Bis(5,5-diphenyl­hydantoinato-κN³)copper(II) 2-methyl-3,4,5,6-tetrahydropyrimidine solvate

The title complex, [Cu(C₁₄H₁₁N₂O₂)₂]·C₅H₁₀N₂, 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.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](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

---

Computing details

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).

(I)

Crystal data

[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) Å^3	T = 298 K
Z = 4	Block, jasmine yellow?
F(000) = 1380	0.58 × 0.21 × 0.13 mm

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.043	H-atom parameters constrained
wR(F^2) = 0.104	w = 1/[σ^2(Fo^2) + (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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4^i	0.86	1.99	2.828 (5)	163
N4—H4···O2^ii	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.