.4427	0.062*
C17	0.6268 (4)	1.1213 (3)	0.4161 (2)	0.0548 (9)
H17	0.6305	1.1583	0.3519	0.066*
C18	0.7412 (3)	1.0327 (3)	0.4545 (2)	0.0440 (8)
C19	0.8579 (4)	0.9930 (3)	0.3999 (2)	0.0575 (10)
H19	0.8650	1.0257	0.3348	0.069*
C20	0.9607 (4)	0.9072 (3)	0.4411 (2)	0.0564 (9)
H20	1.0383	0.8808	0.4050	0.068*
C21	0.9478 (3)	0.8591 (3)	0.5390 (2)	0.0441 (8)
H21	1.0187	0.8006	0.5672	0.053*
C22	0.7362 (3)	0.9792 (2)	0.55167 (19)	0.0334 (6)
C23	0.6164 (3)	1.0133 (2)	0.6105 (2)	0.0327 (6)
C24	0.8312 (3)	1.0342 (2)	0.8058 (2)	0.0493 (8)
H24	0.7444	1.0704	0.7847	0.059*
C25	0.8970 (4)	1.0907 (3)	0.8460 (3)	0.0613 (10)
H25	0.8542	1.1627	0.8517	0.074*
C26	1.0243 (4)	1.0390 (3)	0.8764 (2)	0.0582 (10)
H26	1.0690	1.0754	0.9036	0.070*
C27	1.0882 (3)	0.9310 (3)	0.8667 (2)	0.0446 (8)
C28	1.2243 (4)	0.8718 (3)	0.8922 (2)	0.0572 (10)
H28	1.2724	0.9038	0.9214	0.069*
C29	1.2835 (3)	0.7717 (3)	0.8747 (2)	0.0558 (9)
H29	1.3726	0.7361	0.8907	0.067*
C30	1.2126 (3)	0.7185 (3)	0.8320 (2)	0.0411 (7)
C31	1.2705 (3)	0.6143 (3)	0.8108 (2)	0.0507 (9)
H31	1.3605	0.5769	0.8228	0.061*
C32	1.1947 (3)	0.5686 (3)	0.7729 (2)	0.0503 (8)
H32	1.2318	0.4993	0.7592	0.060*
C33	1.0608 (3)	0.6260 (2)	0.7547 (2)	0.0413 (7)
H33	1.0098	0.5929	0.7295	0.050*
C34	1.0772 (3)	0.7720 (2)	0.80993 (18)	0.0315 (6)
C35	1.0153 (3)	0.8803 (2)	0.82577 (19)	0.0339 (7)
O5	0.8558 (3)	0.6397 (2)	0.53408 (19)	0.0690 (7)
H5C	0.811 (4)	0.664 (3)	0.585 (2)	0.103*
H5D	0.841 (4)	0.582 (3)	0.530 (3)	0.103*
O6	0.6274 (3)	0.5828 (2)	0.4043 (2)	0.0817 (8)
H6A	0.716 (2)	0.560 (4)	0.423 (3)	0.123*
H6B	0.583 (4)	0.592 (4)	0.462 (2)	0.123*
O7	0.4794 (3)	0.5975 (2)	0.57810 (18)	0.0724 (8)
H7A	0.510 (4)	0.612 (3)	0.628 (2)	0.109*
H7B	0.469 (4)	0.532 (2)	0.596 (3)	0.109*
O8	0.2644 (3)	0.7247 (3)	0.4433 (2)	0.0892 (9)
H8A	0.307 (4)	0.726 (4)	0.3862 (19)	0.134*
H8B	0.319 (4)	0.693 (4)	0.489 (2)	0.134*
O9	0.8652 (3)	0.4338 (2)	0.4871 (2)	0.0805 (8)
H9A	0.955 (2)	0.408 (3)	0.480 (3)	0.121*
H9B	0.839 (4)	0.372 (3)	0.505 (3)	0.121*
O10	0.4286 (3)	0.7204 (3)	0.2764 (2)	0.1035 (11)
H10A	0.502 (4)	0.662 (3)	0.299 (3)	0.155*
H10B	0.455 (5)	0.751 (4)	0.217 (2)	0.155*
O11	0.4782 (3)	0.8489 (2)	0.09762 (18)	0.0760 (8)
H11A	0.509 (4)	0.799 (3)	0.064 (3)	0.114*
H11B	0.419 (4)	0.906 (2)	0.072 (3)	0.114*
O12	0.6841 (3)	0.9426 (2)	0.00459 (19)	0.0669 (7)
H12A	0.709 (4)	0.899 (3)	−0.036 (2)	0.100*
H12B	0.621 (3)	0.923 (3)	0.044 (2)	0.100*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0311 (2)	0.03002 (18)	0.03177 (18)	−0.00848 (13)	−0.00302 (13)	−0.00760 (14)
O1	0.0445 (12)	0.0373 (11)	0.0250 (10)	−0.0189 (9)	0.0022 (9)	−0.0082 (9)
O2	0.0489 (14)	0.0705 (16)	0.0451 (13)	−0.0348 (12)	−0.0129 (10)	−0.0054 (11)
O3	0.0493 (13)	0.0363 (11)	0.0311 (11)	−0.0161 (10)	0.0035 (9)	−0.0132 (9)
O4	0.0618 (16)	0.0692 (16)	0.0543 (14)	−0.0286 (12)	0.0277 (12)	−0.0337 (12)
N1	0.0367 (14)	0.0320 (13)	0.0347 (14)	−0.0095 (11)	−0.0034 (11)	−0.0081 (11)
N2	0.0359 (14)	0.0333 (13)	0.0349 (13)	−0.0133 (11)	0.0022 (11)	−0.0081 (11)
N3	0.0417 (15)	0.0329 (13)	0.0349 (13)	−0.0162 (11)	0.0024 (11)	−0.0099 (11)
N4	0.0337 (14)	0.0341 (13)	0.0349 (13)	−0.0127 (11)	−0.0020 (10)	−0.0078 (11)
C1	0.0323 (17)	0.0323 (16)	0.0304 (15)	−0.0097 (12)	0.0002 (13)	−0.0096 (13)
C2	0.0283 (15)	0.0308 (15)	0.0296 (15)	−0.0069 (12)	−0.0019 (12)	−0.0059 (12)
C3	0.0315 (17)	0.0379 (17)	0.0273 (15)	−0.0076 (13)	−0.0046 (13)	−0.0069 (13)
C4	0.0458 (19)	0.0392 (17)	0.0369 (17)	−0.0148 (14)	0.0021 (14)	−0.0037 (14)
C5	0.067 (2)	0.0348 (18)	0.053 (2)	−0.0210 (16)	−0.0033 (17)	−0.0022 (16)
C6	0.063 (2)	0.0231 (15)	0.0451 (19)	−0.0127 (14)	−0.0017 (16)	−0.0045 (14)
C7	0.086 (3)	0.053 (2)	0.052 (2)	−0.022 (2)	−0.001 (2)	−0.0154 (18)
C8	0.104 (4)	0.069 (3)	0.074 (3)	−0.027 (3)	0.026 (3)	−0.033 (2)
C9	0.071 (3)	0.053 (2)	0.117 (4)	−0.011 (2)	0.018 (3)	−0.033 (3)
C10	0.071 (3)	0.055 (2)	0.097 (4)	−0.001 (2)	−0.026 (3)	−0.014 (2)
C11	0.071 (3)	0.050 (2)	0.052 (2)	−0.0040 (18)	−0.0089 (19)	−0.0058 (18)
C12	0.0377 (18)	0.0426 (18)	0.0421 (18)	−0.0076 (14)	0.0028 (14)	−0.0141 (15)
C13	0.040 (2)	0.0449 (19)	0.065 (2)	−0.0035 (15)	−0.0002 (16)	−0.0227 (18)
C14	0.039 (2)	0.0330 (17)	0.075 (3)	0.0000 (14)	−0.0186 (17)	−0.0151 (17)
C15	0.046 (2)	0.0278 (16)	0.0510 (19)	−0.0125 (14)	−0.0182 (15)	−0.0059 (14)
C16	0.063 (2)	0.0353 (18)	0.055 (2)	−0.0164 (16)	−0.0275 (19)	0.0048 (16)
C17	0.081 (3)	0.048 (2)	0.0397 (19)	−0.0322 (19)	−0.0213 (19)	0.0101 (16)
C18	0.060 (2)	0.0456 (19)	0.0342 (17)	−0.0305 (16)	−0.0047 (16)	−0.0011 (15)
C19	0.080 (3)	0.071 (3)	0.0323 (18)	−0.045 (2)	0.0059 (18)	−0.0040 (18)
C20	0.060 (2)	0.075 (3)	0.044 (2)	−0.036 (2)	0.0196 (17)	−0.0186 (19)
C21	0.0420 (19)	0.0479 (19)	0.0459 (19)	−0.0198 (15)	0.0091 (15)	−0.0126 (15)
C22	0.0439 (18)	0.0318 (15)	0.0303 (15)	−0.0186 (13)	−0.0059 (13)	−0.0059 (13)
C23	0.0355 (17)	0.0271 (15)	0.0376 (16)	−0.0108 (12)	−0.0082 (13)	−0.0061 (13)
C24	0.061 (2)	0.0366 (18)	0.053 (2)	−0.0174 (16)	0.0058 (16)	−0.0152 (16)
C25	0.086 (3)	0.043 (2)	0.067 (2)	−0.032 (2)	0.014 (2)	−0.0248 (18)
C26	0.083 (3)	0.070 (3)	0.047 (2)	−0.053 (2)	0.0119 (19)	−0.0249 (19)
C27	0.057 (2)	0.059 (2)	0.0335 (17)	−0.0377 (17)	0.0098 (15)	−0.0165 (15)
C28	0.055 (2)	0.094 (3)	0.045 (2)	−0.049 (2)	−0.0024 (17)	−0.019 (2)
C29	0.039 (2)	0.090 (3)	0.046 (2)	−0.0308 (19)	−0.0063 (16)	−0.010 (2)
C30	0.0326 (18)	0.059 (2)	0.0328 (16)	−0.0188 (15)	−0.0019 (13)	−0.0038 (15)
C31	0.0303 (18)	0.062 (2)	0.048 (2)	−0.0045 (16)	−0.0012 (15)	−0.0011 (17)
C32	0.039 (2)	0.0434 (19)	0.061 (2)	−0.0022 (15)	0.0024 (16)	−0.0129 (17)
C33	0.0380 (18)	0.0367 (17)	0.0501 (19)	−0.0084 (14)	−0.0008 (14)	−0.0153 (15)
C34	0.0323 (16)	0.0402 (17)	0.0239 (14)	−0.0158 (13)	0.0011 (12)	−0.0043 (12)
C35	0.0364 (17)	0.0459 (18)	0.0261 (15)	−0.0231 (14)	0.0030 (12)	−0.0077 (13)
O5	0.0745 (19)	0.079 (2)	0.0643 (17)	−0.0309 (15)	0.0227 (13)	−0.0368 (15)
O6	0.0744 (19)	0.082 (2)	0.077 (2)	−0.0122 (16)	−0.0005 (15)	−0.0100 (17)
O7	0.098 (2)	0.0755 (19)	0.0605 (17)	−0.0413 (16)	−0.0092 (15)	−0.0217 (15)
O8	0.069 (2)	0.098 (2)	0.101 (2)	−0.0231 (17)	−0.0089 (17)	−0.021 (2)
O9	0.0646 (18)	0.088 (2)	0.094 (2)	−0.0234 (16)	0.0010 (16)	−0.0293 (18)
O10	0.101 (3)	0.135 (3)	0.073 (2)	−0.047 (2)	−0.0046 (18)	−0.001 (2)
O11	0.095 (2)	0.0636 (18)	0.0593 (17)	−0.0025 (15)	0.0087 (15)	−0.0275 (14)
O12	0.080 (2)	0.0608 (17)	0.0662 (18)	−0.0227 (14)	0.0030 (13)	−0.0268 (14)

Geometric parameters (Å, º)

Zn1—O1	2.0639 (18)	C16—H16	0.9300
Zn1—O3	2.0654 (19)	C17—C18	1.435 (5)
Zn1—N4	2.165 (2)	C17—H17	0.9300
Zn1—N1	2.173 (2)	C18—C22	1.398 (4)
Zn1—N2	2.185 (2)	C18—C19	1.400 (5)
Zn1—N3	2.196 (2)	C19—C20	1.356 (5)
O1—C1	1.280 (3)	C19—H19	0.9300
O2—C1	1.229 (3)	C20—C21	1.397 (4)
O3—C3	1.276 (3)	C20—H20	0.9300
O4—C3	1.227 (3)	C21—H21	0.9300
N1—C12	1.323 (3)	C22—C23	1.441 (4)
N1—C23	1.348 (3)	C24—C25	1.400 (5)
N2—C21	1.321 (3)	C24—H24	0.9300
N2—C22	1.358 (3)	C25—C26	1.360 (5)
N3—C24	1.321 (4)	C25—H25	0.9300
N3—C35	1.363 (3)	C26—C27	1.399 (5)
N4—C33	1.317 (3)	C26—H26	0.9300
N4—C34	1.361 (3)	C27—C35	1.402 (4)
C1—C2	1.525 (4)	C27—C28	1.434 (5)
C2—C4	1.515 (4)	C28—C29	1.336 (5)
C2—C3	1.534 (4)	C28—H28	0.9300
C2—H2	0.9800	C29—C30	1.428 (4)
C4—C5	1.523 (4)	C29—H29	0.9300
C4—H4A	0.9700	C30—C31	1.403 (4)
C4—H4B	0.9700	C30—C34	1.405 (4)
C5—C6	1.515 (4)	C31—C32	1.352 (4)
C5—H5A	0.9700	C31—H31	0.9300
C5—H5B	0.9700	C32—C33	1.389 (4)
C6—C7	1.371 (4)	C32—H32	0.9300
C6—C11	1.378 (4)	C33—H33	0.9300
C7—C8	1.388 (5)	C34—C35	1.428 (4)
C7—H7	0.9300	O5—H5C	0.89 (2)
C8—C9	1.355 (6)	O5—H5D	0.84 (2)
C8—H8	0.9300	O6—H6A	0.93 (2)
C9—C10	1.368 (6)	O6—H6B	0.91 (3)
C9—H9	0.9300	O7—H7A	0.89 (2)
C10—C11	1.381 (5)	O7—H7B	0.88 (2)
C10—H10	0.9300	O8—H8A	0.88 (2)
C11—H11	0.9300	O8—H8B	0.85 (2)
C12—C13	1.387 (4)	O9—H9A	0.90 (2)
C12—H12	0.9300	O9—H9B	0.91 (2)
C13—C14	1.359 (4)	O10—H10A	0.92 (3)
C13—H13	0.9300	O10—H10B	0.90 (3)
C14—C15	1.399 (4)	O11—H11A	0.87 (2)
C14—H14	0.9300	O11—H11B	0.84 (2)
C15—C23	1.409 (4)	O12—H12A	0.88 (2)
C15—C16	1.420 (4)	O12—H12B	0.88 (2)
C16—C17	1.338 (5)
O1—Zn1—O3	91.19 (7)	C12—C13—H13	120.3
O1—Zn1—N4	96.33 (8)	C13—C14—C15	119.8 (3)
O3—Zn1—N4	98.65 (8)	C13—C14—H14	120.1
O1—Zn1—N1	94.45 (8)	C15—C14—H14	120.1
O3—Zn1—N1	90.08 (8)	C14—C15—C23	117.0 (3)
N4—Zn1—N1	165.96 (8)	C14—C15—C16	123.7 (3)
O1—Zn1—N2	89.32 (8)	C23—C15—C16	119.3 (3)
O3—Zn1—N2	166.85 (8)	C17—C16—C15	121.1 (3)
N4—Zn1—N2	94.36 (8)	C17—C16—H16	119.4
N1—Zn1—N2	76.77 (8)	C15—C16—H16	119.4
O1—Zn1—N3	172.67 (8)	C16—C17—C18	121.6 (3)
O3—Zn1—N3	88.51 (8)	C16—C17—H17	119.2
N4—Zn1—N3	76.49 (9)	C18—C17—H17	119.2
N1—Zn1—N3	92.88 (9)	C22—C18—C19	116.9 (3)
N2—Zn1—N3	92.64 (8)	C22—C18—C17	118.9 (3)
C1—O1—Zn1	121.06 (16)	C19—C18—C17	124.1 (3)
C3—O3—Zn1	125.51 (17)	C20—C19—C18	120.5 (3)
C12—N1—C23	118.2 (2)	C20—C19—H19	119.7
C12—N1—Zn1	127.6 (2)	C18—C19—H19	119.7
C23—N1—Zn1	114.19 (18)	C19—C20—C21	118.8 (3)
C21—N2—C22	118.5 (3)	C19—C20—H20	120.6
C21—N2—Zn1	128.1 (2)	C21—C20—H20	120.6
C22—N2—Zn1	113.29 (18)	N2—C21—C20	122.7 (3)
C24—N3—C35	118.1 (3)	N2—C21—H21	118.6
C24—N3—Zn1	128.4 (2)	C20—C21—H21	118.6
C35—N3—Zn1	113.36 (17)	N2—C22—C18	122.5 (3)
C33—N4—C34	118.1 (2)	N2—C22—C23	118.0 (2)
C33—N4—Zn1	127.74 (19)	C18—C22—C23	119.5 (3)
C34—N4—Zn1	114.17 (18)	N1—C23—C15	122.7 (3)
O2—C1—O1	124.1 (3)	N1—C23—C22	117.8 (2)
O2—C1—C2	119.5 (2)	C15—C23—C22	119.5 (3)
O1—C1—C2	116.4 (2)	N3—C24—C25	122.8 (3)
C4—C2—C1	114.1 (2)	N3—C24—H24	118.6
C4—C2—C3	112.8 (2)	C25—C24—H24	118.6
C1—C2—C3	107.7 (2)	C26—C25—C24	119.1 (3)
C4—C2—H2	107.3	C26—C25—H25	120.4
C1—C2—H2	107.3	C24—C25—H25	120.4
C3—C2—H2	107.3	C25—C26—C27	120.0 (3)
O4—C3—O3	124.3 (3)	C25—C26—H26	120.0
O4—C3—C2	118.4 (3)	C27—C26—H26	120.0
O3—C3—C2	117.3 (2)	C26—C27—C35	117.3 (3)
C2—C4—C5	114.9 (2)	C26—C27—C28	124.0 (3)
C2—C4—H4A	108.5	C35—C27—C28	118.7 (3)
C5—C4—H4A	108.5	C29—C28—C27	121.4 (3)
C2—C4—H4B	108.5	C29—C28—H28	119.3
C5—C4—H4B	108.5	C27—C28—H28	119.3
H4A—C4—H4B	107.5	C28—C29—C30	121.2 (3)
C6—C5—C4	114.2 (3)	C28—C29—H29	119.4
C6—C5—H5A	108.7	C30—C29—H29	119.4
C4—C5—H5A	108.7	C31—C30—C34	117.5 (3)
C6—C5—H5B	108.7	C31—C30—C29	123.5 (3)
C4—C5—H5B	108.7	C34—C30—C29	119.0 (3)
H5A—C5—H5B	107.6	C32—C31—C30	119.5 (3)
C7—C6—C11	117.8 (3)	C32—C31—H31	120.2
C7—C6—C5	120.7 (3)	C30—C31—H31	120.2
C11—C6—C5	121.5 (3)	C31—C32—C33	119.5 (3)
C6—C7—C8	121.0 (4)	C31—C32—H32	120.2
C6—C7—H7	119.5	C33—C32—H32	120.2
C8—C7—H7	119.5	N4—C33—C32	123.2 (3)
C9—C8—C7	120.1 (4)	N4—C33—H33	118.4
C9—C8—H8	119.9	C32—C33—H33	118.4
C7—C8—H8	119.9	N4—C34—C30	122.1 (3)
C8—C9—C10	120.0 (4)	N4—C34—C35	118.2 (2)
C8—C9—H9	120.0	C30—C34—C35	119.7 (3)
C10—C9—H9	120.0	N3—C35—C27	122.6 (3)
C9—C10—C11	119.6 (4)	N3—C35—C34	117.4 (2)
C9—C10—H10	120.2	C27—C35—C34	119.9 (3)
C11—C10—H10	120.2	H5C—O5—H5D	111 (3)
C6—C11—C10	121.4 (4)	H6A—O6—H6B	101 (3)
C6—C11—H11	119.3	H7A—O7—H7B	108 (3)
C10—C11—H11	119.3	H8A—O8—H8B	111 (3)
N1—C12—C13	123.0 (3)	H9A—O9—H9B	104 (3)
N1—C12—H12	118.5	H10A—O10—H10B	105 (3)
C13—C12—H12	118.5	H11A—O11—H11B	116 (3)
C14—C13—C12	119.3 (3)	H12A—O12—H12B	107 (3)
C14—C13—H13	120.3
O3—Zn1—O1—C1	2.3 (2)	C23—N1—C12—C13	−1.1 (4)
N4—Zn1—O1—C1	101.2 (2)	Zn1—N1—C12—C13	−178.3 (2)
N1—Zn1—O1—C1	−87.8 (2)	N1—C12—C13—C14	0.9 (5)
N2—Zn1—O1—C1	−164.5 (2)	C12—C13—C14—C15	−0.4 (5)
N3—Zn1—O1—C1	89.9 (6)	C13—C14—C15—C23	0.2 (4)
O1—Zn1—O3—C3	7.5 (2)	C13—C14—C15—C16	178.3 (3)
N4—Zn1—O3—C3	−89.0 (2)	C14—C15—C16—C17	−179.2 (3)
N1—Zn1—O3—C3	102.0 (2)	C23—C15—C16—C17	−1.2 (4)
N2—Zn1—O3—C3	99.7 (4)	C15—C16—C17—C18	1.8 (5)
N3—Zn1—O3—C3	−165.1 (2)	C16—C17—C18—C22	−1.5 (5)
O1—Zn1—N1—C12	89.4 (2)	C16—C17—C18—C19	176.4 (3)
O3—Zn1—N1—C12	−1.8 (2)	C22—C18—C19—C20	−0.7 (5)
N4—Zn1—N1—C12	−130.6 (3)	C17—C18—C19—C20	−178.6 (3)
N2—Zn1—N1—C12	177.6 (2)	C18—C19—C20—C21	0.1 (5)
N3—Zn1—N1—C12	−90.3 (2)	C22—N2—C21—C20	−0.2 (4)
O1—Zn1—N1—C23	−87.99 (18)	Zn1—N2—C21—C20	177.6 (2)
O3—Zn1—N1—C23	−179.19 (18)	C19—C20—C21—N2	0.4 (5)
N4—Zn1—N1—C23	52.1 (4)	C21—N2—C22—C18	−0.4 (4)
N2—Zn1—N1—C23	0.26 (17)	Zn1—N2—C22—C18	−178.6 (2)
N3—Zn1—N1—C23	92.30 (18)	C21—N2—C22—C23	177.8 (2)
O1—Zn1—N2—C21	−83.2 (2)	Zn1—N2—C22—C23	−0.3 (3)
O3—Zn1—N2—C21	−175.5 (3)	C19—C18—C22—N2	0.8 (4)
N4—Zn1—N2—C21	13.1 (2)	C17—C18—C22—N2	178.9 (3)
N1—Zn1—N2—C21	−177.9 (2)	C19—C18—C22—C23	−177.4 (3)
N3—Zn1—N2—C21	89.8 (2)	C17—C18—C22—C23	0.7 (4)
O1—Zn1—N2—C22	94.77 (18)	C12—N1—C23—C15	0.8 (4)
O3—Zn1—N2—C22	2.4 (5)	Zn1—N1—C23—C15	178.5 (2)
N4—Zn1—N2—C22	−168.94 (18)	C12—N1—C23—C22	−178.2 (2)
N1—Zn1—N2—C22	0.04 (18)	Zn1—N1—C23—C22	−0.5 (3)
N3—Zn1—N2—C22	−92.29 (18)	C14—C15—C23—N1	−0.4 (4)
O1—Zn1—N3—C24	−170.9 (5)	C16—C15—C23—N1	−178.6 (2)
O3—Zn1—N3—C24	−83.1 (2)	C14—C15—C23—C22	178.5 (2)
N4—Zn1—N3—C24	177.6 (3)	C16—C15—C23—C22	0.4 (4)
N1—Zn1—N3—C24	6.9 (3)	N2—C22—C23—N1	0.6 (4)
N2—Zn1—N3—C24	83.8 (3)	C18—C22—C23—N1	178.9 (2)
O1—Zn1—N3—C35	6.4 (7)	N2—C22—C23—C15	−178.4 (2)
O3—Zn1—N3—C35	94.10 (18)	C18—C22—C23—C15	−0.2 (4)
N4—Zn1—N3—C35	−5.16 (17)	C35—N3—C24—C25	−1.4 (4)
N1—Zn1—N3—C35	−175.89 (18)	Zn1—N3—C24—C25	175.7 (2)
N2—Zn1—N3—C35	−99.01 (18)	N3—C24—C25—C26	0.5 (5)
O1—Zn1—N4—C33	5.1 (2)	C24—C25—C26—C27	0.5 (5)
O3—Zn1—N4—C33	97.3 (2)	C25—C26—C27—C35	−0.4 (5)
N1—Zn1—N4—C33	−134.8 (3)	C25—C26—C27—C28	176.7 (3)
N2—Zn1—N4—C33	−84.7 (2)	C26—C27—C28—C29	−174.9 (3)
N3—Zn1—N4—C33	−176.3 (2)	C35—C27—C28—C29	2.2 (5)
O1—Zn1—N4—C34	−175.03 (18)	C27—C28—C29—C30	−1.4 (5)
O3—Zn1—N4—C34	−82.85 (18)	C28—C29—C30—C31	179.0 (3)
N1—Zn1—N4—C34	45.0 (4)	C28—C29—C30—C34	−1.3 (5)
N2—Zn1—N4—C34	95.17 (18)	C34—C30—C31—C32	−1.6 (4)
N3—Zn1—N4—C34	3.50 (17)	C29—C30—C31—C32	178.0 (3)
Zn1—O1—C1—O2	137.5 (2)	C30—C31—C32—C33	0.6 (5)
Zn1—O1—C1—C2	−42.1 (3)	C34—N4—C33—C32	−1.1 (4)
O2—C1—C2—C4	22.5 (4)	Zn1—N4—C33—C32	178.8 (2)
O1—C1—C2—C4	−157.8 (2)	C31—C32—C33—N4	0.8 (5)
O2—C1—C2—C3	−103.6 (3)	C33—N4—C34—C30	−0.1 (4)
O1—C1—C2—C3	76.0 (3)	Zn1—N4—C34—C30	−180.0 (2)
Zn1—O3—C3—O4	−157.1 (2)	C33—N4—C34—C35	178.4 (2)
Zn1—O3—C3—C2	22.6 (3)	Zn1—N4—C34—C35	−1.5 (3)
C4—C2—C3—O4	−10.7 (4)	C31—C30—C34—N4	1.4 (4)
C1—C2—C3—O4	116.2 (3)	C29—C30—C34—N4	−178.3 (3)
C4—C2—C3—O3	169.6 (2)	C31—C30—C34—C35	−177.0 (3)
C1—C2—C3—O3	−63.5 (3)	C29—C30—C34—C35	3.3 (4)
C1—C2—C4—C5	57.4 (3)	C24—N3—C35—C27	1.4 (4)
C3—C2—C4—C5	−179.1 (2)	Zn1—N3—C35—C27	−176.1 (2)
C2—C4—C5—C6	51.1 (4)	C24—N3—C35—C34	−176.3 (2)
C4—C5—C6—C7	−120.2 (3)	Zn1—N3—C35—C34	6.2 (3)
C4—C5—C6—C11	59.8 (4)	C26—C27—C35—N3	−0.5 (4)
C11—C6—C7—C8	0.8 (5)	C28—C27—C35—N3	−177.8 (3)
C5—C6—C7—C8	−179.3 (3)	C26—C27—C35—C34	177.1 (3)
C6—C7—C8—C9	−0.5 (6)	C28—C27—C35—C34	−0.2 (4)
C7—C8—C9—C10	−0.2 (6)	N4—C34—C35—N3	−3.3 (4)
C8—C9—C10—C11	0.6 (6)	C30—C34—C35—N3	175.3 (2)
C7—C6—C11—C10	−0.3 (5)	N4—C34—C35—C27	179.0 (2)
C5—C6—C11—C10	179.7 (3)	C30—C34—C35—C27	−2.5 (4)
C9—C10—C11—C6	−0.4 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O12—H12B···O11	0.88 (2)	2.03 (3)	2.869 (4)	160 (3)
O12—H12A···O3^i	0.88 (2)	2.03 (3)	2.885 (3)	163 (3)
O11—H11B···O12^ii	0.84 (2)	2.05 (3)	2.871 (4)	165 (5)
O11—H11A···O4^i	0.87 (2)	1.81 (2)	2.671 (3)	173 (4)
O10—H10B···O11	0.90 (3)	1.92 (3)	2.798 (4)	166 (5)
O10—H10A···O6	0.92 (3)	1.97 (3)	2.798 (4)	149 (5)
O9—H9B···O8^iii	0.91 (2)	1.89 (2)	2.774 (4)	162 (4)
O9—H9A···O5^iv	0.90 (2)	1.89 (2)	2.787 (4)	178 (4)
O8—H8B···O7	0.85 (2)	2.10 (3)	2.933 (4)	167 (4)
O8—H8A···O10	0.88 (2)	1.91 (3)	2.780 (4)	169 (4)
O7—H7B···O6^iii	0.88 (2)	2.06 (3)	2.875 (4)	153 (4)
O7—H7A···O2	0.89 (2)	1.84 (2)	2.730 (3)	176 (4)
O6—H6B···O7	0.91 (3)	1.88 (3)	2.787 (4)	172 (4)
O6—H6A···O9	0.93 (2)	2.00 (3)	2.814 (4)	145 (4)
O5—H5D···O9	0.84 (2)	2.11 (2)	2.907 (4)	160 (4)
O5—H5C···O1	0.89 (2)	1.91 (2)	2.794 (3)	174 (4)

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