In the crystal structure of the title coordination polymer/co-crystal, {[ZnCl
2(C
18H
18N
4)]·C
18H
18N
4}
n, the tetrahedrally coordinated Zn
II ions are linked by the
N-heterocycle into a linear chain. Another
N-heterocycle present is not coordinated to the metal atom but interacts with the chain through N—H
N and N—H
Cl hydrogen bonds. The butyl chain of the uncoordinated ligand is disordered over three positions in a 0.511 (4):0.289 (5):0.200 (5) ratio.
Supporting information
CCDC reference: 766676
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.007 Å
- Disorder in main residue
- R factor = 0.062
- wR factor = 0.192
- Data-to-parameter ratio = 16.9
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT919_ALERT_3_B Reflection(s) # Likely Affected by the Beamstop 1
Alert level C
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C26
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang .. 7
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 11
PLAT731_ALERT_1_C Bond Calc 0.88(3), Rep 0.876(10) ...... 3.00 su-Ra
N2 -H2 1.555 1.555
PLAT731_ALERT_1_C Bond Calc 0.88(3), Rep 0.878(10) ...... 3.00 su-Ra
N4 -H4 1.555 1.555
PLAT731_ALERT_1_C Bond Calc 0.87(3), Rep 0.875(10) ...... 3.00 su-Ra
N6 -H6 1.555 1.555
PLAT731_ALERT_1_C Bond Calc 0.88(3), Rep 0.879(10) ...... 3.00 su-Ra
N7 -H7 1.555 1.555
PLAT735_ALERT_1_C D-H Calc 0.88(3), Rep 0.880(10) ...... 3.00 su-Ra
N2 -H2 1.555 1.555
PLAT735_ALERT_1_C D-H Calc 0.88(3), Rep 0.880(10) ...... 3.00 su-Ra
N4 -H4 1.555 1.555
PLAT735_ALERT_1_C D-H Calc 0.87(3), Rep 0.880(10) ...... 3.00 su-Ra
N6 -H6 1.555 1.555
PLAT735_ALERT_1_C D-H Calc 0.88(3), Rep 0.880(10) ...... 3.00 su-Ra
N7 -H7 1.555 1.555
PLAT736_ALERT_1_C H...A Calc 1.92(3), Rep 1.920(10) ...... 3.00 su-Ra
H2 -N5 1.555 1.555
PLAT736_ALERT_1_C H...A Calc 1.90(3), Rep 1.900(10) ...... 3.00 su-Ra
H4 -N8 1.555 1.455
PLAT736_ALERT_1_C H...A Calc 2.35(3), Rep 2.350(10) ...... 3.00 su-Ra
H7 -CL2 1.555 2.756
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 32
Alert level G
PLAT301_ALERT_3_G Note: Main Residue Disorder ................... 2.00 Perc.
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 32
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
15 ALERT level C = Check and explain
2 ALERT level G = General alerts; check
11 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
5 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
1,4-Bis(2-benzimidazolyl)butane was synthesized by using a literature method
(van Albada et al., 1995). To a solution of zinc chloride
hexahydrate
(0.25 g, 1 mmol) in ethanol (3 ml) was added an aqueous solution (4 ml) of the
ligand (0.27 g, 1 mmol). The reactants were sealed in a 15-ml Teflon-lined,
stainless-steel Parr bomb. The bomb was heated at 413 K for 3 d. The cool
solution yielded red block single crystals in ca 30% yield.
Carbon-bound hydrogen atoms were generated geometrically and were constrained
to ride on their parent atoms [C–H = 0.95–0.99 Å and Uiso(H) =
1.2Ueq(C)]. The nitrogen-bound ones were located in a difference
Fourier map, and were refined with a N-H distance restraint of 0.88 (1) Å;
their temperature factors were similarly tied.
The butyl chain of the uncoordinated ligand is disordered over three positions
with occupancies of 0.511 (4), 0.289 (5) and 0.200 (5). The 1,2-related distances
were restrained to 1.50 (1) Å and the 1,3-related ones to 2.35 (1) Å.
The final difference Fourier map had a peak in the vicinity of the
disordered atoms.
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).
catena-Poly[[[dichloridozinc(II)]-µ-1,4-bis(1
H-benzimidazol-2-
yl-
κN3)butane] 1,4-bis(1
H-benzimidazol-2-yl)butane solvate]
top
Crystal data top
[ZnCl2(C18H18N4)]·C18H18N4 | F(000) = 1488 |
Mr = 717.00 | Dx = 1.373 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3392 reflections |
a = 8.5321 (5) Å | θ = 2.4–25.2° |
b = 24.119 (2) Å | µ = 0.90 mm−1 |
c = 16.880 (1) Å | T = 173 K |
β = 92.999 (1)° | Block, red |
V = 3468.9 (4) Å3 | 0.45 × 0.30 × 0.20 mm |
Z = 4 | |
Data collection top
Bruker APEXII area-detector diffractometer | 7549 independent reflections |
Radiation source: fine-focus sealed tube | 3855 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.052 |
ϕ and ω scans | θmax = 27.0°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→10 |
Tmin = 0.687, Tmax = 0.840 | k = −30→18 |
17738 measured reflections | l = −19→21 |
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)] = 0.062 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.192 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0962P)2] where P = (Fo2 + 2Fc2)/3 |
7549 reflections | (Δ/σ)max = 0.001 |
448 parameters | Δρmax = 1.10 e Å−3 |
32 restraints | Δρmin = −0.70 e Å−3 |
Crystal data top
[ZnCl2(C18H18N4)]·C18H18N4 | V = 3468.9 (4) Å3 |
Mr = 717.00 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.5321 (5) Å | µ = 0.90 mm−1 |
b = 24.119 (2) Å | T = 173 K |
c = 16.880 (1) Å | 0.45 × 0.30 × 0.20 mm |
β = 92.999 (1)° | |
Data collection top
Bruker APEXII area-detector diffractometer | 7549 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3855 reflections with I > 2σ(I) |
Tmin = 0.687, Tmax = 0.840 | Rint = 0.052 |
17738 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.062 | 32 restraints |
wR(F2) = 0.192 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 1.10 e Å−3 |
7549 reflections | Δρmin = −0.70 e Å−3 |
448 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Zn1 | 0.76884 (6) | 0.443756 (19) | 0.75855 (3) | 0.03034 (19) | |
Cl1 | 0.58239 (17) | 0.39129 (5) | 0.81075 (9) | 0.0579 (4) | |
Cl2 | 0.95928 (16) | 0.39314 (5) | 0.70655 (9) | 0.0518 (4) | |
N1 | 0.6603 (4) | 0.49713 (13) | 0.6803 (2) | 0.0239 (8) | |
N2 | 0.5260 (4) | 0.57190 (14) | 0.6425 (2) | 0.0293 (9) | |
H2 | 0.468 (4) | 0.6019 (11) | 0.637 (3) | 0.035* | |
N3 | −0.1295 (4) | 0.49956 (13) | 0.8346 (2) | 0.0243 (8) | |
N4 | −0.0076 (4) | 0.57767 (15) | 0.8695 (2) | 0.0297 (9) | |
H4 | 0.042 (5) | 0.6091 (10) | 0.864 (3) | 0.036* | |
N5 | 0.3642 (5) | 0.67223 (16) | 0.6438 (2) | 0.0434 (11) | |
N6 | 0.3359 (5) | 0.76206 (16) | 0.6609 (3) | 0.0419 (11) | |
H6 | 0.360 (6) | 0.7956 (9) | 0.677 (3) | 0.050* | |
N7 | 1.1593 (5) | 0.76918 (15) | 0.8373 (2) | 0.0405 (10) | |
H7 | 1.125 (5) | 0.8026 (9) | 0.825 (3) | 0.049* | |
N8 | 1.1417 (5) | 0.67940 (16) | 0.8606 (2) | 0.0388 (10) | |
C1 | 0.6918 (5) | 0.50889 (16) | 0.6017 (2) | 0.0247 (10) | |
C2 | 0.7893 (5) | 0.48250 (19) | 0.5501 (3) | 0.0360 (11) | |
H2a | 0.8472 | 0.4502 | 0.5655 | 0.043* | |
C3 | 0.7981 (6) | 0.5056 (2) | 0.4750 (3) | 0.0437 (13) | |
H3 | 0.8641 | 0.4887 | 0.4383 | 0.052* | |
C4 | 0.7138 (6) | 0.5523 (2) | 0.4520 (3) | 0.0430 (13) | |
H4A | 0.7230 | 0.5667 | 0.4001 | 0.052* | |
C5 | 0.6168 (6) | 0.57815 (19) | 0.5029 (3) | 0.0381 (12) | |
H5 | 0.5585 | 0.6102 | 0.4872 | 0.046* | |
C6 | 0.6070 (5) | 0.55583 (17) | 0.5777 (3) | 0.0284 (10) | |
C7 | 0.5620 (5) | 0.53660 (16) | 0.7022 (3) | 0.0256 (10) | |
C8 | 0.4998 (5) | 0.54272 (18) | 0.7826 (3) | 0.0315 (11) | |
H8A | 0.5665 | 0.5696 | 0.8132 | 0.038* | |
H8B | 0.5093 | 0.5066 | 0.8102 | 0.038* | |
C9 | 0.3315 (5) | 0.56169 (18) | 0.7834 (3) | 0.0339 (11) | |
H9A | 0.3029 | 0.5665 | 0.8390 | 0.041* | |
H9B | 0.3214 | 0.5982 | 0.7567 | 0.041* | |
C10 | 0.2204 (5) | 0.5219 (2) | 0.7431 (3) | 0.0371 (11) | |
H10A | 0.2259 | 0.4864 | 0.7724 | 0.044* | |
H10B | 0.2556 | 0.5147 | 0.6891 | 0.044* | |
C11 | 0.0455 (5) | 0.54116 (19) | 0.7360 (3) | 0.0330 (11) | |
H11A | 0.0410 | 0.5796 | 0.7154 | 0.040* | |
H11B | −0.0131 | 0.5172 | 0.6971 | 0.040* | |
C12 | −0.0323 (5) | 0.53918 (16) | 0.8124 (2) | 0.0243 (10) | |
C13 | −0.1716 (5) | 0.51441 (17) | 0.9110 (3) | 0.0272 (10) | |
C14 | −0.2741 (5) | 0.4896 (2) | 0.9620 (3) | 0.0396 (12) | |
H14 | −0.3266 | 0.4559 | 0.9486 | 0.047* | |
C15 | −0.2956 (6) | 0.5164 (2) | 1.0328 (3) | 0.0509 (15) | |
H15 | −0.3652 | 0.5005 | 1.0686 | 0.061* | |
C16 | −0.2204 (7) | 0.5652 (2) | 1.0538 (3) | 0.0521 (15) | |
H16 | −0.2395 | 0.5822 | 1.1032 | 0.063* | |
C17 | −0.1178 (6) | 0.5895 (2) | 1.0040 (3) | 0.0445 (13) | |
H17 | −0.0646 | 0.6229 | 1.0182 | 0.053* | |
C18 | −0.0950 (5) | 0.56348 (17) | 0.9328 (3) | 0.0287 (10) | |
C19 | 0.2264 (5) | 0.68930 (18) | 0.6044 (3) | 0.0313 (11) | |
C20 | 0.1127 (7) | 0.6592 (2) | 0.5586 (3) | 0.0571 (16) | |
H20 | 0.1210 | 0.6203 | 0.5509 | 0.069* | |
C21 | −0.0121 (7) | 0.6897 (3) | 0.5254 (4) | 0.0686 (19) | |
H21 | −0.0902 | 0.6711 | 0.4932 | 0.082* | |
C22 | −0.0268 (6) | 0.7454 (3) | 0.5375 (4) | 0.0639 (18) | |
H22 | −0.1158 | 0.7640 | 0.5141 | 0.077* | |
C23 | 0.0817 (6) | 0.7754 (2) | 0.5818 (3) | 0.0511 (15) | |
H23 | 0.0705 | 0.8142 | 0.5901 | 0.061* | |
C24 | 0.2081 (5) | 0.74616 (18) | 0.6138 (3) | 0.0315 (11) | |
C25 | 0.4246 (6) | 0.7171 (2) | 0.6767 (3) | 0.0455 (14) | |
C26 | 0.5745 (7) | 0.7182 (3) | 0.7284 (4) | 0.093 (3) | |
H26A | 0.5445 | 0.7204 | 0.7842 | 0.112* | 0.511 (4) |
H26B | 0.6274 | 0.6821 | 0.7221 | 0.112* | 0.511 (4) |
H26C | 0.6509 | 0.7328 | 0.6915 | 0.112* | 0.289 (5) |
H26D | 0.5552 | 0.7495 | 0.7646 | 0.112* | 0.289 (5) |
H26E | 0.5844 | 0.7544 | 0.7561 | 0.112* | 0.200 (5) |
H26F | 0.5717 | 0.6887 | 0.7691 | 0.112* | 0.200 (5) |
C27 | 0.6908 (8) | 0.7616 (3) | 0.7171 (5) | 0.086 (4) | 0.511 (4) |
H27A | 0.6385 | 0.7981 | 0.7125 | 0.103* | 0.511 (4) |
H27B | 0.7453 | 0.7546 | 0.6677 | 0.103* | 0.511 (4) |
C28 | 0.8063 (8) | 0.7613 (3) | 0.7867 (5) | 0.065 (3) | 0.511 (4) |
H28A | 0.8554 | 0.7983 | 0.7933 | 0.078* | 0.511 (4) |
H28B | 0.7525 | 0.7523 | 0.8357 | 0.078* | 0.511 (4) |
C27' | 0.6698 (13) | 0.6826 (6) | 0.7778 (11) | 0.086 (4) | 0.289 (5) |
H27C | 0.7209 | 0.6548 | 0.7447 | 0.103* | 0.289 (5) |
H27D | 0.6033 | 0.6626 | 0.8148 | 0.103* | 0.289 (5) |
C28' | 0.7909 (11) | 0.7148 (8) | 0.8236 (7) | 0.065 (3) | 0.289 (5) |
H28C | 0.8217 | 0.6955 | 0.8738 | 0.078* | 0.289 (5) |
H28D | 0.7506 | 0.7520 | 0.8363 | 0.078* | 0.289 (5) |
C27" | 0.7118 (12) | 0.7096 (11) | 0.6788 (7) | 0.086 (4) | 0.200 (5) |
H27E | 0.6809 | 0.6876 | 0.6310 | 0.103* | 0.200 (5) |
H27F | 0.7540 | 0.7457 | 0.6618 | 0.103* | 0.200 (5) |
C28" | 0.8301 (14) | 0.6796 (6) | 0.7288 (14) | 0.065 (3) | 0.200 (5) |
H28E | 0.7775 | 0.6548 | 0.7659 | 0.078* | 0.200 (5) |
H28F | 0.8959 | 0.6566 | 0.6951 | 0.078* | 0.200 (5) |
C29 | 0.9271 (6) | 0.7194 (3) | 0.7729 (4) | 0.0680 (19) | |
H29A | 0.9552 | 0.7223 | 0.7169 | 0.082* | 0.511 (4) |
H29B | 0.8799 | 0.6823 | 0.7798 | 0.082* | 0.511 (4) |
H29C | 0.9167 | 0.7532 | 0.7397 | 0.082* | 0.289 (5) |
H29D | 0.9303 | 0.6869 | 0.7372 | 0.082* | 0.289 (5) |
H29E | 0.8505 | 0.7369 | 0.8071 | 0.082* | 0.200 (5) |
H29F | 0.9465 | 0.7475 | 0.7319 | 0.082* | 0.200 (5) |
C30 | 1.0769 (6) | 0.7222 (2) | 0.8247 (3) | 0.0421 (13) | |
C31 | 1.2901 (5) | 0.75633 (18) | 0.8853 (3) | 0.0320 (11) | |
C32 | 1.4133 (6) | 0.7881 (2) | 0.9160 (3) | 0.0442 (13) | |
H32 | 1.4210 | 0.8266 | 0.9048 | 0.053* | |
C33 | 1.5239 (6) | 0.7611 (2) | 0.9633 (3) | 0.0548 (16) | |
H33 | 1.6099 | 0.7816 | 0.9863 | 0.066* | |
C34 | 1.5145 (6) | 0.7049 (2) | 0.9788 (3) | 0.0538 (16) | |
H34 | 1.5945 | 0.6878 | 1.0115 | 0.065* | |
C35 | 1.3913 (6) | 0.6729 (2) | 0.9477 (3) | 0.0463 (14) | |
H35 | 1.3850 | 0.6344 | 0.9589 | 0.056* | |
C36 | 1.2775 (5) | 0.69929 (18) | 0.8997 (3) | 0.0328 (11) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Zn1 | 0.0306 (3) | 0.0192 (3) | 0.0406 (4) | 0.0004 (2) | −0.0038 (2) | −0.0001 (2) |
Cl1 | 0.0530 (9) | 0.0321 (7) | 0.0887 (11) | −0.0170 (6) | 0.0056 (8) | 0.0139 (7) |
Cl2 | 0.0455 (8) | 0.0338 (7) | 0.0754 (10) | 0.0136 (6) | −0.0030 (7) | −0.0160 (6) |
N1 | 0.0207 (18) | 0.0230 (18) | 0.028 (2) | 0.0031 (14) | −0.0005 (16) | −0.0037 (15) |
N2 | 0.027 (2) | 0.029 (2) | 0.032 (2) | 0.0114 (16) | 0.0011 (18) | 0.0021 (17) |
N3 | 0.0224 (19) | 0.0229 (18) | 0.027 (2) | −0.0016 (15) | −0.0021 (16) | 0.0008 (15) |
N4 | 0.028 (2) | 0.027 (2) | 0.034 (2) | −0.0068 (16) | 0.0033 (18) | −0.0030 (17) |
N5 | 0.054 (3) | 0.040 (2) | 0.036 (2) | 0.029 (2) | 0.000 (2) | 0.0014 (19) |
N6 | 0.032 (2) | 0.037 (2) | 0.056 (3) | 0.0006 (19) | −0.007 (2) | −0.015 (2) |
N7 | 0.036 (2) | 0.033 (2) | 0.051 (3) | −0.0021 (19) | −0.010 (2) | 0.007 (2) |
N8 | 0.040 (2) | 0.038 (2) | 0.038 (2) | −0.0135 (19) | 0.001 (2) | −0.0025 (18) |
C1 | 0.019 (2) | 0.029 (2) | 0.026 (2) | −0.0010 (17) | −0.0019 (19) | −0.0047 (18) |
C2 | 0.030 (3) | 0.044 (3) | 0.035 (3) | 0.008 (2) | 0.001 (2) | −0.010 (2) |
C3 | 0.037 (3) | 0.063 (3) | 0.032 (3) | 0.008 (3) | 0.006 (2) | −0.012 (3) |
C4 | 0.050 (3) | 0.053 (3) | 0.027 (3) | −0.007 (3) | 0.006 (2) | −0.003 (2) |
C5 | 0.044 (3) | 0.036 (3) | 0.034 (3) | 0.001 (2) | −0.004 (2) | 0.004 (2) |
C6 | 0.027 (2) | 0.027 (2) | 0.031 (3) | −0.0042 (19) | 0.002 (2) | −0.002 (2) |
C7 | 0.021 (2) | 0.025 (2) | 0.031 (3) | 0.0023 (18) | −0.001 (2) | −0.0044 (18) |
C8 | 0.027 (2) | 0.033 (3) | 0.035 (3) | 0.0068 (19) | 0.008 (2) | −0.0011 (19) |
C9 | 0.028 (2) | 0.040 (3) | 0.035 (3) | 0.003 (2) | 0.009 (2) | 0.000 (2) |
C10 | 0.046 (3) | 0.038 (3) | 0.029 (3) | −0.006 (2) | 0.016 (2) | −0.010 (2) |
C11 | 0.029 (3) | 0.042 (3) | 0.029 (3) | −0.002 (2) | 0.003 (2) | −0.002 (2) |
C12 | 0.020 (2) | 0.024 (2) | 0.028 (2) | 0.0036 (17) | −0.0012 (19) | 0.0013 (18) |
C13 | 0.020 (2) | 0.034 (2) | 0.027 (2) | 0.0016 (19) | −0.001 (2) | 0.0052 (19) |
C14 | 0.031 (3) | 0.053 (3) | 0.035 (3) | 0.001 (2) | 0.002 (2) | 0.017 (2) |
C15 | 0.038 (3) | 0.083 (4) | 0.032 (3) | 0.008 (3) | 0.010 (3) | 0.019 (3) |
C16 | 0.048 (3) | 0.076 (4) | 0.033 (3) | 0.015 (3) | 0.004 (3) | −0.002 (3) |
C17 | 0.050 (3) | 0.048 (3) | 0.035 (3) | 0.005 (3) | 0.002 (3) | −0.008 (2) |
C18 | 0.022 (2) | 0.037 (3) | 0.027 (3) | 0.0029 (19) | −0.001 (2) | 0.002 (2) |
C19 | 0.032 (3) | 0.032 (2) | 0.030 (3) | 0.005 (2) | 0.001 (2) | 0.004 (2) |
C20 | 0.068 (4) | 0.042 (3) | 0.061 (4) | −0.017 (3) | 0.003 (3) | −0.012 (3) |
C21 | 0.041 (4) | 0.095 (5) | 0.068 (5) | −0.023 (4) | −0.013 (3) | −0.011 (4) |
C22 | 0.033 (3) | 0.092 (5) | 0.066 (4) | 0.002 (3) | −0.013 (3) | 0.014 (4) |
C23 | 0.033 (3) | 0.052 (3) | 0.068 (4) | 0.010 (2) | −0.006 (3) | 0.017 (3) |
C24 | 0.022 (2) | 0.029 (2) | 0.043 (3) | 0.0016 (18) | −0.006 (2) | 0.003 (2) |
C25 | 0.030 (3) | 0.069 (4) | 0.037 (3) | 0.022 (3) | −0.007 (2) | −0.008 (3) |
C26 | 0.047 (4) | 0.162 (7) | 0.070 (5) | 0.035 (5) | −0.011 (4) | −0.052 (5) |
C27 | 0.072 (6) | 0.078 (6) | 0.106 (7) | −0.007 (6) | −0.017 (6) | 0.014 (6) |
C28 | 0.050 (5) | 0.061 (5) | 0.082 (6) | −0.006 (5) | −0.014 (5) | −0.012 (5) |
C27' | 0.072 (6) | 0.078 (6) | 0.106 (7) | −0.007 (6) | −0.017 (6) | 0.014 (6) |
C28' | 0.050 (5) | 0.061 (5) | 0.082 (6) | −0.006 (5) | −0.014 (5) | −0.012 (5) |
C27" | 0.072 (6) | 0.078 (6) | 0.106 (7) | −0.007 (6) | −0.017 (6) | 0.014 (6) |
C28" | 0.050 (5) | 0.061 (5) | 0.082 (6) | −0.006 (5) | −0.014 (5) | −0.012 (5) |
C29 | 0.045 (4) | 0.097 (5) | 0.061 (4) | −0.019 (3) | −0.011 (3) | 0.030 (3) |
C30 | 0.032 (3) | 0.053 (3) | 0.040 (3) | −0.012 (2) | −0.007 (2) | 0.007 (2) |
C31 | 0.021 (2) | 0.034 (3) | 0.040 (3) | −0.0011 (19) | −0.004 (2) | −0.006 (2) |
C32 | 0.039 (3) | 0.034 (3) | 0.059 (4) | −0.006 (2) | −0.005 (3) | −0.006 (2) |
C33 | 0.034 (3) | 0.056 (4) | 0.073 (4) | −0.006 (3) | −0.012 (3) | −0.019 (3) |
C34 | 0.037 (3) | 0.065 (4) | 0.058 (4) | 0.013 (3) | −0.015 (3) | −0.005 (3) |
C35 | 0.049 (3) | 0.034 (3) | 0.056 (4) | 0.010 (2) | −0.002 (3) | 0.005 (2) |
C36 | 0.026 (3) | 0.033 (3) | 0.039 (3) | −0.003 (2) | 0.000 (2) | −0.002 (2) |
Geometric parameters (Å, º) top
Zn1—N1 | 2.033 (3) | C17—H17 | 0.95 |
Zn1—N3i | 2.024 (3) | C19—C24 | 1.390 (6) |
Zn1—Cl1 | 2.248 (1) | C19—C20 | 1.409 (7) |
Zn1—Cl2 | 2.247 (1) | C20—C21 | 1.387 (8) |
N1—C7 | 1.334 (5) | C20—H20 | 0.95 |
N1—C1 | 1.395 (5) | C21—C22 | 1.365 (8) |
N2—C7 | 1.342 (5) | C21—H21 | 0.95 |
N2—C6 | 1.381 (6) | C22—C23 | 1.368 (8) |
N2—H2 | 0.876 (10) | C22—H22 | 0.95 |
N3—C12 | 1.332 (5) | C23—C24 | 1.375 (6) |
N3—C13 | 1.402 (5) | C23—H23 | 0.95 |
N3—Zn1ii | 2.024 (3) | C25—C26 | 1.511 (7) |
N4—C12 | 1.347 (5) | C26—C27' | 1.423 (9) |
N4—C18 | 1.378 (6) | C26—C27 | 1.460 (7) |
N4—H4 | 0.878 (10) | C26—C27" | 1.490 (10) |
N5—C25 | 1.310 (6) | C26—H26A | 0.99 |
N5—C19 | 1.383 (6) | C26—H26B | 0.99 |
N6—C25 | 1.341 (6) | C26—H26C | 0.99 |
N6—C24 | 1.370 (5) | C26—H26D | 0.99 |
N6—H6 | 0.875 (10) | C26—H26E | 0.99 |
N7—C30 | 1.345 (6) | C26—H26F | 0.99 |
N7—C31 | 1.379 (6) | C27—C28 | 1.4936 |
N7—H7 | 0.879 (10) | C27—H27A | 0.99 |
N8—C30 | 1.305 (6) | C27—H27B | 0.99 |
N8—C36 | 1.388 (6) | C28—C29 | 1.471 (7) |
C1—C2 | 1.390 (6) | C28—H28A | 0.99 |
C1—C6 | 1.392 (5) | C28—H28B | 0.99 |
C2—C3 | 1.391 (7) | C27'—C28' | 1.477 (9) |
C2—H2a | 0.95 | C27'—H27C | 0.99 |
C3—C4 | 1.381 (7) | C27'—H27D | 0.99 |
C3—H3 | 0.95 | C28'—C29 | 1.483 (9) |
C4—C5 | 1.375 (7) | C28'—H28C | 0.99 |
C4—H4A | 0.95 | C28'—H28D | 0.99 |
C5—C6 | 1.378 (6) | C27"—C28" | 1.471 (10) |
C5—H5 | 0.95 | C27"—H27E | 0.99 |
C7—C8 | 1.490 (6) | C27"—H27F | 0.99 |
C8—C9 | 1.508 (6) | C28"—C29 | 1.448 (10) |
C8—H8A | 0.99 | C28"—H28E | 0.99 |
C8—H8B | 0.99 | C28"—H28F | 0.99 |
C9—C10 | 1.488 (6) | C29—C30 | 1.512 (7) |
C9—H9A | 0.99 | C29—H29A | 0.99 |
C9—H9B | 0.99 | C29—H29B | 0.99 |
C10—C11 | 1.561 (6) | C29—H29C | 0.99 |
C10—H10A | 0.99 | C29—H29D | 0.99 |
C10—H10B | 0.99 | C29—H29E | 0.99 |
C11—C12 | 1.482 (6) | C29—H29F | 0.99 |
C11—H11A | 0.99 | C31—C32 | 1.380 (6) |
C11—H11B | 0.99 | C31—C36 | 1.402 (6) |
C13—C18 | 1.392 (6) | C32—C33 | 1.369 (7) |
C13—C14 | 1.394 (6) | C32—H32 | 0.95 |
C14—C15 | 1.378 (7) | C33—C34 | 1.384 (7) |
C14—H14 | 0.95 | C33—H33 | 0.95 |
C15—C16 | 1.379 (7) | C34—C35 | 1.384 (7) |
C15—H15 | 0.95 | C34—H34 | 0.95 |
C16—C17 | 1.376 (7) | C35—C36 | 1.386 (6) |
C16—H16 | 0.95 | C35—H35 | 0.95 |
C17—C18 | 1.379 (6) | | |
| | | |
N3i—Zn1—N1 | 99.03 (13) | C23—C22—H22 | 118.7 |
N3i—Zn1—Cl2 | 108.33 (10) | C22—C23—C24 | 115.9 (5) |
N1—Zn1—Cl2 | 113.83 (10) | C22—C23—H23 | 122.0 |
N3i—Zn1—Cl1 | 114.47 (11) | C24—C23—H23 | 122.0 |
N1—Zn1—Cl1 | 107.68 (11) | N6—C24—C23 | 131.9 (4) |
Cl2—Zn1—Cl1 | 112.84 (6) | N6—C24—C19 | 104.6 (4) |
C7—N1—C1 | 105.9 (3) | C23—C24—C19 | 123.5 (4) |
C7—N1—Zn1 | 122.9 (3) | N5—C25—N6 | 112.3 (4) |
C1—N1—Zn1 | 130.0 (3) | N5—C25—C26 | 124.2 (5) |
C7—N2—C6 | 108.2 (3) | N6—C25—C26 | 123.5 (5) |
C7—N2—H2 | 135 (3) | C27—C26—C25 | 119.8 (6) |
C6—N2—H2 | 117 (3) | C27"—C26—C25 | 109.8 (6) |
C12—N3—C13 | 105.6 (3) | C27—C26—H26A | 107.4 |
C12—N3—Zn1ii | 123.4 (3) | C25—C26—H26A | 107.4 |
C13—N3—Zn1ii | 129.1 (3) | C27—C26—H26B | 107.4 |
C12—N4—C18 | 108.2 (4) | C25—C26—H26B | 107.4 |
C12—N4—H4 | 125 (3) | H26A—C26—H26B | 106.9 |
C18—N4—H4 | 126 (3) | C27'—C26—H26C | 102.0 |
C25—N5—C19 | 105.3 (4) | C25—C26—H26C | 102.0 |
C25—N6—C24 | 108.2 (4) | C27'—C26—H26D | 102.0 |
C25—N6—H6 | 124 (3) | C25—C26—H26D | 102.0 |
C24—N6—H6 | 127 (3) | H26C—C26—H26D | 104.8 |
C30—N7—C31 | 107.7 (4) | C27'—C26—H26E | 102.9 |
C30—N7—H7 | 125 (3) | C27"—C26—H26E | 109.7 |
C31—N7—H7 | 127 (3) | C25—C26—H26E | 109.7 |
C30—N8—C36 | 105.7 (4) | C27"—C26—H26F | 109.7 |
C2—C1—C6 | 120.5 (4) | C25—C26—H26F | 109.7 |
C2—C1—N1 | 130.8 (4) | H26E—C26—H26F | 108.2 |
C6—C1—N1 | 108.7 (4) | C26—C27—C28 | 108.6 (4) |
C1—C2—C3 | 116.8 (4) | C26—C27—H27A | 110.0 |
C1—C2—H2a | 121.6 | C28—C27—H27A | 110.0 |
C3—C2—H2a | 121.6 | C26—C27—H27B | 110.0 |
C4—C3—C2 | 122.1 (5) | C28—C27—H27B | 110.0 |
C4—C3—H3 | 119.0 | H27A—C27—H27B | 108.4 |
C2—C3—H3 | 119.0 | C29—C28—C27 | 108.5 (4) |
C5—C4—C3 | 121.1 (5) | C29—C28—H28A | 110.0 |
C5—C4—H4A | 119.5 | C27—C28—H28A | 110.0 |
C3—C4—H4A | 119.5 | C29—C28—H28B | 110.0 |
C4—C5—C6 | 117.6 (4) | C27—C28—H28B | 110.0 |
C4—C5—H5 | 121.2 | H28A—C28—H28B | 108.4 |
C6—C5—H5 | 121.2 | C26—C27'—C28' | 110.6 (9) |
C5—C6—N2 | 132.3 (4) | C26—C27'—H27C | 109.5 |
C5—C6—C1 | 122.0 (4) | C28'—C27'—H27C | 109.5 |
N2—C6—C1 | 105.7 (4) | C26—C27'—H27D | 109.5 |
N1—C7—N2 | 111.5 (4) | C28'—C27'—H27D | 109.5 |
N1—C7—C8 | 125.6 (4) | H27C—C27'—H27D | 108.1 |
N2—C7—C8 | 122.8 (4) | C27'—C28'—C29 | 106.6 (9) |
C7—C8—C9 | 115.0 (4) | C27'—C28'—H28C | 110.4 |
C7—C8—H8A | 108.5 | C29—C28'—H28C | 110.4 |
C9—C8—H8A | 108.5 | C27'—C28'—H28D | 110.4 |
C7—C8—H8B | 108.5 | C29—C28'—H28D | 110.4 |
C9—C8—H8B | 108.5 | H28C—C28'—H28D | 108.6 |
H8A—C8—H8B | 107.5 | C28"—C27"—C26 | 106.4 (9) |
C10—C9—C8 | 112.6 (4) | C28"—C27"—H27E | 110.5 |
C10—C9—H9A | 109.1 | C26—C27"—H27E | 110.5 |
C8—C9—H9A | 109.1 | C28"—C27"—H27F | 110.5 |
C10—C9—H9B | 109.1 | C26—C27"—H27F | 110.5 |
C8—C9—H9B | 109.1 | H27E—C27"—H27F | 108.6 |
H9A—C9—H9B | 107.8 | C29—C28"—C27" | 109.0 (10) |
C9—C10—C11 | 115.3 (4) | C29—C28"—H28E | 109.9 |
C9—C10—H10A | 108.5 | C27"—C28"—H28E | 109.9 |
C11—C10—H10A | 108.5 | C29—C28"—H28F | 109.9 |
C9—C10—H10B | 108.5 | C27"—C28"—H28F | 109.9 |
C11—C10—H10B | 108.5 | H28E—C28"—H28F | 108.3 |
H10A—C10—H10B | 107.5 | C28—C29—C30 | 117.1 (5) |
C12—C11—C10 | 113.2 (4) | C28'—C29—C30 | 109.5 (6) |
C12—C11—H11A | 108.9 | C28—C29—H29A | 108.0 |
C10—C11—H11A | 108.9 | C30—C29—H29A | 108.0 |
C12—C11—H11B | 108.9 | C28—C29—H29B | 108.0 |
C10—C11—H11B | 108.9 | C30—C29—H29B | 108.0 |
H11A—C11—H11B | 107.8 | H29A—C29—H29B | 107.3 |
N3—C12—N4 | 111.7 (4) | C28"—C29—H29C | 102.8 |
N3—C12—C11 | 125.6 (4) | C28'—C29—H29C | 109.8 |
N4—C12—C11 | 122.7 (4) | C30—C29—H29C | 109.8 |
C18—C13—C14 | 120.1 (4) | C28'—C29—H29D | 109.8 |
C18—C13—N3 | 108.7 (4) | C30—C29—H29D | 109.8 |
C14—C13—N3 | 131.1 (4) | H29C—C29—H29D | 108.2 |
C15—C14—C13 | 116.8 (5) | C28"—C29—H29E | 101.9 |
C15—C14—H14 | 121.6 | C30—C29—H29E | 101.9 |
C13—C14—H14 | 121.6 | C28"—C29—H29F | 101.9 |
C14—C15—C16 | 122.8 (5) | C30—C29—H29F | 101.9 |
C14—C15—H15 | 118.6 | H29E—C29—H29F | 104.7 |
C16—C15—H15 | 118.6 | N8—C30—N7 | 112.8 (4) |
C17—C16—C15 | 120.5 (5) | N8—C30—C29 | 123.9 (5) |
C17—C16—H16 | 119.7 | N7—C30—C29 | 123.3 (5) |
C15—C16—H16 | 119.7 | N7—C31—C32 | 132.3 (4) |
C16—C17—C18 | 117.6 (5) | N7—C31—C36 | 104.8 (4) |
C16—C17—H17 | 121.2 | C32—C31—C36 | 122.9 (4) |
C18—C17—H17 | 121.2 | C33—C32—C31 | 116.3 (5) |
N4—C18—C17 | 132.1 (4) | C33—C32—H32 | 121.8 |
N4—C18—C13 | 105.8 (4) | C31—C32—H32 | 121.8 |
C17—C18—C13 | 122.1 (4) | C32—C33—C34 | 122.0 (5) |
N5—C19—C24 | 109.7 (4) | C32—C33—H33 | 119.0 |
N5—C19—C20 | 130.8 (5) | C34—C33—H33 | 119.0 |
C24—C19—C20 | 119.5 (4) | C33—C34—C35 | 121.7 (5) |
C21—C20—C19 | 116.1 (5) | C33—C34—H34 | 119.2 |
C21—C20—H20 | 121.9 | C35—C34—H34 | 119.2 |
C19—C20—H20 | 121.9 | C34—C35—C36 | 117.4 (5) |
C22—C21—C20 | 122.4 (5) | C34—C35—H35 | 121.3 |
C22—C21—H21 | 118.8 | C36—C35—H35 | 121.3 |
C20—C21—H21 | 118.8 | C35—C36—N8 | 131.4 (4) |
C21—C22—C23 | 122.6 (5) | C35—C36—C31 | 119.6 (4) |
C21—C22—H22 | 118.7 | N8—C36—C31 | 109.1 (4) |
| | | |
N3i—Zn1—N1—C7 | −54.6 (3) | C25—N5—C19—C20 | 180.0 (5) |
Cl2—Zn1—N1—C7 | −169.3 (3) | N5—C19—C20—C21 | −178.7 (5) |
Cl1—Zn1—N1—C7 | 64.8 (3) | C24—C19—C20—C21 | 0.2 (8) |
N3i—Zn1—N1—C1 | 110.9 (3) | C19—C20—C21—C22 | −1.4 (9) |
Cl2—Zn1—N1—C1 | −3.9 (4) | C20—C21—C22—C23 | 1.2 (10) |
Cl1—Zn1—N1—C1 | −129.7 (3) | C21—C22—C23—C24 | 0.2 (9) |
C7—N1—C1—C2 | 178.1 (4) | C25—N6—C24—C23 | 179.2 (6) |
Zn1—N1—C1—C2 | 10.8 (6) | C25—N6—C24—C19 | 1.0 (5) |
C7—N1—C1—C6 | −1.0 (4) | C22—C23—C24—N6 | −179.4 (6) |
Zn1—N1—C1—C6 | −168.3 (3) | C22—C23—C24—C19 | −1.5 (8) |
C6—C1—C2—C3 | 0.6 (6) | N5—C19—C24—N6 | −1.2 (5) |
N1—C1—C2—C3 | −178.4 (4) | C20—C19—C24—N6 | 179.7 (5) |
C1—C2—C3—C4 | −0.4 (7) | N5—C19—C24—C23 | −179.6 (5) |
C2—C3—C4—C5 | 0.0 (8) | C20—C19—C24—C23 | 1.3 (8) |
C3—C4—C5—C6 | 0.1 (7) | C19—N5—C25—N6 | −0.4 (6) |
C4—C5—C6—N2 | 178.1 (5) | C19—N5—C25—C26 | 178.0 (5) |
C4—C5—C6—C1 | 0.1 (7) | C24—N6—C25—N5 | −0.4 (6) |
C7—N2—C6—C5 | −177.7 (5) | C24—N6—C25—C26 | −178.8 (5) |
C7—N2—C6—C1 | 0.5 (5) | N5—C25—C26—C27' | −24.1 (18) |
C2—C1—C6—C5 | −0.5 (6) | N6—C25—C26—C27' | 154.1 (15) |
N1—C1—C6—C5 | 178.7 (4) | N5—C25—C26—C27 | 135.4 (7) |
C2—C1—C6—N2 | −178.9 (4) | N6—C25—C26—C27 | −46.4 (9) |
N1—C1—C6—N2 | 0.3 (4) | N5—C25—C26—C27" | 71.9 (14) |
C1—N1—C7—N2 | 1.4 (5) | N6—C25—C26—C27" | −109.8 (13) |
Zn1—N1—C7—N2 | 169.8 (3) | C25—C26—C27—C28 | 166.7 (4) |
C1—N1—C7—C8 | −177.5 (4) | C26—C27—C28—C29 | 84.5 (6) |
Zn1—N1—C7—C8 | −9.1 (6) | C25—C26—C27'—C28' | −169.7 (9) |
C6—N2—C7—N1 | −1.2 (5) | C26—C27'—C28'—C29 | −87.3 (14) |
C6—N2—C7—C8 | 177.7 (4) | C25—C26—C27"—C28" | −147.5 (10) |
N1—C7—C8—C9 | −142.7 (4) | C26—C27"—C28"—C29 | −88.2 (15) |
N2—C7—C8—C9 | 38.5 (6) | C27"—C28"—C29—C28 | 35.5 (15) |
C7—C8—C9—C10 | 61.9 (5) | C27"—C28"—C29—C30 | −169.5 (9) |
C8—C9—C10—C11 | −175.5 (4) | C27—C28—C29—C30 | 164.5 (4) |
C9—C10—C11—C12 | −73.1 (5) | C27'—C28'—C29—C28 | 100.9 (10) |
C13—N3—C12—N4 | 1.0 (4) | C27'—C28'—C29—C30 | −149.4 (8) |
Zn1ii—N3—C12—N4 | 166.7 (3) | C36—N8—C30—N7 | −0.2 (6) |
C13—N3—C12—C11 | 179.0 (4) | C36—N8—C30—C29 | 178.4 (5) |
Zn1ii—N3—C12—C11 | −15.2 (6) | C31—N7—C30—N8 | 0.2 (6) |
C18—N4—C12—N3 | −1.0 (5) | C31—N7—C30—C29 | −178.4 (5) |
C18—N4—C12—C11 | −179.2 (4) | C28"—C29—C30—N8 | −20 (2) |
C10—C11—C12—N3 | −101.0 (5) | C28—C29—C30—N8 | 132.5 (6) |
C10—C11—C12—N4 | 76.9 (5) | C28'—C29—C30—N8 | 76.2 (10) |
C12—N3—C13—C18 | −0.6 (4) | C28"—C29—C30—N7 | 158.9 (17) |
Zn1ii—N3—C13—C18 | −165.2 (3) | C28—C29—C30—N7 | −49.0 (8) |
C12—N3—C13—C14 | 177.4 (4) | C28'—C29—C30—N7 | −105.3 (9) |
Zn1ii—N3—C13—C14 | 12.8 (6) | C30—N7—C31—C32 | 179.6 (5) |
C18—C13—C14—C15 | 0.8 (6) | C30—N7—C31—C36 | −0.2 (5) |
N3—C13—C14—C15 | −177.0 (4) | N7—C31—C32—C33 | 179.1 (5) |
C13—C14—C15—C16 | −0.3 (7) | C36—C31—C32—C33 | −1.1 (8) |
C14—C15—C16—C17 | −0.4 (8) | C31—C32—C33—C34 | 1.0 (9) |
C15—C16—C17—C18 | 0.6 (7) | C32—C33—C34—C35 | −0.7 (9) |
C12—N4—C18—C17 | −176.8 (5) | C33—C34—C35—C36 | 0.5 (9) |
C12—N4—C18—C13 | 0.6 (5) | C34—C35—C36—N8 | −179.7 (5) |
C16—C17—C18—N4 | 176.9 (5) | C34—C35—C36—C31 | −0.7 (8) |
C16—C17—C18—C13 | −0.1 (7) | C30—N8—C36—C35 | 179.1 (5) |
C14—C13—C18—N4 | −178.3 (4) | C30—N8—C36—C31 | 0.1 (5) |
N3—C13—C18—N4 | 0.0 (4) | N7—C31—C36—C35 | −179.1 (5) |
C14—C13—C18—C17 | −0.6 (6) | C32—C31—C36—C35 | 1.0 (8) |
N3—C13—C18—C17 | 177.7 (4) | N7—C31—C36—N8 | 0.1 (5) |
C25—N5—C19—C24 | 1.0 (6) | C32—C31—C36—N8 | −179.8 (5) |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···N5 | 0.88 (1) | 1.92 (1) | 2.787 (5) | 169 (4) |
N4—H4···N8ii | 0.88 (1) | 1.90 (1) | 2.773 (5) | 175 (4) |
N6—H6···Cl1iii | 0.88 (1) | 2.37 (2) | 3.224 (4) | 167 (5) |
N7—H7···Cl2iv | 0.88 (1) | 2.35 (1) | 3.230 (4) | 178 (4) |
Symmetry codes: (ii) x−1, y, z; (iii) −x+1, y+1/2, −z+3/2; (iv) −x+2, y+1/2, −z+3/2. |
Experimental details
Crystal data |
Chemical formula | [ZnCl2(C18H18N4)]·C18H18N4 |
Mr | 717.00 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 173 |
a, b, c (Å) | 8.5321 (5), 24.119 (2), 16.880 (1) |
β (°) | 92.999 (1) |
V (Å3) | 3468.9 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.90 |
Crystal size (mm) | 0.45 × 0.30 × 0.20 |
|
Data collection |
Diffractometer | Bruker APEXII area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.687, 0.840 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17738, 7549, 3855 |
Rint | 0.052 |
(sin θ/λ)max (Å−1) | 0.640 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.062, 0.192, 1.02 |
No. of reflections | 7549 |
No. of parameters | 448 |
No. of restraints | 32 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 1.10, −0.70 |
Selected bond lengths (Å) topZn1—N1 | 2.033 (3) | Zn1—Cl1 | 2.248 (1) |
Zn1—N3i | 2.024 (3) | Zn1—Cl2 | 2.247 (1) |
Symmetry code: (i) x+1, y, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···N5 | 0.88 (1) | 1.92 (1) | 2.787 (5) | 169 (4) |
N4—H4···N8ii | 0.88 (1) | 1.90 (1) | 2.773 (5) | 175 (4) |
N6—H6···Cl1iii | 0.88 (1) | 2.37 (2) | 3.224 (4) | 167 (5) |
N7—H7···Cl2iv | 0.88 (1) | 2.35 (1) | 3.230 (4) | 178 (4) |
Symmetry codes: (ii) x−1, y, z; (iii) −x+1, y+1/2, −z+3/2; (iv) −x+2, y+1/2, −z+3/2. |