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The title complex, [Cu(C
14H
11N
2O
2)
2]·C
5H
10N
2, contains one [Cu(pht)
2] (pht is 5,5-diphenylhydantoinate) complex molecule and one solvent molecule. The complex shows a three-dimensional network structure assembled by intermolecular N—H
O=C interactions.
Supporting information
CCDC reference: 615689
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.008 Å
- Disorder in solvent or counterion
- R factor = 0.043
- wR factor = 0.104
- Data-to-parameter ratio = 12.7
checkCIF/PLATON results
No syntax errors found
Alert level C
CRYSC01_ALERT_1_C The word below has not been recognised as a standard
identifier.
jasmine
CRYSC01_ALERT_1_C No recognised colour has been given for crystal colour.
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.13 Ratio
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C8
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C12
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C29
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C4
PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for C33'
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.26
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 30.00 Perc.
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C32
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 25.01
From the CIF: _reflns_number_total 5395
Count of symmetry unique reflns 3012
Completeness (_total/calc) 179.12%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 2383
Fraction of Friedel pairs measured 0.791
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
15 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
6 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
5 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).
Crystal data top
[Cu(C15H10N2O2)2]·C5H12N2 | Dx = 1.384 Mg m−3 |
Mr = 664.21 | Melting point: 534 K |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
a = 22.812 (3) Å | Cell parameters from 3729 reflections |
b = 15.958 (2) Å | θ = 2.2–22.6° |
c = 8.7549 (12) Å | µ = 0.73 mm−1 |
V = 3187.1 (8) Å3 | T = 298 K |
Z = 4 | Block, jasmine yellow? |
F(000) = 1380 | 0.58 × 0.21 × 0.13 mm |
Data collection top
CCD area detector diffractometer | 5395 independent reflections |
Radiation source: fine-focus sealed tube | 3701 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.048 |
phi and ω scans | θmax = 25.0°, θmin = 1.8° |
Absorption correction: multi-scan SADABS (Sheldrick, 1996) | h = −21→27 |
Tmin = 0.675, Tmax = 0.911 | k = −18→18 |
16303 measured reflections | l = −10→10 |
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)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.104 | w = 1/[σ2(Fo2) + (0.0398P)2 + 0.9116P] |
S = 1.03 | (Δ/σ)max = 0.004 |
5395 reflections | Δρmax = 0.48 e Å−3 |
425 parameters | Δρmin = −0.25 e Å−3 |
91 restraints | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.035 (16) |
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 | Occ. (<1) |
Cu1 | 0.32372 (2) | 0.60791 (3) | 0.31416 (8) | 0.04248 (16) | |
N1 | 0.32706 (15) | 0.49285 (19) | 0.2822 (4) | 0.0363 (11) | |
N2 | 0.30854 (15) | 0.3666 (2) | 0.1815 (5) | 0.0395 (10) | |
H2 | 0.2880 | 0.3263 | 0.1440 | 0.047* | |
N3 | 0.32717 (14) | 0.72375 (18) | 0.3357 (6) | 0.0387 (10) | |
N4 | 0.30933 (15) | 0.85143 (19) | 0.4305 (5) | 0.0387 (10) | |
H4 | 0.2924 | 0.8907 | 0.4813 | 0.046* | |
N5 | 0.32051 (19) | 0.5645 (3) | 0.8798 (5) | 0.0614 (12) | |
N6 | 0.38268 (19) | 0.5584 (3) | 0.6736 (5) | 0.0577 (12) | |
H6 | 0.3961 | 0.5297 | 0.5982 | 0.069* | |
O1 | 0.41025 (14) | 0.45946 (19) | 0.4205 (4) | 0.0504 (9) | |
O2 | 0.24975 (13) | 0.47716 (18) | 0.1140 (4) | 0.0442 (8) | |
O3 | 0.40708 (14) | 0.75345 (18) | 0.1862 (4) | 0.0470 (8) | |
O4 | 0.24862 (15) | 0.74440 (17) | 0.5010 (4) | 0.0598 (10) | |
C1 | 0.37114 (19) | 0.4423 (2) | 0.3304 (7) | 0.0393 (11) | |
C2 | 0.2913 (2) | 0.4468 (3) | 0.1863 (6) | 0.0384 (12) | |
C3 | 0.36646 (19) | 0.3566 (3) | 0.2481 (6) | 0.0382 (12) | |
C4 | 0.3706 (2) | 0.2850 (3) | 0.3614 (5) | 0.0424 (13) | |
C5 | 0.3221 (3) | 0.2568 (3) | 0.4354 (7) | 0.0709 (17) | |
H5 | 0.2856 | 0.2793 | 0.4116 | 0.085* | |
C6 | 0.3266 (3) | 0.1938 (4) | 0.5478 (8) | 0.095 (2) | |
H6A | 0.2932 | 0.1757 | 0.5992 | 0.114* | |
C7 | 0.3792 (4) | 0.1599 (4) | 0.5808 (9) | 0.098 (2) | |
H7 | 0.3823 | 0.1177 | 0.6536 | 0.117* | |
C8 | 0.4275 (4) | 0.1879 (5) | 0.5067 (8) | 0.106 (3) | |
H8 | 0.4638 | 0.1641 | 0.5287 | 0.127* | |
C9 | 0.4240 (3) | 0.2508 (4) | 0.3999 (7) | 0.0717 (17) | |
H9 | 0.4580 | 0.2704 | 0.3533 | 0.086* | |
C10 | 0.41114 (19) | 0.3542 (3) | 0.1179 (6) | 0.0413 (12) | |
C11 | 0.4176 (3) | 0.2833 (3) | 0.0321 (6) | 0.0701 (17) | |
H11 | 0.3978 | 0.2346 | 0.0595 | 0.084* | |
C12 | 0.4537 (4) | 0.2836 (4) | −0.0961 (8) | 0.097 (2) | |
H12 | 0.4588 | 0.2342 | −0.1509 | 0.116* | |
C13 | 0.4813 (3) | 0.3535 (5) | −0.1429 (8) | 0.085 (2) | |
H13 | 0.5042 | 0.3530 | −0.2308 | 0.102* | |
C14 | 0.4753 (2) | 0.4244 (4) | −0.0601 (8) | 0.0751 (18) | |
H14 | 0.4945 | 0.4730 | −0.0908 | 0.090* | |
C15 | 0.4408 (2) | 0.4253 (3) | 0.0701 (7) | 0.0590 (15) | |
H15 | 0.4375 | 0.4745 | 0.1264 | 0.071* | |
C16 | 0.36888 (19) | 0.7742 (2) | 0.2748 (5) | 0.0360 (12) | |
C17 | 0.29113 (19) | 0.7710 (2) | 0.4301 (6) | 0.0360 (11) | |
C18 | 0.36022 (17) | 0.8643 (2) | 0.3363 (6) | 0.0336 (11) | |
C19 | 0.34646 (18) | 0.9288 (3) | 0.2102 (6) | 0.0357 (11) | |
C20 | 0.3430 (2) | 0.9089 (3) | 0.0582 (6) | 0.0561 (14) | |
H20 | 0.3516 | 0.8548 | 0.0256 | 0.067* | |
C21 | 0.3265 (2) | 0.9697 (4) | −0.0473 (7) | 0.0677 (16) | |
H21 | 0.3248 | 0.9563 | −0.1506 | 0.081* | |
C22 | 0.3127 (2) | 1.0486 (3) | −0.0003 (8) | 0.0666 (17) | |
H22 | 0.3008 | 1.0885 | −0.0714 | 0.080* | |
C23 | 0.3161 (2) | 1.0692 (3) | 0.1488 (8) | 0.0617 (16) | |
H23 | 0.3073 | 1.1235 | 0.1799 | 0.074* | |
C24 | 0.3327 (2) | 1.0098 (3) | 0.2558 (6) | 0.0505 (14) | |
H24 | 0.3346 | 1.0243 | 0.3586 | 0.061* | |
C25 | 0.41449 (19) | 0.8877 (2) | 0.4291 (6) | 0.0402 (11) | |
C26 | 0.4644 (2) | 0.9157 (3) | 0.3551 (7) | 0.0585 (16) | |
H26 | 0.4639 | 0.9235 | 0.2498 | 0.070* | |
C27 | 0.5150 (3) | 0.9320 (3) | 0.4365 (10) | 0.080 (2) | |
H27 | 0.5485 | 0.9505 | 0.3859 | 0.096* | |
C28 | 0.5160 (3) | 0.9209 (4) | 0.5926 (11) | 0.091 (2) | |
H28 | 0.5499 | 0.9318 | 0.6481 | 0.109* | |
C29 | 0.4667 (4) | 0.8940 (4) | 0.6639 (8) | 0.091 (2) | |
H29 | 0.4671 | 0.8864 | 0.7692 | 0.109* | |
C30 | 0.4162 (2) | 0.8777 (3) | 0.5840 (7) | 0.0589 (15) | |
H30 | 0.3829 | 0.8598 | 0.6358 | 0.071* | |
C31 | 0.3435 (2) | 0.5239 (3) | 0.7638 (6) | 0.0516 (14) | |
C32 | 0.3247 (3) | 0.4371 (3) | 0.7320 (8) | 0.0719 (17) | |
H32A | 0.3455 | 0.4161 | 0.6446 | 0.108* | |
H32B | 0.2833 | 0.4363 | 0.7119 | 0.108* | |
H32C | 0.3331 | 0.4024 | 0.8190 | 0.108* | |
C33 | 0.3369 (3) | 0.6512 (4) | 0.9112 (8) | 0.0853 (18) | 0.675 (7) |
H33A | 0.3363 | 0.6605 | 1.0207 | 0.102* | 0.675 (7) |
H33B | 0.3083 | 0.6883 | 0.8651 | 0.102* | 0.675 (7) |
C34 | 0.3964 (5) | 0.6725 (6) | 0.8512 (12) | 0.079 (3) | 0.675 (7) |
H34A | 0.4017 | 0.7327 | 0.8542 | 0.094* | 0.675 (7) |
H34B | 0.4259 | 0.6472 | 0.9162 | 0.094* | 0.675 (7) |
C35 | 0.4042 (3) | 0.6431 (4) | 0.6960 (7) | 0.0750 (17) | 0.675 (7) |
H35A | 0.4456 | 0.6449 | 0.6705 | 0.090* | 0.675 (7) |
H35B | 0.3837 | 0.6805 | 0.6269 | 0.090* | 0.675 (7) |
C33' | 0.3369 (3) | 0.6512 (4) | 0.9112 (8) | 0.0853 (18) | 0.325 (7) |
H33C | 0.3030 | 0.6812 | 0.9492 | 0.102* | 0.325 (7) |
H33D | 0.3667 | 0.6521 | 0.9902 | 0.102* | 0.325 (7) |
C34' | 0.3566 (11) | 0.6885 (12) | 0.792 (3) | 0.073 (4) | 0.325 (7) |
H34C | 0.3725 | 0.7421 | 0.8242 | 0.087* | 0.325 (7) |
H34D | 0.3236 | 0.7002 | 0.7257 | 0.087* | 0.325 (7) |
C35' | 0.4042 (3) | 0.6431 (4) | 0.6960 (7) | 0.0750 (17) | 0.325 (7) |
H35C | 0.4096 | 0.6710 | 0.5986 | 0.090* | 0.325 (7) |
H35D | 0.4413 | 0.6425 | 0.7499 | 0.090* | 0.325 (7) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0499 (3) | 0.0243 (2) | 0.0532 (3) | −0.0009 (2) | 0.0037 (4) | −0.0130 (3) |
N1 | 0.0371 (19) | 0.0277 (17) | 0.044 (3) | −0.0014 (16) | 0.002 (2) | −0.0120 (18) |
N2 | 0.038 (2) | 0.0263 (19) | 0.054 (3) | −0.0024 (16) | −0.0091 (19) | −0.0065 (18) |
N3 | 0.0418 (19) | 0.0244 (15) | 0.050 (3) | 0.0000 (16) | 0.004 (2) | −0.012 (2) |
N4 | 0.048 (2) | 0.0198 (17) | 0.048 (3) | 0.0004 (16) | 0.016 (2) | −0.0130 (17) |
N5 | 0.064 (3) | 0.076 (3) | 0.044 (3) | −0.005 (2) | 0.004 (2) | −0.013 (2) |
N6 | 0.065 (3) | 0.058 (3) | 0.049 (3) | −0.006 (2) | 0.013 (2) | −0.019 (2) |
O1 | 0.047 (2) | 0.0452 (19) | 0.059 (2) | −0.0028 (15) | −0.006 (2) | −0.0199 (17) |
O2 | 0.0465 (19) | 0.0329 (17) | 0.053 (2) | 0.0029 (15) | −0.0029 (18) | −0.0054 (15) |
O3 | 0.0445 (19) | 0.0398 (18) | 0.057 (2) | 0.0085 (15) | 0.0116 (18) | −0.0108 (17) |
O4 | 0.062 (2) | 0.0320 (17) | 0.085 (3) | −0.0096 (16) | 0.030 (2) | −0.0125 (18) |
C1 | 0.034 (2) | 0.039 (2) | 0.045 (3) | −0.0080 (19) | 0.007 (3) | −0.009 (3) |
C2 | 0.039 (3) | 0.031 (3) | 0.045 (3) | 0.001 (2) | 0.010 (2) | −0.007 (2) |
C3 | 0.040 (3) | 0.029 (2) | 0.046 (3) | −0.006 (2) | 0.001 (2) | −0.013 (2) |
C4 | 0.054 (3) | 0.033 (2) | 0.040 (3) | −0.004 (2) | −0.003 (2) | −0.010 (2) |
C5 | 0.064 (4) | 0.069 (4) | 0.080 (5) | −0.021 (3) | −0.014 (4) | 0.022 (3) |
C6 | 0.105 (6) | 0.099 (5) | 0.080 (5) | −0.042 (5) | −0.012 (4) | 0.038 (4) |
C7 | 0.151 (8) | 0.076 (5) | 0.066 (5) | 0.003 (5) | −0.011 (6) | 0.023 (4) |
C8 | 0.119 (6) | 0.135 (7) | 0.065 (5) | 0.061 (5) | −0.005 (5) | 0.030 (5) |
C9 | 0.069 (4) | 0.088 (4) | 0.058 (4) | 0.023 (3) | 0.004 (3) | 0.018 (3) |
C10 | 0.041 (3) | 0.034 (3) | 0.049 (3) | 0.008 (2) | 0.000 (3) | −0.005 (2) |
C11 | 0.116 (5) | 0.046 (3) | 0.049 (4) | 0.012 (3) | 0.024 (3) | −0.007 (3) |
C12 | 0.160 (7) | 0.064 (4) | 0.066 (5) | 0.047 (4) | 0.025 (5) | −0.012 (4) |
C13 | 0.082 (4) | 0.100 (5) | 0.072 (5) | 0.038 (4) | 0.021 (4) | 0.008 (4) |
C14 | 0.051 (4) | 0.088 (4) | 0.087 (5) | −0.009 (3) | 0.007 (4) | 0.001 (4) |
C15 | 0.051 (3) | 0.056 (3) | 0.070 (4) | −0.007 (3) | 0.017 (3) | −0.011 (3) |
C16 | 0.035 (3) | 0.026 (2) | 0.047 (4) | 0.0049 (19) | −0.004 (2) | −0.007 (2) |
C17 | 0.036 (3) | 0.031 (2) | 0.042 (3) | 0.001 (2) | 0.006 (2) | −0.007 (2) |
C18 | 0.032 (2) | 0.0296 (19) | 0.040 (3) | 0.0000 (16) | 0.005 (2) | −0.003 (2) |
C19 | 0.030 (2) | 0.034 (2) | 0.044 (3) | −0.006 (2) | −0.001 (2) | 0.003 (2) |
C20 | 0.060 (3) | 0.053 (3) | 0.055 (4) | 0.010 (2) | −0.010 (3) | −0.007 (3) |
C21 | 0.075 (4) | 0.082 (4) | 0.047 (4) | 0.012 (3) | −0.008 (3) | 0.008 (3) |
C22 | 0.056 (4) | 0.064 (4) | 0.079 (5) | 0.008 (3) | −0.006 (3) | 0.025 (4) |
C23 | 0.060 (4) | 0.036 (3) | 0.090 (5) | 0.007 (2) | 0.008 (3) | 0.008 (3) |
C24 | 0.056 (3) | 0.032 (2) | 0.064 (4) | 0.001 (2) | 0.006 (3) | 0.001 (2) |
C25 | 0.045 (3) | 0.027 (2) | 0.049 (3) | 0.002 (2) | −0.006 (3) | −0.008 (2) |
C26 | 0.047 (3) | 0.050 (3) | 0.079 (5) | −0.004 (2) | −0.011 (3) | 0.004 (3) |
C27 | 0.050 (4) | 0.067 (4) | 0.123 (7) | −0.006 (3) | −0.017 (4) | −0.019 (4) |
C28 | 0.072 (5) | 0.079 (5) | 0.122 (7) | 0.012 (4) | −0.052 (5) | −0.042 (5) |
C29 | 0.107 (6) | 0.096 (5) | 0.070 (5) | 0.008 (5) | −0.043 (5) | −0.020 (4) |
C30 | 0.066 (4) | 0.061 (4) | 0.050 (4) | −0.006 (3) | −0.012 (3) | −0.011 (3) |
C31 | 0.048 (3) | 0.057 (3) | 0.050 (4) | −0.009 (3) | −0.007 (3) | −0.002 (3) |
C32 | 0.072 (4) | 0.068 (4) | 0.075 (4) | −0.015 (3) | 0.004 (3) | −0.005 (3) |
C33 | 0.094 (4) | 0.084 (4) | 0.078 (4) | −0.015 (3) | 0.026 (3) | −0.038 (3) |
C34 | 0.087 (6) | 0.069 (5) | 0.080 (7) | −0.027 (5) | 0.023 (5) | −0.033 (5) |
C35 | 0.094 (4) | 0.067 (3) | 0.064 (4) | −0.021 (3) | 0.015 (3) | −0.019 (3) |
C33' | 0.094 (4) | 0.084 (4) | 0.078 (4) | −0.015 (3) | 0.026 (3) | −0.038 (3) |
C34' | 0.093 (8) | 0.062 (7) | 0.064 (9) | −0.016 (8) | 0.025 (8) | −0.017 (7) |
C35' | 0.094 (4) | 0.067 (3) | 0.064 (4) | −0.021 (3) | 0.015 (3) | −0.019 (3) |
Geometric parameters (Å, º) top
Cu1—N1 | 1.859 (3) | C14—C15 | 1.386 (8) |
Cu1—N3 | 1.860 (3) | C14—H14 | 0.9300 |
N1—C1 | 1.357 (5) | C15—H15 | 0.9300 |
N1—C2 | 1.383 (5) | C16—C18 | 1.547 (5) |
N2—C2 | 1.340 (5) | C18—C25 | 1.527 (6) |
N2—C3 | 1.453 (5) | C18—C19 | 1.542 (7) |
N2—H2 | 0.8600 | C19—C20 | 1.370 (7) |
N3—C16 | 1.356 (5) | C19—C24 | 1.390 (6) |
N3—C17 | 1.388 (5) | C20—C21 | 1.392 (7) |
N4—C17 | 1.349 (5) | C20—H20 | 0.9300 |
N4—C18 | 1.439 (5) | C21—C22 | 1.362 (7) |
N4—H4 | 0.8600 | C21—H21 | 0.9300 |
N5—C31 | 1.314 (6) | C22—C23 | 1.349 (8) |
N5—C33 | 1.460 (7) | C22—H22 | 0.9300 |
N6—C31 | 1.313 (6) | C23—C24 | 1.386 (7) |
N6—C35 | 1.451 (6) | C23—H23 | 0.9300 |
N6—H6 | 0.8600 | C24—H24 | 0.9300 |
O1—C1 | 1.222 (5) | C25—C30 | 1.366 (7) |
O2—C2 | 1.238 (5) | C25—C26 | 1.385 (6) |
O3—C16 | 1.213 (5) | C26—C27 | 1.381 (7) |
O4—C17 | 1.227 (5) | C26—H26 | 0.9300 |
C1—C3 | 1.549 (6) | C27—C28 | 1.378 (10) |
C3—C4 | 1.517 (6) | C27—H27 | 0.9300 |
C3—C10 | 1.530 (6) | C28—C29 | 1.357 (10) |
C4—C5 | 1.359 (7) | C28—H28 | 0.9300 |
C4—C9 | 1.377 (7) | C29—C30 | 1.371 (8) |
C5—C6 | 1.411 (8) | C29—H29 | 0.9300 |
C5—H5 | 0.9300 | C30—H30 | 0.9300 |
C6—C7 | 1.348 (9) | C31—C32 | 1.476 (7) |
C6—H6A | 0.9300 | C32—H32A | 0.9600 |
C7—C8 | 1.355 (10) | C32—H32B | 0.9600 |
C7—H7 | 0.9300 | C32—H32C | 0.9600 |
C8—C9 | 1.374 (8) | C33—C34 | 1.493 (10) |
C8—H8 | 0.9300 | C33—H33A | 0.9700 |
C9—H9 | 0.9300 | C33—H33B | 0.9700 |
C10—C11 | 1.367 (7) | C34—C35 | 1.448 (11) |
C10—C15 | 1.386 (6) | C34—H34A | 0.9700 |
C11—C12 | 1.393 (8) | C34—H34B | 0.9700 |
C11—H11 | 0.9300 | C35—H35A | 0.9700 |
C12—C13 | 1.345 (9) | C35—H35B | 0.9700 |
C12—H12 | 0.9300 | C34'—H34C | 0.9700 |
C13—C14 | 1.351 (8) | C34'—H34D | 0.9700 |
C13—H13 | 0.9300 | | |
| | | |
N1—Cu1—N3 | 174.44 (16) | N4—C18—C25 | 112.6 (4) |
C1—N1—C2 | 108.1 (3) | N4—C18—C19 | 110.0 (3) |
C1—N1—Cu1 | 124.8 (3) | C25—C18—C19 | 112.5 (3) |
C2—N1—Cu1 | 126.3 (3) | N4—C18—C16 | 99.8 (3) |
C2—N2—C3 | 111.1 (3) | C25—C18—C16 | 108.0 (3) |
C2—N2—H2 | 124.5 | C19—C18—C16 | 113.4 (4) |
C3—N2—H2 | 124.5 | C20—C19—C24 | 118.8 (5) |
C16—N3—C17 | 109.1 (3) | C20—C19—C18 | 123.5 (4) |
C16—N3—Cu1 | 125.5 (3) | C24—C19—C18 | 117.5 (4) |
C17—N3—Cu1 | 125.1 (3) | C19—C20—C21 | 119.9 (5) |
C17—N4—C18 | 112.5 (3) | C19—C20—H20 | 120.1 |
C17—N4—H4 | 123.7 | C21—C20—H20 | 120.1 |
C18—N4—H4 | 123.7 | C22—C21—C20 | 120.5 (6) |
C31—N5—C33 | 120.7 (5) | C22—C21—H21 | 119.8 |
C31—N6—C35 | 122.7 (4) | C20—C21—H21 | 119.8 |
C31—N6—H6 | 118.7 | C23—C22—C21 | 120.3 (5) |
C35—N6—H6 | 118.7 | C23—C22—H22 | 119.8 |
O1—C1—N1 | 127.5 (4) | C21—C22—H22 | 119.8 |
O1—C1—C3 | 123.3 (4) | C22—C23—C24 | 120.2 (5) |
N1—C1—C3 | 109.2 (4) | C22—C23—H23 | 119.9 |
O2—C2—N2 | 125.7 (4) | C24—C23—H23 | 119.9 |
O2—C2—N1 | 123.7 (4) | C23—C24—C19 | 120.3 (5) |
N2—C2—N1 | 110.7 (4) | C23—C24—H24 | 119.9 |
N2—C3—C4 | 113.7 (4) | C19—C24—H24 | 119.9 |
N2—C3—C10 | 108.0 (4) | C30—C25—C26 | 118.6 (5) |
C4—C3—C10 | 115.3 (4) | C30—C25—C18 | 121.6 (5) |
N2—C3—C1 | 98.8 (3) | C26—C25—C18 | 119.8 (5) |
C4—C3—C1 | 110.9 (4) | C27—C26—C25 | 120.4 (6) |
C10—C3—C1 | 108.8 (4) | C27—C26—H26 | 119.8 |
C5—C4—C9 | 118.2 (5) | C25—C26—H26 | 119.8 |
C5—C4—C3 | 120.7 (5) | C28—C27—C26 | 120.1 (7) |
C9—C4—C3 | 120.9 (5) | C28—C27—H27 | 119.9 |
C4—C5—C6 | 120.6 (6) | C26—C27—H27 | 119.9 |
C4—C5—H5 | 119.7 | C29—C28—C27 | 118.9 (6) |
C6—C5—H5 | 119.7 | C29—C28—H28 | 120.6 |
C7—C6—C5 | 120.1 (7) | C27—C28—H28 | 120.6 |
C7—C6—H6A | 120.0 | C28—C29—C30 | 121.4 (7) |
C5—C6—H6A | 120.0 | C28—C29—H29 | 119.3 |
C6—C7—C8 | 119.3 (7) | C30—C29—H29 | 119.3 |
C6—C7—H7 | 120.4 | C25—C30—C29 | 120.6 (6) |
C8—C7—H7 | 120.4 | C25—C30—H30 | 119.7 |
C7—C8—C9 | 121.3 (7) | C29—C30—H30 | 119.7 |
C7—C8—H8 | 119.3 | N6—C31—N5 | 122.0 (5) |
C9—C8—H8 | 119.3 | N6—C31—C32 | 118.6 (5) |
C8—C9—C4 | 120.5 (6) | N5—C31—C32 | 119.5 (5) |
C8—C9—H9 | 119.8 | C31—C32—H32A | 109.5 |
C4—C9—H9 | 119.8 | C31—C32—H32B | 109.5 |
C11—C10—C15 | 117.4 (5) | H32A—C32—H32B | 109.5 |
C11—C10—C3 | 120.1 (4) | C31—C32—H32C | 109.5 |
C15—C10—C3 | 122.0 (4) | H32A—C32—H32C | 109.5 |
C10—C11—C12 | 120.2 (6) | H32B—C32—H32C | 109.5 |
C10—C11—H11 | 119.9 | N5—C33—C34 | 112.5 (5) |
C12—C11—H11 | 119.9 | N5—C33—H33A | 109.1 |
C13—C12—C11 | 121.7 (6) | C34—C33—H33A | 109.1 |
C13—C12—H12 | 119.1 | N5—C33—H33B | 109.1 |
C11—C12—H12 | 119.1 | C34—C33—H33B | 109.1 |
C12—C13—C14 | 118.9 (6) | H33A—C33—H33B | 107.8 |
C12—C13—H13 | 120.5 | C35—C34—C33 | 111.6 (8) |
C14—C13—H13 | 120.5 | C35—C34—H34A | 109.3 |
C13—C14—C15 | 120.5 (6) | C33—C34—H34A | 109.3 |
C13—C14—H14 | 119.8 | C35—C34—H34B | 109.3 |
C15—C14—H14 | 119.8 | C33—C34—H34B | 109.3 |
C14—C15—C10 | 121.2 (5) | H34A—C34—H34B | 108.0 |
C14—C15—H15 | 119.4 | C34—C35—N6 | 112.7 (6) |
C10—C15—H15 | 119.4 | C34—C35—H35A | 109.0 |
O3—C16—N3 | 126.4 (4) | N6—C35—H35A | 109.0 |
O3—C16—C18 | 124.6 (4) | C34—C35—H35B | 109.0 |
N3—C16—C18 | 109.0 (4) | N6—C35—H35B | 109.0 |
O4—C17—N4 | 124.8 (4) | H35A—C35—H35B | 107.8 |
O4—C17—N3 | 125.5 (4) | H34C—C34'—H34D | 107.2 |
N4—C17—N3 | 109.6 (4) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O4i | 0.86 | 1.99 | 2.828 (5) | 163 |
N4—H4···O2ii | 0.86 | 2.04 | 2.902 (4) | 176 |
N6—H6···O1 | 0.86 | 1.94 | 2.792 (5) | 169 |
Symmetry codes: (i) −x+1/2, y−1/2, z−1/2; (ii) −x+1/2, y+1/2, z+1/2. |
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