Crystal structure of 5,5-bis­(4-methyl­benz­yl)pyrimidine-2,4,6(1H,3H,5H)-trione monohydrate

Reaction of 4-methyl benzyl chloride with barbituric acid gave 5,5-bis­(4-methyl­benz­yl)pyrimidine-2,4,6(1H,3H,5H)-trione, which crystallized with two mol­ecules in its asymmetric unit along with two solvent water mol­ecules. A hydrogen-bonded sheet is formed by a combination of N—H...O and O_water—H...O hydrogen bonds, which are further inter­connected by C—H...π_ar­yl inter­actions, leading to a three-dimensional supra­molecular architecture.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.049
• wR factor = 0.135
• Data-to-parameter ratio = 17.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent  C     Ueq(max)/Ueq(min) Range        3.5 Ratio
PLAT220_ALERT_2_C Large Non-Solvent  C     Ueq(max)/Ueq(min) Range        4.0 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H    Uiso(max)/Uiso(min) ..        4.2 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H    Uiso(max)/Uiso(min) ..        4.6 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C1     --  C6      ..        5.2 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C4     --  C7      ..        6.5 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C8     --  C11     ..        5.5 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C14    --  C15     ..        7.0 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C17    --  C18     ..        6.5 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N4     --  C29     ..        5.5 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C21    --  C39     ..        6.0 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C35    --  C36     ..        6.6 su
PLAT241_ALERT_2_C High      Ueq as Compared to Neighbors for .....        C17 Check
PLAT241_ALERT_2_C High      Ueq as Compared to Neighbors for .....        C26 Check
PLAT241_ALERT_2_C High      Ueq as Compared to Neighbors for .....        C35 Check
PLAT242_ALERT_2_C Low       Ueq as Compared to Neighbors for .....         C1 Check
PLAT242_ALERT_2_C Low       Ueq as Compared to Neighbors for .....        C16 Check
PLAT242_ALERT_2_C Low       Ueq as Compared to Neighbors for .....        C21 Check
PLAT242_ALERT_2_C Low       Ueq as Compared to Neighbors for .....        C33 Check
PLAT242_ALERT_2_C Low       Ueq as Compared to Neighbors for .....        C36 Check
PLAT245_ALERT_2_C U(iso) H1B     Smaller than U(eq) O1      by ...      0.028 AngSq
PLAT245_ALERT_2_C U(iso) H2B     Smaller than U(eq) O2      by ...      0.020 AngSq
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0050 Ang.
PLAT761_ALERT_1_C CIF Contains no X-H Bonds ......................     Please Check
PLAT762_ALERT_1_C CIF Contains no X-Y-H or H-Y-H Angles ..........     Please Check
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      8.171 Check
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.457 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          4 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          2 Note
PLAT915_ALERT_3_C Low Friedel Pair Coverage ......................         88 %

Alert level G
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...         10 Report
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          4 Report
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          4 Note
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          3 Note
              H2 O
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         29 Note
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2014 Note
PLAT910_ALERT_3_G Missing # of FCF Reflections Below Th(Min) .....          1 Report
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         26 Note
PLAT916_ALERT_2_G Hooft y and Flack x Parameter values differ by .       0.40 Check
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......     Please Check

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
  30 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  12 ALERT level G = General information/check it is not something unexpected

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  22 ALERT type 2 Indicator that the structure model may be wrong or deficient
  10 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   3 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX2 (Bruker, 2009); cell refinement: APEX2 and SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus and XPREP (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

5,5-Bis(4-methylbenzyl)pyrimidine-2,4,6(1H,3H,5H)-trione monohydrate

Crystal data

C20H20N2O3·H2O	Prism
Mr = 354.40	Dx = 1.183 Mg m^−3
Orthorhombic, Pca21	Melting point: 443 K
Hall symbol: P 2c -2ac	Mo Kα radiation, λ = 0.71073 Å
a = 13.0920 (17) Å	Cell parameters from 138 reflections
b = 19.198 (3) Å	θ = 1.9–27.5°
c = 15.827 (2) Å	µ = 0.08 mm^−1
V = 3978.1 (9) Å^3	T = 296 K
Z = 8	Prism, colourless
F(000) = 1504	0.39 × 0.27 × 0.19 mm

Data collection

Bruker APEXII diffractometer	4909 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.057
Graphite monochromator	θmax = 27.5°, θmin = 1.9°
phi and φ scans	h = −16→16
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −24→24
Tmin = 0.973, Tmax = 0.984	l = −19→20
61392 measured reflections	1 standard reflections every 1 reflections
8543 independent reflections	intensity decay: 1%

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)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.135	w = 1/[σ^2(Fo^2) + (0.0724P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.98	(Δ/σ)max < 0.001
8543 reflections	Δρmax = 0.20 e Å^−3
489 parameters	Δρmin = −0.14 e Å^−3
29 restraints	Absolute structure: Flack (1983), 4587 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.1 (1)

Special details

Experimental. All the solvents employed were of analytical grade. Starting materials and reagents were purchased from Sigma Chemical co. (Saint Louis, USA). The reaction progress was monitored by thin layer chromatography using TLC Silica gel 60 F254 (Merck), and spots were visualized by using ultraviolet light of 254 nm. Melting point was determined by using open capillary and uncorrected value is given. 1H-NMR spectrum was recorded on Jeol-400 MHz NMR instrument using CDCl3/DMSO-d6 as solvent. Chemical shift values were expressed in δ (p.p.m.) relative to tetramethylsilane (TMS) as an internal reference standard. Mass spectrum of the compound was recorded on Shimadzu LC-2010EV with ESI probe.

1H-NMR spectral data of I clearly indicated the formation of I. In the spectrum, a singlet at δ (p.p.m.) value 2.23 corresponds to the two para-methyl groups, while, a singlet signal at δ (p.p.m.) value 3.22 is for four alkyl protons (two CH2 groups) and two doublets at 6.93 and 7.07 corresponds to the eight aromatic protons. Two NH protons of the barbituric acid moiety appeared at δ value 7.85 as a singlet. Mass spectrum of I gave a peak with (m/z) value = 335.0 which exactly matches with its calculated mass.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
C6	0.8772 (3)	0.7536 (2)	0.0448 (3)	0.1148 (12)
H6	0.8098	0.7382	0.0448	0.138*
C19	0.9200 (4)	0.6505 (2)	0.1358 (3)	0.174 (2)
H19A	0.9340	0.6568	0.1949	0.262*
H19B	0.9595	0.6122	0.1147	0.262*
H19C	0.8487	0.6409	0.1281	0.262*
C39	0.8413 (4)	0.8470 (2)	0.2588 (3)	0.205 (3)
H39A	0.8257	0.8861	0.2944	0.308*
H39B	0.8045	0.8512	0.2066	0.308*
H39C	0.9133	0.8461	0.2474	0.308*
C40	0.7798 (5)	0.1883 (2)	0.2643 (4)	0.192 (2)
H40A	0.8105	0.1576	0.3049	0.288*
H40B	0.8263	0.1956	0.2182	0.288*
H40C	0.7179	0.1678	0.2434	0.288*
H2B	0.520 (2)	0.5106 (14)	0.109 (2)	0.088 (10)*
H2A	0.583 (3)	0.513 (2)	0.036 (4)	0.156 (19)*
H1A	1.225 (2)	0.9802 (12)	0.272 (2)	0.092 (10)*
H1B	1.1706 (19)	1.0021 (12)	0.342 (2)	0.070 (8)*
C1	0.9482 (4)	0.7161 (2)	0.0883 (3)	0.1193 (12)
C2	1.0471 (4)	0.7405 (2)	0.0846 (2)	0.1205 (13)
H2	1.0982	0.7152	0.1115	0.145*
C3	1.0739 (3)	0.8016 (2)	0.0421 (2)	0.1027 (11)
H3	1.1413	0.8168	0.0427	0.123*
C4	1.0001 (2)	0.83994 (14)	−0.00130 (15)	0.0727 (7)
C5	0.9012 (2)	0.81420 (17)	0.0001 (2)	0.0877 (9)
H5	0.8500	0.8376	−0.0291	0.105*
C7	1.02806 (17)	0.90622 (13)	−0.04658 (16)	0.0715 (7)
H7A	0.9901	0.9082	−0.0992	0.086*
H7B	1.1001	0.9044	−0.0608	0.086*
C8	1.00757 (17)	0.97436 (13)	0.00349 (16)	0.0563 (6)
C9	0.89331 (16)	0.98272 (13)	0.01741 (17)	0.0522 (6)
C10	0.91876 (18)	1.00450 (11)	0.1679 (2)	0.0510 (6)
C11	1.06796 (15)	0.97321 (12)	0.08499 (16)	0.0561 (6)
C12	1.04400 (17)	1.03834 (13)	−0.04920 (18)	0.0678 (7)
H12A	1.1174	1.0350	−0.0565	0.081*
H12B	1.0132	1.0356	−0.1048	0.081*
C13	1.01968 (17)	1.10829 (15)	−0.01215 (17)	0.0685 (7)
C14	0.9285 (2)	1.14188 (16)	−0.0302 (2)	0.0845 (8)
H14	0.8828	1.1210	−0.0673	0.101*
C15	0.9035 (3)	1.2049 (2)	0.0051 (3)	0.1032 (11)
H15	0.8415	1.2257	−0.0085	0.124*
C16	0.9688 (4)	1.23778 (19)	0.0602 (3)	0.1149 (12)
C17	1.0608 (4)	1.2054 (2)	0.0784 (3)	0.1245 (14)
H17	1.1066	1.2268	0.1152	0.149*
C18	1.0859 (2)	1.14120 (18)	0.0425 (2)	0.0941 (9)
H18	1.1481	1.1204	0.0556	0.113*
C20	0.9419 (4)	1.3093 (2)	0.0984 (4)	0.180 (2)
H20A	0.9712	1.3131	0.1538	0.270*
H20B	0.8690	1.3139	0.1022	0.270*
H20C	0.9687	1.3456	0.0629	0.270*
C21	0.8100 (4)	0.7794 (2)	0.3035 (3)	0.1294 (14)
C22	0.8734 (3)	0.7433 (2)	0.3546 (3)	0.1207 (12)
H22	0.9391	0.7598	0.3642	0.145*
C23	0.8418 (2)	0.68184 (19)	0.3932 (2)	0.0984 (11)
H23	0.8869	0.6585	0.4287	0.118*
C24	0.7465 (2)	0.65484 (16)	0.38039 (18)	0.0820 (8)
C25	0.6804 (3)	0.6924 (2)	0.3298 (2)	0.1110 (12)
H25	0.6142	0.6764	0.3210	0.133*
C26	0.7127 (4)	0.7546 (2)	0.2916 (3)	0.1376 (16)
H26	0.6674	0.7794	0.2577	0.165*
C27	0.71252 (17)	0.58865 (16)	0.42374 (18)	0.0824 (9)
H27A	0.6397	0.5916	0.4342	0.099*
H27B	0.7464	0.5857	0.4781	0.099*
C28	0.73450 (17)	0.52040 (14)	0.37356 (17)	0.0655 (7)
C29	0.67384 (16)	0.52234 (14)	0.29184 (18)	0.0635 (6)
C30	0.82374 (18)	0.49247 (12)	0.20860 (19)	0.0514 (6)
C31	0.84770 (17)	0.51243 (15)	0.35966 (18)	0.0630 (7)
C32	0.69710 (19)	0.45597 (16)	0.42547 (17)	0.0812 (8)
H32A	0.7295	0.4571	0.4806	0.097*
H32B	0.6240	0.4601	0.4342	0.097*
C33	0.7185 (2)	0.38700 (16)	0.38549 (18)	0.0784 (8)
C34	0.8099 (2)	0.3523 (2)	0.3962 (2)	0.1020 (10)
H34	0.8596	0.3716	0.4311	0.122*
C35	0.8296 (4)	0.2887 (3)	0.3557 (4)	0.1307 (16)
H35	0.8928	0.2673	0.3622	0.157*
C36	0.7556 (5)	0.2579 (2)	0.3061 (3)	0.1243 (12)
C37	0.6641 (4)	0.2918 (2)	0.2993 (3)	0.1226 (13)
H37	0.6127	0.2711	0.2676	0.147*
C38	0.6443 (2)	0.3541 (2)	0.3365 (2)	0.0993 (10)
H38	0.5808	0.3750	0.3293	0.119*
N1	1.01988 (13)	0.98950 (10)	0.15858 (17)	0.0572 (6)
HN1	1.0568	0.9904	0.2035	0.069*
N2	0.85962 (14)	0.99882 (10)	0.09608 (16)	0.0534 (5)
HN2	0.7952	1.0062	0.1017	0.064*
N3	0.88084 (14)	0.49787 (10)	0.28006 (15)	0.0558 (6)
HN3	0.9455	0.4913	0.2743	0.067*
N4	0.72171 (13)	0.50664 (10)	0.21786 (16)	0.0584 (6)
HN4	0.6847	0.5055	0.1730	0.070*
O1	1.16630 (18)	0.99390 (14)	0.2863 (2)	0.0976 (8)
O2	0.57806 (19)	0.51299 (15)	0.0904 (2)	0.1084 (10)
O3	0.88202 (13)	1.02084 (10)	0.23583 (12)	0.0709 (5)
O4	1.15820 (10)	0.95863 (10)	0.08464 (13)	0.0775 (5)
O5	0.83276 (12)	0.97775 (9)	−0.04055 (11)	0.0726 (5)
O6	0.86065 (13)	0.47823 (10)	0.14088 (12)	0.0709 (5)
O7	0.58342 (12)	0.53645 (12)	0.29178 (14)	0.0953 (6)
O8	0.90867 (13)	0.51705 (12)	0.41774 (13)	0.0874 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C6	0.137 (3)	0.088 (3)	0.119 (3)	−0.038 (2)	−0.003 (2)	−0.026 (2)
C19	0.312 (6)	0.093 (3)	0.119 (3)	−0.044 (3)	0.006 (4)	−0.005 (2)
C39	0.362 (8)	0.094 (3)	0.159 (4)	−0.046 (4)	0.014 (5)	−0.006 (3)
C40	0.294 (7)	0.109 (3)	0.172 (5)	0.019 (4)	0.044 (5)	0.025 (3)
C1	0.190 (4)	0.088 (3)	0.080 (2)	−0.001 (3)	−0.010 (3)	−0.019 (2)
C2	0.179 (4)	0.103 (3)	0.079 (2)	0.028 (3)	−0.022 (3)	0.003 (2)
C3	0.113 (2)	0.108 (3)	0.087 (2)	0.022 (2)	−0.009 (2)	−0.009 (2)
C4	0.0893 (18)	0.0841 (18)	0.0448 (15)	0.0125 (16)	0.0001 (14)	−0.0115 (14)
C5	0.094 (2)	0.087 (2)	0.082 (2)	−0.0126 (17)	−0.0143 (17)	−0.0221 (18)
C7	0.0651 (14)	0.105 (2)	0.0445 (16)	0.0115 (13)	0.0061 (12)	−0.0133 (15)
C8	0.0431 (11)	0.0879 (17)	0.0379 (13)	−0.0012 (12)	0.0014 (10)	0.0050 (13)
C9	0.0401 (12)	0.0792 (15)	0.0375 (16)	−0.0035 (10)	−0.0045 (11)	0.0052 (11)
C10	0.0432 (12)	0.0672 (15)	0.0426 (18)	−0.0026 (9)	0.0024 (13)	0.0077 (11)
C11	0.0365 (11)	0.0798 (16)	0.0520 (15)	−0.0043 (11)	0.0038 (11)	0.0030 (13)
C12	0.0529 (12)	0.097 (2)	0.0537 (16)	−0.0022 (12)	0.0092 (12)	0.0155 (15)
C13	0.0573 (13)	0.094 (2)	0.0543 (18)	−0.0113 (13)	−0.0003 (12)	0.0191 (15)
C14	0.0796 (18)	0.086 (2)	0.088 (2)	−0.0055 (15)	−0.0074 (15)	0.0160 (17)
C15	0.101 (2)	0.099 (3)	0.110 (3)	−0.002 (2)	0.006 (2)	0.029 (2)
C16	0.172 (4)	0.086 (3)	0.086 (3)	0.002 (3)	0.017 (3)	0.014 (2)
C17	0.178 (4)	0.114 (3)	0.082 (3)	−0.035 (3)	−0.038 (3)	0.011 (2)
C18	0.095 (2)	0.098 (2)	0.089 (2)	−0.0124 (18)	−0.0202 (17)	0.0148 (18)
C20	0.275 (6)	0.117 (3)	0.148 (4)	0.007 (3)	0.036 (4)	−0.011 (3)
C21	0.192 (4)	0.114 (3)	0.083 (3)	−0.010 (3)	−0.015 (3)	−0.039 (2)
C22	0.140 (3)	0.099 (3)	0.123 (3)	−0.013 (2)	−0.010 (3)	−0.030 (3)
C23	0.095 (2)	0.108 (3)	0.091 (3)	0.004 (2)	−0.0182 (18)	−0.036 (2)
C24	0.0795 (17)	0.115 (2)	0.0511 (16)	0.0048 (17)	−0.0033 (15)	−0.0236 (17)
C25	0.114 (2)	0.130 (3)	0.089 (3)	0.009 (2)	−0.034 (2)	−0.026 (2)
C26	0.203 (5)	0.109 (3)	0.100 (3)	0.015 (3)	−0.054 (3)	−0.018 (3)
C27	0.0600 (15)	0.135 (3)	0.0525 (18)	0.0095 (15)	0.0060 (12)	−0.0218 (18)
C28	0.0446 (12)	0.114 (2)	0.0377 (15)	−0.0038 (13)	0.0058 (11)	−0.0082 (15)
C29	0.0391 (12)	0.1030 (19)	0.0486 (15)	−0.0098 (12)	−0.0013 (11)	0.0014 (14)
C30	0.0467 (13)	0.0750 (16)	0.0327 (16)	−0.0054 (10)	−0.0042 (12)	0.0004 (10)
C31	0.0447 (13)	0.108 (2)	0.0363 (16)	−0.0031 (12)	−0.0027 (12)	−0.0025 (13)
C32	0.0672 (14)	0.133 (3)	0.0432 (15)	−0.0126 (16)	0.0118 (13)	0.0041 (17)
C33	0.0753 (17)	0.112 (2)	0.0479 (17)	−0.0106 (16)	0.0049 (14)	0.0165 (17)
C34	0.084 (2)	0.125 (3)	0.096 (2)	−0.0012 (19)	−0.0010 (18)	0.034 (2)
C35	0.127 (3)	0.118 (4)	0.147 (4)	0.027 (3)	0.024 (3)	0.053 (3)
C36	0.171 (4)	0.105 (3)	0.097 (3)	−0.002 (3)	0.026 (3)	0.011 (2)
C37	0.146 (4)	0.123 (3)	0.099 (3)	−0.004 (3)	−0.008 (3)	0.008 (3)
C38	0.101 (2)	0.113 (3)	0.084 (2)	−0.0056 (19)	−0.0081 (18)	0.004 (2)
N1	0.0406 (10)	0.0901 (14)	0.0408 (15)	−0.0008 (8)	−0.0098 (10)	0.0026 (10)
N2	0.0325 (9)	0.0872 (14)	0.0405 (14)	0.0011 (7)	−0.0005 (10)	0.0027 (8)
N3	0.0336 (10)	0.0979 (15)	0.0360 (15)	−0.0022 (8)	0.0001 (10)	−0.0017 (9)
N4	0.0423 (11)	0.0982 (15)	0.0347 (14)	−0.0044 (8)	−0.0038 (10)	−0.0027 (9)
O1	0.0577 (12)	0.192 (2)	0.0431 (15)	0.0075 (11)	−0.0041 (12)	−0.0181 (12)
O2	0.0582 (13)	0.223 (3)	0.0443 (16)	0.0125 (12)	−0.0046 (12)	0.0058 (14)
O3	0.0593 (10)	0.1132 (14)	0.0402 (11)	0.0041 (9)	0.0053 (8)	−0.0093 (9)
O4	0.0389 (8)	0.1202 (15)	0.0733 (12)	0.0012 (8)	−0.0007 (8)	−0.0006 (11)
O5	0.0535 (9)	0.1195 (15)	0.0448 (11)	−0.0020 (9)	−0.0080 (9)	−0.0004 (10)
O6	0.0649 (10)	0.1105 (14)	0.0373 (11)	0.0007 (9)	0.0047 (8)	−0.0088 (10)
O7	0.0366 (9)	0.174 (2)	0.0751 (13)	−0.0020 (10)	−0.0013 (9)	−0.0119 (13)
O8	0.0517 (9)	0.1655 (18)	0.0449 (11)	0.0017 (10)	−0.0126 (9)	−0.0159 (11)

Geometric parameters (Å, º)

C6—C1	1.363 (5)	C16—C20	1.541 (6)
C6—C5	1.397 (5)	C17—C18	1.396 (5)
C19—C1	1.513 (6)	C21—C22	1.351 (6)
C39—C21	1.534 (6)	C21—C26	1.373 (5)
C40—C36	1.524 (6)	C22—C23	1.392 (5)
C1—C2	1.378 (6)	C23—C24	1.367 (4)
C2—C3	1.396 (5)	C24—C25	1.383 (5)
C3—C4	1.396 (4)	C24—C27	1.511 (4)
C4—C5	1.386 (4)	C25—C26	1.403 (6)
C4—C7	1.506 (4)	C27—C28	1.559 (4)
C7—C8	1.553 (3)	C28—C31	1.506 (3)
C8—C11	1.513 (3)	C28—C29	1.518 (4)
C8—C9	1.521 (3)	C28—C32	1.564 (4)
C8—C12	1.559 (4)	C29—O7	1.214 (3)
C9—O5	1.216 (3)	C29—N4	1.362 (4)
C9—N2	1.357 (3)	C30—O6	1.207 (3)
C10—O3	1.218 (3)	C30—N3	1.360 (3)
C10—N1	1.363 (3)	C30—N4	1.371 (3)
C10—N2	1.380 (4)	C31—O8	1.221 (3)
C11—O4	1.214 (2)	C31—N3	1.361 (4)
C11—N1	1.360 (3)	C32—C33	1.494 (4)
C12—C13	1.500 (4)	C33—C34	1.380 (4)
C13—C18	1.378 (4)	C33—C38	1.393 (4)
C13—C14	1.386 (4)	C34—C35	1.403 (6)
C14—C15	1.372 (5)	C35—C36	1.380 (6)
C15—C16	1.374 (5)	C36—C37	1.368 (6)
C16—C17	1.387 (6)	C37—C38	1.358 (6)
C1—C6—C5	122.8 (4)	C26—C21—C39	118.6 (5)
C6—C1—C2	116.1 (4)	C21—C22—C23	121.0 (4)
C6—C1—C19	121.7 (5)	C24—C23—C22	121.9 (3)
C2—C1—C19	122.2 (5)	C23—C24—C25	117.3 (3)
C1—C2—C3	122.8 (4)	C23—C24—C27	121.4 (3)
C4—C3—C2	120.4 (4)	C25—C24—C27	121.2 (3)
C5—C4—C3	116.8 (3)	C24—C25—C26	120.4 (4)
C5—C4—C7	122.4 (3)	C21—C26—C25	121.0 (4)
C3—C4—C7	120.8 (3)	C24—C27—C28	114.9 (2)
C4—C5—C6	121.0 (3)	C31—C28—C29	113.1 (2)
C4—C7—C8	115.3 (2)	C31—C28—C27	110.0 (2)
C11—C8—C9	113.1 (2)	C29—C28—C27	108.5 (2)
C11—C8—C7	109.4 (2)	C31—C28—C32	107.7 (2)
C9—C8—C7	109.44 (19)	C29—C28—C32	107.7 (2)
C11—C8—C12	107.91 (19)	C27—C28—C32	109.8 (2)
C9—C8—C12	107.17 (18)	O7—C29—N4	119.8 (2)
C7—C8—C12	109.7 (2)	O7—C29—C28	121.1 (2)
O5—C9—N2	119.9 (2)	N4—C29—C28	119.10 (19)
O5—C9—C8	121.6 (2)	O6—C30—N3	122.4 (2)
N2—C9—C8	118.5 (2)	O6—C30—N4	122.0 (2)
O3—C10—N1	122.3 (3)	N3—C30—N4	115.6 (2)
O3—C10—N2	121.7 (2)	O8—C31—N3	120.2 (2)
N1—C10—N2	116.0 (2)	O8—C31—C28	121.7 (2)
O4—C11—N1	120.5 (2)	N3—C31—C28	118.0 (2)
O4—C11—C8	120.5 (2)	C33—C32—C28	114.8 (2)
N1—C11—C8	119.00 (18)	C34—C33—C38	117.0 (3)
C13—C12—C8	115.6 (2)	C34—C33—C32	122.5 (3)
C18—C13—C14	117.2 (3)	C38—C33—C32	120.5 (3)
C18—C13—C12	121.5 (2)	C33—C34—C35	121.6 (4)
C14—C13—C12	121.3 (3)	C36—C35—C34	120.3 (4)
C15—C14—C13	122.2 (3)	C37—C36—C35	117.0 (4)
C14—C15—C16	121.0 (4)	C37—C36—C40	124.4 (6)
C15—C16—C17	117.8 (4)	C35—C36—C40	118.5 (6)
C15—C16—C20	121.1 (4)	C38—C37—C36	123.6 (4)
C17—C16—C20	121.1 (5)	C37—C38—C33	120.5 (3)
C16—C17—C18	121.0 (4)	C11—N1—C10	126.2 (2)
C13—C18—C17	120.8 (3)	C9—N2—C10	126.29 (19)
C22—C21—C26	118.3 (5)	C30—N3—C31	127.6 (2)
C22—C21—C39	123.1 (5)	C29—N4—C30	125.7 (2)
C5—C6—C1—C2	−1.3 (5)	C39—C21—C26—C25	179.0 (4)
C5—C6—C1—C19	−179.7 (3)	C24—C25—C26—C21	0.0 (6)
C6—C1—C2—C3	2.7 (6)	C23—C24—C27—C28	−90.5 (3)
C19—C1—C2—C3	−178.9 (3)	C25—C24—C27—C28	93.0 (3)
C1—C2—C3—C4	−2.0 (5)	C24—C27—C28—C31	60.9 (3)
C2—C3—C4—C5	−0.2 (4)	C24—C27—C28—C29	−63.3 (3)
C2—C3—C4—C7	179.4 (3)	C24—C27—C28—C32	179.3 (2)
C3—C4—C5—C6	1.5 (4)	C31—C28—C29—O7	−171.5 (3)
C7—C4—C5—C6	−178.1 (3)	C27—C28—C29—O7	−49.2 (3)
C1—C6—C5—C4	−0.7 (5)	C32—C28—C29—O7	69.6 (3)
C5—C4—C7—C8	82.6 (3)	C31—C28—C29—N4	9.8 (3)
C3—C4—C7—C8	−97.0 (3)	C27—C28—C29—N4	132.0 (2)
C4—C7—C8—C11	59.5 (3)	C32—C28—C29—N4	−109.2 (3)
C4—C7—C8—C9	−64.9 (3)	C29—C28—C31—O8	172.4 (3)
C4—C7—C8—C12	177.7 (2)	C27—C28—C31—O8	50.9 (3)
C11—C8—C9—O5	−172.6 (2)	C32—C28—C31—O8	−68.7 (3)
C7—C8—C9—O5	−50.3 (3)	C29—C28—C31—N3	−9.4 (3)
C12—C8—C9—O5	68.6 (3)	C27—C28—C31—N3	−130.8 (3)
C11—C8—C9—N2	10.0 (3)	C32—C28—C31—N3	109.5 (3)
C7—C8—C9—N2	132.3 (2)	C31—C28—C32—C33	−57.5 (3)
C12—C8—C9—N2	−108.8 (2)	C29—C28—C32—C33	64.8 (3)
C9—C8—C11—O4	171.2 (2)	C27—C28—C32—C33	−177.3 (2)
C7—C8—C11—O4	48.9 (3)	C28—C32—C33—C34	86.1 (3)
C12—C8—C11—O4	−70.4 (3)	C28—C32—C33—C38	−95.3 (3)
C9—C8—C11—N1	−9.5 (3)	C38—C33—C34—C35	3.6 (5)
C7—C8—C11—N1	−131.8 (2)	C32—C33—C34—C35	−177.7 (3)
C12—C8—C11—N1	108.9 (2)	C33—C34—C35—C36	−2.5 (6)
C11—C8—C12—C13	−66.5 (2)	C34—C35—C36—C37	−0.3 (7)
C9—C8—C12—C13	55.6 (3)	C34—C35—C36—C40	−179.1 (4)
C7—C8—C12—C13	174.32 (19)	C35—C36—C37—C38	1.9 (7)
C8—C12—C13—C18	89.4 (3)	C40—C36—C37—C38	−179.4 (4)
C8—C12—C13—C14	−89.2 (3)	C36—C37—C38—C33	−0.6 (7)
C18—C13—C14—C15	−0.7 (4)	C34—C33—C38—C37	−2.1 (5)
C12—C13—C14—C15	178.0 (3)	C32—C33—C38—C37	179.2 (3)
C13—C14—C15—C16	0.2 (5)	O4—C11—N1—C10	−177.7 (2)
C14—C15—C16—C17	0.5 (6)	C8—C11—N1—C10	3.0 (3)
C14—C15—C16—C20	178.6 (4)	O3—C10—N1—C11	−177.6 (2)
C15—C16—C17—C18	−0.6 (6)	N2—C10—N1—C11	3.6 (3)
C20—C16—C17—C18	−178.7 (4)	O5—C9—N2—C10	178.3 (2)
C14—C13—C18—C17	0.6 (4)	C8—C9—N2—C10	−4.3 (3)
C12—C13—C18—C17	−178.1 (3)	O3—C10—N2—C9	178.3 (2)
C16—C17—C18—C13	0.0 (6)	N1—C10—N2—C9	−2.9 (3)
C26—C21—C22—C23	1.2 (6)	O6—C30—N3—C31	−178.9 (3)
C39—C21—C22—C23	−179.4 (4)	N4—C30—N3—C31	3.3 (3)
C21—C22—C23—C24	0.8 (6)	O8—C31—N3—C30	−178.5 (2)
C22—C23—C24—C25	−2.4 (5)	C28—C31—N3—C30	3.3 (4)
C22—C23—C24—C27	−179.0 (3)	O7—C29—N4—C30	177.3 (2)
C23—C24—C25—C26	1.9 (5)	C28—C29—N4—C30	−3.9 (4)
C27—C24—C25—C26	178.5 (3)	O6—C30—N4—C29	179.2 (2)
C22—C21—C26—C25	−1.6 (6)	N3—C30—N4—C29	−2.9 (3)

Hydrogen-bond geometry (Å, º)

Cg is the centroid of the C13–C18 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···O1	0.86	1.94	2.787 (4)	167
O1—H1A···O3^i	0.84 (3)	2.13 (3)	2.949 (3)	162
O1—H1B···O5^ii	0.90 (3)	1.90 (3)	2.794 (4)	175
N2—HN2···O4^iii	0.86	1.94	2.767 (2)	162
O2—H2A···O8^iv	0.86 (6)	1.88 (6)	2.739 (4)	177
O2—H2B···O6^v	0.82 (3)	2.16 (3)	2.961 (3)	169
N3—HN3···O7^vi	0.86	1.90	2.739 (2)	164
N4—HN4···O2	0.86	1.92	2.761 (4)	166
C22—H22···Cg^vii	0.93	2.97	3.5693	124

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