metal-organic compounds
The N-heterocycle in the title compound, [Zn(C4H4O4)(C19H12N4)]n, chelates to the ZnII ion; adjacent Zn ions are linked through three O atoms of the succinate anions into a ribbon. Adjacent ribbons are further linked by N—HO hydrogen bonding, forming layers. The Zn center shows a square-pyramidal coordination.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806049452/xu2171sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806049452/xu2171Isup2.hkl |
CCDC reference: 630535
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.007 Å
- R factor = 0.055
- wR factor = 0.152
- Data-to-parameter ratio = 14.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.62 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C12 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT731_ALERT_1_C Bond Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Ra N3 -H3N 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Ra N3 -H3N 1.555 1.555
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 4 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 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Computing details top
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2006).
Poly-[[(2-phenyl-1H-1,3,7,8,-tetraazacyclopenta[l]phenanthrene)zinc(II)]- µ3-succinato] top
Crystal data top
[Zn(C4H4O4)(C19H12N4)] | F(000) = 1952 |
Mr = 477.77 | Dx = 1.675 Mg m−3 |
Orthorhombic, Pcca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2a 2ac | Cell parameters from 16211 reflections |
a = 13.819 (2) Å | θ = 3.3–27.5° |
b = 9.757 (2) Å | µ = 1.34 mm−1 |
c = 28.098 (2) Å | T = 293 K |
V = 3788.5 (10) Å3 | Block, pale yellow |
Z = 8 | 0.33 × 0.31 × 0.27 mm |
Data collection top
Rigaku RAXIS-RAPID IP diffractometer | 4342 independent reflections |
Radiation source: fine-focus sealed tube | 2419 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.088 |
ω scans | θmax = 27.5°, θmin = 3.3° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −17→17 |
Tmin = 0.666, Tmax = 0.714 | k = −12→10 |
32856 measured reflections | l = −36→36 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.152 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.96 | w = 1/[σ2(Fo2) + (0.0837P)2] where P = (Fo2 + 2Fc2)/3 |
4342 reflections | (Δ/σ)max = 0.001 |
293 parameters | Δρmax = 0.69 e Å−3 |
1 restraint | Δρmin = −0.62 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Zn1 | 0.63096 (3) | 0.88445 (5) | 0.598065 (15) | 0.04069 (18) | |
N1 | 0.6285 (2) | 0.9175 (3) | 0.67188 (11) | 0.0404 (7) | |
N2 | 0.6302 (2) | 0.6836 (3) | 0.62554 (11) | 0.0436 (8) | |
N3 | 0.6248 (3) | 0.6490 (4) | 0.81905 (12) | 0.0472 (9) | |
H3N | 0.609 (3) | 0.697 (4) | 0.8431 (10) | 0.046 (13)* | |
N4 | 0.6260 (2) | 0.4536 (4) | 0.77927 (13) | 0.0512 (9) | |
O1 | 0.5163 (2) | 0.8744 (3) | 0.55746 (10) | 0.0560 (8) | |
O2 | 0.4105 (3) | 0.8480 (4) | 0.61422 (11) | 0.0686 (10) | |
O3 | 0.3382 (2) | 0.9107 (3) | 0.40849 (10) | 0.0495 (7) | |
O4 | 0.2230 (2) | 0.8338 (3) | 0.45520 (10) | 0.0523 (8) | |
C1 | 0.4328 (3) | 0.8615 (4) | 0.57249 (15) | 0.0455 (10) | |
C2 | 0.3534 (3) | 0.8649 (6) | 0.53489 (16) | 0.0684 (15) | |
H2A | 0.3054 | 0.7964 | 0.5431 | 0.082* | |
H2B | 0.3219 | 0.9537 | 0.5365 | 0.082* | |
C3 | 0.3833 (3) | 0.8416 (6) | 0.48617 (16) | 0.0623 (13) | |
H3A | 0.4063 | 0.7479 | 0.4838 | 0.075* | |
H3B | 0.4380 | 0.9010 | 0.4797 | 0.075* | |
C4 | 0.3100 (3) | 0.8632 (4) | 0.44758 (14) | 0.0444 (10) | |
C5 | 0.6279 (3) | 0.8035 (4) | 0.69854 (13) | 0.0368 (8) | |
C6 | 0.6268 (3) | 1.0349 (5) | 0.69327 (15) | 0.0470 (10) | |
H6 | 0.6270 | 1.1141 | 0.6748 | 0.056* | |
C7 | 0.6245 (3) | 1.0481 (5) | 0.74245 (15) | 0.0503 (11) | |
H7 | 0.6236 | 1.1346 | 0.7563 | 0.060* | |
C8 | 0.6236 (3) | 0.9347 (5) | 0.77003 (15) | 0.0479 (10) | |
H8 | 0.6219 | 0.9422 | 0.8030 | 0.057* | |
C9 | 0.6253 (3) | 0.8077 (4) | 0.74865 (13) | 0.0384 (9) | |
C10 | 0.6255 (3) | 0.6809 (4) | 0.77157 (14) | 0.0417 (9) | |
C11 | 0.6248 (3) | 0.5109 (5) | 0.82143 (15) | 0.0497 (11) | |
C12 | 0.6218 (3) | 0.4391 (5) | 0.86639 (16) | 0.0525 (11) | |
C13 | 0.6246 (4) | 0.5038 (7) | 0.90915 (18) | 0.0781 (17) | |
H13 | 0.6308 | 0.5986 | 0.9104 | 0.094* | |
C14 | 0.6183 (4) | 0.4289 (8) | 0.9510 (2) | 0.094 (2) | |
H14 | 0.6200 | 0.4747 | 0.9800 | 0.112* | |
C15 | 0.6099 (4) | 0.2949 (7) | 0.9506 (2) | 0.0819 (19) | |
H15 | 0.6060 | 0.2456 | 0.9789 | 0.098* | |
C16 | 0.6070 (5) | 0.2312 (7) | 0.9085 (2) | 0.096 (2) | |
H16 | 0.6007 | 0.1364 | 0.9078 | 0.116* | |
C17 | 0.6131 (4) | 0.3016 (6) | 0.8661 (2) | 0.0809 (17) | |
H17 | 0.6113 | 0.2543 | 0.8373 | 0.097* | |
C18 | 0.6267 (3) | 0.5596 (4) | 0.74824 (15) | 0.0439 (9) | |
C19 | 0.6268 (3) | 0.5540 (4) | 0.69750 (14) | 0.0430 (9) | |
C20 | 0.6263 (3) | 0.4364 (5) | 0.67061 (17) | 0.0541 (11) | |
H20 | 0.6259 | 0.3514 | 0.6856 | 0.065* | |
C21 | 0.6264 (3) | 0.4434 (5) | 0.62287 (18) | 0.0591 (12) | |
H21 | 0.6243 | 0.3639 | 0.6047 | 0.071* | |
C22 | 0.6298 (3) | 0.5706 (5) | 0.60115 (16) | 0.0532 (11) | |
H22 | 0.6319 | 0.5753 | 0.5681 | 0.064* | |
C23 | 0.6284 (3) | 0.6766 (4) | 0.67358 (13) | 0.0386 (8) |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.0492 (3) | 0.0477 (3) | 0.0251 (2) | −0.0018 (2) | −0.0013 (2) | 0.0006 (2) |
N1 | 0.0516 (19) | 0.0413 (19) | 0.0281 (16) | −0.0014 (16) | −0.0012 (15) | −0.0017 (14) |
N2 | 0.057 (2) | 0.045 (2) | 0.0284 (17) | 0.0024 (17) | 0.0024 (16) | −0.0035 (15) |
N3 | 0.057 (2) | 0.053 (2) | 0.0317 (19) | 0.0024 (19) | 0.0063 (17) | 0.0088 (17) |
N4 | 0.056 (2) | 0.052 (2) | 0.045 (2) | 0.0038 (18) | 0.0012 (18) | 0.0127 (17) |
O1 | 0.0527 (18) | 0.079 (2) | 0.0366 (16) | −0.0034 (16) | −0.0093 (13) | 0.0082 (15) |
O2 | 0.079 (2) | 0.097 (3) | 0.0298 (16) | −0.001 (2) | −0.0010 (16) | −0.0005 (17) |
O3 | 0.0684 (19) | 0.0479 (18) | 0.0321 (16) | 0.0002 (15) | 0.0030 (13) | −0.0011 (13) |
O4 | 0.0565 (18) | 0.060 (2) | 0.0402 (16) | −0.0071 (15) | −0.0109 (14) | 0.0113 (14) |
C1 | 0.056 (3) | 0.046 (3) | 0.034 (2) | 0.006 (2) | −0.0007 (19) | 0.0024 (19) |
C2 | 0.056 (3) | 0.109 (5) | 0.040 (3) | 0.012 (3) | −0.010 (2) | −0.009 (3) |
C3 | 0.059 (3) | 0.089 (4) | 0.039 (2) | 0.011 (2) | −0.006 (2) | 0.005 (2) |
C4 | 0.059 (3) | 0.044 (3) | 0.030 (2) | 0.000 (2) | −0.0050 (19) | −0.0040 (18) |
C5 | 0.040 (2) | 0.041 (2) | 0.0292 (19) | −0.0020 (19) | −0.0013 (16) | 0.0003 (16) |
C6 | 0.062 (3) | 0.044 (2) | 0.036 (2) | −0.002 (2) | 0.004 (2) | 0.0011 (18) |
C7 | 0.074 (3) | 0.039 (2) | 0.038 (2) | −0.006 (2) | 0.003 (2) | −0.0038 (18) |
C8 | 0.057 (3) | 0.058 (3) | 0.029 (2) | 0.000 (2) | 0.0047 (19) | −0.0036 (19) |
C9 | 0.040 (2) | 0.047 (2) | 0.0280 (19) | −0.003 (2) | 0.0002 (17) | 0.0038 (17) |
C10 | 0.045 (2) | 0.049 (2) | 0.030 (2) | 0.002 (2) | −0.0008 (17) | 0.0033 (19) |
C11 | 0.053 (3) | 0.057 (3) | 0.038 (2) | 0.001 (2) | 0.000 (2) | 0.010 (2) |
C12 | 0.050 (3) | 0.063 (3) | 0.044 (3) | −0.002 (2) | 0.002 (2) | 0.023 (2) |
C13 | 0.105 (5) | 0.079 (4) | 0.050 (3) | −0.011 (3) | 0.001 (3) | 0.025 (3) |
C14 | 0.135 (6) | 0.099 (5) | 0.047 (3) | 0.004 (4) | 0.000 (3) | 0.022 (3) |
C15 | 0.074 (4) | 0.105 (5) | 0.067 (4) | 0.006 (3) | 0.004 (3) | 0.050 (4) |
C16 | 0.136 (6) | 0.068 (4) | 0.084 (5) | −0.001 (4) | −0.002 (4) | 0.036 (4) |
C17 | 0.107 (5) | 0.076 (4) | 0.059 (3) | 0.003 (3) | 0.004 (3) | 0.027 (3) |
C18 | 0.048 (2) | 0.044 (2) | 0.040 (2) | −0.0006 (19) | 0.002 (2) | 0.0083 (18) |
C19 | 0.046 (2) | 0.044 (2) | 0.038 (2) | 0.000 (2) | 0.0027 (19) | −0.0002 (18) |
C20 | 0.066 (3) | 0.041 (2) | 0.056 (3) | −0.001 (2) | 0.001 (2) | 0.001 (2) |
C21 | 0.080 (3) | 0.045 (3) | 0.053 (3) | 0.001 (2) | 0.004 (3) | −0.014 (2) |
C22 | 0.070 (3) | 0.051 (3) | 0.038 (2) | 0.002 (2) | 0.003 (2) | −0.008 (2) |
C23 | 0.042 (2) | 0.040 (2) | 0.033 (2) | −0.0001 (19) | −0.0002 (17) | −0.0014 (17) |
Geometric parameters (Å, º) top
Zn1—O1 | 1.955 (3) | C6—H6 | 0.9300 |
Zn1—O3i | 2.052 (3) | C7—C8 | 1.351 (6) |
Zn1—O4ii | 2.025 (3) | C7—H7 | 0.9300 |
Zn1—N1 | 2.099 (3) | C8—C9 | 1.377 (6) |
Zn1—N2 | 2.106 (3) | C8—H8 | 0.9300 |
N1—C6 | 1.294 (5) | C9—C10 | 1.394 (6) |
N1—C5 | 1.341 (5) | C10—C18 | 1.353 (6) |
N2—C22 | 1.298 (6) | C11—C12 | 1.445 (6) |
N2—C23 | 1.352 (5) | C12—C17 | 1.347 (8) |
N3—C11 | 1.349 (6) | C12—C13 | 1.358 (7) |
N3—C10 | 1.370 (5) | C13—C14 | 1.387 (7) |
N3—H3N | 0.850 (10) | C13—H13 | 0.9300 |
N4—C11 | 1.310 (6) | C14—C15 | 1.313 (9) |
N4—C18 | 1.353 (5) | C14—H14 | 0.9300 |
O1—C1 | 1.235 (5) | C15—C16 | 1.337 (8) |
O2—C1 | 1.220 (5) | C15—H15 | 0.9300 |
O3—C4 | 1.254 (5) | C16—C17 | 1.379 (7) |
O4—C4 | 1.254 (5) | C16—H16 | 0.9300 |
C1—C2 | 1.523 (6) | C17—H17 | 0.9300 |
C2—C3 | 1.448 (6) | C18—C19 | 1.427 (6) |
C2—H2A | 0.9700 | C19—C23 | 1.372 (6) |
C2—H2B | 0.9700 | C19—C20 | 1.373 (6) |
C3—C4 | 1.499 (6) | C20—C21 | 1.343 (6) |
C3—H3A | 0.9700 | C20—H20 | 0.9300 |
C3—H3B | 0.9700 | C21—C22 | 1.384 (7) |
C5—C9 | 1.409 (5) | C21—H21 | 0.9300 |
C5—C23 | 1.423 (5) | C22—H22 | 0.9300 |
C6—C7 | 1.388 (6) | ||
O1—Zn1—O4ii | 93.8 (1) | C6—C7—H7 | 120.2 |
O1—Zn1—O3i | 99.5 (1) | C7—C8—C9 | 119.1 (4) |
O1—Zn1—N1 | 124.8 (1) | C7—C8—H8 | 120.4 |
O1—Zn1—N2 | 99.4 (1) | C9—C8—H8 | 120.4 |
O3i—Zn1—O4ii | 92.3 (1) | C8—C9—C10 | 126.6 (4) |
O3i—Zn1—N1 | 86.7 (1) | C8—C9—C5 | 117.6 (4) |
O3i—Zn1—N2 | 160.1 (1) | C10—C9—C5 | 115.8 (4) |
O4ii—Zn1—N1 | 141.0 (1) | C18—C10—N3 | 105.8 (4) |
O4ii—Zn1—N2 | 92.7 (1) | C18—C10—C9 | 123.5 (4) |
N1—Zn1—N2 | 77.3 (1) | N3—C10—C9 | 130.6 (4) |
C6—N1—C5 | 118.3 (4) | N4—C11—N3 | 112.4 (4) |
C6—N1—Zn1 | 126.5 (3) | N4—C11—C12 | 125.8 (4) |
C5—N1—Zn1 | 115.1 (3) | N3—C11—C12 | 121.8 (4) |
C22—N2—C23 | 118.9 (4) | C17—C12—C13 | 118.1 (5) |
C22—N2—Zn1 | 126.6 (3) | C17—C12—C11 | 118.6 (5) |
C23—N2—Zn1 | 114.4 (3) | C13—C12—C11 | 123.2 (5) |
C11—N3—C10 | 106.0 (4) | C12—C13—C14 | 120.3 (6) |
C11—N3—H3N | 121 (3) | C12—C13—H13 | 119.9 |
C10—N3—H3N | 130 (3) | C14—C13—H13 | 119.9 |
C11—N4—C18 | 104.9 (4) | C15—C14—C13 | 121.5 (6) |
C1—O1—Zn1 | 124.2 (3) | C15—C14—H14 | 119.2 |
C4—O3—Zn1i | 120.2 (3) | C13—C14—H14 | 119.2 |
C4—O4—Zn1iii | 114.8 (3) | C14—C15—C16 | 118.2 (5) |
O2—C1—O1 | 125.2 (4) | C14—C15—H15 | 120.9 |
O2—C1—C2 | 119.2 (4) | C16—C15—H15 | 120.9 |
O1—C1—C2 | 115.7 (4) | C15—C16—C17 | 122.2 (7) |
C3—C2—C1 | 116.5 (4) | C15—C16—H16 | 118.9 |
C3—C2—H2A | 108.2 | C17—C16—H16 | 118.9 |
C1—C2—H2A | 108.2 | C12—C17—C16 | 119.7 (6) |
C3—C2—H2B | 108.2 | C12—C17—H17 | 120.1 |
C1—C2—H2B | 108.2 | C16—C17—H17 | 120.1 |
H2A—C2—H2B | 107.3 | N4—C18—C10 | 110.9 (4) |
C2—C3—C4 | 118.0 (4) | N4—C18—C19 | 127.9 (4) |
C2—C3—H3A | 107.8 | C10—C18—C19 | 121.2 (4) |
C4—C3—H3A | 107.8 | C23—C19—C20 | 117.3 (4) |
C2—C3—H3B | 107.8 | C23—C19—C18 | 117.1 (4) |
C4—C3—H3B | 107.8 | C20—C19—C18 | 125.6 (4) |
H3A—C3—H3B | 107.2 | C21—C20—C19 | 120.5 (4) |
O4—C4—O3 | 122.1 (4) | C21—C20—H20 | 119.8 |
O4—C4—C3 | 119.5 (4) | C19—C20—H20 | 119.8 |
O3—C4—C3 | 118.4 (4) | C20—C21—C22 | 119.1 (4) |
N1—C5—C9 | 122.3 (4) | C20—C21—H21 | 120.5 |
N1—C5—C23 | 116.5 (3) | C22—C21—H21 | 120.5 |
C9—C5—C23 | 121.2 (4) | N2—C22—C21 | 121.9 (4) |
N1—C6—C7 | 123.0 (4) | N2—C22—H22 | 119.0 |
N1—C6—H6 | 118.5 | C21—C22—H22 | 119.0 |
C7—C6—H6 | 118.5 | N2—C23—C19 | 122.3 (4) |
C8—C7—C6 | 119.7 (4) | N2—C23—C5 | 116.6 (3) |
C8—C7—H7 | 120.2 | C19—C23—C5 | 121.1 (4) |
O1—Zn1—N1—C6 | −86.5 (4) | C5—C9—C10—C18 | −0.8 (6) |
O4ii—Zn1—N1—C6 | 102.4 (4) | C8—C9—C10—N3 | −0.6 (7) |
O3i—Zn1—N1—C6 | 12.7 (3) | C5—C9—C10—N3 | 179.0 (4) |
N2—Zn1—N1—C6 | −179.2 (3) | C18—N4—C11—N3 | 0.0 (5) |
O1—Zn1—N1—C5 | 92.8 (3) | C18—N4—C11—C12 | 178.7 (4) |
O4ii—Zn1—N1—C5 | −78.3 (3) | C10—N3—C11—N4 | 0.3 (5) |
O3i—Zn1—N1—C5 | −167.9 (3) | C10—N3—C11—C12 | −178.5 (4) |
N2—Zn1—N1—C5 | 0.1 (3) | N4—C11—C12—C17 | −4.6 (7) |
O1—Zn1—N2—C22 | 55.2 (4) | N3—C11—C12—C17 | 174.1 (4) |
O4ii—Zn1—N2—C22 | −39.0 (4) | N4—C11—C12—C13 | 177.3 (5) |
O3i—Zn1—N2—C22 | −143.5 (4) | N3—C11—C12—C13 | −4.1 (7) |
N1—Zn1—N2—C22 | 179.0 (4) | C17—C12—C13—C14 | −0.2 (9) |
O1—Zn1—N2—C23 | −123.6 (3) | C11—C12—C13—C14 | 177.9 (5) |
O4ii—Zn1—N2—C23 | 142.1 (3) | C12—C13—C14—C15 | 0.3 (10) |
O3i—Zn1—N2—C23 | 37.6 (5) | C13—C14—C15—C16 | −0.3 (10) |
N1—Zn1—N2—C23 | 0.2 (3) | C14—C15—C16—C17 | 0.4 (10) |
O4ii—Zn1—O1—C1 | 160.5 (3) | C13—C12—C17—C16 | 0.3 (8) |
O3i—Zn1—O1—C1 | −106.5 (3) | C11—C12—C17—C16 | −178.0 (5) |
N1—Zn1—O1—C1 | −13.9 (4) | C15—C16—C17—C12 | −0.4 (10) |
N2—Zn1—O1—C1 | 67.2 (4) | C11—N4—C18—C10 | −0.3 (5) |
Zn1—O1—C1—O2 | −3.0 (6) | C11—N4—C18—C19 | −179.1 (4) |
Zn1—O1—C1—C2 | 176.2 (3) | N3—C10—C18—N4 | 0.5 (5) |
O2—C1—C2—C3 | −162.8 (5) | C9—C10—C18—N4 | −179.6 (4) |
O1—C1—C2—C3 | 17.9 (7) | N3—C10—C18—C19 | 179.4 (4) |
C1—C2—C3—C4 | −171.7 (4) | C9—C10—C18—C19 | −0.7 (6) |
Zn1iii—O4—C4—O3 | −5.2 (5) | N4—C18—C19—C23 | −179.5 (4) |
Zn1iii—O4—C4—C3 | 174.8 (3) | C10—C18—C19—C23 | 1.8 (6) |
Zn1i—O3—C4—O4 | 103.4 (4) | N4—C18—C19—C20 | −0.1 (7) |
Zn1i—O3—C4—C3 | −76.5 (5) | C10—C18—C19—C20 | −178.8 (4) |
C2—C3—C4—O4 | −35.1 (7) | C23—C19—C20—C21 | −0.6 (6) |
C2—C3—C4—O3 | 144.9 (5) | C18—C19—C20—C21 | 180.0 (4) |
C6—N1—C5—C9 | 0.0 (5) | C19—C20—C21—C22 | 1.8 (7) |
Zn1—N1—C5—C9 | −179.4 (3) | C23—N2—C22—C21 | 0.8 (6) |
C6—N1—C5—C23 | 179.1 (3) | Zn1—N2—C22—C21 | −178.0 (3) |
Zn1—N1—C5—C23 | −0.3 (4) | C20—C21—C22—N2 | −1.9 (7) |
C5—N1—C6—C7 | 0.2 (6) | C22—N2—C23—C19 | 0.4 (6) |
Zn1—N1—C6—C7 | 179.5 (3) | Zn1—N2—C23—C19 | 179.4 (3) |
N1—C6—C7—C8 | −0.3 (7) | C22—N2—C23—C5 | −179.3 (4) |
C6—C7—C8—C9 | 0.2 (6) | Zn1—N2—C23—C5 | −0.4 (4) |
C7—C8—C9—C10 | 179.5 (4) | C20—C19—C23—N2 | −0.5 (6) |
C7—C8—C9—C5 | −0.1 (6) | C18—C19—C23—N2 | 178.9 (4) |
N1—C5—C9—C8 | −0.1 (6) | C20—C19—C23—C5 | 179.2 (4) |
C23—C5—C9—C8 | −179.1 (3) | C18—C19—C23—C5 | −1.3 (6) |
N1—C5—C9—C10 | −179.6 (3) | N1—C5—C23—N2 | 0.4 (5) |
C23—C5—C9—C10 | 1.3 (5) | C9—C5—C23—N2 | 179.6 (4) |
C11—N3—C10—C18 | −0.5 (5) | N1—C5—C23—C19 | −179.3 (4) |
C11—N3—C10—C9 | 179.7 (4) | C9—C5—C23—C19 | −0.2 (6) |
C8—C9—C10—C18 | 179.6 (4) |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x+1/2, y, −z+1; (iii) x−1/2, y, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3N···O2iv | 0.85 (1) | 1.92 (2) | 2.743 (5) | 163 (4) |
Symmetry code: (iv) −x+1, y, −z+3/2. |