Bis(5,5-diphenyl­hydantoinato-κN3)bis­(1H-imidazole-κN3)copper(II) monohydrate

Xu, X.-Y.; Xu, T.-T.; Ma, H.-P.; Hu, X.-L.; Wang, D.-Q.

doi:10.1107/S1600536806028509

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Bis(5,5-diphenylhydantoinato-κN³)bis(1H-imidazole-κN³)copper(II) monohydrate

X.-Y. Xu, T.-T. Xu, H.-P. Ma, X.-L. Hu and D.-Q. Wang

In the title compound, [Cu(C₁₅H₁₁N₂O₂)₂(C₃H₄N₂)₂]·H₂O, the Cu^II ion has a distorted square-planar CuN₄ coordination environment. The crystal structure is stabilized by intermolecular hydrogen bonding.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806028509/xu2067sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806028509/xu2067Isup2.hkl Contains datablock I

CCDC reference: 618345

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.010 Å
R factor = 0.049
wR factor = 0.134
Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.91 Ratio

Alert level C
PLAT034_ALERT_1_C No Flack Parameter Given. Z .GT. Si, NonCentro .          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT220_ALERT_2_C Large Non-Solvent    N     Ueq(max)/Ueq(min) ...       2.77 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.37 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C6
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        C32
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N5
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C4
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C19
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         10
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      46.00 A   3 

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               6182
           Count of symmetry unique reflns         3518
           Completeness (_total/calc)            175.72%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2664
           Fraction of Friedel pairs measured     0.757
           Are heavy atom types Z>Si present        yes

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   9 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 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, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL'.

Bis(5,5-diphenylhydantoinato-κN³)bis(1H-imidazole-κN³)copper(II) monohydrate top

Crystal data top

[Cu(C₁₅H₁₁N₂O₂)₂(C₃H₄N₂)₂]·H₂O	F(000) = 1492
M_r = 720.24	D_x = 1.357 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: p 2ac 2ab	Cell parameters from 3376 reflections
a = 8.615 (2) Å	θ = 2.5–19.6°
b = 16.576 (3) Å	µ = 0.67 mm⁻¹
c = 24.680 (4) Å	T = 298 K
V = 3524.4 (12) Å³	Prism, red
Z = 4	0.38 × 0.21 × 0.11 mm

Data collection top

Bruker APEX area-dectector diffractometer	6182 independent reflections
Radiation source: fine-focus sealed tube	3915 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.061
φ and ω scans	θ_max = 25.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −10→10
T_min = 0.784, T_max = 0.930	k = −15→19
18479 measured reflections	l = −29→27

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.134	H-atom parameters constrained
S = 0.97	w = 1/[σ²(F_o²) + (0.0594P)² + 1.5734P] where P = (F_o² + 2F_c²)/3
6182 reflections	(Δ/σ)_max = 0.001
451 parameters	Δρ_max = 0.53 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cu1	0.58596 (8)	0.69500 (4)	0.85289 (2)	0.0434 (2)
N1	0.5636 (6)	0.5773 (2)	0.86204 (16)	0.0444 (11)
N2	0.5427 (5)	0.4479 (2)	0.83651 (16)	0.0480 (13)
H2	0.5134	0.4065	0.8181	0.058*
N3	0.6159 (5)	0.8104 (3)	0.83714 (14)	0.0385 (10)
N4	0.6543 (5)	0.9285 (2)	0.79484 (17)	0.0410 (12)
H4	0.6542	0.9639	0.7694	0.049*
N5	0.4273 (7)	0.7204 (3)	0.90784 (17)	0.0580 (13)
N6	0.3015 (9)	0.7253 (5)	0.9838 (2)	0.106 (3)
H6	0.2695	0.7116	1.0155	0.127*
N7	0.7812 (7)	0.6745 (3)	0.8120 (2)	0.0610 (15)
N8	1.0276 (7)	0.6759 (3)	0.7900 (3)	0.088 (2)
H8	1.1254	0.6862	0.7916	0.106*
O1	0.7063 (6)	0.5611 (2)	0.93947 (17)	0.0708 (13)
O2	0.4388 (5)	0.5458 (2)	0.78171 (14)	0.0527 (11)
O3	0.7520 (5)	0.8341 (2)	0.91491 (15)	0.0615 (12)
O4	0.5168 (4)	0.83038 (19)	0.75082 (14)	0.0478 (10)
O5	0.3464 (5)	0.6992 (3)	0.77890 (19)	0.0871 (15)
H1	0.4009	0.7346	0.7628	0.131*
H3	0.3829	0.6541	0.7686	0.131*
C1	0.6410 (7)	0.5345 (3)	0.9003 (2)	0.0502 (16)
C2	0.5074 (7)	0.5248 (3)	0.8233 (2)	0.0414 (13)
C3	0.6355 (6)	0.4433 (3)	0.8852 (2)	0.0425 (14)
C4	0.5571 (7)	0.3977 (3)	0.9304 (2)	0.0424 (14)
C5	0.4007 (9)	0.3859 (4)	0.9305 (3)	0.078 (2)
H5	0.3431	0.4030	0.9008	0.094*
C6	0.3249 (10)	0.3496 (5)	0.9732 (4)	0.095 (3)
H6A	0.2178	0.3427	0.9720	0.114*
C7	0.4058 (11)	0.3240 (4)	1.0165 (3)	0.079 (2)
H7	0.3551	0.2990	1.0452	0.094*
C8	0.5592 (11)	0.3348 (4)	1.0181 (2)	0.077 (2)
H8A	0.6159	0.3174	1.0479	0.093*
C9	0.6344 (8)	0.3722 (4)	0.9748 (2)	0.070 (2)
H9	0.7412	0.3798	0.9765	0.084*
C10	0.7951 (8)	0.4098 (4)	0.8708 (2)	0.0520 (16)
C11	0.9198 (9)	0.4582 (4)	0.8620 (3)	0.077 (2)
H11	0.9109	0.5136	0.8671	0.093*
C12	1.0618 (10)	0.4254 (7)	0.8452 (4)	0.103 (3)
H12	1.1469	0.4590	0.8400	0.124*
C13	1.0758 (11)	0.3457 (7)	0.8366 (3)	0.093 (3)
H13	1.1700	0.3243	0.8251	0.111*
C14	0.9535 (11)	0.2972 (6)	0.8445 (3)	0.096 (3)
H14	0.9631	0.2421	0.8384	0.115*
C15	0.8122 (9)	0.3287 (4)	0.8620 (3)	0.076 (2)
H15	0.7285	0.2943	0.8677	0.092*
C16	0.6971 (7)	0.8568 (3)	0.8710 (2)	0.0435 (14)
C17	0.5881 (7)	0.8548 (3)	0.79071 (19)	0.0351 (11)
C18	0.7258 (6)	0.9405 (3)	0.8476 (2)	0.0383 (12)
C19	0.9017 (7)	0.9537 (3)	0.8429 (2)	0.0420 (13)
C20	0.9832 (8)	0.9216 (4)	0.8004 (3)	0.0576 (17)
H20	0.9311	0.8942	0.7730	0.069*
C21	1.1425 (9)	0.9297 (5)	0.7982 (3)	0.074 (2)
H21	1.1970	0.9070	0.7694	0.088*
C22	1.2201 (9)	0.9700 (5)	0.8371 (4)	0.086 (3)
H22	1.3273	0.9760	0.8349	0.103*
C23	1.1417 (9)	1.0016 (5)	0.8793 (4)	0.095 (3)
H23	1.1954	1.0287	0.9065	0.114*
C24	0.9797 (8)	0.9942 (4)	0.8827 (3)	0.077 (2)
H24	0.9261	1.0165	0.9118	0.092*
C25	0.6439 (7)	1.0073 (4)	0.8787 (2)	0.0492 (16)
C26	0.6231 (7)	1.0808 (3)	0.8547 (3)	0.0640 (18)
H26	0.6635	1.0900	0.8203	0.077*
C27	0.5430 (9)	1.1417 (4)	0.8807 (4)	0.089 (3)
H27	0.5285	1.1910	0.8635	0.107*
C28	0.4854 (9)	1.1301 (5)	0.9313 (4)	0.088 (3)
H28	0.4319	1.1712	0.9488	0.106*
C29	0.5065 (10)	1.0585 (6)	0.9557 (3)	0.092 (3)
H29	0.4684	1.0505	0.9906	0.110*
C30	0.5845 (9)	0.9965 (4)	0.9296 (2)	0.0692 (18)
H30	0.5967	0.9471	0.9469	0.083*
C31	0.4011 (9)	0.6846 (4)	0.9536 (2)	0.0723 (19)
H31	0.4468	0.6362	0.9640	0.087*
C32	0.2585 (13)	0.7920 (6)	0.9563 (4)	0.137 (4)
H32	0.1903	0.8321	0.9677	0.165*
C33	0.3348 (10)	0.7883 (5)	0.9091 (3)	0.110 (3)
H33	0.3266	0.8260	0.8813	0.132*
C34	0.9184 (9)	0.7023 (4)	0.8238 (3)	0.0691 (17)
H34	0.9380	0.7368	0.8528	0.083*
C35	0.9550 (10)	0.6300 (4)	0.7528 (4)	0.093 (3)
H35	1.0002	0.6043	0.7233	0.112*
C36	0.8038 (11)	0.6288 (4)	0.7668 (3)	0.087 (2)
H36	0.7264	0.6009	0.7484	0.104*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0588 (4)	0.0314 (3)	0.0402 (3)	−0.0075 (4)	0.0066 (4)	0.0001 (3)
N1	0.061 (3)	0.028 (2)	0.045 (2)	−0.009 (2)	−0.006 (3)	0.001 (2)
N2	0.066 (3)	0.026 (2)	0.052 (3)	−0.004 (2)	−0.022 (2)	−0.0017 (19)
N3	0.045 (3)	0.038 (2)	0.032 (2)	−0.006 (2)	−0.0011 (18)	0.000 (2)
N4	0.052 (3)	0.034 (2)	0.037 (2)	−0.008 (2)	−0.010 (2)	0.006 (2)
N5	0.079 (4)	0.052 (3)	0.043 (3)	0.000 (3)	0.017 (3)	0.009 (2)
N6	0.122 (6)	0.135 (7)	0.061 (4)	−0.008 (5)	0.047 (4)	0.015 (4)
N7	0.070 (4)	0.040 (3)	0.073 (4)	−0.007 (3)	0.021 (3)	−0.006 (3)
N8	0.065 (4)	0.061 (4)	0.138 (5)	0.005 (3)	0.041 (4)	0.000 (4)
O1	0.094 (4)	0.057 (3)	0.062 (3)	−0.018 (3)	−0.033 (3)	−0.006 (2)
O2	0.072 (3)	0.038 (2)	0.047 (2)	0.003 (2)	−0.022 (2)	0.0051 (17)
O3	0.080 (3)	0.060 (3)	0.044 (2)	−0.008 (2)	−0.016 (2)	0.0094 (19)
O4	0.063 (3)	0.038 (2)	0.042 (2)	−0.0105 (18)	−0.0102 (19)	−0.0026 (17)
O5	0.090 (4)	0.044 (2)	0.128 (4)	0.004 (3)	0.040 (3)	0.003 (3)
C1	0.063 (5)	0.040 (3)	0.048 (3)	−0.012 (3)	−0.016 (3)	−0.001 (3)
C2	0.050 (4)	0.030 (3)	0.045 (3)	−0.007 (3)	−0.002 (3)	−0.001 (3)
C3	0.046 (4)	0.041 (3)	0.040 (3)	−0.008 (3)	−0.011 (3)	0.005 (3)
C4	0.050 (4)	0.030 (3)	0.047 (3)	−0.006 (3)	−0.002 (3)	0.002 (2)
C5	0.059 (5)	0.087 (5)	0.089 (5)	−0.001 (4)	−0.003 (4)	0.031 (4)
C6	0.059 (5)	0.111 (7)	0.114 (7)	−0.006 (5)	0.017 (5)	0.033 (6)
C7	0.093 (6)	0.067 (5)	0.075 (5)	−0.006 (5)	0.027 (5)	0.005 (4)
C8	0.101 (6)	0.084 (5)	0.047 (4)	0.003 (5)	−0.007 (4)	0.016 (3)
C9	0.064 (5)	0.093 (5)	0.053 (4)	−0.018 (4)	−0.008 (3)	0.019 (4)
C10	0.054 (4)	0.062 (4)	0.040 (3)	−0.004 (3)	−0.008 (3)	0.009 (3)
C11	0.055 (4)	0.083 (5)	0.094 (5)	−0.010 (5)	−0.011 (5)	0.014 (4)
C12	0.067 (6)	0.134 (8)	0.108 (6)	0.002 (6)	−0.007 (6)	0.018 (6)
C13	0.066 (5)	0.155 (9)	0.057 (4)	0.011 (7)	0.000 (4)	0.006 (5)
C14	0.102 (7)	0.100 (6)	0.086 (5)	0.048 (6)	0.006 (5)	−0.017 (5)
C15	0.082 (5)	0.066 (5)	0.082 (5)	0.008 (4)	−0.001 (4)	−0.003 (4)
C16	0.049 (4)	0.044 (3)	0.037 (3)	−0.006 (3)	0.000 (3)	0.003 (3)
C17	0.037 (3)	0.031 (3)	0.037 (3)	0.004 (3)	0.000 (3)	−0.003 (2)
C18	0.045 (3)	0.030 (3)	0.040 (3)	−0.004 (2)	−0.002 (3)	−0.004 (3)
C19	0.043 (3)	0.032 (3)	0.051 (3)	−0.004 (3)	−0.002 (3)	−0.001 (2)
C20	0.061 (5)	0.058 (4)	0.054 (4)	−0.002 (3)	0.005 (3)	−0.001 (3)
C21	0.059 (5)	0.082 (5)	0.081 (5)	0.011 (4)	0.020 (4)	0.005 (4)
C22	0.044 (5)	0.084 (6)	0.129 (8)	−0.002 (4)	0.001 (5)	0.013 (5)
C23	0.054 (5)	0.098 (6)	0.133 (8)	−0.013 (5)	−0.023 (5)	−0.036 (6)
C24	0.056 (5)	0.086 (5)	0.089 (5)	−0.011 (4)	−0.004 (4)	−0.039 (4)
C25	0.043 (4)	0.048 (4)	0.057 (4)	−0.004 (3)	−0.005 (3)	−0.014 (3)
C26	0.074 (5)	0.033 (3)	0.085 (4)	−0.004 (3)	0.009 (4)	−0.007 (3)
C27	0.075 (6)	0.046 (4)	0.148 (8)	−0.005 (4)	0.001 (5)	−0.026 (5)
C28	0.058 (5)	0.075 (6)	0.132 (8)	0.008 (4)	0.001 (5)	−0.046 (6)
C29	0.084 (6)	0.110 (7)	0.082 (5)	0.008 (6)	0.017 (4)	−0.030 (5)
C30	0.073 (5)	0.068 (4)	0.067 (4)	0.008 (5)	0.005 (4)	−0.011 (3)
C31	0.084 (5)	0.077 (5)	0.056 (4)	−0.008 (5)	0.004 (4)	0.012 (4)
C32	0.158 (10)	0.119 (7)	0.134 (8)	0.056 (8)	0.100 (7)	0.049 (7)
C33	0.134 (8)	0.093 (6)	0.103 (6)	0.044 (6)	0.074 (6)	0.037 (5)
C34	0.070 (5)	0.043 (3)	0.094 (4)	0.001 (4)	0.023 (4)	−0.009 (3)
C35	0.093 (7)	0.066 (5)	0.121 (7)	−0.006 (4)	0.060 (6)	−0.016 (5)
C36	0.102 (7)	0.067 (5)	0.093 (6)	−0.014 (5)	0.040 (5)	−0.010 (4)

Geometric parameters (Å, º) top

Cu1—N1	1.974 (4)	C10—C11	1.359 (9)
Cu1—N3	1.969 (4)	C10—C15	1.370 (8)
Cu1—N5	1.971 (5)	C11—C12	1.402 (11)
Cu1—N7	1.990 (5)	C11—H11	0.9300
N1—C1	1.356 (6)	C12—C13	1.343 (11)
N1—C2	1.381 (6)	C12—H12	0.9300
N2—C2	1.351 (6)	C13—C14	1.340 (11)
N2—C3	1.444 (6)	C13—H13	0.9300
N2—H2	0.8600	C14—C15	1.393 (10)
N3—C16	1.334 (6)	C14—H14	0.9300
N3—C17	1.383 (6)	C15—H15	0.9300
N4—C17	1.351 (6)	C16—C18	1.524 (7)
N4—C18	1.455 (6)	C18—C25	1.519 (7)
N4—H4	0.8600	C18—C19	1.535 (8)
N5—C31	1.296 (7)	C19—C24	1.367 (8)
N5—C33	1.380 (9)	C19—C20	1.369 (8)
N6—C31	1.321 (9)	C20—C21	1.380 (9)
N6—C32	1.350 (10)	C20—H20	0.9300
N6—H6	0.8600	C21—C22	1.348 (10)
N7—C34	1.302 (8)	C21—H21	0.9300
N7—C36	1.362 (8)	C22—C23	1.348 (11)
N8—C34	1.332 (8)	C22—H22	0.9300
N8—C35	1.348 (9)	C23—C24	1.403 (10)
N8—H8	0.8600	C23—H23	0.9300
O1—C1	1.203 (6)	C24—H24	0.9300
O2—C2	1.234 (6)	C25—C26	1.367 (8)
O3—C16	1.240 (6)	C25—C30	1.370 (8)
O4—C17	1.229 (6)	C26—C27	1.381 (9)
O5—H1	0.8500	C26—H26	0.9300
O5—H3	0.8499	C27—C28	1.356 (11)
C1—C3	1.557 (7)	C27—H27	0.9300
C3—C4	1.509 (7)	C28—C29	1.344 (11)
C3—C10	1.524 (8)	C28—H28	0.9300
C4—C9	1.348 (8)	C29—C30	1.387 (9)
C4—C5	1.361 (9)	C29—H29	0.9300
C5—C6	1.376 (9)	C30—H30	0.9300
C5—H5	0.9300	C31—H31	0.9300
C6—C7	1.345 (11)	C32—C33	1.338 (10)
C6—H6A	0.9300	C32—H32	0.9300
C7—C8	1.335 (11)	C33—H33	0.9300
C7—H7	0.9300	C34—H34	0.9300
C8—C9	1.395 (9)	C35—C36	1.348 (10)
C8—H8A	0.9300	C35—H35	0.9300
C9—H9	0.9300	C36—H36	0.9300

N3—Cu1—N5	91.10 (17)	C13—C14—C15	120.5 (8)
N3—Cu1—N1	174.78 (17)	C13—C14—H14	119.7
N5—Cu1—N1	93.71 (18)	C15—C14—H14	119.7
N3—Cu1—N7	87.41 (18)	C10—C15—C14	120.7 (8)
N5—Cu1—N7	166.2 (2)	C10—C15—H15	119.6
N1—Cu1—N7	88.40 (19)	C14—C15—H15	119.6
C1—N1—C2	109.0 (4)	O3—C16—N3	125.0 (5)
C1—N1—Cu1	123.3 (4)	O3—C16—C18	123.0 (5)
C2—N1—Cu1	125.3 (3)	N3—C16—C18	111.8 (4)
C2—N2—C3	112.1 (4)	O4—C17—N4	124.7 (4)
C2—N2—H2	124.0	O4—C17—N3	125.1 (4)
C3—N2—H2	124.0	N4—C17—N3	110.2 (4)
C16—N3—C17	107.7 (4)	N4—C18—C25	110.8 (4)
C16—N3—Cu1	120.3 (3)	N4—C18—C16	98.4 (4)
C17—N3—Cu1	131.2 (3)	C25—C18—C16	113.4 (5)
C17—N4—C18	111.7 (4)	N4—C18—C19	111.7 (4)
C17—N4—H4	124.1	C25—C18—C19	113.1 (4)
C18—N4—H4	124.1	C16—C18—C19	108.6 (4)
C31—N5—C33	104.7 (6)	C24—C19—C20	119.2 (6)
C31—N5—Cu1	128.6 (5)	C24—C19—C18	120.0 (5)
C33—N5—Cu1	126.2 (4)	C20—C19—C18	120.6 (5)
C31—N6—C32	108.2 (6)	C19—C20—C21	120.2 (7)
C31—N6—H6	125.9	C19—C20—H20	119.9
C32—N6—H6	125.9	C21—C20—H20	119.9
C34—N7—C36	104.5 (6)	C22—C21—C20	120.8 (8)
C34—N7—Cu1	126.4 (5)	C22—C21—H21	119.6
C36—N7—Cu1	129.1 (5)	C20—C21—H21	119.6
C34—N8—C35	106.6 (7)	C23—C22—C21	119.7 (7)
C34—N8—H8	126.7	C23—C22—H22	120.2
C35—N8—H8	126.7	C21—C22—H22	120.2
H1—O5—H3	105.4	C22—C23—C24	120.7 (8)
O1—C1—N1	126.6 (5)	C22—C23—H23	119.6
O1—C1—C3	124.3 (5)	C24—C23—H23	119.6
N1—C1—C3	109.0 (4)	C19—C24—C23	119.3 (7)
O2—C2—N2	125.1 (5)	C19—C24—H24	120.3
O2—C2—N1	124.5 (5)	C23—C24—H24	120.3
N2—C2—N1	110.4 (5)	C26—C25—C30	117.7 (6)
N2—C3—C4	113.2 (4)	C26—C25—C18	119.5 (5)
N2—C3—C10	109.0 (4)	C30—C25—C18	122.8 (6)
C4—C3—C10	113.2 (5)	C25—C26—C27	121.0 (7)
N2—C3—C1	99.5 (4)	C25—C26—H26	119.5
C4—C3—C1	108.8 (4)	C27—C26—H26	119.5
C10—C3—C1	112.4 (5)	C28—C27—C26	120.5 (8)
C9—C4—C5	116.3 (6)	C28—C27—H27	119.8
C9—C4—C3	122.4 (6)	C26—C27—H27	119.8
C5—C4—C3	121.1 (5)	C29—C28—C27	119.3 (8)
C4—C5—C6	122.3 (7)	C29—C28—H28	120.3
C4—C5—H5	118.9	C27—C28—H28	120.3
C6—C5—H5	118.9	C28—C29—C30	120.7 (8)
C7—C6—C5	119.9 (8)	C28—C29—H29	119.6
C7—C6—H6A	120.0	C30—C29—H29	119.6
C5—C6—H6A	120.0	C25—C30—C29	120.8 (7)
C8—C7—C6	119.6 (7)	C25—C30—H30	119.6
C8—C7—H7	120.2	C29—C30—H30	119.6
C6—C7—H7	120.2	N5—C31—N6	111.8 (7)
C7—C8—C9	119.8 (7)	N5—C31—H31	124.1
C7—C8—H8A	120.1	N6—C31—H31	124.1
C9—C8—H8A	120.1	C33—C32—N6	105.4 (8)
C4—C9—C8	122.1 (7)	C33—C32—H32	127.3
C4—C9—H9	119.0	N6—C32—H32	127.3
C8—C9—H9	119.0	C32—C33—N5	109.9 (7)
C11—C10—C15	118.0 (7)	C32—C33—H33	125.1
C11—C10—C3	122.4 (6)	N5—C33—H33	125.1
C15—C10—C3	119.4 (6)	N7—C34—N8	112.6 (6)
C10—C11—C12	120.5 (8)	N7—C34—H34	123.7
C10—C11—H11	119.7	N8—C34—H34	123.7
C12—C11—H11	119.7	C36—C35—N8	106.4 (7)
C13—C12—C11	120.5 (9)	C36—C35—H35	126.8
C13—C12—H12	119.8	N8—C35—H35	126.8
C11—C12—H12	119.8	C35—C36—N7	109.9 (8)
C14—C13—C12	119.7 (9)	C35—C36—H36	125.1
C14—C13—H13	120.1	N7—C36—H36	125.1
C12—C13—H13	120.1

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4ⁱ	0.86	2.13	2.950 (5)	158
N4—H4···O2ⁱⁱ	0.86	2.02	2.827 (5)	156
N6—H6···O3ⁱⁱⁱ	0.86	1.88	2.720 (7)	164
N8—H8···O5^iv	0.86	1.94	2.787 (7)	167
O5—H1···O4	0.85	1.90	2.714 (6)	160
O5—H3···O2	0.85	1.89	2.665 (6)	152

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+1, y+1/2, −z+3/2; (iii) x−1/2, −y+3/2, −z+2; (iv) x+1, y, z.

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