trans-Bis(5,5-di­phenyl­hydantoinato)­bis(2-phenyl­ethyl­amine)copper(II)

The title compound, [Cu(C₁₅H₁₁N₂O₂)₂(C₈H₁₁N)₂], has its metal atom in a square-planar trans-CuN₄ coordination environment; the Cu^II atom lies on a center of symmetry. The 5,5-di­phenyl­hydantoinate and 2-phenyl­ethyl­amine ligands behave as monodentate ligands and bind through their N atoms. The crystal structure is stabilized by N—H...O=C intermolecular hydrogen bonds [N...O = 2.864 (3) Å].

Key indicators

• Single-crystal X-ray study
• T = 297 K
• R factor = 0.047
• wR factor = 0.152
• Data-to-parameter ratio = 11.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.70 mm
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.05 Ratio
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....        C17

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: WinAFC Diffractometer Control Software (Rigaku, 1999); cell refinement: WinAFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 2001); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.

(I)

Crystal data

[Cu(C15H11N2O2)2(C8H11N)2]	F(000) = 846.0
Mr = 808.42	Dx = 1.330 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 11.050 (9) Å	θ = 10.4–13.0°
b = 18.502 (10) Å	µ = 0.59 mm^−1
c = 9.916 (5) Å	T = 297 K
β = 95.08 (5)°	Prismatic, red violet
V = 2019 (2) Å^3	0.70 × 0.50 × 0.30 mm
Z = 2

Data collection

Rigaku AFC-7R diffractometer	Rint = 0.034
ω–2θ scans	θmax = 27.5°
Absorption correction: ψ scan (North et al., 1968)	h = −14→14
Tmin = 0.708, Tmax = 0.837	k = 0→24
5357 measured reflections	l = −12→5
4643 independent reflections	3 standard reflections every 150 reflections
4635 reflections with I > 2σ(I)	intensity decay: 3.3%

Refinement

Refinement on F^2	H-atom parameters not refined
R[F^2 > 2σ(F^2)] = 0.047	w = 1/[σ^2(Fo^2) + (0.0561P)^2 + 2.676P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.152	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.55 e Å^−3
4635 reflections	Δρmin = −0.94 e Å^−3
259 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cu1	0.5000	0.5000	0.5000	0.0351 (2)
O1	0.5641 (2)	0.4876 (1)	0.8337 (2)	0.0410 (6)
O2	0.2446 (2)	0.5762 (2)	0.5626 (2)	0.0493 (6)
N1	0.4205 (2)	0.5272 (1)	0.6639 (2)	0.0324 (5)
N2	0.3783 (2)	0.5292 (2)	0.8807 (2)	0.0359 (6)
N3	0.4551 (3)	0.5961 (2)	0.4112 (3)	0.0571 (9)
C1	0.4629 (3)	0.5120 (2)	0.7974 (3)	0.0306 (6)
C2	0.3073 (3)	0.5544 (2)	0.6623 (3)	0.0328 (6)
C3	0.2658 (3)	0.5544 (2)	0.8083 (3)	0.0315 (6)
C4	0.1621 (3)	0.5005 (2)	0.8200 (3)	0.0357 (6)
C5	0.1554 (4)	0.4625 (2)	0.9407 (4)	0.0501 (9)
C6	0.0613 (4)	0.4156 (3)	0.9560 (5)	0.067 (1)
C7	−0.0274 (5)	0.4042 (3)	0.8544 (6)	0.077 (1)
C8	−0.0235 (5)	0.4416 (3)	0.7349 (6)	0.080 (1)
C9	0.0709 (4)	0.4893 (2)	0.7166 (4)	0.060 (1)
C10	0.2296 (3)	0.6297 (2)	0.8513 (3)	0.0332 (6)
C11	0.1283 (3)	0.6632 (2)	0.7886 (4)	0.0463 (8)
C12	0.0938 (4)	0.7313 (2)	0.8297 (4)	0.058 (1)
C13	0.1582 (4)	0.7663 (2)	0.9324 (5)	0.058 (1)
C14	0.2577 (4)	0.7335 (2)	0.9962 (5)	0.065 (1)
C15	0.2947 (3)	0.6656 (2)	0.9568 (4)	0.0500 (9)
C16	0.5543 (5)	0.6455 (2)	0.3803 (4)	0.063 (1)
C17	0.5145 (5)	0.7021 (3)	0.2760 (5)	0.078 (1)
C18	0.6172 (4)	0.7484 (2)	0.2325 (4)	0.058 (1)
C19	0.6264 (5)	0.8207 (3)	0.2679 (4)	0.071 (1)
C20	0.7157 (6)	0.8641 (3)	0.2243 (6)	0.084 (2)
C21	0.7990 (5)	0.8357 (4)	0.1445 (7)	0.094 (2)
C22	0.7926 (5)	0.7635 (4)	0.1077 (7)	0.089 (2)
C23	0.7029 (5)	0.7209 (2)	0.1523 (5)	0.068 (1)
H1	0.3904	0.5254	0.9765	0.0431*
H2	0.2167	0.4692	1.0130	0.0601*
H3	0.0582	0.3905	1.0393	0.0806*
H4	−0.0911	0.3709	0.8657	0.0921*
H5	−0.0860	0.4347	0.6641	0.0957*
H6	0.0730	0.5143	0.6331	0.0725*
H7	0.0816	0.6395	0.7167	0.0556*
H8	0.0239	0.7537	0.7851	0.0697*
H9	0.1344	0.8131	0.9595	0.0699*
H10	0.3026	0.7575	1.0691	0.0775*
H11	0.3647	0.6438	1.0022	0.0600*
H12	0.4087	0.5860	0.3280	0.0685*
H13	0.4061	0.6213	0.4696	0.0685*
H14	0.5840	0.6692	0.4615	0.0760*
H15	0.6176	0.6177	0.3472	0.0760*
H16	0.4770	0.6784	0.1982	0.0934*
H17	0.4570	0.7329	0.3131	0.0934*
H18	0.5695	0.8408	0.3239	0.0853*
H19	0.7198	0.9137	0.2492	0.1011*
H20	0.8612	0.8655	0.1144	0.1125*
H21	0.8500	0.7437	0.0520	0.1066*
H22	0.6993	0.6713	0.1277	0.0816*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0545 (3)	0.0380 (3)	0.0132 (2)	0.0096 (3)	0.0061 (2)	0.0032 (2)
O1	0.040 (1)	0.064 (2)	0.0186 (9)	0.017 (1)	0.0019 (8)	0.0029 (9)
O2	0.052 (1)	0.069 (2)	0.025 (1)	0.015 (1)	−0.0043 (10)	0.014 (1)
N1	0.044 (1)	0.041 (1)	0.0122 (10)	0.009 (1)	0.0007 (9)	0.0021 (9)
N2	0.038 (1)	0.055 (2)	0.014 (1)	0.014 (1)	0.0020 (9)	0.005 (1)
N3	0.098 (3)	0.050 (2)	0.026 (1)	0.028 (2)	0.022 (1)	0.011 (1)
C1	0.038 (2)	0.040 (2)	0.014 (1)	0.006 (1)	0.000 (1)	0.002 (1)
C2	0.042 (2)	0.038 (2)	0.018 (1)	0.005 (1)	0.000 (1)	0.004 (1)
C3	0.034 (2)	0.043 (2)	0.017 (1)	0.008 (1)	0.002 (1)	0.004 (1)
C4	0.041 (2)	0.031 (1)	0.036 (1)	0.006 (1)	0.008 (1)	−0.003 (1)
C5	0.055 (2)	0.053 (2)	0.044 (2)	0.008 (2)	0.019 (2)	0.012 (2)
C6	0.070 (3)	0.058 (3)	0.079 (3)	−0.002 (2)	0.037 (2)	0.008 (2)
C7	0.076 (3)	0.057 (3)	0.103 (4)	−0.025 (2)	0.041 (3)	−0.018 (3)
C8	0.075 (3)	0.080 (3)	0.083 (3)	−0.031 (3)	0.003 (3)	−0.026 (3)
C9	0.063 (2)	0.069 (3)	0.049 (2)	−0.021 (2)	−0.001 (2)	−0.004 (2)
C10	0.036 (2)	0.037 (2)	0.028 (1)	0.000 (1)	0.007 (1)	0.003 (1)
C11	0.052 (2)	0.043 (2)	0.042 (2)	0.011 (2)	−0.006 (2)	−0.001 (1)
C12	0.062 (2)	0.052 (2)	0.059 (2)	0.017 (2)	−0.002 (2)	0.003 (2)
C13	0.074 (3)	0.030 (2)	0.071 (3)	0.007 (2)	0.010 (2)	−0.006 (2)
C14	0.069 (3)	0.057 (3)	0.066 (3)	−0.007 (2)	−0.008 (2)	−0.019 (2)
C15	0.049 (2)	0.050 (2)	0.050 (2)	0.004 (2)	−0.007 (2)	−0.011 (2)
C16	0.103 (3)	0.046 (2)	0.036 (2)	−0.002 (2)	−0.018 (2)	0.006 (2)
C17	0.105 (4)	0.071 (3)	0.059 (3)	0.022 (3)	0.016 (3)	0.029 (2)
C18	0.084 (3)	0.054 (2)	0.037 (2)	0.017 (2)	−0.001 (2)	0.014 (2)
C19	0.107 (4)	0.063 (3)	0.042 (2)	0.022 (3)	0.000 (2)	−0.001 (2)
C20	0.093 (4)	0.066 (3)	0.086 (4)	0.006 (3)	−0.033 (3)	−0.019 (3)
C21	0.056 (3)	0.085 (4)	0.135 (5)	−0.010 (3)	−0.021 (3)	0.011 (4)
C22	0.058 (3)	0.095 (4)	0.114 (4)	0.013 (3)	0.014 (3)	0.001 (4)
C23	0.086 (3)	0.054 (3)	0.063 (3)	0.023 (2)	0.005 (2)	−0.001 (2)

Geometric parameters (Å, º)

Cu1—N1	1.979 (2)	C10—C15	1.386 (5)
Cu1—N3	2.026 (3)	C11—C12	1.388 (6)
O1—C1	1.230 (4)	C11—H7	0.950
O2—C2	1.225 (4)	C12—C13	1.355 (6)
N1—C1	1.393 (3)	C12—H8	0.950
N1—C2	1.347 (4)	C13—C14	1.362 (6)
N2—C1	1.340 (4)	C13—H9	0.950
N2—C3	1.457 (4)	C14—C15	1.387 (6)
N2—H1	0.950	C14—H10	0.950
N3—C16	1.480 (6)	C15—H11	0.950
N3—H12	0.950	C16—C17	1.510 (6)
N3—H13	0.950	C16—H14	0.950
C2—C3	1.556 (4)	C16—H15	0.950
C3—C4	1.531 (4)	C17—C18	1.515 (7)
C3—C10	1.521 (4)	C17—H16	0.950
C4—C5	1.395 (5)	C17—H17	0.950
C4—C9	1.388 (5)	C18—C19	1.385 (7)
C5—C6	1.374 (6)	C18—C23	1.387 (7)
C5—H2	0.950	C19—C20	1.372 (8)
C6—C7	1.358 (7)	C19—H18	0.950
C6—H3	0.950	C20—C21	1.371 (9)
C7—C8	1.376 (8)	C20—H19	0.950
C7—H4	0.950	C21—C22	1.384 (9)
C8—C9	1.390 (7)	C21—H20	0.950
C8—H5	0.950	C22—C23	1.370 (8)
C9—H6	0.950	C22—H21	0.950
C10—C11	1.379 (5)	C23—H22	0.950
N1—Cu1—N3	91.4 (1)	C11—C10—C15	118.1 (3)
N1—Cu1—N3^i	88.6 (1)	C10—C11—C12	120.6 (3)
Cu1—N1—C1	126.3 (2)	C10—C11—H7	119.7
Cu1—N1—C2	124.4 (2)	C12—C11—H7	119.7
C1—N1—C2	108.7 (2)	C11—C12—C13	121.0 (4)
C1—N2—C3	112.6 (2)	C11—C12—H8	119.5
C1—N2—H1	123.7	C13—C12—H8	119.5
C3—N2—H1	123.7	C12—C13—C14	118.9 (4)
Cu1—N3—C16	118.3 (3)	C12—C13—H9	120.5
Cu1—N3—H12	107.2	C14—C13—H9	120.5
Cu1—N3—H13	107.2	C13—C14—C15	121.3 (4)
C16—N3—H12	107.2	C13—C14—H10	119.4
C16—N3—H13	107.2	C15—C14—H10	119.4
H12—N3—H13	109.5	C10—C15—C14	120.1 (3)
O1—C1—N1	124.9 (3)	C10—C15—H11	120.0
O1—C1—N2	125.0 (2)	C14—C15—H11	120.0
N1—C1—N2	110.1 (2)	N3—C16—C17	113.2 (4)
O2—C2—N1	126.2 (3)	N3—C16—H14	108.5
O2—C2—C3	124.0 (3)	N3—C16—H15	108.5
N1—C2—C3	109.8 (2)	C17—C16—H14	108.5
N2—C3—C2	98.6 (2)	C17—C16—H15	108.5
N2—C3—C4	111.5 (3)	H14—C16—H15	109.5
N2—C3—C10	112.9 (2)	C16—C17—C18	114.0 (4)
C2—C3—C4	110.8 (2)	C16—C17—H16	108.3
C2—C3—C10	111.6 (2)	C16—C17—H17	108.3
C4—C3—C10	111.0 (3)	C18—C17—H16	108.3
C3—C4—C5	119.3 (3)	C18—C17—H17	108.3
C3—C4—C9	122.7 (3)	H16—C17—H17	109.5
C5—C4—C9	117.9 (3)	C17—C18—C19	121.0 (4)
C4—C5—C6	120.7 (3)	C17—C18—C23	121.5 (4)
C4—C5—H2	119.6	C19—C18—C23	117.5 (4)
C6—C5—H2	119.6	C18—C19—C20	121.6 (5)
C5—C6—C7	121.3 (5)	C18—C19—H18	119.2
C5—C6—H3	119.3	C20—C19—H18	119.2
C7—C6—H3	119.3	C19—C20—C21	119.7 (5)
C6—C7—C8	119.0 (5)	C19—C20—H19	120.2
C6—C7—H4	120.5	C21—C20—H19	120.2
C8—C7—H4	120.5	C20—C21—C22	120.1 (6)
C7—C8—C9	120.9 (5)	C20—C21—H20	119.9
C7—C8—H5	119.6	C22—C21—H20	119.9
C9—C8—H5	119.6	C21—C22—C23	119.4 (5)
C4—C9—C8	120.1 (4)	C21—C22—H21	120.3
C4—C9—H6	119.9	C23—C22—H21	120.3
C8—C9—H6	119.9	C18—C23—C22	121.6 (5)
C3—C10—C11	120.6 (3)	C18—C23—H22	119.2
C3—C10—C15	121.3 (3)	C22—C23—H22	119.2
Cu1—N1—C1—O1	9.9 (4)	C2—C3—C4—C5	144.7 (3)
Cu1—N1—C1—N2	−171.2 (2)	C2—C3—C4—C9	−37.5 (4)
Cu1—N1—C2—O2	−11.6 (5)	C2—C3—C10—C11	67.1 (4)
Cu1—N1—C2—C3	168.5 (2)	C2—C3—C10—C15	−115.0 (3)
Cu1—N1^i—C1^i—O1^i	−9.9 (4)	C3—C4—C5—C6	177.9 (4)
Cu1—N1^i—C1^i—N2^i	171.2 (2)	C3—C4—C9—C8	−177.6 (4)
Cu1—N1^i—C2^i—O2^i	11.6 (5)	C3—C10—C11—C12	178.7 (3)
Cu1—N1^i—C2^i—C3^i	−168.5 (2)	C3—C10—C15—C14	−178.3 (3)
Cu1—N3—C16—C17	161.0 (3)	C4—C3—C10—C11	−57.0 (4)
Cu1—N3^i—C16^i—C17^i	−161.0 (3)	C4—C3—C10—C15	121.0 (3)
O1—C1—N1—C2	−178.9 (3)	C4—C5—C6—C7	0.5 (7)
O1—C1—N2—C3	−177.9 (3)	C4—C9—C8—C7	−0.9 (7)
O2—C2—N1—C1	176.9 (3)	C5—C4—C3—C10	−90.7 (4)
O2—C2—C3—N2	−175.4 (3)	C5—C4—C9—C8	0.2 (6)
O2—C2—C3—C4	67.6 (4)	C5—C6—C7—C8	−1.2 (8)
O2—C2—C3—C10	−56.5 (4)	C6—C5—C4—C9	0.0 (6)
N1—Cu1—N3—C16	116.4 (3)	C6—C7—C8—C9	1.3 (8)
N1—Cu1—N3^i—C16^i	63.6 (3)	C9—C4—C3—C10	87.0 (4)
N1—C1—N2—C3	3.3 (4)	C10—C11—C12—C13	−0.3 (6)
N1—C2—C3—N2	4.5 (3)	C10—C15—C14—C13	−0.5 (7)
N1—C2—C3—C4	−112.5 (3)	C11—C10—C15—C14	−0.3 (5)
N1—C2—C3—C10	123.4 (3)	C11—C12—C13—C14	−0.5 (7)
N2—C1—N1—C2	0.0 (3)	C12—C11—C10—C15	0.6 (5)
N2—C3—C4—C5	36.0 (4)	C12—C13—C14—C15	0.9 (7)
N2—C3—C4—C9	−146.2 (3)	C16—C17—C18—C19	−110.7 (5)
N2—C3—C10—C11	177.1 (3)	C16—C17—C18—C23	71.5 (5)
N2—C3—C10—C15	−4.9 (4)	C17—C18—C19—C20	−177.0 (4)
N3—Cu1—N1—C1	−140.8 (3)	C17—C18—C23—C22	177.0 (5)
N3—Cu1—N1—C2	49.3 (3)	C18—C19—C20—C21	−0.6 (8)
N3—Cu1—N1^i—C1^i	−39.2 (3)	C18—C23—C22—C21	0.7 (8)
N3—Cu1—N1^i—C2^i	130.7 (3)	C19—C18—C23—C22	−0.9 (7)
N3—C16—C17—C18	−174.1 (3)	C19—C20—C21—C22	0.3 (9)
C1—N1—C2—C3	−3.0 (3)	C20—C19—C18—C23	0.9 (7)
C1—N2—C3—C2	−4.6 (3)	C20—C21—C22—C23	−0.4 (9)
C1—N2—C3—C4	111.9 (3)	C20—C21—C22—C23	−0.4 (9)
C1—N2—C3—C10	−122.5 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H13···O2	0.95	2.24	2.901 (4)	126
N3—H12···O1^i	0.95	2.15	2.872 (3)	132
N2—H1···O1^ii	0.95	1.92	2.864 (3)	172

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z+2.