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Diffraction results obtained at 100 and 291 K, the former at high resolution, are reported for the title compound, [Cu(C10H9N4O2S)2(NH3)2] or [Cu(sulfa)2(NH3)2] [Hsulfa is 4-amino-N-(pyrimidin-2-yl)benzenesulfonamide]. The CuII cation is coordinated by two N-atom donors from a bidentate sulfa ligand, by two ammonia molecules in the equatorial plane and by a monohapto (η1) sulfadiazine at the apex of a distorted square pyramid. The present interpretation and two earlier reports [Brown, Cook & Sengier (1987). Acta Cryst. C43, 2332–2334; Tommasino, Renaud, Luneau & Pilet (2011). Polyhedron, 30, 1663–1670] disagree about the nature and geometry of the ligands. The relationship between the present result and the former is discussed, and evidence is provided that the latter erroneously assigned an ammine as an aqua ligand.
Supporting information
CCDC references: 962283; 962284
For both compounds, data collection: SMART (Bruker, 2003); cell refinement: SMART (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2012 (Sheldrick, 2008).
(I_100K) Bis[4-amino-
N-(pyrimidin-2-yl)benzenesulfonamido]diamminecopper(II)
top
Crystal data top
[Cu(C10H9N4O2S)2(NH3)2] | F(000) = 1228 |
Mr = 596.15 | Dx = 1.643 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 9589 reflections |
a = 13.662 (1) Å | θ = 2.2–46.3° |
b = 12.6329 (10) Å | µ = 1.13 mm−1 |
c = 13.9651 (11) Å | T = 100 K |
V = 2410.2 (3) Å3 | Prism, green |
Z = 4 | 0.20 × 0.20 × 0.18 mm |
Data collection top
Bruker D8 difrractometer with APEX CCD area-detector diffractometer | 28306 independent reflections |
Radiation source: Incoatec microsource | 21743 reflections with I > 2σ(I) |
Multilayer optics monochromator | Rint = 0.073 |
ω scans | θmax = 54.7°, θmin = 2.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −30→31 |
Tmin = 0.805, Tmax = 0.822 | k = −28→24 |
120975 measured reflections | l = −32→26 |
Refinement top
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)] = 0.046 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.101 | w = 1/[σ2(Fo2) + (0.0269P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max = 0.001 |
28306 reflections | Δρmax = 0.69 e Å−3 |
374 parameters | Δρmin = −0.86 e Å−3 |
1 restraint | Absolute structure: Flack (1983), with 12765 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.007 (4) |
Special details top
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 (Å2) top | x | y | z | Uiso*/Ueq | |
Cu1 | 0.741201 (8) | 0.557896 (10) | 0.073138 (12) | 0.01261 (2) | |
S1 | 0.901026 (18) | 0.84377 (2) | 0.14662 (2) | 0.01469 (4) | |
S2 | 0.799364 (16) | 0.42730 (2) | 0.27749 (2) | 0.01185 (3) | |
O1 | 0.97693 (7) | 0.82183 (8) | 0.21739 (8) | 0.01878 (14) | |
O2 | 0.80848 (6) | 0.87903 (8) | 0.18816 (9) | 0.02217 (18) | |
O3 | 0.76641 (6) | 0.33030 (7) | 0.32199 (7) | 0.01626 (13) | |
O4 | 0.77162 (6) | 0.52554 (7) | 0.32347 (7) | 0.01645 (13) | |
N1 | 0.90299 (6) | 0.57648 (7) | 0.03814 (8) | 0.01372 (12) | |
N2 | 1.03858 (6) | 0.69572 (8) | 0.04945 (8) | 0.01558 (14) | |
N3 | 0.87444 (6) | 0.74761 (7) | 0.08076 (9) | 0.01599 (14) | |
N4 | 1.01570 (8) | 1.22284 (10) | −0.07789 (10) | 0.02146 (19) | |
H4A | 1.0573 (18) | 1.2607 (19) | −0.0516 (19) | 0.030 (6)* | |
H4B | 1.0222 (18) | 1.211 (2) | −0.136 (2) | 0.033 (7)* | |
N5 | 0.74515 (6) | 0.40431 (7) | 0.01501 (7) | 0.01325 (12) | |
N6 | 0.78328 (7) | 0.25797 (7) | 0.11756 (8) | 0.01474 (13) | |
N7 | 0.76006 (6) | 0.43850 (7) | 0.16942 (7) | 0.01325 (12) | |
N8 | 1.23325 (6) | 0.41895 (8) | 0.25963 (8) | 0.01615 (14) | |
H8A | 1.2553 (16) | 0.475 (2) | 0.2401 (19) | 0.027 (6)* | |
H8B | 1.2565 (16) | 0.362 (2) | 0.2382 (19) | 0.029 (7)* | |
N9 | 0.69446 (9) | 0.64133 (10) | −0.03758 (9) | 0.01935 (17) | |
H9A | 0.638 (2) | 0.654 (2) | −0.031 (2) | 0.058 (10)* | |
H9B | 0.6984 (18) | 0.615 (2) | −0.093 (2) | 0.031 (7)* | |
H9C | 0.724 (2) | 0.704 (3) | −0.041 (2) | 0.053 (9)* | |
N10 | 0.68953 (7) | 0.66133 (8) | 0.16855 (8) | 0.01536 (14) | |
H10A | 0.6241 (18) | 0.6806 (18) | 0.1666 (19) | 0.031 (7)* | |
H10B | 0.7264 (16) | 0.7200 (19) | 0.1636 (17) | 0.022 (6)* | |
H10C | 0.6993 (17) | 0.6350 (19) | 0.2243 (18) | 0.025 (6)* | |
C1 | 0.94222 (7) | 0.67304 (8) | 0.05590 (8) | 0.01308 (14) | |
C2 | 0.96446 (7) | 0.49919 (9) | 0.01275 (9) | 0.01614 (16) | |
H2 | 0.9385 | 0.4313 | −0.0019 | 0.019* | |
C3 | 1.06475 (8) | 0.51432 (9) | 0.00700 (10) | 0.01692 (17) | |
H3 | 1.1082 | 0.4585 | −0.0094 | 0.020* | |
C4 | 1.09803 (7) | 0.61576 (9) | 0.02657 (9) | 0.01647 (16) | |
H4 | 1.1664 | 0.6290 | 0.0235 | 0.020* | |
C5 | 0.94407 (6) | 0.94991 (8) | 0.07638 (11) | 0.01534 (14) | |
C6 | 0.92687 (8) | 0.95415 (9) | −0.02154 (10) | 0.01755 (17) | |
H6 | 0.8966 | 0.8961 | −0.0530 | 0.021* | |
C7 | 0.95400 (8) | 1.04324 (10) | −0.07352 (10) | 0.01786 (17) | |
H7 | 0.9436 | 1.0450 | −0.1408 | 0.021* | |
C8 | 0.99671 (7) | 1.13088 (9) | −0.02758 (10) | 0.01639 (16) | |
C9 | 1.01518 (7) | 1.12503 (9) | 0.07094 (11) | 0.01751 (15) | |
H9 | 1.0456 | 1.1829 | 0.1026 | 0.021* | |
C10 | 0.98940 (8) | 1.03553 (9) | 0.12266 (9) | 0.01692 (16) | |
H10 | 1.0024 | 1.0322 | 0.1894 | 0.020* | |
C11 | 0.76427 (6) | 0.36031 (8) | 0.10190 (8) | 0.01237 (13) | |
C12 | 0.74385 (8) | 0.34130 (10) | −0.06131 (9) | 0.01617 (15) | |
H12 | 0.7309 | 0.3702 | −0.1228 | 0.019* | |
C13 | 0.76132 (9) | 0.23324 (10) | −0.05170 (10) | 0.01854 (18) | |
H13 | 0.7601 | 0.1870 | −0.1054 | 0.022* | |
C14 | 0.78058 (8) | 0.19629 (9) | 0.03955 (10) | 0.01729 (17) | |
H14 | 0.7926 | 0.1227 | 0.0474 | 0.021* | |
C15 | 0.92722 (6) | 0.42428 (8) | 0.27180 (8) | 0.01280 (13) | |
C16 | 0.97930 (7) | 0.51905 (8) | 0.26304 (8) | 0.01402 (14) | |
H16 | 0.9452 | 0.5845 | 0.2601 | 0.017* | |
C17 | 1.08049 (7) | 0.51761 (8) | 0.25871 (9) | 0.01445 (14) | |
H17 | 1.1156 | 0.5822 | 0.2532 | 0.017* | |
C18 | 1.13163 (7) | 0.42084 (8) | 0.26238 (8) | 0.01351 (14) | |
C19 | 1.07845 (7) | 0.32624 (8) | 0.27179 (10) | 0.01591 (16) | |
H19 | 1.1122 | 0.2606 | 0.2751 | 0.019* | |
C20 | 0.97683 (7) | 0.32800 (8) | 0.27632 (10) | 0.01518 (15) | |
H20 | 0.9413 | 0.2637 | 0.2825 | 0.018* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.01399 (3) | 0.01147 (4) | 0.01236 (4) | 0.00202 (3) | −0.00025 (4) | −0.00013 (4) |
S1 | 0.01316 (7) | 0.01306 (9) | 0.01786 (11) | 0.00013 (6) | 0.00156 (8) | −0.00218 (8) |
S2 | 0.01272 (7) | 0.01202 (8) | 0.01082 (8) | 0.00059 (6) | −0.00021 (7) | −0.00088 (7) |
O1 | 0.0194 (3) | 0.0194 (4) | 0.0175 (4) | −0.0004 (2) | −0.0019 (3) | −0.0001 (3) |
O2 | 0.0168 (3) | 0.0181 (4) | 0.0316 (5) | 0.0010 (2) | 0.0085 (3) | −0.0056 (3) |
O3 | 0.0168 (3) | 0.0164 (3) | 0.0156 (3) | −0.0021 (2) | 0.0001 (2) | 0.0034 (3) |
O4 | 0.0178 (3) | 0.0166 (3) | 0.0150 (3) | 0.0039 (2) | −0.0001 (2) | −0.0047 (3) |
N1 | 0.0132 (2) | 0.0118 (3) | 0.0161 (4) | −0.0010 (2) | 0.0005 (2) | −0.0017 (3) |
N2 | 0.0124 (2) | 0.0142 (3) | 0.0202 (4) | −0.0014 (2) | 0.0016 (2) | −0.0011 (3) |
N3 | 0.0134 (2) | 0.0125 (3) | 0.0221 (4) | 0.00013 (19) | 0.0003 (3) | −0.0034 (3) |
N4 | 0.0231 (4) | 0.0197 (4) | 0.0216 (5) | −0.0045 (3) | −0.0005 (4) | 0.0019 (4) |
N5 | 0.0150 (3) | 0.0123 (3) | 0.0125 (3) | −0.0007 (2) | −0.0008 (2) | −0.0011 (2) |
N6 | 0.0177 (3) | 0.0109 (3) | 0.0156 (4) | 0.0018 (2) | 0.0002 (3) | −0.0010 (3) |
N7 | 0.0159 (3) | 0.0118 (3) | 0.0121 (3) | 0.0013 (2) | −0.0016 (2) | −0.0013 (2) |
N8 | 0.0139 (3) | 0.0161 (3) | 0.0185 (4) | −0.0007 (2) | 0.0005 (3) | −0.0008 (3) |
N9 | 0.0227 (4) | 0.0186 (4) | 0.0168 (4) | 0.0060 (3) | 0.0020 (3) | 0.0025 (3) |
N10 | 0.0156 (3) | 0.0139 (3) | 0.0165 (4) | 0.0016 (2) | 0.0006 (3) | −0.0012 (3) |
C1 | 0.0125 (2) | 0.0123 (3) | 0.0144 (4) | −0.0011 (2) | 0.0005 (2) | −0.0005 (3) |
C2 | 0.0154 (3) | 0.0141 (4) | 0.0189 (4) | −0.0006 (2) | 0.0026 (3) | −0.0035 (3) |
C3 | 0.0153 (3) | 0.0160 (4) | 0.0194 (5) | 0.0001 (3) | 0.0032 (3) | −0.0028 (3) |
C4 | 0.0135 (3) | 0.0172 (4) | 0.0187 (5) | −0.0007 (3) | 0.0026 (3) | −0.0005 (3) |
C5 | 0.0150 (3) | 0.0131 (3) | 0.0179 (4) | 0.0000 (2) | −0.0003 (4) | −0.0027 (3) |
C6 | 0.0192 (3) | 0.0156 (4) | 0.0179 (5) | −0.0019 (3) | −0.0020 (3) | −0.0033 (3) |
C7 | 0.0195 (4) | 0.0180 (4) | 0.0161 (4) | −0.0018 (3) | −0.0015 (3) | −0.0007 (3) |
C8 | 0.0148 (3) | 0.0160 (4) | 0.0183 (5) | −0.0009 (3) | −0.0002 (3) | −0.0005 (3) |
C9 | 0.0187 (3) | 0.0151 (3) | 0.0188 (4) | −0.0026 (2) | −0.0019 (4) | −0.0019 (4) |
C10 | 0.0185 (3) | 0.0155 (4) | 0.0168 (4) | −0.0017 (3) | −0.0018 (3) | −0.0016 (3) |
C11 | 0.0128 (3) | 0.0114 (3) | 0.0130 (4) | −0.0002 (2) | 0.0000 (2) | −0.0013 (3) |
C12 | 0.0184 (3) | 0.0174 (4) | 0.0128 (4) | −0.0019 (3) | −0.0008 (3) | −0.0027 (3) |
C13 | 0.0231 (4) | 0.0161 (4) | 0.0164 (5) | −0.0007 (3) | 0.0003 (3) | −0.0062 (3) |
C14 | 0.0187 (3) | 0.0130 (4) | 0.0202 (5) | 0.0006 (3) | 0.0012 (3) | −0.0032 (3) |
C15 | 0.0134 (2) | 0.0114 (3) | 0.0136 (4) | 0.0003 (2) | −0.0008 (3) | −0.0006 (3) |
C16 | 0.0153 (3) | 0.0116 (3) | 0.0151 (4) | 0.0003 (2) | −0.0002 (3) | 0.0004 (3) |
C17 | 0.0151 (3) | 0.0127 (3) | 0.0156 (4) | −0.0012 (2) | 0.0000 (3) | 0.0002 (3) |
C18 | 0.0132 (3) | 0.0141 (3) | 0.0132 (4) | −0.0001 (2) | 0.0003 (2) | −0.0004 (3) |
C19 | 0.0143 (3) | 0.0125 (3) | 0.0210 (5) | 0.0006 (2) | −0.0008 (3) | −0.0004 (3) |
C20 | 0.0141 (3) | 0.0119 (3) | 0.0196 (4) | −0.0001 (2) | −0.0008 (3) | 0.0003 (3) |
Geometric parameters (Å, º) top
Cu1—N9 | 1.9772 (12) | N10—H10A | 0.93 (2) |
Cu1—N10 | 1.9952 (10) | N10—H10B | 0.90 (2) |
Cu1—N7 | 2.0370 (10) | N10—H10C | 0.86 (3) |
Cu1—N5 | 2.1039 (10) | C2—C3 | 1.3857 (14) |
Cu1—N1 | 2.2759 (8) | C2—H2 | 0.95 |
Cu1—C11 | 2.5478 (10) | C3—C4 | 1.3868 (16) |
S1—O1 | 1.4592 (10) | C3—H3 | 0.95 |
S1—O2 | 1.4606 (9) | C4—H4 | 0.95 |
S1—N3 | 1.5663 (10) | C5—C6 | 1.389 (2) |
S1—C5 | 1.7624 (13) | C5—C10 | 1.4039 (16) |
S2—O3 | 1.4458 (9) | C6—C7 | 1.3895 (18) |
S2—O4 | 1.4479 (9) | C6—H6 | 0.95 |
S2—N7 | 1.6081 (10) | C7—C8 | 1.4065 (17) |
S2—C15 | 1.7490 (9) | C7—H7 | 0.95 |
N1—C2 | 1.3359 (14) | C8—C9 | 1.401 (2) |
N1—C1 | 1.3552 (13) | C9—C10 | 1.3871 (17) |
N2—C4 | 1.3350 (14) | C9—H9 | 0.95 |
N2—C1 | 1.3502 (12) | C10—H10 | 0.95 |
N3—C1 | 1.3659 (13) | C12—C13 | 1.3923 (18) |
N4—C8 | 1.3822 (17) | C12—H12 | 0.95 |
N4—H4A | 0.83 (2) | C13—C14 | 1.3824 (19) |
N4—H4B | 0.83 (3) | C13—H13 | 0.95 |
N5—C12 | 1.3304 (15) | C14—H14 | 0.95 |
N5—C11 | 1.3600 (15) | C15—C20 | 1.3938 (14) |
N6—C11 | 1.3367 (13) | C15—C16 | 1.3981 (14) |
N6—C14 | 1.3399 (16) | C16—C17 | 1.3838 (14) |
N7—C11 | 1.3668 (14) | C16—H16 | 0.95 |
N8—C18 | 1.3890 (12) | C17—C18 | 1.4090 (15) |
N8—H8A | 0.82 (3) | C17—H17 | 0.95 |
N8—H8B | 0.84 (3) | C18—C19 | 1.4047 (15) |
N9—H9A | 0.79 (3) | C19—C20 | 1.3898 (13) |
N9—H9B | 0.84 (3) | C19—H19 | 0.95 |
N9—H9C | 0.89 (3) | C20—H20 | 0.95 |
| | | |
N9—Cu1—N10 | 93.37 (5) | N1—C2—C3 | 122.42 (10) |
N9—Cu1—N7 | 162.13 (5) | N1—C2—H2 | 118.8 |
N10—Cu1—N7 | 95.10 (4) | C3—C2—H2 | 118.8 |
N9—Cu1—N5 | 101.43 (5) | C2—C3—C4 | 116.12 (10) |
N10—Cu1—N5 | 150.54 (4) | C2—C3—H3 | 121.9 |
N7—Cu1—N5 | 64.44 (4) | C4—C3—H3 | 121.9 |
N9—Cu1—N1 | 95.21 (4) | N2—C4—C3 | 123.15 (9) |
N10—Cu1—N1 | 114.80 (4) | N2—C4—H4 | 118.4 |
N7—Cu1—N1 | 95.47 (4) | C3—C4—H4 | 118.4 |
N5—Cu1—N1 | 89.28 (3) | C6—C5—C10 | 119.89 (11) |
N9—Cu1—C11 | 133.27 (5) | C6—C5—S1 | 121.40 (8) |
N10—Cu1—C11 | 125.46 (4) | C10—C5—S1 | 118.50 (11) |
N7—Cu1—C11 | 32.31 (4) | C5—C6—C7 | 120.04 (11) |
N5—Cu1—C11 | 32.24 (4) | C5—C6—H6 | 120.0 |
N1—Cu1—C11 | 90.85 (3) | C7—C6—H6 | 120.0 |
O1—S1—O2 | 113.84 (7) | C6—C7—C8 | 120.66 (12) |
O1—S1—N3 | 114.53 (6) | C6—C7—H7 | 119.7 |
O2—S1—N3 | 105.60 (5) | C8—C7—H7 | 119.7 |
O1—S1—C5 | 106.52 (6) | N4—C8—C9 | 120.66 (11) |
O2—S1—C5 | 106.13 (6) | N4—C8—C7 | 120.50 (12) |
N3—S1—C5 | 109.92 (6) | C9—C8—C7 | 118.77 (11) |
O3—S2—O4 | 117.02 (6) | C10—C9—C8 | 120.58 (11) |
O3—S2—N7 | 111.96 (5) | C10—C9—H9 | 119.7 |
O4—S2—N7 | 104.68 (5) | C8—C9—H9 | 119.7 |
O3—S2—C15 | 108.18 (5) | C9—C10—C5 | 120.02 (12) |
O4—S2—C15 | 107.48 (5) | C9—C10—H10 | 120.0 |
N7—S2—C15 | 107.02 (5) | C5—C10—H10 | 120.0 |
C2—N1—C1 | 117.24 (8) | N6—C11—N5 | 125.35 (10) |
C2—N1—Cu1 | 126.31 (7) | N6—C11—N7 | 126.46 (10) |
C1—N1—Cu1 | 115.96 (6) | N5—C11—N7 | 108.19 (9) |
C4—N2—C1 | 116.65 (9) | N6—C11—Cu1 | 175.88 (7) |
C1—N3—S1 | 121.80 (7) | N5—C11—Cu1 | 55.61 (5) |
C8—N4—H4A | 112.9 (17) | N7—C11—Cu1 | 52.81 (5) |
C8—N4—H4B | 111.7 (18) | N5—C12—C13 | 120.47 (12) |
H4A—N4—H4B | 117 (2) | N5—C12—H12 | 119.8 |
C12—N5—C11 | 118.22 (10) | C13—C12—H12 | 119.8 |
C12—N5—Cu1 | 149.38 (9) | C14—C13—C12 | 116.91 (11) |
C11—N5—Cu1 | 92.15 (6) | C14—C13—H13 | 121.5 |
C11—N6—C14 | 115.09 (10) | C12—C13—H13 | 121.5 |
C11—N7—S2 | 124.74 (8) | N6—C14—C13 | 123.94 (11) |
C11—N7—Cu1 | 94.88 (7) | N6—C14—H14 | 118.0 |
S2—N7—Cu1 | 136.63 (5) | C13—C14—H14 | 118.0 |
C18—N8—H8A | 111.3 (16) | C20—C15—C16 | 120.25 (8) |
C18—N8—H8B | 113.7 (16) | C20—C15—S2 | 120.18 (7) |
H8A—N8—H8B | 119 (2) | C16—C15—S2 | 119.58 (7) |
Cu1—N9—H9A | 109 (2) | C17—C16—C15 | 120.06 (9) |
Cu1—N9—H9B | 119.1 (18) | C17—C16—H16 | 120.0 |
H9A—N9—H9B | 105 (3) | C15—C16—H16 | 120.0 |
Cu1—N9—H9C | 112 (2) | C16—C17—C18 | 120.35 (9) |
H9A—N9—H9C | 105 (3) | C16—C17—H17 | 119.8 |
H9B—N9—H9C | 106 (3) | C18—C17—H17 | 119.8 |
Cu1—N10—H10A | 119.6 (16) | N8—C18—C19 | 120.33 (9) |
Cu1—N10—H10B | 106.9 (15) | N8—C18—C17 | 120.63 (9) |
H10A—N10—H10B | 108.8 (19) | C19—C18—C17 | 119.01 (8) |
Cu1—N10—H10C | 107.3 (16) | C20—C19—C18 | 120.49 (9) |
H10A—N10—H10C | 106 (2) | C20—C19—H19 | 119.8 |
H10B—N10—H10C | 108 (2) | C18—C19—H19 | 119.8 |
N2—C1—N1 | 124.36 (9) | C19—C20—C15 | 119.84 (9) |
N2—C1—N3 | 122.11 (9) | C19—C20—H20 | 120.1 |
N1—C1—N3 | 113.53 (8) | C15—C20—H20 | 120.1 |
| | | |
N9—Cu1—N1—C2 | −114.39 (11) | S1—C5—C6—C7 | 174.22 (9) |
N10—Cu1—N1—C2 | 149.45 (10) | C5—C6—C7—C8 | −1.61 (17) |
N7—Cu1—N1—C2 | 51.26 (11) | C6—C7—C8—N4 | −174.29 (11) |
N5—Cu1—N1—C2 | −12.98 (11) | C6—C7—C8—C9 | 2.64 (17) |
C11—Cu1—N1—C2 | 19.22 (11) | N4—C8—C9—C10 | 175.21 (11) |
N9—Cu1—N1—C1 | 73.88 (9) | C7—C8—C9—C10 | −1.72 (16) |
N10—Cu1—N1—C1 | −22.28 (10) | C8—C9—C10—C5 | −0.21 (17) |
N7—Cu1—N1—C1 | −120.47 (8) | C6—C5—C10—C9 | 1.27 (16) |
N5—Cu1—N1—C1 | 175.29 (9) | S1—C5—C10—C9 | −173.47 (8) |
C11—Cu1—N1—C1 | −152.51 (8) | C14—N6—C11—N5 | −1.40 (15) |
O1—S1—N3—C1 | −31.47 (12) | C14—N6—C11—N7 | 178.23 (9) |
O2—S1—N3—C1 | −157.53 (10) | C14—N6—C11—Cu1 | −103.5 (12) |
C5—S1—N3—C1 | 88.39 (11) | C12—N5—C11—N6 | 0.83 (15) |
N9—Cu1—N5—C12 | 14.94 (15) | Cu1—N5—C11—N6 | −175.11 (9) |
N10—Cu1—N5—C12 | 133.62 (14) | C12—N5—C11—N7 | −178.86 (9) |
N7—Cu1—N5—C12 | −176.64 (15) | Cu1—N5—C11—N7 | 5.20 (7) |
N1—Cu1—N5—C12 | −80.22 (15) | C12—N5—C11—Cu1 | 175.94 (10) |
C11—Cu1—N5—C12 | −172.96 (18) | S2—N7—C11—N6 | 13.68 (15) |
N9—Cu1—N5—C11 | −172.10 (6) | Cu1—N7—C11—N6 | 174.93 (9) |
N10—Cu1—N5—C11 | −53.42 (10) | S2—N7—C11—N5 | −166.64 (7) |
N7—Cu1—N5—C11 | −3.67 (5) | Cu1—N7—C11—N5 | −5.39 (8) |
N1—Cu1—N5—C11 | 92.74 (6) | S2—N7—C11—Cu1 | −161.25 (10) |
O3—S2—N7—C11 | −47.39 (10) | N9—Cu1—C11—N6 | 115.5 (12) |
O4—S2—N7—C11 | −175.12 (8) | N10—Cu1—C11—N6 | −104.1 (12) |
C15—S2—N7—C11 | 70.99 (9) | N7—Cu1—C11—N6 | −81.3 (12) |
O3—S2—N7—Cu1 | 160.41 (7) | N5—Cu1—C11—N6 | 104.9 (12) |
O4—S2—N7—Cu1 | 32.67 (9) | N1—Cu1—C11—N6 | 17.6 (12) |
C15—S2—N7—Cu1 | −81.22 (8) | N9—Cu1—C11—N5 | 10.67 (8) |
N9—Cu1—N7—C11 | 43.54 (16) | N10—Cu1—C11—N5 | 151.00 (6) |
N10—Cu1—N7—C11 | 161.53 (6) | N7—Cu1—C11—N5 | 173.79 (9) |
N5—Cu1—N7—C11 | 3.67 (5) | N1—Cu1—C11—N5 | −87.30 (6) |
N1—Cu1—N7—C11 | −82.90 (6) | N9—Cu1—C11—N7 | −163.12 (7) |
N9—Cu1—N7—S2 | −159.08 (11) | N10—Cu1—C11—N7 | −22.79 (7) |
N10—Cu1—N7—S2 | −41.09 (8) | N5—Cu1—C11—N7 | −173.79 (9) |
N5—Cu1—N7—S2 | 161.05 (9) | N1—Cu1—C11—N7 | 98.91 (6) |
N1—Cu1—N7—S2 | 74.48 (8) | C11—N5—C12—C13 | 0.24 (15) |
C11—Cu1—N7—S2 | 157.38 (12) | Cu1—N5—C12—C13 | 172.25 (10) |
C4—N2—C1—N1 | −1.95 (18) | N5—C12—C13—C14 | −0.59 (17) |
C4—N2—C1—N3 | 178.58 (12) | C11—N6—C14—C13 | 0.97 (16) |
C2—N1—C1—N2 | 0.09 (18) | C12—C13—C14—N6 | −0.04 (18) |
Cu1—N1—C1—N2 | 172.60 (9) | O3—S2—C15—C20 | 21.45 (12) |
C2—N1—C1—N3 | 179.60 (11) | O4—S2—C15—C20 | 148.66 (10) |
Cu1—N1—C1—N3 | −7.89 (13) | N7—S2—C15—C20 | −99.36 (11) |
S1—N3—C1—N2 | −28.67 (17) | O3—S2—C15—C16 | −158.33 (10) |
S1—N3—C1—N1 | 151.82 (9) | O4—S2—C15—C16 | −31.11 (11) |
C1—N1—C2—C3 | 1.83 (19) | N7—S2—C15—C16 | 80.86 (10) |
Cu1—N1—C2—C3 | −169.80 (10) | C20—C15—C16—C17 | 0.07 (18) |
N1—C2—C3—C4 | −1.8 (2) | S2—C15—C16—C17 | 179.85 (9) |
C1—N2—C4—C3 | 1.98 (19) | C15—C16—C17—C18 | 0.46 (18) |
C2—C3—C4—N2 | −0.2 (2) | C16—C17—C18—N8 | −178.95 (11) |
O1—S1—C5—C6 | 142.19 (9) | C16—C17—C18—C19 | −0.85 (17) |
O2—S1—C5—C6 | −96.17 (10) | N8—C18—C19—C20 | 178.82 (12) |
N3—S1—C5—C6 | 17.57 (10) | C17—C18—C19—C20 | 0.72 (19) |
O1—S1—C5—C10 | −43.16 (10) | C18—C19—C20—C15 | −0.2 (2) |
O2—S1—C5—C10 | 78.48 (9) | C16—C15—C20—C19 | −0.21 (19) |
N3—S1—C5—C10 | −167.77 (8) | S2—C15—C20—C19 | −179.98 (10) |
C10—C5—C6—C7 | −0.36 (16) | | |
(I_291K) Bis[4-amino-
N-(pyrimidin-2-yl)benzenesulfonamido]diamminecopper(II)
top
Crystal data top
[Cu(C10H9N4O2S)2(NH3)2] | F(000) = 1228 |
Mr = 596.15 | Dx = 1.616 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 2038 reflections |
a = 13.7824 (11) Å | θ = 2.6–18.7° |
b = 12.5795 (10) Å | µ = 1.11 mm−1 |
c = 14.1313 (11) Å | T = 291 K |
V = 2450.0 (3) Å3 | Prism, green |
Z = 4 | 0.20 × 0.20 × 0.18 mm |
Data collection top
Bruker D8 diffractometer with APEX CCD area-detector | 4910 independent reflections |
Radiation source: Incoatec microsource | 4143 reflections with I > 2σ(I) |
Multilayer optics monochromator | Rint = 0.069 |
ω scans | θmax = 26.4°, θmin = 2.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −17→15 |
Tmin = 0.808, Tmax = 0.825 | k = −15→15 |
21202 measured reflections | l = −17→16 |
Refinement top
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)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.092 | w = 1/[σ2(Fo2) + (0.0269P)2 + 0.3577P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
4910 reflections | Δρmax = 0.50 e Å−3 |
336 parameters | Δρmin = −0.28 e Å−3 |
1 restraint | Absolute structure: Flack (1983), with 2302 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.009 (14) |
Special details top
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 (Å2) top | x | y | z | Uiso*/Ueq | |
Cu1 | 0.74175 (3) | 0.55727 (3) | 0.07404 (4) | 0.03452 (13) | |
S1 | 0.90252 (8) | 0.84389 (8) | 0.14936 (9) | 0.0394 (3) | |
S2 | 0.79898 (7) | 0.42673 (7) | 0.27642 (7) | 0.0309 (2) | |
O1 | 0.9782 (2) | 0.8226 (2) | 0.2186 (2) | 0.0484 (8) | |
O2 | 0.8118 (2) | 0.8804 (2) | 0.1907 (3) | 0.0568 (9) | |
O3 | 0.7668 (2) | 0.3298 (2) | 0.3202 (2) | 0.0411 (7) | |
O4 | 0.7714 (2) | 0.5255 (2) | 0.3210 (2) | 0.0415 (7) | |
N1 | 0.9024 (2) | 0.5770 (2) | 0.0393 (2) | 0.0325 (8) | |
N2 | 1.0373 (2) | 0.6952 (2) | 0.0515 (3) | 0.0388 (9) | |
N3 | 0.8753 (2) | 0.7467 (2) | 0.0856 (3) | 0.0389 (8) | |
N4 | 1.0154 (3) | 1.2187 (3) | −0.0788 (3) | 0.0552 (11) | |
H4A | 1.0545 | 1.2606 | −0.0435 | 0.083* | |
H4B | 1.0314 | 1.2013 | −0.1389 | 0.083* | |
N5 | 0.7458 (2) | 0.4025 (3) | 0.0167 (2) | 0.0309 (8) | |
N6 | 0.7831 (2) | 0.2569 (3) | 0.1183 (2) | 0.0361 (8) | |
N7 | 0.7611 (2) | 0.4379 (2) | 0.1682 (2) | 0.0297 (8) | |
N8 | 1.2286 (2) | 0.4198 (3) | 0.2620 (3) | 0.0402 (9) | |
H8A | 1.2543 | 0.4835 | 0.2421 | 0.060* | |
H8B | 1.2603 | 0.3567 | 0.2482 | 0.060* | |
N9 | 0.6923 (3) | 0.6367 (3) | −0.0367 (3) | 0.0520 (11) | |
H9A | 0.6289 | 0.6476 | −0.0301 | 0.078* | |
H9B | 0.7031 | 0.5992 | −0.0891 | 0.078* | |
H9C | 0.7227 | 0.6989 | −0.0408 | 0.078* | |
N10 | 0.6905 (2) | 0.6609 (3) | 0.1668 (3) | 0.0391 (9) | |
H10A | 0.6285 | 0.6744 | 0.1540 | 0.059* | |
H10B | 0.7246 | 0.7208 | 0.1633 | 0.059* | |
H10C | 0.6954 | 0.6340 | 0.2249 | 0.059* | |
C1 | 0.9413 (3) | 0.6732 (3) | 0.0591 (3) | 0.0318 (9) | |
C2 | 0.9639 (3) | 0.5012 (3) | 0.0120 (3) | 0.0403 (10) | |
H2 | 0.9386 | 0.4351 | −0.0042 | 0.048* | |
C3 | 1.0620 (3) | 0.5154 (3) | 0.0065 (3) | 0.0411 (10) | |
H3 | 1.1037 | 0.4603 | −0.0098 | 0.049* | |
C4 | 1.0952 (3) | 0.6148 (3) | 0.0264 (3) | 0.0399 (10) | |
H4 | 1.1615 | 0.6274 | 0.0223 | 0.048* | |
C5 | 0.9447 (3) | 0.9490 (3) | 0.0784 (4) | 0.0361 (9) | |
C6 | 0.9279 (3) | 0.9511 (3) | −0.0175 (3) | 0.0458 (11) | |
H6 | 0.8986 | 0.8935 | −0.0471 | 0.055* | |
C7 | 0.9550 (3) | 1.0400 (3) | −0.0700 (4) | 0.0465 (11) | |
H7 | 0.9448 | 1.0407 | −0.1351 | 0.056* | |
C8 | 0.9970 (3) | 1.1271 (3) | −0.0266 (3) | 0.0399 (10) | |
C9 | 1.0147 (3) | 1.1235 (3) | 0.0699 (4) | 0.0441 (10) | |
H9 | 1.0433 | 1.1814 | 0.0998 | 0.053* | |
C10 | 0.9902 (3) | 1.0347 (3) | 0.1219 (3) | 0.0421 (11) | |
H10 | 1.0042 | 1.0321 | 0.1862 | 0.051* | |
C11 | 0.7650 (3) | 0.3588 (3) | 0.1025 (3) | 0.0278 (9) | |
C12 | 0.7444 (3) | 0.3382 (4) | −0.0577 (3) | 0.0408 (10) | |
H12 | 0.7326 | 0.3660 | −0.1176 | 0.049* | |
C13 | 0.7604 (3) | 0.2308 (4) | −0.0473 (4) | 0.0464 (12) | |
H13 | 0.7584 | 0.1849 | −0.0988 | 0.056* | |
C14 | 0.7791 (3) | 0.1949 (3) | 0.0419 (3) | 0.0416 (11) | |
H14 | 0.7898 | 0.1225 | 0.0500 | 0.050* | |
C15 | 0.9263 (3) | 0.4236 (3) | 0.2708 (3) | 0.0290 (8) | |
C16 | 0.9776 (3) | 0.5185 (3) | 0.2639 (3) | 0.0339 (9) | |
H16 | 0.9443 | 0.5828 | 0.2622 | 0.041* | |
C17 | 1.0768 (3) | 0.5178 (3) | 0.2596 (3) | 0.0359 (9) | |
H17 | 1.1103 | 0.5816 | 0.2538 | 0.043* | |
C18 | 1.1283 (3) | 0.4216 (3) | 0.2639 (3) | 0.0337 (9) | |
C19 | 1.0754 (3) | 0.3273 (3) | 0.2718 (3) | 0.0394 (10) | |
H19 | 1.1081 | 0.2627 | 0.2741 | 0.047* | |
C20 | 0.9756 (3) | 0.3282 (3) | 0.2762 (3) | 0.0375 (9) | |
H20 | 0.9416 | 0.2648 | 0.2828 | 0.045* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0373 (3) | 0.0335 (2) | 0.0327 (3) | 0.00779 (19) | 0.0004 (3) | −0.0002 (3) |
S1 | 0.0330 (6) | 0.0359 (5) | 0.0493 (7) | 0.0007 (4) | 0.0051 (5) | −0.0070 (5) |
S2 | 0.0298 (5) | 0.0347 (5) | 0.0280 (5) | 0.0031 (4) | −0.0009 (4) | −0.0032 (4) |
O1 | 0.052 (2) | 0.0492 (18) | 0.0438 (18) | −0.0025 (14) | −0.0047 (16) | 0.0036 (15) |
O2 | 0.0416 (19) | 0.0480 (19) | 0.081 (3) | 0.0072 (15) | 0.0251 (17) | −0.0141 (17) |
O3 | 0.0386 (17) | 0.0472 (18) | 0.0374 (17) | −0.0077 (13) | 0.0017 (14) | 0.0030 (15) |
O4 | 0.0393 (18) | 0.0495 (17) | 0.0358 (17) | 0.0110 (13) | −0.0021 (14) | −0.0126 (14) |
N1 | 0.0299 (18) | 0.0320 (17) | 0.0356 (19) | −0.0012 (13) | −0.0007 (14) | −0.0024 (14) |
N2 | 0.0267 (18) | 0.0368 (17) | 0.053 (3) | −0.0023 (14) | 0.0057 (16) | −0.0025 (16) |
N3 | 0.0281 (17) | 0.0334 (16) | 0.055 (2) | −0.0008 (13) | −0.0018 (18) | −0.0074 (18) |
N4 | 0.058 (3) | 0.057 (2) | 0.051 (2) | −0.010 (2) | −0.003 (2) | 0.002 (2) |
N5 | 0.0302 (19) | 0.0342 (19) | 0.028 (2) | 0.0003 (14) | −0.0016 (14) | −0.0041 (15) |
N6 | 0.039 (2) | 0.0323 (17) | 0.037 (2) | 0.0028 (15) | 0.0035 (16) | −0.0050 (15) |
N7 | 0.0310 (19) | 0.0287 (17) | 0.0295 (19) | 0.0027 (13) | −0.0063 (15) | −0.0064 (14) |
N8 | 0.0307 (19) | 0.0429 (19) | 0.047 (2) | −0.0007 (15) | 0.0038 (17) | 0.0022 (17) |
N9 | 0.065 (3) | 0.050 (2) | 0.041 (2) | 0.023 (2) | 0.004 (2) | 0.0035 (19) |
N10 | 0.033 (2) | 0.0356 (18) | 0.048 (2) | 0.0054 (15) | 0.0008 (18) | −0.0013 (17) |
C1 | 0.029 (2) | 0.0353 (19) | 0.031 (2) | −0.0023 (15) | −0.0017 (18) | −0.0004 (17) |
C2 | 0.041 (3) | 0.035 (2) | 0.045 (3) | −0.0055 (19) | 0.001 (2) | −0.0101 (19) |
C3 | 0.037 (2) | 0.041 (2) | 0.046 (3) | 0.0016 (19) | 0.011 (2) | −0.006 (2) |
C4 | 0.028 (2) | 0.050 (3) | 0.041 (2) | −0.0050 (19) | 0.0056 (19) | 0.002 (2) |
C5 | 0.029 (2) | 0.0332 (18) | 0.047 (2) | 0.0015 (16) | −0.001 (2) | −0.007 (2) |
C6 | 0.047 (3) | 0.042 (2) | 0.048 (3) | −0.004 (2) | −0.008 (2) | −0.010 (2) |
C7 | 0.046 (3) | 0.053 (3) | 0.041 (3) | −0.003 (2) | −0.004 (2) | −0.008 (2) |
C8 | 0.035 (2) | 0.041 (2) | 0.044 (3) | 0.0036 (19) | 0.003 (2) | 0.001 (2) |
C9 | 0.044 (2) | 0.038 (2) | 0.051 (3) | −0.0076 (17) | 0.000 (3) | −0.008 (2) |
C10 | 0.037 (3) | 0.050 (3) | 0.040 (3) | 0.0016 (19) | −0.009 (2) | −0.005 (2) |
C11 | 0.0196 (19) | 0.0317 (19) | 0.032 (2) | 0.0009 (15) | 0.0023 (16) | −0.0045 (15) |
C12 | 0.033 (2) | 0.053 (3) | 0.036 (3) | −0.0059 (19) | −0.0018 (19) | −0.007 (2) |
C13 | 0.050 (3) | 0.042 (3) | 0.047 (3) | 0.000 (2) | −0.003 (2) | −0.021 (2) |
C14 | 0.040 (3) | 0.033 (2) | 0.052 (3) | −0.0001 (18) | 0.002 (2) | −0.011 (2) |
C15 | 0.030 (2) | 0.0322 (18) | 0.025 (2) | 0.0027 (15) | −0.0016 (18) | −0.0005 (16) |
C16 | 0.040 (2) | 0.0295 (19) | 0.032 (2) | 0.0052 (16) | −0.0041 (19) | −0.0027 (18) |
C17 | 0.039 (2) | 0.035 (2) | 0.034 (2) | −0.0058 (17) | −0.0011 (19) | 0.0017 (18) |
C18 | 0.034 (2) | 0.042 (2) | 0.026 (2) | 0.0007 (18) | 0.0014 (19) | −0.0016 (18) |
C19 | 0.036 (2) | 0.034 (2) | 0.048 (3) | 0.0074 (17) | −0.004 (2) | 0.001 (2) |
C20 | 0.033 (2) | 0.033 (2) | 0.046 (3) | −0.0018 (16) | −0.001 (2) | 0.000 (2) |
Geometric parameters (Å, º) top
Cu1—N9 | 1.978 (4) | N10—H10A | 0.89 |
Cu1—N10 | 1.979 (3) | N10—H10B | 0.89 |
Cu1—N7 | 2.024 (3) | N10—H10C | 0.89 |
Cu1—N5 | 2.110 (4) | C2—C3 | 1.366 (6) |
Cu1—N1 | 2.281 (3) | C2—H2 | 0.93 |
Cu1—C11 | 2.549 (4) | C3—C4 | 1.360 (6) |
S1—O2 | 1.454 (3) | C3—H3 | 0.93 |
S1—O1 | 1.456 (3) | C4—H4 | 0.93 |
S1—N3 | 1.565 (3) | C5—C6 | 1.374 (7) |
S1—C5 | 1.759 (5) | C5—C10 | 1.390 (6) |
S2—O3 | 1.438 (3) | C6—C7 | 1.393 (6) |
S2—O4 | 1.443 (3) | C6—H6 | 0.93 |
S2—N7 | 1.622 (4) | C7—C8 | 1.384 (6) |
S2—C15 | 1.756 (4) | C7—H7 | 0.93 |
N1—C2 | 1.333 (5) | C8—C9 | 1.385 (7) |
N1—C1 | 1.353 (4) | C9—C10 | 1.379 (6) |
N2—C4 | 1.336 (5) | C9—H9 | 0.93 |
N2—C1 | 1.356 (5) | C10—H10 | 0.93 |
N3—C1 | 1.349 (5) | C12—C13 | 1.376 (6) |
N4—C8 | 1.391 (5) | C12—H12 | 0.93 |
N4—H4A | 0.90 | C13—C14 | 1.364 (7) |
N4—H4B | 0.90 | C13—H13 | 0.93 |
N5—C12 | 1.327 (5) | C14—H14 | 0.93 |
N5—C11 | 1.357 (5) | C15—C20 | 1.383 (5) |
N6—C11 | 1.326 (5) | C15—C16 | 1.391 (5) |
N6—C14 | 1.332 (5) | C16—C17 | 1.368 (6) |
N7—C11 | 1.361 (5) | C16—H16 | 0.93 |
N8—C18 | 1.382 (5) | C17—C18 | 1.405 (5) |
N8—H8A | 0.92 | C17—H17 | 0.93 |
N8—H8B | 0.93 | C18—C19 | 1.397 (5) |
N9—H9A | 0.89 | C19—C20 | 1.376 (5) |
N9—H9B | 0.89 | C19—H19 | 0.93 |
N9—H9C | 0.89 | C20—H20 | 0.93 |
| | | |
N9—Cu1—N10 | 93.94 (14) | N1—C2—C3 | 123.5 (4) |
N9—Cu1—N7 | 160.09 (16) | N1—C2—H2 | 118.3 |
N10—Cu1—N7 | 95.76 (14) | C3—C2—H2 | 118.3 |
N9—Cu1—N5 | 99.85 (15) | C4—C3—C2 | 116.2 (4) |
N10—Cu1—N5 | 150.68 (14) | C4—C3—H3 | 121.9 |
N7—Cu1—N5 | 64.16 (14) | C2—C3—H3 | 121.9 |
N9—Cu1—N1 | 96.28 (15) | N2—C4—C3 | 123.4 (4) |
N10—Cu1—N1 | 114.65 (13) | N2—C4—H4 | 118.3 |
N7—Cu1—N1 | 95.40 (12) | C3—C4—H4 | 118.3 |
N5—Cu1—N1 | 89.53 (11) | C6—C5—C10 | 119.8 (4) |
N9—Cu1—C11 | 131.50 (15) | C6—C5—S1 | 121.4 (3) |
N10—Cu1—C11 | 125.83 (13) | C10—C5—S1 | 118.7 (4) |
N7—Cu1—C11 | 32.10 (12) | C5—C6—C7 | 119.7 (4) |
N5—Cu1—C11 | 32.15 (13) | C5—C6—H6 | 120.1 |
N1—Cu1—C11 | 91.07 (11) | C7—C6—H6 | 120.1 |
O2—S1—O1 | 113.8 (2) | C8—C7—C6 | 120.8 (4) |
O2—S1—N3 | 105.80 (18) | C8—C7—H7 | 119.6 |
O1—S1—N3 | 114.53 (18) | C6—C7—H7 | 119.6 |
O2—S1—C5 | 106.03 (19) | C7—C8—C9 | 118.9 (4) |
O1—S1—C5 | 106.54 (19) | C7—C8—N4 | 119.8 (4) |
N3—S1—C5 | 109.8 (2) | C9—C8—N4 | 121.2 (4) |
O3—S2—O4 | 117.44 (18) | C10—C9—C8 | 120.5 (4) |
O3—S2—N7 | 112.33 (17) | C10—C9—H9 | 119.7 |
O4—S2—N7 | 104.61 (17) | C8—C9—H9 | 119.7 |
O3—S2—C15 | 108.01 (17) | C9—C10—C5 | 120.2 (5) |
O4—S2—C15 | 107.55 (17) | C9—C10—H10 | 119.9 |
N7—S2—C15 | 106.28 (18) | C5—C10—H10 | 119.9 |
C2—N1—C1 | 116.6 (3) | N6—C11—N5 | 125.4 (3) |
C2—N1—Cu1 | 127.0 (3) | N6—C11—N7 | 126.8 (4) |
C1—N1—Cu1 | 115.9 (2) | N5—C11—N7 | 107.8 (3) |
C4—N2—C1 | 116.7 (3) | N6—C11—Cu1 | 176.3 (3) |
C1—N3—S1 | 122.2 (3) | N5—C11—Cu1 | 55.81 (19) |
C8—N4—H4A | 107.4 | N7—C11—Cu1 | 52.2 (2) |
C8—N4—H4B | 110.0 | N5—C12—C13 | 120.8 (4) |
H4A—N4—H4B | 120.9 | N5—C12—H12 | 119.6 |
C12—N5—C11 | 117.7 (3) | C13—C12—H12 | 119.6 |
C12—N5—Cu1 | 150.1 (3) | C14—C13—C12 | 117.0 (4) |
C11—N5—Cu1 | 92.0 (2) | C14—C13—H13 | 121.5 |
C11—N6—C14 | 114.9 (3) | C12—C13—H13 | 121.5 |
C11—N7—S2 | 124.6 (3) | N6—C14—C13 | 124.3 (4) |
C11—N7—Cu1 | 95.7 (2) | N6—C14—H14 | 117.9 |
S2—N7—Cu1 | 136.56 (18) | C13—C14—H14 | 117.9 |
C18—N8—H8A | 112.1 | C20—C15—C16 | 119.9 (3) |
C18—N8—H8B | 119.3 | C20—C15—S2 | 120.5 (3) |
H8A—N8—H8B | 120.1 | C16—C15—S2 | 119.5 (3) |
Cu1—N9—H9A | 109.5 | C17—C16—C15 | 120.4 (3) |
Cu1—N9—H9B | 109.5 | C17—C16—H16 | 119.8 |
H9A—N9—H9B | 109.5 | C15—C16—H16 | 119.8 |
Cu1—N9—H9C | 109.5 | C16—C17—C18 | 120.6 (4) |
H9A—N9—H9C | 109.5 | C16—C17—H17 | 119.7 |
H9B—N9—H9C | 109.5 | C18—C17—H17 | 119.7 |
Cu1—N10—H10A | 109.5 | N8—C18—C19 | 120.7 (4) |
Cu1—N10—H10B | 109.5 | N8—C18—C17 | 121.3 (4) |
H10A—N10—H10B | 109.5 | C19—C18—C17 | 118.1 (4) |
Cu1—N10—H10C | 109.5 | C20—C19—C18 | 121.3 (3) |
H10A—N10—H10C | 109.5 | C20—C19—H19 | 119.4 |
H10B—N10—H10C | 109.5 | C18—C19—H19 | 119.4 |
N3—C1—N1 | 113.7 (3) | C19—C20—C15 | 119.7 (3) |
N3—C1—N2 | 122.7 (3) | C19—C20—H20 | 120.1 |
N1—C1—N2 | 123.5 (3) | C15—C20—H20 | 120.1 |
| | | |
N9—Cu1—N1—C2 | −111.1 (4) | S1—C5—C6—C7 | 174.4 (3) |
N10—Cu1—N1—C2 | 151.7 (3) | C5—C6—C7—C8 | −1.3 (7) |
N7—Cu1—N1—C2 | 52.8 (4) | C6—C7—C8—C9 | 2.1 (7) |
N5—Cu1—N1—C2 | −11.2 (3) | C6—C7—C8—N4 | −174.2 (4) |
C11—Cu1—N1—C2 | 20.9 (4) | C7—C8—C9—C10 | −0.4 (6) |
N9—Cu1—N1—C1 | 77.1 (3) | N4—C8—C9—C10 | 175.7 (4) |
N10—Cu1—N1—C1 | −20.2 (3) | C8—C9—C10—C5 | −2.0 (7) |
N7—Cu1—N1—C1 | −119.1 (3) | C6—C5—C10—C9 | 2.8 (6) |
N5—Cu1—N1—C1 | 177.0 (3) | S1—C5—C10—C9 | −172.9 (3) |
C11—Cu1—N1—C1 | −150.9 (3) | C14—N6—C11—N5 | −1.7 (6) |
O2—S1—N3—C1 | −159.4 (3) | C14—N6—C11—N7 | 177.6 (4) |
O1—S1—N3—C1 | −33.2 (4) | C14—N6—C11—Cu1 | −109 (4) |
C5—S1—N3—C1 | 86.6 (4) | C12—N5—C11—N6 | 0.5 (6) |
N9—Cu1—N5—C12 | 15.9 (6) | Cu1—N5—C11—N6 | −175.7 (3) |
N10—Cu1—N5—C12 | 132.7 (5) | C12—N5—C11—N7 | −178.9 (3) |
N7—Cu1—N5—C12 | −176.6 (6) | Cu1—N5—C11—N7 | 4.9 (3) |
N1—Cu1—N5—C12 | −80.4 (6) | C12—N5—C11—Cu1 | 176.2 (4) |
C11—Cu1—N5—C12 | −173.2 (7) | S2—N7—C11—N6 | 12.8 (6) |
N9—Cu1—N5—C11 | −171.0 (2) | Cu1—N7—C11—N6 | 175.5 (3) |
N10—Cu1—N5—C11 | −54.1 (4) | S2—N7—C11—N5 | −167.8 (3) |
N7—Cu1—N5—C11 | −3.5 (2) | Cu1—N7—C11—N5 | −5.1 (3) |
N1—Cu1—N5—C11 | 92.7 (2) | S2—N7—C11—Cu1 | −162.7 (4) |
O3—S2—N7—C11 | −46.0 (4) | N9—Cu1—C11—N6 | 122 (4) |
O4—S2—N7—C11 | −174.4 (3) | N10—Cu1—C11—N6 | −99 (4) |
C15—S2—N7—C11 | 71.9 (3) | N7—Cu1—C11—N6 | −76 (4) |
O3—S2—N7—Cu1 | 159.5 (2) | N5—Cu1—C11—N6 | 110 (5) |
O4—S2—N7—Cu1 | 31.1 (3) | N1—Cu1—C11—N6 | 22 (4) |
C15—S2—N7—Cu1 | −82.6 (3) | N9—Cu1—C11—N5 | 11.9 (3) |
N9—Cu1—N7—C11 | 42.3 (5) | N10—Cu1—C11—N5 | 150.7 (2) |
N10—Cu1—N7—C11 | 161.1 (2) | N7—Cu1—C11—N5 | 174.1 (3) |
N5—Cu1—N7—C11 | 3.5 (2) | N1—Cu1—C11—N5 | −87.4 (2) |
N1—Cu1—N7—C11 | −83.4 (2) | N9—Cu1—C11—N7 | −162.2 (2) |
N9—Cu1—N7—S2 | −158.5 (3) | N10—Cu1—C11—N7 | −23.4 (3) |
N10—Cu1—N7—S2 | −39.8 (3) | N5—Cu1—C11—N7 | −174.1 (3) |
N5—Cu1—N7—S2 | 162.6 (3) | N1—Cu1—C11—N7 | 98.5 (2) |
N1—Cu1—N7—S2 | 75.7 (3) | C11—N5—C12—C13 | 1.0 (6) |
C11—Cu1—N7—S2 | 159.1 (4) | Cu1—N5—C12—C13 | 173.3 (4) |
S1—N3—C1—N1 | 154.4 (3) | N5—C12—C13—C14 | −1.2 (6) |
S1—N3—C1—N2 | −26.8 (6) | C11—N6—C14—C13 | 1.5 (6) |
C2—N1—C1—N3 | 179.5 (4) | C12—C13—C14—N6 | −0.2 (7) |
Cu1—N1—C1—N3 | −7.8 (5) | O3—S2—C15—C20 | 20.8 (4) |
C2—N1—C1—N2 | 0.7 (6) | O4—S2—C15—C20 | 148.4 (4) |
Cu1—N1—C1—N2 | 173.4 (3) | N7—S2—C15—C20 | −100.0 (4) |
C4—N2—C1—N3 | 178.7 (4) | O3—S2—C15—C16 | −157.1 (3) |
C4—N2—C1—N1 | −2.6 (6) | O4—S2—C15—C16 | −29.4 (4) |
C1—N1—C2—C3 | 2.3 (6) | N7—S2—C15—C16 | 82.2 (4) |
Cu1—N1—C2—C3 | −169.5 (3) | C20—C15—C16—C17 | 2.0 (7) |
N1—C2—C3—C4 | −3.1 (7) | S2—C15—C16—C17 | 179.9 (3) |
C1—N2—C4—C3 | 1.7 (7) | C15—C16—C17—C18 | −1.3 (6) |
C2—C3—C4—N2 | 1.0 (7) | C16—C17—C18—N8 | −178.4 (4) |
O2—S1—C5—C6 | −97.1 (4) | C16—C17—C18—C19 | 0.6 (6) |
O1—S1—C5—C6 | 141.3 (3) | N8—C18—C19—C20 | 178.3 (4) |
N3—S1—C5—C6 | 16.8 (4) | C17—C18—C19—C20 | −0.7 (7) |
O2—S1—C5—C10 | 78.6 (3) | C18—C19—C20—C15 | 1.4 (7) |
O1—S1—C5—C10 | −43.0 (4) | C16—C15—C20—C19 | −2.1 (7) |
N3—S1—C5—C10 | −167.6 (3) | S2—C15—C20—C19 | −179.9 (3) |
C10—C5—C6—C7 | −1.2 (6) | | |
Coordination and hydrogen bonds (Å) of (I) at 100 and 291 K topCoordination bonds (Å) | 100 K | 291 K |
Cu1—N1 | 2.2759 (8) | 2.281 (4) |
Cu1—N5 | 2.1039 (10) | 2.110 (5) |
Cu1—N7 | 2.0370 (10) | 2.024 (5) |
Cu1—N9 | 1.9772 (12) | 1.978 (5) |
Cu1—N10 | 1.9952 (10) | 1.979 (5) |
| | |
Hydrogen bonds | | |
D—H···A | D···A at 100 K | D···A at 291 K |
N4—H4B···O1i | 2.9158 (18) | 2.911 (7) |
N8—H8A···O2ii | 2.9267 (14) | 2.941 (6) |
N8—H8B···O3iii | 3.2982 (14) | 3.288 (6) |
N8—H8B···N6iii | 3.0658 (15) | 3.103 (7) |
N9—H9A···N2iv | 3.2016 (16) | 3.254 (7) |
N9—H9B···N8v | 3.0944 (17) | 3.128 (8) |
N9—H9C···O3vi | 3.1354 (16) | 3.211 (7) |
N10—H10A···O1iv | 2.9911 (14) | 3.023 (6) |
N10—H10A···N2iv | 3.2063 (14) | 3.223 (7) |
N10—H10B···O2 | 3.2062 (14) | 3.246 (6) |
N10—H10B···N3 | 3.0121 (14) | 2.995 (6) |
N10—H10C···O4 | 2.9801 (14) | 2.982 (7) |
Symmetry codes: (i) -x+2, -y+2, z-1/2;
(ii) x+1/2, -y+3/2, z;
(iii) x+1/2, -y+1/2, z;
(iv) x-1/2, -y+3/2, z;
(v) -x+2, -y+2, z-1/2;
(vi) -x+3/2, y+1/2, z-1/2. |
Comparison of lattice parameters for [Cu(sulfa)2(L1)(L2)] topPublished as | Cu(sulfa)2(NH3)2 | Cu(sulfa)2(NH3)(OH2) | Cu(sulfa)2(NH3)2 |
Reference | Brown et al. (1987) | Tommasino et al. (2011) | This work, T = 291 K |
Space group | Pn21a | Pna21 | Pna21 |
a (Å) | 13.915 (5) | 13.735 (2) | 13.7824 (11) |
b (Å) | 14.356 (5) | 12.588 (2) | 12.5795 (10) |
c (Å) | 12.659 (5) | 14.139 (2) | 14.1313 (11) |
V (Å3) | 2528.81 | 2444.6 (4) | 2450.0 (3) |
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