research communications
Open access
The molecular and crystal structure of a cadmium complex of naphthalene-1,5-disulfonate and o-phenylenediamine was studied and Hirshfeld surfaces and fingerprint plots were generated to investigate the various intermolecular interactions.
Keywords: crystal structure; cadmium complex; o-phenylenediamine; naphthalene-1,5-disulfonate; Hirshfeld surface analysis.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989023010125/dj2067sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2056989023010125/dj2067Isup2.hkl |
CCDC reference: 2257108
Key indicators
Structure: I- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.023
- wR factor = 0.061
- Data-to-parameter ratio = 12.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT420_ALERT_2_C D-H Bond Without Acceptor N1 --H1A . Please Check PLAT420_ALERT_2_C D-H Bond Without Acceptor N2 --H2B . Please Check PLAT420_ALERT_2_C D-H Bond Without Acceptor N4 --H4B . Please Check
Alert level G PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K) 293 Check PLAT200_ALERT_1_G Reported _diffrn_ambient_temperature ..... (K) 293 Check PLAT794_ALERT_5_G Tentative Bond Valency for Cd1 (II) . 1.87 Info PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 13 Note PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ........... 4.9 Low PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 9 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 3 ALERT level C = Check. Ensure it is not caused by an omission or oversight 6 ALERT level G = General information/check it is not something unexpected 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 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 1 ALERT type 5 Informative message, check
Computing details top
Bis(benzene-1,2-diamine-κ2N,N')bis(benzene-1,2-diamine-κN)cadmium(II) naphthalene-1,5-disulfonate top
Crystal data top
[Cd(C6H8N2)4](C10H6O6S2) | F(000) = 1704 |
Mr = 831.24 | Dx = 1.582 Mg m−3 |
Monoclinic, C2/c | Cu Kα radiation, λ = 1.54184 Å |
a = 23.5743 (2) Å | Cell parameters from 13387 reflections |
b = 7.7286 (1) Å | θ = 3.9–71.3° |
c = 19.7260 (2) Å | µ = 6.62 mm−1 |
β = 103.858 (1)° | T = 293 K |
V = 3489.39 (7) Å3 | Block, colourless |
Z = 4 | 0.3 × 0.26 × 0.2 mm |
Data collection top
XtaLAB Synergy, Single source at home/near, HyPix3000 diffractometer | 3390 independent reflections |
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source | 3298 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.030 |
Detector resolution: 10.0000 pixels mm-1 | θmax = 71.4°, θmin = 3.9° |
ω scans | h = −23→28 |
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2023) | k = −9→9 |
Tmin = 0.698, Tmax = 1.000 | l = −24→24 |
16542 measured reflections |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.023 | w = 1/[σ2(Fo2) + (0.0374P)2 + 1.6331P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.061 | (Δ/σ)max = 0.001 |
S = 1.04 | Δρmax = 0.29 e Å−3 |
3390 reflections | Δρmin = −0.51 e Å−3 |
264 parameters | Extinction correction: SHELXL2018/3 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.00060 (3) |
Primary atom site location: dual |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Cd1 | 0.500000 | 0.30368 (2) | 0.750000 | 0.03390 (8) | |
S1 | 0.57283 (2) | 0.75940 (6) | 0.64093 (2) | 0.03278 (11) | |
O3 | 0.63434 (6) | 0.7592 (2) | 0.67223 (8) | 0.0538 (4) | |
O2 | 0.53752 (7) | 0.82032 (19) | 0.68767 (7) | 0.0461 (4) | |
O1 | 0.55070 (7) | 0.59515 (18) | 0.60921 (8) | 0.0471 (3) | |
N3 | 0.55688 (7) | 0.5428 (2) | 0.81048 (8) | 0.0324 (3) | |
N1 | 0.56647 (7) | 0.2566 (2) | 0.68088 (9) | 0.0359 (3) | |
N2 | 0.57034 (7) | 0.0874 (2) | 0.80405 (10) | 0.0412 (4) | |
C17 | 0.50295 (7) | 0.9405 (2) | 0.52814 (8) | 0.0264 (3) | |
C7 | 0.61049 (7) | 0.5314 (2) | 0.86432 (8) | 0.0320 (4) | |
N4 | 0.55812 (9) | 0.3778 (3) | 0.93793 (11) | 0.0553 (5) | |
C15 | 0.60837 (7) | 0.9911 (2) | 0.55757 (9) | 0.0334 (4) | |
H15 | 0.645358 | 0.968869 | 0.585633 | 0.040* | |
C16 | 0.56084 (7) | 0.9092 (2) | 0.57062 (8) | 0.0277 (3) | |
C13 | 0.54760 (8) | 1.1410 (3) | 0.46009 (9) | 0.0341 (4) | |
H13 | 0.543889 | 1.218105 | 0.423086 | 0.041* | |
C14 | 0.60174 (8) | 1.1089 (3) | 0.50191 (10) | 0.0382 (4) | |
H14 | 0.634285 | 1.165022 | 0.493536 | 0.046* | |
C12 | 0.60984 (8) | 0.4504 (3) | 0.92721 (9) | 0.0391 (4) | |
C6 | 0.62457 (8) | 0.1375 (2) | 0.78897 (10) | 0.0361 (4) | |
C1 | 0.62273 (8) | 0.2241 (2) | 0.72671 (10) | 0.0348 (4) | |
C2 | 0.67355 (10) | 0.2866 (3) | 0.71257 (13) | 0.0493 (5) | |
H2 | 0.672048 | 0.345609 | 0.671084 | 0.059* | |
C8 | 0.66153 (9) | 0.5986 (3) | 0.85278 (11) | 0.0468 (5) | |
H8 | 0.661275 | 0.653233 | 0.810709 | 0.056* | |
C5 | 0.67805 (9) | 0.1121 (3) | 0.83592 (12) | 0.0506 (5) | |
H5 | 0.679763 | 0.052972 | 0.877417 | 0.061* | |
C11 | 0.66247 (10) | 0.4376 (3) | 0.97790 (12) | 0.0572 (6) | |
H11 | 0.663070 | 0.383961 | 1.020270 | 0.069* | |
C3 | 0.72678 (10) | 0.2621 (4) | 0.75990 (16) | 0.0609 (6) | |
H3 | 0.760948 | 0.304468 | 0.750326 | 0.073* | |
C4 | 0.72872 (10) | 0.1742 (3) | 0.82129 (15) | 0.0619 (7) | |
H4 | 0.764382 | 0.156738 | 0.853024 | 0.074* | |
C9 | 0.71343 (10) | 0.5848 (4) | 0.90398 (14) | 0.0677 (7) | |
H9 | 0.747926 | 0.630189 | 0.896406 | 0.081* | |
C10 | 0.71319 (11) | 0.5032 (4) | 0.96591 (14) | 0.0718 (8) | |
H10 | 0.747871 | 0.492453 | 1.000044 | 0.086* | |
H3A | 0.5610 (10) | 0.613 (4) | 0.7782 (13) | 0.049 (7)* | |
H2A | 0.5562 (12) | 0.003 (4) | 0.7824 (14) | 0.063 (8)* | |
H1A | 0.5530 (11) | 0.162 (4) | 0.6578 (13) | 0.051 (7)* | |
H1B | 0.5681 (12) | 0.337 (4) | 0.6538 (15) | 0.064 (9)* | |
H3B | 0.5317 (11) | 0.593 (3) | 0.8244 (13) | 0.054 (7)* | |
H4A | 0.5264 (13) | 0.448 (4) | 0.9240 (14) | 0.064 (8)* | |
H2B | 0.5746 (12) | 0.072 (4) | 0.8486 (16) | 0.071 (9)* | |
H4B | 0.5614 (16) | 0.361 (5) | 0.980 (2) | 0.102 (13)* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Cd1 | 0.02348 (11) | 0.03120 (12) | 0.04631 (12) | 0.000 | 0.00697 (7) | 0.000 |
S1 | 0.0289 (2) | 0.0389 (2) | 0.0286 (2) | 0.00213 (17) | 0.00313 (16) | 0.00811 (16) |
O3 | 0.0305 (7) | 0.0741 (10) | 0.0503 (9) | 0.0027 (7) | −0.0035 (6) | 0.0233 (8) |
O2 | 0.0478 (8) | 0.0612 (10) | 0.0323 (7) | 0.0017 (6) | 0.0153 (6) | 0.0050 (6) |
O1 | 0.0549 (9) | 0.0323 (7) | 0.0501 (8) | 0.0017 (6) | 0.0044 (6) | 0.0089 (6) |
N3 | 0.0312 (8) | 0.0332 (8) | 0.0283 (7) | 0.0007 (6) | −0.0019 (6) | 0.0012 (6) |
N1 | 0.0329 (8) | 0.0379 (9) | 0.0361 (8) | 0.0067 (7) | 0.0064 (6) | −0.0009 (7) |
N2 | 0.0349 (8) | 0.0400 (10) | 0.0458 (10) | 0.0000 (7) | 0.0041 (7) | 0.0097 (8) |
C17 | 0.0245 (8) | 0.0272 (8) | 0.0277 (7) | 0.0021 (6) | 0.0070 (6) | 0.0004 (6) |
C7 | 0.0308 (9) | 0.0319 (9) | 0.0299 (8) | 0.0015 (7) | 0.0003 (6) | −0.0013 (7) |
N4 | 0.0487 (11) | 0.0661 (13) | 0.0476 (11) | −0.0084 (10) | 0.0048 (8) | 0.0217 (10) |
C15 | 0.0237 (8) | 0.0391 (10) | 0.0359 (9) | 0.0002 (7) | 0.0039 (6) | 0.0026 (7) |
C16 | 0.0265 (8) | 0.0303 (8) | 0.0259 (7) | 0.0031 (6) | 0.0059 (6) | 0.0006 (6) |
C13 | 0.0298 (8) | 0.0371 (9) | 0.0359 (9) | −0.0002 (7) | 0.0091 (7) | 0.0108 (7) |
C14 | 0.0251 (8) | 0.0428 (11) | 0.0475 (10) | −0.0044 (7) | 0.0103 (7) | 0.0090 (8) |
C12 | 0.0384 (10) | 0.0393 (10) | 0.0351 (9) | 0.0002 (8) | 0.0001 (7) | 0.0038 (8) |
C6 | 0.0292 (9) | 0.0315 (9) | 0.0449 (10) | 0.0043 (7) | 0.0035 (7) | 0.0007 (8) |
C1 | 0.0274 (9) | 0.0344 (9) | 0.0421 (10) | 0.0066 (7) | 0.0072 (7) | −0.0038 (7) |
C2 | 0.0404 (11) | 0.0536 (13) | 0.0580 (13) | 0.0055 (9) | 0.0196 (10) | 0.0023 (10) |
C8 | 0.0370 (10) | 0.0579 (13) | 0.0454 (11) | −0.0042 (9) | 0.0096 (8) | 0.0041 (9) |
C5 | 0.0380 (11) | 0.0556 (14) | 0.0517 (12) | 0.0084 (9) | −0.0022 (9) | 0.0069 (10) |
C11 | 0.0511 (13) | 0.0697 (15) | 0.0404 (11) | 0.0033 (11) | −0.0091 (9) | 0.0125 (10) |
C3 | 0.0315 (11) | 0.0721 (16) | 0.0802 (18) | −0.0003 (11) | 0.0158 (11) | −0.0033 (14) |
C4 | 0.0299 (11) | 0.0720 (17) | 0.0753 (17) | 0.0078 (10) | −0.0039 (10) | −0.0017 (13) |
C9 | 0.0311 (11) | 0.093 (2) | 0.0735 (16) | −0.0103 (12) | 0.0026 (10) | 0.0021 (15) |
C10 | 0.0386 (12) | 0.098 (2) | 0.0636 (16) | 0.0009 (13) | −0.0183 (11) | 0.0066 (14) |
Geometric parameters (Å, º) top
Cd1—N3i | 2.4230 (15) | N4—H4B | 0.82 (4) |
Cd1—N3 | 2.4230 (15) | C15—H15 | 0.9300 |
Cd1—N1i | 2.3388 (16) | C15—C16 | 1.364 (2) |
Cd1—N1 | 2.3388 (16) | C15—C14 | 1.406 (3) |
Cd1—N2 | 2.4153 (17) | C13—H13 | 0.9300 |
Cd1—N2i | 2.4153 (17) | C13—C14 | 1.366 (2) |
S1—O3 | 1.4335 (15) | C14—H14 | 0.9300 |
S1—O2 | 1.4601 (15) | C12—C11 | 1.398 (3) |
S1—O1 | 1.4556 (15) | C6—C1 | 1.390 (3) |
S1—C16 | 1.7765 (16) | C6—C5 | 1.388 (3) |
N3—C7 | 1.446 (2) | C1—C2 | 1.381 (3) |
N3—H3A | 0.86 (3) | C2—H2 | 0.9300 |
N3—H3B | 0.81 (3) | C2—C3 | 1.386 (3) |
N1—C1 | 1.437 (2) | C8—H8 | 0.9300 |
N1—H1A | 0.88 (3) | C8—C9 | 1.392 (3) |
N1—H1B | 0.83 (3) | C5—H5 | 0.9300 |
N2—C6 | 1.434 (2) | C5—C4 | 1.380 (4) |
N2—H2A | 0.81 (3) | C11—H11 | 0.9300 |
N2—H2B | 0.87 (3) | C11—C10 | 1.370 (4) |
C17—C17ii | 1.423 (3) | C3—H3 | 0.9300 |
C17—C16 | 1.440 (2) | C3—C4 | 1.380 (4) |
C17—C13ii | 1.415 (2) | C4—H4 | 0.9300 |
C7—C12 | 1.393 (3) | C9—H9 | 0.9300 |
C7—C8 | 1.379 (3) | C9—C10 | 1.376 (4) |
N4—C12 | 1.403 (3) | C10—H10 | 0.9300 |
N4—H4A | 0.91 (3) | ||
N3i—Cd1—N3 | 80.58 (7) | H4A—N4—H4B | 106 (3) |
N1i—Cd1—N3 | 101.57 (6) | C16—C15—H15 | 119.8 |
N1i—Cd1—N3i | 92.10 (6) | C16—C15—C14 | 120.34 (15) |
N1—Cd1—N3i | 101.57 (6) | C14—C15—H15 | 119.8 |
N1—Cd1—N3 | 92.10 (6) | C17—C16—S1 | 121.00 (12) |
N1i—Cd1—N1 | 162.11 (10) | C15—C16—S1 | 117.74 (12) |
N1—Cd1—N2 | 70.41 (6) | C15—C16—C17 | 121.26 (15) |
N1—Cd1—N2i | 96.90 (6) | C17ii—C13—H13 | 119.3 |
N1i—Cd1—N2 | 96.89 (6) | C14—C13—C17ii | 121.44 (16) |
N1i—Cd1—N2i | 70.41 (6) | C14—C13—H13 | 119.3 |
N2—Cd1—N3 | 94.02 (6) | C15—C14—H14 | 119.9 |
N2—Cd1—N3i | 170.30 (6) | C13—C14—C15 | 120.15 (16) |
N2i—Cd1—N3i | 94.02 (6) | C13—C14—H14 | 119.9 |
N2i—Cd1—N3 | 170.30 (6) | C7—C12—N4 | 120.60 (17) |
N2—Cd1—N2i | 92.41 (9) | C7—C12—C11 | 118.13 (19) |
O3—S1—O2 | 113.53 (10) | C11—C12—N4 | 121.22 (19) |
O3—S1—O1 | 113.92 (10) | C1—C6—N2 | 118.20 (16) |
O3—S1—C16 | 107.01 (9) | C5—C6—N2 | 122.42 (19) |
O2—S1—C16 | 105.95 (8) | C5—C6—C1 | 119.26 (18) |
O1—S1—O2 | 110.66 (9) | C6—C1—N1 | 117.96 (17) |
O1—S1—C16 | 105.00 (8) | C2—C1—N1 | 121.76 (19) |
Cd1—N3—H3A | 105.4 (16) | C2—C1—C6 | 120.12 (19) |
Cd1—N3—H3B | 99.6 (19) | C1—C2—H2 | 119.8 |
C7—N3—Cd1 | 126.76 (11) | C1—C2—C3 | 120.4 (2) |
C7—N3—H3A | 110.4 (16) | C3—C2—H2 | 119.8 |
C7—N3—H3B | 111.3 (18) | C7—C8—H8 | 119.9 |
H3A—N3—H3B | 100 (2) | C7—C8—C9 | 120.1 (2) |
Cd1—N1—H1A | 102.8 (16) | C9—C8—H8 | 119.9 |
Cd1—N1—H1B | 114 (2) | C6—C5—H5 | 119.8 |
C1—N1—Cd1 | 107.87 (12) | C4—C5—C6 | 120.3 (2) |
C1—N1—H1A | 110.1 (17) | C4—C5—H5 | 119.8 |
C1—N1—H1B | 111 (2) | C12—C11—H11 | 119.6 |
H1A—N1—H1B | 111 (3) | C10—C11—C12 | 120.8 (2) |
Cd1—N2—H2A | 100 (2) | C10—C11—H11 | 119.6 |
Cd1—N2—H2B | 116.2 (19) | C2—C3—H3 | 120.2 |
C6—N2—Cd1 | 105.88 (12) | C4—C3—C2 | 119.5 (2) |
C6—N2—H2A | 113 (2) | C4—C3—H3 | 120.2 |
C6—N2—H2B | 110.7 (19) | C5—C4—H4 | 119.8 |
H2A—N2—H2B | 111 (3) | C3—C4—C5 | 120.4 (2) |
C17ii—C17—C16 | 117.68 (18) | C3—C4—H4 | 119.8 |
C13ii—C17—C17ii | 119.12 (18) | C8—C9—H9 | 120.3 |
C13ii—C17—C16 | 123.20 (15) | C10—C9—C8 | 119.3 (2) |
C12—C7—N3 | 119.18 (16) | C10—C9—H9 | 120.3 |
C8—C7—N3 | 119.98 (17) | C11—C10—C9 | 120.8 (2) |
C8—C7—C12 | 120.84 (17) | C11—C10—H10 | 119.6 |
C12—N4—H4A | 113.3 (18) | C9—C10—H10 | 119.6 |
C12—N4—H4B | 110 (3) | ||
Cd1—N3—C7—C12 | −62.9 (2) | C17ii—C13—C14—C15 | 0.8 (3) |
Cd1—N3—C7—C8 | 116.43 (18) | C7—C12—C11—C10 | 0.0 (4) |
Cd1—N1—C1—C6 | 33.6 (2) | C7—C8—C9—C10 | 0.2 (4) |
Cd1—N1—C1—C2 | −141.87 (17) | N4—C12—C11—C10 | 177.5 (3) |
Cd1—N2—C6—C1 | −31.2 (2) | C16—C15—C14—C13 | −0.6 (3) |
Cd1—N2—C6—C5 | 144.82 (18) | C13ii—C17—C16—S1 | 1.4 (2) |
O3—S1—C16—C17 | −179.81 (14) | C13ii—C17—C16—C15 | −179.75 (17) |
O3—S1—C16—C15 | 1.27 (17) | C14—C15—C16—S1 | 178.96 (14) |
O2—S1—C16—C17 | −58.37 (15) | C14—C15—C16—C17 | 0.0 (3) |
O2—S1—C16—C15 | 122.71 (15) | C12—C7—C8—C9 | 0.6 (3) |
O1—S1—C16—C17 | 58.79 (15) | C12—C11—C10—C9 | 0.7 (5) |
O1—S1—C16—C15 | −120.12 (15) | C6—C1—C2—C3 | 0.7 (3) |
N3—C7—C12—N4 | 1.2 (3) | C6—C5—C4—C3 | 0.0 (4) |
N3—C7—C12—C11 | 178.65 (19) | C1—C6—C5—C4 | 0.9 (3) |
N3—C7—C8—C9 | −178.7 (2) | C1—C2—C3—C4 | 0.1 (4) |
N1—C1—C2—C3 | 176.0 (2) | C2—C3—C4—C5 | −0.5 (4) |
N2—C6—C1—N1 | −0.6 (3) | C8—C7—C12—N4 | −178.1 (2) |
N2—C6—C1—C2 | 174.92 (19) | C8—C7—C12—C11 | −0.7 (3) |
N2—C6—C5—C4 | −175.1 (2) | C8—C9—C10—C11 | −0.8 (5) |
C17ii—C17—C16—S1 | −178.68 (15) | C5—C6—C1—N1 | −176.70 (19) |
C17ii—C17—C16—C15 | 0.2 (3) | C5—C6—C1—C2 | −1.2 (3) |
Symmetry codes: (i) −x+1, y, −z+3/2; (ii) −x+1, −y+2, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O2 | 0.86 (3) | 2.36 (3) | 3.185 (2) | 160 (2) |
N2—H2A···O2iii | 0.81 (3) | 2.30 (3) | 3.046 (3) | 154 (3) |
N1—H1B···O1 | 0.83 (3) | 2.18 (3) | 2.955 (2) | 156 (3) |
N3—H3B···O2i | 0.81 (3) | 2.37 (3) | 3.097 (2) | 150 (2) |
N4—H4A···O1i | 0.91 (3) | 2.11 (3) | 3.021 (3) | 176 (3) |
Symmetry codes: (i) −x+1, y, −z+3/2; (iii) x, y−1, z. |