Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805025328/br6209sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805025328/br6209Isup2.hkl |
CCDC reference: 269152
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.020 Å Some non-H atoms missing
- Disorder in main residue
- R factor = 0.064
- wR factor = 0.209
- Data-to-parameter ratio = 15.6
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT341_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ... 20 PLAT432_ALERT_2_B Short Inter X...Y Contact Br1 .. C28 .. 3.11 Ang.
Alert level C CHEMW01_ALERT_1_C The ratio of given/expected molecular weight as calculated from the _chemical_formula_sum lies outside the range 0.99 <> 1.01 Calculated formula weight = 625.0214 Formula weight given = 611.2600 CHEMW01_ALERT_1_C The difference between the given and expected weight for compound is greater 1 mass unit. Check that all hydrogen atoms have been taken into account. PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ? PLAT077_ALERT_4_C Unitcell contains non-integer number of atoms .. ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O2 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C12 PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for C27 PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for C29 PLAT301_ALERT_3_C Main Residue Disorder ......................... 1.00 Perc. PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C27 - C28 ... 1.35 Ang. PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C29 - C30 ... 1.34 Ang. PLAT731_ALERT_1_C Bond Calc 0.84(6), Rep 0.84(2) ...... 3.00 su-Rat O1W -H1W 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 1.35(3), Rep 1.348(10) ...... 3.00 su-Rat C27 -C28 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 1.34(3), Rep 1.335(10) ...... 3.00 su-Rat C29 -C30 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.84(6), Rep 0.84(2) ...... 3.00 su-Rat O1W -H1W 1.555 1.555 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C52 H35.34 Br0.66 N8 O4 Zn2
Alert level G FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the _chemical_formula_sum and _chemical_formula_moiety. This is usually due to the moiety formula being in the wrong format. Atom count from _chemical_formula_sum: C30 H30.67 Br0.33 N5 O4.5 Z Atom count from _chemical_formula_moiety:C30 H30.67 Br0.33 N4 O4.5 Z FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C30 H30.67 Br0.33 N5 O4.5 Zn1 Atom count from the _atom_site data: C30 H30.67 Br0.33 N4 O4.5 Zn1 CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected. CELLZ01_ALERT_1_G ALERT: Large difference may be due to a symmetry error - see SYMMG tests From the CIF: _cell_formula_units_Z 8 From the CIF: _chemical_formula_sum C30 H30.67 Br0.33 N5 O4.5 Zn1 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 240.00 240.00 0.00 H 245.36 245.36 0.00 Br 2.64 2.64 0.00 N 40.00 32.00 8.00 O 36.00 36.00 0.00 Zn 8.00 8.00 0.00 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 25.99 From the CIF: _reflns_number_total 4727 Count of symmetry unique reflns 2953 Completeness (_total/calc) 160.07% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1774 Fraction of Friedel pairs measured 0.601 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 21 ALERT level C = Check and explain 5 ALERT level G = General alerts; check 15 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 2 ALERT type 3 Indicator that the structure quality may be low 5 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXL97.
[Zn(C13H9N2O)(C13H8.67Br0.33N2O)]·2C2H6O·0.5H2O | F(000) = 2531 |
Mr = 611.26 | Dx = 1.396 Mg m−3 |
Orthorhombic, Iba2 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: I 2 -2c | Cell parameters from 1648 reflections |
a = 32.459 (3) Å | θ = 2.3–26.1° |
b = 9.408 (1) Å | µ = 1.35 mm−1 |
c = 19.053 (2) Å | T = 293 K |
V = 5818.5 (10) Å3 | Plate, colorless |
Z = 8 | 0.36 × 0.26 × 0.05 mm |
Bruker APEX area-detector diffractometer | 4727 independent reflections |
Radiation source: fine-focus sealed tube | 2387 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.068 |
φ and ω scans | θmax = 26.0°, θmin = 1.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −40→31 |
Tmin = 0.643, Tmax = 0.936 | k = −11→10 |
12802 measured reflections | l = −18→23 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.065 | H-atom parameters constrained |
wR(F2) = 0.209 | w = 1/[σ2(Fo2) + (0.1164P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.95 | (Δ/σ)max < 0.001 |
4727 reflections | Δρmax = 0.61 e Å−3 |
303 parameters | Δρmin = −0.54 e Å−3 |
33 restraints | Absolute structure: Flack (1983), 1772 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.01 (3) |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Br1 | 0.48567 (15) | −0.3818 (4) | 0.5435 (3) | 0.155 (2) | 0.33 |
Zn1 | 0.34497 (3) | 0.23178 (9) | 0.50481 (10) | 0.0664 (3) | |
O1 | 0.34597 (15) | 0.0265 (6) | 0.4892 (3) | 0.0675 (17) | |
O2 | 0.34726 (18) | 0.3489 (8) | 0.4225 (4) | 0.084 (2) | |
N1 | 0.3903 (2) | 0.2287 (7) | 0.5722 (4) | 0.065 (2) | |
N2 | 0.4408 (2) | 0.1415 (9) | 0.6351 (5) | 0.079 (2) | |
H2A | 0.4590 | 0.0826 | 0.6503 | 0.094* | |
N3 | 0.2906 (2) | 0.2948 (8) | 0.5336 (4) | 0.067 (2) | |
N4 | 0.2277 (2) | 0.3849 (7) | 0.5199 (4) | 0.0598 (19) | |
H4A | 0.2077 | 0.4336 | 0.5025 | 0.072* | |
C1 | 0.37820 (16) | −0.0599 (5) | 0.5044 (4) | 0.070 (2) | |
C2 | 0.37687 (18) | −0.1931 (6) | 0.4729 (3) | 0.081 (3) | |
H2B | 0.3551 | −0.2166 | 0.4433 | 0.097* | |
C3 | 0.4080 (2) | −0.2911 (5) | 0.4856 (4) | 0.099 (4) | |
H3A | 0.4071 | −0.3802 | 0.4645 | 0.119* | |
C4 | 0.4405 (2) | −0.2560 (7) | 0.5299 (5) | 0.101 (4) | |
H4 | 0.4614 | −0.3216 | 0.5384 | 0.122* | 0.67 |
C5 | 0.44185 (17) | −0.1229 (7) | 0.5614 (4) | 0.086 (3) | |
H5A | 0.4636 | −0.0994 | 0.5910 | 0.103* | |
C6 | 0.41069 (17) | −0.0248 (5) | 0.5487 (4) | 0.068 (2) | |
C7 | 0.4138 (2) | 0.1143 (9) | 0.5840 (5) | 0.059 (2) | |
C8 | 0.4032 (2) | 0.3315 (7) | 0.6199 (3) | 0.073 (3) | |
C9 | 0.3888 (2) | 0.4680 (7) | 0.6332 (4) | 0.098 (3) | |
H9A | 0.3673 | 0.5050 | 0.6067 | 0.117* | |
C10 | 0.4066 (2) | 0.5492 (7) | 0.6861 (5) | 0.103 (4) | |
H10A | 0.3970 | 0.6406 | 0.6950 | 0.123* | |
C11 | 0.4388 (2) | 0.4939 (9) | 0.7256 (4) | 0.112 (4) | |
H11A | 0.4507 | 0.5482 | 0.7610 | 0.135* | |
C12 | 0.4532 (2) | 0.3574 (9) | 0.7124 (4) | 0.120 (5) | |
H12A | 0.4748 | 0.3204 | 0.7388 | 0.144* | |
C13 | 0.4354 (2) | 0.2762 (6) | 0.6595 (4) | 0.084 (3) | |
C14 | 0.31875 (16) | 0.4465 (6) | 0.4021 (3) | 0.064 (2) | |
C15 | 0.33007 (16) | 0.5283 (7) | 0.3445 (3) | 0.070 (2) | |
H15A | 0.3558 | 0.5160 | 0.3240 | 0.083* | |
C16 | 0.3029 (2) | 0.6285 (7) | 0.3175 (3) | 0.087 (3) | |
H16A | 0.3105 | 0.6832 | 0.2790 | 0.104* | |
C17 | 0.2644 (2) | 0.6469 (6) | 0.3481 (4) | 0.084 (3) | |
H17A | 0.2462 | 0.7140 | 0.3301 | 0.101* | |
C18 | 0.25307 (15) | 0.5651 (7) | 0.4057 (3) | 0.072 (2) | |
H18A | 0.2273 | 0.5774 | 0.4262 | 0.086* | |
C19 | 0.28025 (17) | 0.4649 (6) | 0.4327 (3) | 0.062 (2) | |
C20 | 0.2666 (2) | 0.3800 (8) | 0.4958 (5) | 0.059 (2) | |
C21 | 0.26540 (15) | 0.2432 (6) | 0.5853 (3) | 0.059 (2) | |
C22 | 0.27404 (16) | 0.1525 (7) | 0.6410 (3) | 0.085 (3) | |
H22A | 0.3004 | 0.1157 | 0.6465 | 0.102* | |
C23 | 0.2432 (2) | 0.1169 (7) | 0.6885 (3) | 0.085 (3) | |
H23A | 0.2490 | 0.0562 | 0.7258 | 0.101* | |
C24 | 0.20378 (19) | 0.1720 (8) | 0.6803 (3) | 0.092 (3) | |
H24A | 0.1832 | 0.1481 | 0.7121 | 0.110* | |
C25 | 0.19514 (14) | 0.2626 (7) | 0.6247 (4) | 0.082 (3) | |
H25A | 0.1687 | 0.2995 | 0.6192 | 0.099* | |
C26 | 0.22595 (17) | 0.2983 (6) | 0.5772 (3) | 0.059 (2) | |
O1W | 0.5000 | 0.0000 | 0.7192 (5) | 0.082 (3) | |
H1W | 0.515 (2) | 0.053 (8) | 0.744 (2) | 0.098* | |
O3 | 0.4645 (4) | 0.8148 (12) | 0.8117 (6) | 0.156 (4) | |
H3O | 0.4393 | 0.8147 | 0.8082 | 0.233* | |
O4 | 0.3802 (4) | 0.8127 (13) | 0.8128 (6) | 0.171 (5) | |
H4O | 0.3696 | 0.7591 | 0.8415 | 0.257* | |
C27 | 0.4754 (9) | 0.822 (2) | 0.8810 (9) | 0.260 (7) | |
H27A | 0.5049 | 0.8342 | 0.8856 | 0.312* | |
H27B | 0.4617 | 0.9010 | 0.9036 | 0.312* | |
C28 | 0.4636 (8) | 0.698 (2) | 0.9106 (10) | 0.260 (7) | |
H28A | 0.4690 | 0.7012 | 0.9601 | 0.390* | |
H28B | 0.4787 | 0.6211 | 0.8899 | 0.390* | |
H28C | 0.4346 | 0.6840 | 0.9030 | 0.390* | |
C29 | 0.3574 (7) | 0.935 (2) | 0.8083 (15) | 0.260 (7) | |
H29A | 0.3295 | 0.9139 | 0.7933 | 0.312* | |
H29B | 0.3562 | 0.9818 | 0.8537 | 0.312* | |
C30 | 0.3758 (7) | 1.020 (2) | 0.7616 (15) | 0.260 (7) | |
H30A | 0.3613 | 1.1084 | 0.7588 | 0.390* | |
H30B | 0.3757 | 0.9746 | 0.7164 | 0.390* | |
H30C | 0.4038 | 1.0370 | 0.7759 | 0.390* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.150 (4) | 0.118 (3) | 0.199 (5) | 0.079 (3) | −0.073 (4) | −0.061 (3) |
Zn1 | 0.0567 (5) | 0.0719 (6) | 0.0707 (6) | 0.0027 (4) | −0.0004 (6) | 0.0004 (8) |
O1 | 0.054 (3) | 0.077 (3) | 0.071 (5) | −0.003 (3) | −0.008 (3) | 0.007 (3) |
O2 | 0.062 (4) | 0.101 (5) | 0.091 (5) | 0.016 (3) | 0.022 (4) | 0.019 (4) |
N1 | 0.064 (4) | 0.053 (4) | 0.079 (5) | −0.003 (4) | 0.006 (4) | −0.011 (4) |
N2 | 0.061 (5) | 0.075 (5) | 0.101 (7) | 0.018 (4) | −0.021 (5) | −0.017 (5) |
N3 | 0.070 (5) | 0.073 (5) | 0.056 (4) | −0.001 (4) | −0.006 (4) | 0.002 (4) |
N4 | 0.052 (4) | 0.072 (4) | 0.055 (5) | 0.010 (3) | 0.002 (3) | −0.004 (4) |
C1 | 0.073 (5) | 0.071 (5) | 0.068 (5) | −0.003 (4) | 0.002 (6) | −0.010 (7) |
C2 | 0.083 (7) | 0.068 (6) | 0.091 (7) | −0.007 (5) | 0.002 (5) | −0.022 (6) |
C3 | 0.113 (9) | 0.068 (6) | 0.116 (13) | 0.028 (6) | 0.004 (7) | −0.016 (7) |
C4 | 0.083 (7) | 0.107 (9) | 0.115 (11) | 0.027 (6) | −0.021 (7) | −0.017 (8) |
C5 | 0.072 (6) | 0.082 (7) | 0.104 (9) | 0.014 (5) | −0.003 (5) | −0.017 (7) |
C6 | 0.048 (5) | 0.080 (6) | 0.076 (6) | −0.001 (4) | 0.002 (4) | −0.001 (5) |
C7 | 0.050 (5) | 0.055 (5) | 0.072 (6) | 0.001 (4) | −0.003 (4) | −0.017 (5) |
C8 | 0.067 (6) | 0.064 (6) | 0.089 (7) | −0.005 (5) | 0.003 (5) | −0.018 (6) |
C9 | 0.085 (7) | 0.075 (7) | 0.134 (11) | 0.001 (6) | −0.015 (7) | −0.001 (8) |
C10 | 0.095 (8) | 0.091 (8) | 0.122 (10) | 0.002 (6) | −0.032 (7) | −0.046 (8) |
C11 | 0.096 (8) | 0.115 (9) | 0.125 (11) | 0.000 (8) | −0.006 (7) | −0.068 (9) |
C12 | 0.079 (8) | 0.123 (10) | 0.157 (13) | −0.014 (7) | −0.032 (7) | −0.062 (10) |
C13 | 0.061 (6) | 0.098 (8) | 0.093 (8) | −0.012 (6) | −0.004 (5) | −0.018 (7) |
C14 | 0.064 (6) | 0.063 (5) | 0.066 (6) | −0.003 (4) | 0.000 (5) | −0.002 (5) |
C15 | 0.078 (6) | 0.076 (6) | 0.055 (6) | −0.002 (5) | 0.017 (5) | −0.002 (5) |
C16 | 0.136 (10) | 0.067 (7) | 0.058 (6) | −0.019 (6) | 0.013 (6) | −0.002 (5) |
C17 | 0.103 (8) | 0.081 (7) | 0.068 (7) | 0.015 (6) | 0.005 (6) | 0.020 (6) |
C18 | 0.077 (6) | 0.068 (6) | 0.070 (6) | 0.010 (5) | 0.004 (5) | −0.002 (5) |
C19 | 0.058 (5) | 0.070 (6) | 0.059 (5) | −0.010 (4) | 0.006 (4) | −0.003 (5) |
C20 | 0.063 (5) | 0.057 (4) | 0.058 (6) | 0.003 (4) | 0.007 (5) | 0.000 (5) |
C21 | 0.053 (5) | 0.053 (5) | 0.069 (6) | −0.002 (4) | −0.001 (4) | 0.011 (4) |
C22 | 0.076 (7) | 0.092 (7) | 0.087 (8) | −0.010 (6) | 0.006 (6) | −0.012 (7) |
C23 | 0.084 (7) | 0.110 (9) | 0.060 (7) | 0.012 (6) | 0.012 (6) | 0.023 (6) |
C24 | 0.095 (9) | 0.108 (9) | 0.072 (7) | −0.012 (7) | 0.012 (6) | 0.016 (7) |
C25 | 0.078 (7) | 0.088 (7) | 0.080 (8) | 0.005 (5) | 0.014 (5) | 0.009 (6) |
C26 | 0.056 (5) | 0.056 (5) | 0.064 (6) | −0.001 (4) | 0.011 (4) | 0.001 (5) |
O1W | 0.063 (6) | 0.098 (8) | 0.085 (7) | −0.011 (5) | 0.000 | 0.000 |
O3 | 0.167 (9) | 0.152 (8) | 0.147 (10) | −0.050 (8) | 0.060 (7) | −0.013 (8) |
O4 | 0.203 (12) | 0.146 (9) | 0.166 (11) | −0.042 (8) | 0.082 (9) | 0.020 (8) |
C27 | 0.281 (15) | 0.259 (15) | 0.240 (16) | −0.050 (13) | 0.010 (13) | 0.076 (13) |
C28 | 0.281 (15) | 0.259 (15) | 0.240 (16) | −0.050 (13) | 0.010 (13) | 0.076 (13) |
C29 | 0.281 (15) | 0.259 (15) | 0.240 (16) | −0.050 (13) | 0.010 (13) | 0.076 (13) |
C30 | 0.281 (15) | 0.259 (15) | 0.240 (16) | −0.050 (13) | 0.010 (13) | 0.076 (13) |
Br1—C4 | 1.901 (6) | C14—C15 | 1.3900 |
Zn1—O2 | 1.917 (7) | C14—C19 | 1.3900 |
Zn1—N3 | 1.942 (8) | C15—C16 | 1.3900 |
Zn1—N1 | 1.953 (8) | C15—H15A | 0.9300 |
Zn1—O1 | 1.954 (6) | C16—C17 | 1.3900 |
O1—C1 | 1.357 (7) | C16—H16A | 0.9300 |
O2—C14 | 1.360 (8) | C17—C18 | 1.3900 |
N1—C7 | 1.338 (10) | C17—H17A | 0.9300 |
N1—C8 | 1.392 (9) | C18—C19 | 1.3900 |
N2—C7 | 1.335 (11) | C18—H18A | 0.9300 |
N2—C13 | 1.361 (9) | C19—C20 | 1.509 (10) |
N2—H2A | 0.8600 | C21—C22 | 1.3900 |
N3—C20 | 1.329 (11) | C21—C26 | 1.3900 |
N3—C21 | 1.370 (9) | C22—C23 | 1.3900 |
N4—C20 | 1.344 (10) | C22—H22A | 0.9300 |
N4—C26 | 1.364 (7) | C23—C24 | 1.3900 |
N4—H4A | 0.8600 | C23—H23A | 0.9300 |
C1—C2 | 1.3900 | C24—C25 | 1.3900 |
C1—C6 | 1.3900 | C24—H24A | 0.9300 |
C2—C3 | 1.3900 | C25—C26 | 1.3900 |
C2—H2B | 0.9300 | C25—H25A | 0.9300 |
C3—C4 | 1.3900 | O1W—H1W | 0.84 (2) |
C3—H3A | 0.9300 | O3—C27 | 1.368 (10) |
C4—C5 | 1.3900 | O3—H3O | 0.8200 |
C4—H4 | 0.9300 | O4—C29 | 1.372 (10) |
C5—C6 | 1.3900 | O4—H4O | 0.8200 |
C5—H5A | 0.9300 | C27—C28 | 1.348 (10) |
C6—C7 | 1.475 (9) | C27—H27A | 0.9700 |
C8—C9 | 1.3900 | C27—H27B | 0.9700 |
C8—C13 | 1.3900 | C28—H28A | 0.9600 |
C9—C10 | 1.3900 | C28—H28B | 0.9600 |
C9—H9A | 0.9300 | C28—H28C | 0.9600 |
C10—C11 | 1.3900 | C29—C30 | 1.335 (10) |
C10—H10A | 0.9300 | C29—H29A | 0.9700 |
C11—C12 | 1.3900 | C29—H29B | 0.9700 |
C11—H11A | 0.9300 | C30—H30A | 0.9600 |
C12—C13 | 1.3900 | C30—H30B | 0.9600 |
C12—H12A | 0.9300 | C30—H30C | 0.9600 |
O2—Zn1—N3 | 95.2 (3) | C15—C14—C19 | 120.0 |
O2—Zn1—N1 | 121.1 (3) | C16—C15—C14 | 120.0 |
N3—Zn1—N1 | 120.3 (3) | C16—C15—H15A | 120.0 |
O2—Zn1—O1 | 116.3 (3) | C14—C15—H15A | 120.0 |
N3—Zn1—O1 | 111.1 (3) | C17—C16—C15 | 120.0 |
N1—Zn1—O1 | 94.2 (3) | C17—C16—H16A | 120.0 |
C1—O1—Zn1 | 125.0 (4) | C15—C16—H16A | 120.0 |
C14—O2—Zn1 | 126.5 (5) | C16—C17—C18 | 120.0 |
C7—N1—C8 | 106.1 (7) | C16—C17—H17A | 120.0 |
C7—N1—Zn1 | 123.5 (6) | C18—C17—H17A | 120.0 |
C8—N1—Zn1 | 130.2 (5) | C19—C18—C17 | 120.0 |
C7—N2—C13 | 110.0 (7) | C19—C18—H18A | 120.0 |
C7—N2—H2A | 125.0 | C17—C18—H18A | 120.0 |
C13—N2—H2A | 125.0 | C18—C19—C14 | 120.0 |
C20—N3—C21 | 104.7 (7) | C18—C19—C20 | 117.8 (5) |
C20—N3—Zn1 | 124.3 (6) | C14—C19—C20 | 122.2 (5) |
C21—N3—Zn1 | 129.6 (5) | N3—C20—N4 | 112.7 (8) |
C20—N4—C26 | 107.0 (6) | N3—C20—C19 | 125.3 (7) |
C20—N4—H4A | 126.5 | N4—C20—C19 | 122.0 (7) |
C26—N4—H4A | 126.5 | N3—C21—C22 | 130.3 (5) |
O1—C1—C2 | 115.1 (5) | N3—C21—C26 | 109.7 (5) |
O1—C1—C6 | 124.9 (5) | C22—C21—C26 | 120.0 |
C2—C1—C6 | 120.0 | C21—C22—C23 | 120.0 |
C1—C2—C3 | 120.0 | C21—C22—H22A | 120.0 |
C1—C2—H2B | 120.0 | C23—C22—H22A | 120.0 |
C3—C2—H2B | 120.0 | C22—C23—C24 | 120.0 |
C4—C3—C2 | 120.0 | C22—C23—H23A | 120.0 |
C4—C3—H3A | 120.0 | C24—C23—H23A | 120.0 |
C2—C3—H3A | 120.0 | C23—C24—C25 | 120.0 |
C3—C4—C5 | 120.0 | C23—C24—H24A | 120.0 |
C3—C4—Br1 | 121.3 (4) | C25—C24—H24A | 120.0 |
C5—C4—Br1 | 118.6 (4) | C26—C25—C24 | 120.0 |
C3—C4—H4 | 120.0 | C26—C25—H25A | 120.0 |
C5—C4—H4 | 120.0 | C24—C25—H25A | 120.0 |
C4—C5—C6 | 120.0 | N4—C26—C25 | 134.1 (5) |
C4—C5—H5A | 120.0 | N4—C26—C21 | 105.9 (5) |
C6—C5—H5A | 120.0 | C25—C26—C21 | 120.0 |
C5—C6—C1 | 120.0 | C27—O3—H3O | 109.5 |
C5—C6—C7 | 117.3 (5) | C29—O4—H4O | 109.5 |
C1—C6—C7 | 122.7 (5) | C28—C27—O3 | 107.0 (10) |
N2—C7—N1 | 110.1 (7) | C28—C27—H27A | 110.3 |
N2—C7—C6 | 123.2 (7) | O3—C27—H27A | 110.3 |
N1—C7—C6 | 126.7 (8) | C28—C27—H27B | 110.3 |
C9—C8—C13 | 120.0 | O3—C27—H27B | 110.3 |
C9—C8—N1 | 131.3 (5) | H27A—C27—H27B | 108.6 |
C13—C8—N1 | 108.7 (5) | C27—C28—H28A | 109.5 |
C10—C9—C8 | 120.0 | C27—C28—H28B | 109.5 |
C10—C9—H9A | 120.0 | H28A—C28—H28B | 109.5 |
C8—C9—H9A | 120.0 | C27—C28—H28C | 109.5 |
C9—C10—C11 | 120.0 | H28A—C28—H28C | 109.5 |
C9—C10—H10A | 120.0 | H28B—C28—H28C | 109.5 |
C11—C10—H10A | 120.0 | C30—C29—O4 | 107.5 (10) |
C12—C11—C10 | 120.0 | C30—C29—H29A | 110.2 |
C12—C11—H11A | 120.0 | O4—C29—H29A | 110.2 |
C10—C11—H11A | 120.0 | C30—C29—H29B | 110.2 |
C11—C12—C13 | 120.0 | O4—C29—H29B | 110.2 |
C11—C12—H12A | 120.0 | H29A—C29—H29B | 108.5 |
C13—C12—H12A | 120.0 | C29—C30—H30A | 109.5 |
N2—C13—C12 | 134.8 (6) | C29—C30—H30B | 109.5 |
N2—C13—C8 | 105.1 (6) | H30A—C30—H30B | 109.5 |
C12—C13—C8 | 120.0 | C29—C30—H30C | 109.5 |
O2—C14—C15 | 114.8 (5) | H30A—C30—H30C | 109.5 |
O2—C14—C19 | 125.1 (5) | H30B—C30—H30C | 109.5 |
O2—Zn1—O1—C1 | 108.7 (6) | C9—C10—C11—C12 | 0.0 |
N3—Zn1—O1—C1 | −143.9 (6) | C10—C11—C12—C13 | 0.0 |
N1—Zn1—O1—C1 | −19.1 (6) | C7—N2—C13—C12 | 177.3 (7) |
N3—Zn1—O2—C14 | 4.4 (7) | C7—N2—C13—C8 | −0.3 (9) |
N1—Zn1—O2—C14 | −125.9 (6) | C11—C12—C13—N2 | −177.3 (10) |
O1—Zn1—O2—C14 | 121.0 (6) | C11—C12—C13—C8 | 0.0 |
O2—Zn1—N1—C7 | −114.2 (7) | C9—C8—C13—N2 | 178.0 (7) |
N3—Zn1—N1—C7 | 127.4 (7) | N1—C8—C13—N2 | −0.5 (7) |
O1—Zn1—N1—C7 | 10.0 (7) | C9—C8—C13—C12 | 0.0 |
O2—Zn1—N1—C8 | 71.3 (8) | N1—C8—C13—C12 | −178.5 (6) |
N3—Zn1—N1—C8 | −47.1 (8) | Zn1—O2—C14—C15 | 173.1 (4) |
O1—Zn1—N1—C8 | −164.5 (7) | Zn1—O2—C14—C19 | −9.0 (9) |
O2—Zn1—N3—C20 | 6.2 (7) | O2—C14—C15—C16 | 178.0 (6) |
N1—Zn1—N3—C20 | 137.0 (7) | C19—C14—C15—C16 | 0.0 |
O1—Zn1—N3—C20 | −114.6 (7) | C14—C15—C16—C17 | 0.0 |
O2—Zn1—N3—C21 | 171.0 (7) | C15—C16—C17—C18 | 0.0 |
N1—Zn1—N3—C21 | −58.2 (8) | C16—C17—C18—C19 | 0.0 |
O1—Zn1—N3—C21 | 50.2 (7) | C17—C18—C19—C14 | 0.0 |
Zn1—O1—C1—C2 | −163.8 (4) | C17—C18—C19—C20 | 179.4 (6) |
Zn1—O1—C1—C6 | 17.1 (8) | O2—C14—C19—C18 | −177.8 (7) |
O1—C1—C2—C3 | −179.1 (7) | C15—C14—C19—C18 | 0.0 |
C6—C1—C2—C3 | 0.0 | O2—C14—C19—C20 | 2.9 (7) |
C1—C2—C3—C4 | 0.0 | C15—C14—C19—C20 | −179.4 (6) |
C2—C3—C4—C5 | 0.0 | C21—N3—C20—N4 | −0.5 (9) |
C2—C3—C4—Br1 | −175.5 (7) | Zn1—N3—C20—N4 | 167.4 (6) |
C3—C4—C5—C6 | 0.0 | C21—N3—C20—C19 | 179.0 (7) |
Br1—C4—C5—C6 | 175.6 (7) | Zn1—N3—C20—C19 | −13.1 (12) |
C4—C5—C6—C1 | 0.0 | C26—N4—C20—N3 | 0.2 (9) |
C4—C5—C6—C7 | 179.7 (7) | C26—N4—C20—C19 | −179.3 (6) |
O1—C1—C6—C5 | 179.0 (8) | C18—C19—C20—N3 | −170.3 (7) |
C2—C1—C6—C5 | 0.0 | C14—C19—C20—N3 | 9.1 (11) |
O1—C1—C6—C7 | −0.7 (8) | C18—C19—C20—N4 | 9.1 (10) |
C2—C1—C6—C7 | −179.7 (7) | C14—C19—C20—N4 | −171.5 (6) |
C13—N2—C7—N1 | 1.0 (11) | C20—N3—C21—C22 | −178.1 (6) |
C13—N2—C7—C6 | −177.5 (8) | Zn1—N3—C21—C22 | 14.8 (10) |
C8—N1—C7—N2 | −1.3 (10) | C20—N3—C21—C26 | 0.6 (7) |
Zn1—N1—C7—N2 | −176.9 (6) | Zn1—N3—C21—C26 | −166.5 (5) |
C8—N1—C7—C6 | 177.1 (8) | N3—C21—C22—C23 | 178.6 (8) |
Zn1—N1—C7—C6 | 1.5 (13) | C26—C21—C22—C23 | 0.0 |
C5—C6—C7—N2 | −11.0 (11) | C21—C22—C23—C24 | 0.0 |
C1—C6—C7—N2 | 168.7 (7) | C22—C23—C24—C25 | 0.0 |
C5—C6—C7—N1 | 170.8 (8) | C23—C24—C25—C26 | 0.0 |
C1—C6—C7—N1 | −9.5 (12) | C20—N4—C26—C25 | 178.2 (6) |
C7—N1—C8—C9 | −177.2 (7) | C20—N4—C26—C21 | 0.1 (7) |
Zn1—N1—C8—C9 | −2.0 (11) | C24—C25—C26—N4 | −177.8 (8) |
C7—N1—C8—C13 | 1.1 (8) | C24—C25—C26—C21 | 0.0 |
Zn1—N1—C8—C13 | 176.3 (5) | N3—C21—C26—N4 | −0.5 (6) |
C13—C8—C9—C10 | 0.0 | C22—C21—C26—N4 | 178.4 (6) |
N1—C8—C9—C10 | 178.2 (8) | N3—C21—C26—C25 | −178.8 (6) |
C8—C9—C10—C11 | 0.0 | C22—C21—C26—C25 | 0.0 |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W···O3i | 0.84 (2) | 1.91 (3) | 2.733 (11) | 165 (8) |
O4—H4O···O2ii | 0.82 | 1.98 | 2.797 (12) | 171 |
O3—H3O···O4 | 0.82 | 1.92 | 2.738 (16) | 173 |
N2—H2A···O1W | 0.86 | 2.02 | 2.833 (9) | 157 |
N4—H4A···O1iii | 0.86 | 1.97 | 2.799 (8) | 163 |
Symmetry codes: (i) −x+1, −y+1, z; (ii) x, −y+1, z+1/2; (iii) −x+1/2, y+1/2, z. |
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