Crystal structure of methyl 4-(4-hy­droxy­phen­yl)-6-methyl-2-oxo-1,2,3,4-tetra­hydro­pyrimidine-5-carboxyl­ate monohydrate

The title hydrate crystallizes with two formula units in the asymmetric unit (Z′ = 2). The organic mol­ecules form a dimer, linked by a pair of N—H...O hydrogen bonds. Further hydrogen bonding together with weak C—H...π and π–π inter­actions further consolidates the packing, generating a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.038
• wR factor = 0.099
• Data-to-parameter ratio = 10.5

checkCIF/PLATON results

No syntax errors found



Alert level A
DIFF019_ALERT_1_A  _diffrn_standards_number is missing
            Number of standards used in measurement.
DIFF020_ALERT_1_A  _diffrn_standards_interval_count and
            _diffrn_standards_interval_time are missing. Number of measurements
            between standards or time (min) between standards.
DIFF022_ALERT_1_A  _diffrn_standards_decay_% is missing
            Percentage decrease in standards intensity.

Alert level C
PLAT222_ALERT_3_C Non-Solvent Resd 1   H Uiso(max)/Uiso(min) Range        4.2 Ratio
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      3.125 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          7 Report

Alert level G
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          2 Note
              C13 H14 N2 O4
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          4 Note
              H2 O
PLAT793_ALERT_4_G The Model has Chirality at C4      (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C17     (Centro SPGR)          R Verify
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           4 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          3 Note
PLAT933_ALERT_2_G Number of OMIT records in Embedded RES .........          2 Note
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......     Please Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density          13 Note

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

   3 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
   4 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al. (2008); software used to prepare material for publication: SHELXL2014/7 (Sheldrick, 2015).

Methyl 4-(4-hydroxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate monohydrate

Crystal data

C13H14N2O4·H2O	Z = 4
Mr = 280.28	F(000) = 592
Triclinic, P1	Dx = 1.431 Mg m^−3
a = 10.7527 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.6731 (6) Å	Cell parameters from 740 reflections
c = 12.4456 (7) Å	θ = 2.2–30.1°
α = 98.236 (2)°	µ = 0.11 mm^−1
β = 112.374 (1)°	T = 150 K
γ = 108.944 (2)°	Plate, colorless
V = 1301.16 (13) Å^3	0.23 × 0.20 × 0.15 mm

Data collection

Bruker Kappa APEXII DUO diffractometer	5116 independent reflections
Radiation source: fine-focus sealed tube	4387 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
ω scans	θmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −13→13
Tmin = 0.926, Tmax = 0.934	k = −14→14
21716 measured reflections	l = −15→15

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: difference Fourier map
wR(F^2) = 0.099	All H-atom parameters refined
S = 1.04	w = 1/[σ^2(Fo^2) + (0.046P)^2 + 0.5474P] where P = (Fo^2 + 2Fc^2)/3
5116 reflections	(Δ/σ)max = 0.001
489 parameters	Δρmax = 0.23 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
C1	0.39164 (15)	0.54081 (12)	0.87596 (12)	0.0139 (3)
C2	0.60979 (15)	0.53784 (13)	0.86203 (12)	0.0148 (3)
C3	0.53110 (14)	0.42096 (12)	0.77764 (12)	0.0136 (3)
C4	0.36594 (14)	0.34937 (12)	0.73347 (12)	0.0133 (3)
C5	0.60417 (15)	0.35855 (12)	0.72784 (13)	0.0153 (3)
C6	0.56565 (17)	0.17576 (14)	0.58648 (15)	0.0209 (3)
C7	0.77354 (16)	0.61333 (15)	0.91932 (15)	0.0213 (3)
C8	0.26914 (14)	0.32159 (12)	0.59847 (12)	0.0135 (3)
C9	0.16677 (15)	0.19821 (12)	0.52680 (13)	0.0147 (3)
C10	0.07261 (15)	0.17160 (12)	0.40490 (13)	0.0153 (3)
C11	0.07936 (15)	0.26965 (13)	0.35266 (12)	0.0142 (3)
C12	0.18128 (15)	0.39416 (13)	0.42297 (13)	0.0155 (3)
C13	0.27411 (15)	0.41876 (13)	0.54497 (13)	0.0155 (3)
C14	0.62129 (15)	0.92206 (13)	1.09772 (12)	0.0144 (3)
C15	0.40117 (15)	0.90446 (13)	1.12011 (12)	0.0149 (3)
C16	0.46382 (15)	1.02900 (13)	1.18448 (12)	0.0149 (3)
C17	0.62246 (15)	1.11457 (12)	1.21918 (12)	0.0142 (3)
C18	0.37813 (15)	1.08432 (13)	1.22405 (13)	0.0179 (3)
C19	0.37283 (19)	1.26713 (15)	1.32473 (17)	0.0253 (3)
C20	0.24606 (16)	0.81093 (14)	1.07923 (14)	0.0209 (3)
C21	0.72322 (14)	1.15937 (12)	1.35558 (12)	0.0134 (3)
C22	0.81179 (15)	1.28805 (12)	1.41893 (13)	0.0154 (3)
C23	0.90581 (15)	1.32811 (12)	1.54268 (13)	0.0160 (3)
C24	0.91207 (14)	1.23915 (13)	1.60557 (12)	0.0146 (3)
C25	0.82479 (15)	1.10980 (13)	1.54369 (13)	0.0146 (3)
C26	0.73188 (14)	1.07151 (12)	1.41985 (13)	0.0140 (3)
N1	0.53814 (13)	0.59703 (11)	0.90574 (11)	0.0163 (3)
N2	0.31652 (13)	0.42046 (11)	0.80401 (11)	0.0153 (3)
N3	0.48323 (13)	0.85228 (11)	1.08401 (11)	0.0162 (3)
N4	0.68018 (13)	1.04716 (11)	1.15386 (11)	0.0154 (3)
O1	0.33372 (11)	0.59969 (9)	0.91804 (9)	0.0185 (2)
O2	0.73271 (11)	0.40171 (9)	0.74845 (10)	0.0225 (2)
O3	0.50735 (11)	0.24088 (9)	0.64955 (9)	0.0191 (2)
O4	−0.01614 (11)	0.23932 (9)	0.23188 (9)	0.0178 (2)
O5	−0.03765 (13)	0.44197 (10)	0.16905 (11)	0.0253 (3)
O6	0.68445 (10)	0.86842 (9)	1.05711 (9)	0.0181 (2)
O7	0.25613 (12)	1.02650 (11)	1.21377 (13)	0.0372 (3)
O8	0.45133 (11)	1.21067 (9)	1.27839 (10)	0.0215 (2)
O9	1.00441 (11)	1.28271 (9)	1.72845 (9)	0.0182 (2)
O10	1.02933 (13)	1.10134 (11)	1.82525 (11)	0.0279 (3)
H2	0.3460 (16)	0.2653 (14)	0.7513 (13)	0.012 (4)*
H4	0.6248 (16)	1.1903 (14)	1.1908 (14)	0.013 (4)*
H6C	0.801 (2)	0.695 (2)	0.9685 (19)	0.042 (6)*
H6A	0.6325 (19)	0.1504 (15)	0.6451 (15)	0.020 (4)*
H6B	0.618 (2)	0.2300 (17)	0.5497 (17)	0.032 (5)*
H7A	0.473 (2)	0.1020 (18)	0.5170 (18)	0.037 (5)*
H7B	0.810 (2)	0.6203 (19)	0.8581 (19)	0.043 (6)*
H7C	0.823 (2)	0.572 (2)	0.971 (2)	0.050 (6)*
H9	0.1627 (17)	0.1297 (15)	0.5647 (14)	0.014 (4)*
H10	0.0015 (18)	0.0858 (15)	0.3535 (15)	0.017 (4)*
H12	0.1873 (18)	0.4638 (16)	0.3874 (15)	0.023 (4)*
H13	0.3430 (18)	0.5067 (16)	0.5956 (15)	0.022 (4)*
H19A	0.272 (2)	1.2425 (19)	1.2587 (19)	0.041 (5)*
H19B	0.430 (2)	1.355 (2)	1.354 (2)	0.050 (6)*
H19C	0.369 (2)	1.2410 (18)	1.3956 (18)	0.035 (5)*
H20A	0.224 (2)	0.8036 (18)	1.1506 (19)	0.040 (5)*
H20B	0.176 (2)	0.8369 (18)	1.0264 (18)	0.035 (5)*
H20C	0.232 (2)	0.725 (2)	1.0365 (19)	0.043 (6)*
H22	0.8056 (18)	1.3477 (16)	1.3726 (15)	0.022 (4)*
H23	0.9677 (18)	1.4181 (16)	1.5872 (15)	0.019 (4)*
H25	0.8305 (18)	1.0473 (15)	1.5905 (15)	0.020 (4)*
H26	0.6728 (17)	0.9814 (15)	1.3765 (14)	0.014 (4)*
H1N	0.587 (2)	0.6755 (18)	0.9547 (16)	0.025 (4)*
H3N	0.442 (2)	0.7732 (19)	1.0363 (18)	0.034 (5)*
H2N	0.220 (2)	0.3872 (16)	0.7813 (16)	0.024 (4)*
H4N	0.769 (2)	1.0913 (17)	1.1660 (16)	0.025 (5)*
H1O	−0.017 (2)	0.308 (2)	0.2135 (19)	0.045 (6)*
H2O	1.007 (2)	1.218 (2)	1.759 (2)	0.047 (6)*
H3O	−0.126 (3)	0.447 (2)	0.147 (2)	0.049 (6)*
H4O	0.033 (2)	0.513 (2)	0.1929 (19)	0.040 (6)*
H5O	0.954 (3)	1.045 (2)	1.824 (2)	0.050 (6)*
H6O	1.115 (3)	1.097 (2)	1.870 (2)	0.048 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0135 (7)	0.0148 (6)	0.0126 (6)	0.0056 (5)	0.0053 (5)	0.0037 (5)
C2	0.0130 (7)	0.0171 (7)	0.0149 (7)	0.0068 (5)	0.0060 (5)	0.0064 (5)
C3	0.0112 (6)	0.0138 (6)	0.0153 (7)	0.0050 (5)	0.0053 (5)	0.0056 (5)
C4	0.0118 (6)	0.0104 (6)	0.0175 (7)	0.0041 (5)	0.0075 (5)	0.0021 (5)
C5	0.0140 (7)	0.0136 (6)	0.0176 (7)	0.0055 (5)	0.0065 (6)	0.0058 (5)
C6	0.0216 (8)	0.0187 (7)	0.0271 (8)	0.0102 (6)	0.0155 (7)	0.0031 (6)
C7	0.0136 (7)	0.0198 (7)	0.0219 (8)	0.0025 (6)	0.0057 (6)	−0.0002 (6)
C8	0.0104 (6)	0.0133 (6)	0.0171 (7)	0.0055 (5)	0.0071 (5)	0.0021 (5)
C9	0.0139 (7)	0.0123 (6)	0.0196 (7)	0.0061 (5)	0.0091 (6)	0.0039 (5)
C10	0.0120 (7)	0.0112 (6)	0.0192 (7)	0.0035 (5)	0.0067 (6)	−0.0008 (5)
C11	0.0111 (6)	0.0171 (7)	0.0147 (7)	0.0067 (5)	0.0066 (5)	0.0019 (5)
C12	0.0140 (7)	0.0137 (6)	0.0190 (7)	0.0056 (5)	0.0079 (6)	0.0051 (5)
C13	0.0112 (6)	0.0111 (6)	0.0201 (7)	0.0026 (5)	0.0061 (6)	0.0010 (5)
C14	0.0125 (6)	0.0160 (6)	0.0116 (6)	0.0059 (5)	0.0026 (5)	0.0034 (5)
C15	0.0121 (7)	0.0191 (7)	0.0117 (6)	0.0066 (5)	0.0038 (5)	0.0041 (5)
C16	0.0119 (7)	0.0173 (7)	0.0157 (7)	0.0063 (5)	0.0060 (5)	0.0052 (5)
C17	0.0137 (7)	0.0128 (6)	0.0169 (7)	0.0061 (5)	0.0074 (6)	0.0038 (5)
C18	0.0142 (7)	0.0180 (7)	0.0205 (7)	0.0067 (6)	0.0072 (6)	0.0050 (6)
C19	0.0263 (9)	0.0200 (8)	0.0398 (10)	0.0132 (7)	0.0224 (8)	0.0086 (7)
C20	0.0140 (7)	0.0191 (7)	0.0216 (8)	0.0023 (6)	0.0065 (6)	−0.0007 (6)
C21	0.0100 (6)	0.0131 (6)	0.0173 (7)	0.0048 (5)	0.0074 (5)	0.0015 (5)
C22	0.0150 (7)	0.0126 (6)	0.0207 (7)	0.0057 (5)	0.0104 (6)	0.0041 (5)
C23	0.0134 (7)	0.0098 (6)	0.0214 (7)	0.0021 (5)	0.0089 (6)	−0.0012 (5)
C24	0.0101 (6)	0.0163 (6)	0.0153 (7)	0.0050 (5)	0.0062 (5)	−0.0008 (5)
C25	0.0120 (6)	0.0142 (6)	0.0187 (7)	0.0058 (5)	0.0079 (6)	0.0041 (5)
C26	0.0110 (6)	0.0095 (6)	0.0190 (7)	0.0028 (5)	0.0068 (5)	0.0008 (5)
N1	0.0130 (6)	0.0115 (6)	0.0173 (6)	0.0017 (5)	0.0051 (5)	−0.0016 (5)
N2	0.0101 (6)	0.0147 (6)	0.0172 (6)	0.0030 (5)	0.0060 (5)	0.0001 (5)
N3	0.0128 (6)	0.0126 (6)	0.0178 (6)	0.0032 (5)	0.0053 (5)	−0.0005 (5)
N4	0.0119 (6)	0.0142 (6)	0.0175 (6)	0.0034 (5)	0.0071 (5)	0.0013 (5)
O1	0.0154 (5)	0.0168 (5)	0.0201 (5)	0.0061 (4)	0.0074 (4)	−0.0002 (4)
O2	0.0129 (5)	0.0211 (5)	0.0301 (6)	0.0053 (4)	0.0101 (4)	0.0021 (4)
O3	0.0158 (5)	0.0139 (5)	0.0264 (6)	0.0052 (4)	0.0114 (4)	0.0000 (4)
O4	0.0158 (5)	0.0165 (5)	0.0148 (5)	0.0042 (4)	0.0039 (4)	0.0023 (4)
O5	0.0141 (6)	0.0149 (5)	0.0356 (6)	0.0039 (5)	0.0036 (5)	0.0026 (5)
O6	0.0150 (5)	0.0169 (5)	0.0202 (5)	0.0072 (4)	0.0073 (4)	0.0008 (4)
O7	0.0200 (6)	0.0253 (6)	0.0613 (9)	0.0033 (5)	0.0247 (6)	−0.0035 (6)
O8	0.0200 (5)	0.0154 (5)	0.0342 (6)	0.0086 (4)	0.0173 (5)	0.0051 (4)
O9	0.0152 (5)	0.0160 (5)	0.0152 (5)	0.0027 (4)	0.0041 (4)	−0.0005 (4)
O10	0.0135 (6)	0.0255 (6)	0.0367 (7)	0.0048 (5)	0.0054 (5)	0.0119 (5)

Geometric parameters (Å, º)

C1—O1	1.2481 (17)	C15—C20	1.4984 (19)
C1—N2	1.3342 (17)	C16—C18	1.4659 (19)
C1—N1	1.3653 (18)	C16—C17	1.5177 (19)
C2—C3	1.3579 (19)	C17—N4	1.4776 (17)
C2—N1	1.3872 (18)	C17—C21	1.5188 (19)
C2—C7	1.4973 (19)	C17—H4	0.994 (15)
C3—C5	1.4647 (19)	C18—O7	1.2105 (18)
C3—C4	1.5218 (18)	C18—O8	1.3444 (17)
C4—N2	1.4745 (17)	C19—O8	1.4499 (17)
C4—C8	1.5182 (19)	C19—H19A	0.99 (2)
C4—H2	1.009 (15)	C19—H19B	0.94 (2)
C5—O2	1.2127 (17)	C19—H19C	0.98 (2)
C5—O3	1.3548 (17)	C20—H20A	1.01 (2)
C6—O3	1.4491 (17)	C20—H20B	0.96 (2)
C6—H6A	0.968 (17)	C20—H20C	1.00 (2)
C6—H6B	0.989 (19)	C21—C26	1.3931 (19)
C6—H7A	1.03 (2)	C21—C22	1.3946 (19)
C7—H6C	0.95 (2)	C22—C23	1.384 (2)
C7—H7B	0.98 (2)	C22—H22	0.968 (17)
C7—H7C	0.96 (2)	C23—C24	1.391 (2)
C8—C9	1.3917 (19)	C23—H23	0.975 (17)
C8—C13	1.3918 (19)	C24—O9	1.3699 (17)
C9—C10	1.384 (2)	C24—C25	1.3965 (19)
C9—H9	0.982 (16)	C25—C26	1.383 (2)
C10—C11	1.3904 (19)	C25—H25	0.999 (17)
C10—H10	0.972 (16)	C26—H26	0.971 (16)
C11—O4	1.3696 (16)	N1—H1N	0.878 (19)
C11—C12	1.3966 (19)	N2—H2N	0.890 (19)
C12—C13	1.385 (2)	N3—H3N	0.88 (2)
C12—H12	0.976 (17)	N4—H4N	0.867 (19)
C13—H13	0.983 (17)	O4—H1O	0.86 (2)
C14—O6	1.2472 (17)	O5—H3O	0.91 (2)
C14—N4	1.3386 (18)	O5—H4O	0.83 (2)
C14—N3	1.3706 (18)	O9—H2O	0.90 (2)
C15—C16	1.3523 (19)	O10—H5O	0.86 (3)
C15—N3	1.3869 (18)	O10—H6O	0.90 (2)
O1—C1—N2	122.43 (12)	N4—C17—C16	109.46 (11)
O1—C1—N1	120.57 (12)	N4—C17—C21	109.83 (11)
N2—C1—N1	116.97 (12)	C16—C17—C21	113.17 (11)
C3—C2—N1	119.80 (12)	N4—C17—H4	106.2 (9)
C3—C2—C7	126.65 (13)	C16—C17—H4	109.2 (9)
N1—C2—C7	113.53 (12)	C21—C17—H4	108.7 (9)
C2—C3—C5	120.57 (12)	O7—C18—O8	121.30 (13)
C2—C3—C4	121.63 (12)	O7—C18—C16	126.02 (13)
C5—C3—C4	117.78 (11)	O8—C18—C16	112.66 (12)
N2—C4—C8	108.71 (10)	O8—C19—H19A	109.5 (12)
N2—C4—C3	109.65 (11)	O8—C19—H19B	106.2 (14)
C8—C4—C3	115.47 (11)	H19A—C19—H19B	112.9 (18)
N2—C4—H2	105.7 (9)	O8—C19—H19C	110.4 (11)
C8—C4—H2	107.5 (9)	H19A—C19—H19C	111.3 (16)
C3—C4—H2	109.4 (9)	H19B—C19—H19C	106.4 (17)
O2—C5—O3	121.53 (13)	C15—C20—H20A	111.6 (12)
O2—C5—C3	127.41 (13)	C15—C20—H20B	111.1 (12)
O3—C5—C3	111.05 (11)	H20A—C20—H20B	106.6 (16)
O3—C6—H6A	107.7 (10)	C15—C20—H20C	109.4 (12)
O3—C6—H6B	112.2 (11)	H20A—C20—H20C	107.8 (16)
H6A—C6—H6B	110.0 (14)	H20B—C20—H20C	110.3 (16)
O3—C6—H7A	103.6 (11)	C26—C21—C22	118.39 (13)
H6A—C6—H7A	115.1 (14)	C26—C21—C17	120.28 (12)
H6B—C6—H7A	108.1 (15)	C22—C21—C17	121.31 (12)
C2—C7—H6C	110.7 (12)	C23—C22—C21	121.08 (13)
C2—C7—H7B	112.1 (12)	C23—C22—H22	121.6 (10)
H6C—C7—H7B	109.6 (17)	C21—C22—H22	117.3 (10)
C2—C7—H7C	109.8 (13)	C22—C23—C24	119.74 (12)
H6C—C7—H7C	107.8 (18)	C22—C23—H23	121.3 (9)
H7B—C7—H7C	106.7 (17)	C24—C23—H23	119.0 (10)
C9—C8—C13	118.41 (13)	O9—C24—C23	118.02 (12)
C9—C8—C4	120.22 (12)	O9—C24—C25	121.92 (12)
C13—C8—C4	121.27 (12)	C23—C24—C25	120.06 (13)
C10—C9—C8	121.23 (13)	C26—C25—C24	119.37 (12)
C10—C9—H9	120.3 (9)	C26—C25—H25	121.7 (10)
C8—C9—H9	118.5 (9)	C24—C25—H25	118.9 (10)
C9—C10—C11	119.66 (12)	C25—C26—C21	121.36 (12)
C9—C10—H10	122.1 (9)	C25—C26—H26	119.4 (9)
C11—C10—H10	118.2 (9)	C21—C26—H26	119.3 (9)
O4—C11—C10	117.81 (12)	C1—N1—C2	123.79 (12)
O4—C11—C12	122.17 (12)	C1—N1—H1N	115.9 (12)
C10—C11—C12	120.02 (13)	C2—N1—H1N	120.3 (12)
C13—C12—C11	119.37 (13)	C1—N2—C4	126.69 (12)
C13—C12—H12	119.8 (10)	C1—N2—H2N	115.7 (11)
C11—C12—H12	120.8 (10)	C4—N2—H2N	115.6 (11)
C12—C13—C8	121.30 (12)	C14—N3—C15	123.93 (12)
C12—C13—H13	119.6 (10)	C14—N3—H3N	114.0 (13)
C8—C13—H13	119.1 (10)	C15—N3—H3N	120.9 (13)
O6—C14—N4	123.48 (13)	C14—N4—C17	126.51 (12)
O6—C14—N3	119.81 (12)	C14—N4—H4N	117.2 (12)
N4—C14—N3	116.70 (12)	C17—N4—H4N	115.1 (12)
C16—C15—N3	119.54 (12)	C5—O3—C6	115.32 (11)
C16—C15—C20	127.09 (13)	C11—O4—H1O	109.9 (14)
N3—C15—C20	113.36 (12)	H3O—O5—H4O	112.6 (19)
C15—C16—C18	119.77 (12)	C18—O8—C19	113.98 (11)
C15—C16—C17	122.02 (12)	C24—O9—H2O	111.0 (15)
C18—C16—C17	118.21 (12)	H5O—O10—H6O	113 (2)
N1—C2—C3—C5	178.24 (12)	C15—C16—C18—O8	−175.05 (12)
C7—C2—C3—C5	−3.6 (2)	C17—C16—C18—O8	5.71 (18)
N1—C2—C3—C4	−2.98 (19)	N4—C17—C21—C26	−68.68 (15)
C7—C2—C3—C4	175.15 (13)	C16—C17—C21—C26	53.97 (16)
C2—C3—C4—N2	−5.41 (17)	N4—C17—C21—C22	109.60 (14)
C5—C3—C4—N2	173.40 (11)	C16—C17—C21—C22	−127.75 (13)
C2—C3—C4—C8	117.77 (14)	C26—C21—C22—C23	−0.2 (2)
C5—C3—C4—C8	−63.42 (15)	C17—C21—C22—C23	−178.55 (12)
C2—C3—C5—O2	−3.9 (2)	C21—C22—C23—C24	−0.3 (2)
C4—C3—C5—O2	177.25 (13)	C22—C23—C24—O9	−178.78 (12)
C2—C3—C5—O3	177.24 (12)	C22—C23—C24—C25	0.6 (2)
C4—C3—C5—O3	−1.58 (17)	O9—C24—C25—C26	179.01 (12)
N2—C4—C8—C9	−108.73 (13)	C23—C24—C25—C26	−0.4 (2)
C3—C4—C8—C9	127.59 (13)	C24—C25—C26—C21	−0.2 (2)
N2—C4—C8—C13	67.52 (16)	C22—C21—C26—C25	0.5 (2)
C3—C4—C8—C13	−56.15 (17)	C17—C21—C26—C25	178.83 (12)
C13—C8—C9—C10	0.6 (2)	O1—C1—N1—C2	−179.62 (12)
C4—C8—C9—C10	176.94 (12)	N2—C1—N1—C2	2.45 (19)
C8—C9—C10—C11	−0.3 (2)	C3—C2—N1—C1	5.2 (2)
C9—C10—C11—O4	−179.75 (12)	C7—C2—N1—C1	−173.19 (13)
C9—C10—C11—C12	0.3 (2)	O1—C1—N2—C4	169.09 (12)
O4—C11—C12—C13	179.50 (12)	N1—C1—N2—C4	−13.0 (2)
C10—C11—C12—C13	−0.6 (2)	C8—C4—N2—C1	−113.04 (14)
C11—C12—C13—C8	0.8 (2)	C3—C4—N2—C1	14.04 (18)
C9—C8—C13—C12	−0.8 (2)	O6—C14—N3—C15	−176.36 (12)
C4—C8—C13—C12	−177.17 (12)	N4—C14—N3—C15	2.68 (19)
N3—C15—C16—C18	−179.33 (12)	C16—C15—N3—C14	−7.4 (2)
C20—C15—C16—C18	1.5 (2)	C20—C15—N3—C14	171.83 (12)
N3—C15—C16—C17	−0.1 (2)	O6—C14—N4—C17	−170.82 (12)
C20—C15—C16—C17	−179.25 (13)	N3—C14—N4—C17	10.18 (19)
C15—C16—C17—N4	10.20 (18)	C16—C17—N4—C14	−15.85 (18)
C18—C16—C17—N4	−170.57 (11)	C21—C17—N4—C14	108.97 (14)
C15—C16—C17—C21	−112.65 (14)	O2—C5—O3—C6	−4.45 (19)
C18—C16—C17—C21	66.57 (15)	C3—C5—O3—C6	174.46 (11)
C15—C16—C18—O7	6.7 (2)	O7—C18—O8—C19	1.7 (2)
C17—C16—C18—O7	−172.58 (15)	C16—C18—O8—C19	−176.70 (12)

Hydrogen-bond geometry (Å, º)

Cg1 and Cg2 are the centroids of the C8–C13 and C21–C26 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O6	0.878 (19)	2.10 (2)	2.9762 (16)	173.1 (17)
N3—H3N···O1	0.88 (2)	1.98 (2)	2.8626 (16)	174 (2)
N2—H2N···O9^i	0.89 (2)	2.02 (2)	2.8971 (19)	170.0 (18)
N4—H4N···O4^ii	0.87 (2)	2.13 (2)	2.9738 (19)	163.4 (18)
O4—H1O···O5	0.87 (2)	1.78 (2)	2.6473 (16)	175 (2)
O9—H2O···O10	0.90 (2)	1.73 (2)	2.6189 (17)	174.7 (19)
O5—H4O···O2^iii	0.84 (2)	2.15 (2)	2.8549 (19)	141 (2)
O5—H3O···O1^iv	0.91 (3)	1.91 (3)	2.786 (2)	162 (2)
C20—H20C···O5^iv	1.00 (2)	2.56 (2)	3.332 (2)	133.7 (17)
C26—H26···O3^v	0.971 (17)	2.571 (18)	3.4607 (18)	152.4 (14)
C6—H6B···Cg2^vi	0.989 (19)	2.70 (2)	3.392 (2)	127.1 (16)
C19—H19C···Cg1^vii	0.98 (2)	2.84 (2)	3.395 (2)	116.5 (16)

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