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In the title complex, [Cu(C9H7NO3)(C12H10N2)2]ClO4·2H2O, the Cu atom exhibits a significantly distorted octa­hedral geometry as a result of the Jahn–Teller effect and the chelating influence of the ligands. In the crystal structure, the mol­ecules are linked by hydrogen bonds into one-dimensional double chains, which are further linked into two-dimensional layers by π–π stacking inter­actions between neighbouring aromatic ligands.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680603618X/jh2034sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680603618X/jh2034Isup2.hkl
Contains datablock I

CCDC reference: 624889

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in solvent or counterion
  • R factor = 0.038
  • wR factor = 0.090
  • Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl1 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 36.00 Perc. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 31.20 Deg. O6A -CL1 -O6 1.555 1.555 1.555 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3 H2 O
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 0 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2003); software used to prepare material for publication: SHELXTL.

(Hippurato-κ2O,O')bis(1,10-phenanthroline-κ2N,N')copper(II) perchlorate dihydrate top
Crystal data top
[Cu(C9H7NO3)(C12H10N2)2]ClO4·2H2OF(000) = 1516
Mr = 737.59Dx = 1.525 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4500 reflections
a = 16.8105 (13) Åθ = 2.5–27.5°
b = 10.1481 (8) ŵ = 0.83 mm1
c = 19.6316 (14) ÅT = 298 K
β = 106.370 (4)°Prism, blue
V = 3213.3 (4) Å30.34 × 0.28 × 0.26 mm
Z = 4
Data collection top
Bruker SMART CCD APEX-II
diffractometer
8015 independent reflections
Radiation source: fine-focus sealed tube4850 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.050
Detector resolution: 8.35 pixels mm-1θmax = 28.4°, θmin = 2.2°
ω scansh = 2221
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1313
Tmin = 0.752, Tmax = 0.811l = 2626
33934 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.03P)2 + 0.7P]
where P = (Fo2 + 2Fc2)/3
8015 reflections(Δ/σ)max = 0.029
493 parametersΔρmax = 0.35 e Å3
86 restraintsΔρmin = 0.37 e Å3
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
xyzUiso*/UeqOcc. (<1)
Cu10.247836 (17)0.95800 (3)0.481603 (15)0.05131 (11)
Cl10.35921 (5)0.00382 (8)0.14713 (4)0.0743 (2)
O50.3310 (6)0.0347 (6)0.0759 (3)0.137 (3)0.526 (8)
O60.4148 (6)0.0914 (8)0.1907 (5)0.160 (4)0.526 (8)
O70.3021 (5)0.0442 (11)0.1776 (5)0.194 (5)0.526 (8)
O80.4124 (5)0.1053 (8)0.1511 (4)0.172 (4)0.526 (8)
O5A0.2819 (4)0.0654 (8)0.1174 (6)0.171 (4)0.474 (8)
O6A0.3773 (6)0.0893 (10)0.2037 (5)0.142 (4)0.474 (8)
O7A0.3460 (7)0.1169 (7)0.1654 (6)0.189 (5)0.474 (8)
O8A0.4095 (7)0.0256 (11)0.1064 (6)0.211 (5)0.474 (8)
O10.24614 (9)1.04110 (15)0.38773 (8)0.0507 (4)
O20.14518 (9)0.89715 (17)0.34763 (9)0.0613 (5)
O30.13557 (11)1.29407 (18)0.29441 (10)0.0713 (5)
O1W0.0641 (2)1.5089 (3)0.36329 (18)0.1348 (11)
H1WA0.053 (3)1.572 (6)0.328 (3)0.202*
H1WB0.102 (3)1.467 (5)0.347 (3)0.202*
O2W0.03451 (17)0.7173 (2)0.26562 (13)0.0711 (6)
H2WA0.0101 (18)0.744 (3)0.2470 (16)0.083 (12)*
H2WB0.0639 (19)0.773 (3)0.2834 (18)0.088 (13)*
N10.21895 (13)1.1587 (2)0.25544 (10)0.0603 (5)
H1c0.26141.15160.23940.072*
N20.18108 (12)1.1059 (2)0.50337 (10)0.0555 (5)
N30.17989 (11)0.8531 (2)0.53567 (10)0.0512 (5)
N40.31764 (11)0.80707 (19)0.46832 (9)0.0494 (5)
N50.36506 (12)1.0145 (2)0.55542 (10)0.0528 (5)
C10.18940 (13)0.9893 (2)0.33862 (13)0.0469 (6)
C20.17408 (17)1.0408 (2)0.26354 (13)0.0613 (7)
H2A0.18820.97170.23480.074*
H2B0.11531.05830.24450.074*
C30.19661 (16)1.2779 (3)0.27197 (12)0.0548 (6)
C40.24854 (16)1.3908 (3)0.26128 (12)0.0551 (6)
C50.33219 (18)1.3778 (3)0.26646 (14)0.0681 (7)
H5A0.35781.29600.27660.082*
C60.3779 (2)1.4865 (4)0.25649 (16)0.0855 (10)
H6A0.43431.47780.26130.103*
C70.3402 (3)1.6058 (4)0.23966 (16)0.0931 (11)
H7A0.37061.67740.23110.112*
C80.2577 (2)1.6210 (3)0.23526 (16)0.0933 (11)
H8A0.23261.70310.22470.112*
C90.21196 (18)1.5137 (3)0.24663 (14)0.0718 (8)
H9A0.15631.52440.24440.086*
C100.18220 (18)1.2312 (3)0.48540 (15)0.0715 (8)
H10A0.21691.25700.45840.086*
C110.1331 (2)1.3266 (3)0.50548 (16)0.0791 (9)
H11A0.13551.41420.49230.095*
C120.08176 (18)1.2889 (3)0.54463 (16)0.0752 (9)
H12A0.04931.35150.55880.090*
C130.07750 (15)1.1573 (3)0.56363 (13)0.0597 (7)
C140.02176 (16)1.1064 (4)0.60051 (14)0.0705 (8)
H14A0.01361.16380.61470.085*
C150.01954 (16)0.9780 (4)0.61490 (14)0.0713 (8)
H15A0.01730.94820.63900.086*
C160.07213 (14)0.8855 (3)0.59429 (12)0.0584 (7)
C170.07309 (18)0.7497 (3)0.60731 (14)0.0714 (8)
H17A0.03710.71360.63060.086*
C180.12631 (19)0.6715 (3)0.58593 (14)0.0735 (8)
H18A0.12780.58150.59500.088*
C190.17905 (17)0.7261 (3)0.55018 (14)0.0639 (7)
H19A0.21530.67060.53590.077*
C200.12725 (13)0.9323 (3)0.55800 (11)0.0493 (6)
C210.12918 (14)1.0687 (3)0.54193 (12)0.0510 (6)
C220.29293 (16)0.7049 (3)0.42546 (13)0.0590 (7)
H22A0.23700.69700.40130.071*
C230.34747 (18)0.6098 (3)0.41531 (13)0.0658 (7)
H23A0.32800.53850.38550.079*
C240.42926 (18)0.6210 (3)0.44909 (14)0.0647 (7)
H24A0.46660.55970.44070.078*
C250.54225 (17)0.7436 (3)0.53543 (17)0.0742 (8)
H25A0.58200.68400.52980.089*
C260.56577 (17)0.8452 (3)0.57995 (17)0.0783 (9)
H26A0.62140.85420.60490.094*
C270.50772 (15)0.9402 (3)0.59011 (14)0.0618 (7)
C280.52854 (19)1.0504 (3)0.63461 (15)0.0772 (9)
H28A0.58311.06340.66150.093*
C290.4689 (2)1.1381 (3)0.63842 (14)0.0784 (9)
H29A0.48241.21140.66780.094*
C300.38738 (17)1.1176 (3)0.59810 (13)0.0653 (7)
H30A0.34711.17840.60120.078*
C310.42413 (14)0.9267 (2)0.55164 (12)0.0495 (6)
C320.39912 (14)0.8164 (2)0.50480 (11)0.0478 (6)
C330.45771 (15)0.7244 (3)0.49641 (14)0.0570 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.05481 (18)0.0533 (2)0.04946 (19)0.00270 (14)0.02070 (13)0.00611 (14)
Cl10.0698 (5)0.0678 (5)0.0857 (6)0.0034 (4)0.0224 (4)0.0037 (4)
O50.179 (7)0.153 (5)0.074 (3)0.016 (5)0.028 (4)0.024 (3)
O60.175 (7)0.121 (5)0.155 (7)0.047 (5)0.000 (5)0.001 (5)
O70.168 (6)0.221 (9)0.251 (8)0.023 (6)0.153 (6)0.013 (6)
O80.186 (6)0.150 (6)0.206 (7)0.078 (5)0.096 (5)0.002 (5)
O5A0.093 (4)0.185 (7)0.221 (8)0.052 (4)0.021 (5)0.077 (6)
O6A0.195 (8)0.137 (6)0.129 (5)0.032 (5)0.103 (5)0.066 (4)
O7A0.203 (8)0.083 (5)0.249 (9)0.018 (5)0.012 (7)0.079 (5)
O8A0.236 (8)0.247 (9)0.235 (9)0.025 (7)0.204 (8)0.035 (7)
O10.0484 (9)0.0580 (10)0.0461 (9)0.0072 (8)0.0142 (7)0.0044 (8)
O20.0484 (9)0.0638 (11)0.0717 (12)0.0112 (9)0.0168 (8)0.0041 (9)
O30.0599 (11)0.0628 (12)0.0912 (14)0.0012 (9)0.0210 (10)0.0014 (10)
O1W0.200 (3)0.104 (2)0.120 (2)0.028 (2)0.077 (2)0.0314 (17)
O2W0.0670 (14)0.0685 (15)0.0755 (15)0.0039 (13)0.0165 (12)0.0101 (12)
N10.0781 (14)0.0539 (13)0.0528 (13)0.0050 (11)0.0248 (11)0.0003 (10)
N20.0600 (12)0.0537 (13)0.0538 (12)0.0013 (10)0.0177 (10)0.0075 (10)
N30.0539 (11)0.0584 (13)0.0438 (11)0.0005 (10)0.0179 (9)0.0062 (9)
N40.0510 (11)0.0579 (13)0.0400 (11)0.0054 (9)0.0142 (9)0.0029 (9)
N50.0593 (12)0.0621 (13)0.0389 (11)0.0070 (10)0.0172 (9)0.0030 (10)
C10.0397 (12)0.0498 (14)0.0540 (15)0.0056 (11)0.0177 (11)0.0021 (11)
C20.0769 (17)0.0524 (16)0.0500 (15)0.0044 (13)0.0102 (13)0.0037 (12)
C30.0615 (16)0.0542 (16)0.0425 (14)0.0016 (13)0.0043 (12)0.0033 (11)
C40.0664 (16)0.0567 (16)0.0381 (13)0.0051 (13)0.0078 (11)0.0005 (11)
C50.0817 (19)0.0716 (19)0.0568 (16)0.0065 (16)0.0291 (14)0.0101 (14)
C60.092 (2)0.108 (3)0.069 (2)0.030 (2)0.0437 (18)0.0220 (19)
C70.128 (3)0.095 (3)0.0540 (19)0.048 (2)0.0222 (19)0.0003 (18)
C80.120 (3)0.067 (2)0.067 (2)0.019 (2)0.0154 (19)0.0177 (16)
C90.0740 (18)0.0623 (18)0.0623 (18)0.0055 (15)0.0086 (14)0.0125 (14)
C100.087 (2)0.0590 (19)0.0738 (19)0.0019 (15)0.0307 (16)0.0075 (15)
C110.101 (2)0.0536 (18)0.079 (2)0.0100 (17)0.0188 (18)0.0113 (15)
C120.0739 (19)0.081 (2)0.0656 (19)0.0199 (17)0.0117 (15)0.0224 (16)
C130.0546 (15)0.0753 (19)0.0440 (14)0.0125 (13)0.0051 (12)0.0129 (13)
C140.0526 (15)0.112 (3)0.0477 (16)0.0184 (17)0.0150 (12)0.0151 (16)
C150.0510 (15)0.117 (3)0.0479 (16)0.0035 (17)0.0171 (12)0.0020 (17)
C160.0472 (13)0.091 (2)0.0364 (13)0.0051 (14)0.0104 (11)0.0068 (13)
C170.0722 (18)0.095 (2)0.0485 (16)0.0216 (17)0.0204 (14)0.0004 (15)
C180.097 (2)0.0706 (19)0.0576 (17)0.0183 (17)0.0293 (16)0.0003 (15)
C190.0803 (18)0.0587 (18)0.0562 (16)0.0031 (14)0.0253 (14)0.0033 (13)
C200.0463 (13)0.0659 (17)0.0332 (12)0.0024 (12)0.0072 (10)0.0077 (11)
C210.0464 (13)0.0682 (18)0.0365 (12)0.0041 (12)0.0086 (10)0.0119 (11)
C220.0644 (15)0.0621 (17)0.0473 (15)0.0116 (13)0.0105 (12)0.0064 (12)
C230.089 (2)0.0586 (17)0.0480 (15)0.0192 (15)0.0172 (14)0.0020 (12)
C240.0800 (19)0.0588 (18)0.0638 (17)0.0262 (15)0.0343 (15)0.0180 (14)
C250.0550 (16)0.077 (2)0.095 (2)0.0110 (15)0.0278 (16)0.0343 (18)
C260.0469 (15)0.094 (2)0.089 (2)0.0066 (16)0.0106 (15)0.0382 (19)
C270.0539 (15)0.0764 (19)0.0531 (16)0.0131 (14)0.0118 (12)0.0228 (14)
C280.0665 (18)0.100 (3)0.0573 (18)0.0336 (18)0.0038 (14)0.0147 (17)
C290.094 (2)0.088 (2)0.0497 (17)0.036 (2)0.0143 (16)0.0061 (15)
C300.0811 (18)0.0706 (19)0.0462 (15)0.0156 (15)0.0214 (13)0.0093 (13)
C310.0509 (13)0.0606 (16)0.0393 (13)0.0063 (12)0.0167 (11)0.0108 (11)
C320.0510 (13)0.0557 (15)0.0407 (13)0.0030 (11)0.0196 (11)0.0118 (11)
C330.0574 (15)0.0610 (17)0.0582 (16)0.0107 (13)0.0252 (12)0.0229 (13)
Geometric parameters (Å, º) top
Cu1—N41.9908 (19)C8—C91.387 (4)
Cu1—N21.991 (2)C8—H8A0.9300
Cu1—O12.0195 (16)C9—H9A0.9300
Cu1—N32.061 (2)C10—C111.399 (4)
Cu1—N52.1685 (19)C10—H10A0.9300
Cu1—O22.7782 (17)C11—C121.362 (4)
Cl1—O7A1.312 (6)C11—H11A0.9300
Cl1—O8A1.335 (6)C12—C131.394 (4)
Cl1—O71.357 (6)C12—H12A0.9300
Cl1—O6A1.374 (6)C13—C211.398 (3)
Cl1—O51.380 (5)C13—C141.432 (4)
Cl1—O61.394 (7)C14—C151.336 (4)
Cl1—O81.411 (5)C14—H14A0.9300
Cl1—O5A1.412 (5)C15—C161.424 (4)
O1—C11.264 (3)C15—H15A0.9300
O2—C11.238 (3)C16—C201.401 (3)
O3—C31.236 (3)C16—C171.401 (4)
O1W—H1WA0.92 (5)C17—C181.348 (4)
O1W—H1WB0.90 (5)C17—H17A0.9300
O2W—H2WA0.79 (3)C18—C191.391 (4)
O2W—H2WB0.77 (3)C18—H18A0.9300
N1—C31.334 (3)C19—H19A0.9300
N1—C21.446 (3)C20—C211.422 (3)
N1—H1c0.8600C22—C231.384 (3)
N2—C101.321 (3)C22—H22A0.9300
N2—C211.360 (3)C23—C241.353 (4)
N3—C191.321 (3)C23—H23A0.9300
N3—C201.357 (3)C24—C331.393 (4)
N4—C221.326 (3)C24—H24A0.9300
N4—C321.358 (3)C25—C261.338 (4)
N5—C301.327 (3)C25—C331.425 (4)
N5—C311.352 (3)C25—H25A0.9300
C1—C21.516 (3)C26—C271.425 (4)
C2—H2A0.9700C26—H26A0.9300
C2—H2B0.9700C27—C281.401 (4)
C3—C41.491 (3)C27—C311.402 (3)
C4—C91.385 (4)C28—C291.359 (4)
C4—C51.387 (4)C28—H28A0.9300
C5—C61.389 (4)C29—C301.391 (4)
C5—H5A0.9300C29—H29A0.9300
C6—C71.363 (5)C30—H30A0.9300
C6—H6A0.9300C31—C321.434 (3)
C7—C81.374 (5)C32—C331.401 (3)
C7—H7A0.9300
N4—Cu1—N2175.32 (8)C6—C7—C8120.4 (3)
N4—Cu1—O193.38 (7)C6—C7—H7A119.8
N2—Cu1—O190.98 (8)C8—C7—H7A119.8
N4—Cu1—N395.88 (8)C7—C8—C9119.8 (3)
N2—Cu1—N381.46 (9)C7—C8—H8A120.1
O1—Cu1—N3144.91 (7)C9—C8—H8A120.1
N4—Cu1—N580.37 (8)C4—C9—C8120.4 (3)
N2—Cu1—N596.79 (8)C4—C9—H9A119.8
O1—Cu1—N5106.02 (7)C8—C9—H9A119.8
N3—Cu1—N5108.88 (7)N2—C10—C11122.5 (3)
O2—Cu1—N5153.69 (6)N2—C10—H10A118.8
O2—Cu1—N486.38 (6)C11—C10—H10A118.8
O2—Cu1—N394.95 (6)C12—C11—C10118.9 (3)
O2—Cu1—N297.67 (7)C12—C11—H11A120.6
O2—Cu1—O151.95 (6)C10—C11—H11A120.6
O7A—Cl1—O8A120.1 (7)C11—C12—C13120.6 (3)
O7A—Cl1—O749.4 (5)C11—C12—H12A119.7
O8A—Cl1—O7165.8 (6)C13—C12—H12A119.7
O7A—Cl1—O6A112.6 (6)C12—C13—C21116.9 (3)
O8A—Cl1—O6A110.2 (5)C12—C13—C14124.8 (3)
O7—Cl1—O6A83.9 (5)C21—C13—C14118.2 (3)
O7A—Cl1—O5116.9 (5)C15—C14—C13121.3 (3)
O8A—Cl1—O556.7 (5)C15—C14—H14A119.3
O7—Cl1—O5116.4 (5)C13—C14—H14A119.3
O6A—Cl1—O5127.6 (6)C14—C15—C16121.7 (3)
O7A—Cl1—O6124.3 (6)C14—C15—H15A119.1
O8A—Cl1—O680.4 (6)C16—C15—H15A119.1
O7—Cl1—O6113.2 (5)C20—C16—C17116.8 (3)
O6A—Cl1—O631.2 (5)C20—C16—C15118.3 (3)
O5—Cl1—O6117.1 (5)C17—C16—C15124.9 (3)
O7A—Cl1—O853.5 (5)C18—C17—C16119.8 (3)
O8A—Cl1—O870.5 (5)C18—C17—H17A120.1
O7—Cl1—O8102.1 (5)C16—C17—H17A120.1
O6A—Cl1—O8117.3 (6)C17—C18—C19119.7 (3)
O5—Cl1—O8105.4 (4)C17—C18—H18A120.1
O6—Cl1—O899.3 (5)C19—C18—H18A120.1
O7A—Cl1—O5A108.6 (5)N3—C19—C18123.0 (3)
O8A—Cl1—O5A110.1 (6)N3—C19—H19A118.5
O7—Cl1—O5A70.0 (5)C18—C19—H19A118.5
O6A—Cl1—O5A91.3 (6)N3—C20—C16123.3 (2)
O5—Cl1—O5A57.8 (4)N3—C20—C21116.6 (2)
O6—Cl1—O5A110.6 (6)C16—C20—C21120.1 (2)
O8—Cl1—O5A149.9 (5)N2—C21—C13122.8 (2)
C1—O1—Cu1109.64 (15)N2—C21—C20116.9 (2)
H1WA—O1W—H1WB95 (5)C13—C21—C20120.3 (2)
H2WA—O2W—H2WB111 (3)N4—C22—C23122.4 (2)
C3—N1—C2122.1 (2)N4—C22—H22A118.8
C3—N1—H1c118.9C23—C22—H22A118.8
C2—N1—H1c118.9C24—C23—C22119.6 (3)
C10—N2—C21118.4 (2)C24—C23—H23A120.2
C10—N2—Cu1128.10 (19)C22—C23—H23A120.2
C21—N2—Cu1113.48 (17)C23—C24—C33120.1 (2)
C19—N3—C20117.4 (2)C23—C24—H24A120.0
C19—N3—Cu1131.03 (18)C33—C24—H24A120.0
C20—N3—Cu1111.52 (16)C26—C25—C33121.5 (3)
C22—N4—C32118.6 (2)C26—C25—H25A119.2
C22—N4—Cu1126.43 (16)C33—C25—H25A119.2
C32—N4—Cu1114.90 (15)C25—C26—C27121.7 (3)
C30—N5—C31118.3 (2)C25—C26—H26A119.2
C30—N5—Cu1132.25 (19)C27—C26—H26A119.2
C31—N5—Cu1109.41 (15)C28—C27—C31116.8 (3)
O2—C1—O1124.0 (2)C28—C27—C26124.5 (3)
O2—C1—C2117.1 (2)C31—C27—C26118.7 (3)
O1—C1—C2118.9 (2)C29—C28—C27119.9 (3)
N1—C2—C1116.2 (2)C29—C28—H28A120.1
N1—C2—H2A108.2C27—C28—H28A120.1
C1—C2—H2A108.2C28—C29—C30119.7 (3)
N1—C2—H2B108.2C28—C29—H29A120.2
C1—C2—H2B108.2C30—C29—H29A120.2
H2A—C2—H2B107.4N5—C30—C29122.3 (3)
O3—C3—N1121.7 (2)N5—C30—H30A118.8
O3—C3—C4121.7 (2)C29—C30—H30A118.8
N1—C3—C4116.5 (2)N5—C31—C27123.1 (2)
C9—C4—C5118.9 (3)N5—C31—C32117.5 (2)
C9—C4—C3118.6 (2)C27—C31—C32119.4 (2)
C5—C4—C3122.6 (2)N4—C32—C33122.0 (2)
C6—C5—C4120.2 (3)N4—C32—C31117.6 (2)
C6—C5—H5A119.9C33—C32—C31120.5 (2)
C4—C5—H5A119.9C24—C33—C32117.4 (2)
C7—C6—C5120.2 (3)C24—C33—C25124.4 (3)
C7—C6—H6A119.9C32—C33—C25118.2 (3)
C5—C6—H6A119.9
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1WA···O2Wi0.92 (6)1.89 (6)2.803 (4)172 (5)
O1W—H1WB···O30.90 (5)2.19 (5)2.990 (4)148 (5)
O2W—H2WA···O3ii0.78 (3)2.10 (3)2.876 (3)172 (3)
O2W—H2WB···O20.77 (3)2.02 (3)2.774 (3)169 (3)
Symmetry codes: (i) x, y+1, z; (ii) x, y1/2, z+1/2.
 

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