Ethyl 6-methyl-2-oxo-4-phenyl-1,2,3,4-tetra­hydro­pyrimidine-5-carboxyl­ate

The title compound, C₁₄H₁₆N₂O₃, is chiral. There are two mol­ecules in the asymmetric unit, which are related by an approximate non-crystallographic twofold screw axis. Mol­ecules of the title compound are linked by inter­molecular N—H...O hydrogen-bond inter­actions involving the H atoms of the amino groups and O atoms of the keto groups, thus forming a zigzag structure.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.010 Å
• R factor = 0.062
• wR factor = 0.180
• Data-to-parameter ratio = 7.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.57
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.83 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.18 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.21 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.60 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O4     -   C27     ..       5.57 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C13
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C27
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         10

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           25.00
           From the CIF: _reflns_number_total               2505
           Count of symmetry unique reflns         2549
           Completeness (_total/calc)             98.27%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C20    = .          S

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000) and DIAMOND (Brandenburg, 2004); software used to prepare material for publication: SHELXTL.

Ethyl 6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Crystal data

C14H16N2O3	Dx = 1.299 Mg m^−3
Mr = 260.29	Melting point: 475 K
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 11.516 (3) Å	Cell parameters from 1277 reflections
b = 7.429 (2) Å	θ = 2.5–22.2°
c = 16.101 (3) Å	µ = 0.09 mm^−1
β = 104.878 (3)°	T = 298 K
V = 1331.3 (6) Å^3	Needle, colourless
Z = 4	0.52 × 0.11 × 0.08 mm
F(000) = 552

Data collection

Bruker SMART CCD area-detector diffractometer	2505 independent reflections
Radiation source: fine-focus sealed tube	1614 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.056
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→10
Tmin = 0.954, Tmax = 0.993	k = −8→8
6562 measured reflections	l = −17→19

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)] = 0.062	H-atom parameters constrained
wR(F^2) = 0.180	w = 1/[σ^2(Fo^2) + (0.0758P)^2 + 0.0608P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
2505 reflections	Δρmax = 0.35 e Å^−3
331 parameters	Δρmin = −0.46 e Å^−3
52 restraints	Absolute structure: Flack (1983), with how many Friedel pairs?
Primary atom site location: structure-invariant direct methods

Special details

Experimental. Spectroscopic analysis: ¹H NMR (DMSO-d₆, 360 MHz, δ, p.p.m.): 9.21 (br, 1H), 7.3 (br, 1H), 7.03–7.32 (m, 5H), 5.11 (s, 1H), 3.91 (q, 2H), 2.30 (s, 3H), 1.09 (t, 3H). Elemental analysis, calculated for C₁₄H₁₆N₂O₃: C 64.60, H 6.19, N 10.76%; found: C 64.25, H 6.21, N 10.68%.

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
N1	0.9344 (4)	0.6919 (7)	0.1671 (3)	0.0369 (12)
H1	0.9113	0.5908	0.1423	0.044*
N2	0.9317 (4)	1.0012 (7)	0.1613 (3)	0.0393 (13)
H2	0.9386	1.0978	0.1335	0.047*
N3	0.8265 (4)	0.4923 (7)	0.9486 (3)	0.0387 (12)
H3	0.8365	0.5925	0.9763	0.046*
N4	0.8286 (4)	0.1844 (7)	0.9499 (3)	0.0346 (12)
H4	0.8657	0.0874	0.9707	0.042*
O1	1.0867 (4)	1.0324 (7)	0.4129 (2)	0.0525 (12)
O2	1.1080 (5)	0.7377 (8)	0.4360 (3)	0.0722 (16)
O3	0.8841 (3)	0.8362 (6)	0.0388 (2)	0.0418 (10)
O4	0.6659 (4)	0.1739 (7)	0.6949 (2)	0.0576 (13)
O5	0.6833 (4)	0.4698 (7)	0.6751 (3)	0.0607 (14)
O6	0.9123 (3)	0.3432 (6)	1.0718 (2)	0.0437 (10)
C1	1.0700 (6)	0.8628 (10)	0.3881 (4)	0.0439 (15)
C2	0.9997 (5)	0.8469 (9)	0.2987 (3)	0.0340 (13)
C3	0.9899 (5)	0.6910 (9)	0.2543 (3)	0.0355 (14)
C4	1.0329 (6)	0.5094 (9)	0.2882 (4)	0.0489 (17)
H4A	1.0764	0.4547	0.2513	0.073*
H4B	0.9652	0.4355	0.2900	0.073*
H4C	1.0847	0.5212	0.3451	0.073*
C5	0.9142 (5)	0.8461 (8)	0.1180 (3)	0.0321 (12)
C6	0.9399 (5)	1.0170 (8)	0.2532 (3)	0.0354 (14)
H6	0.9914	1.1202	0.2758	0.042*
C7	0.8171 (5)	1.0481 (8)	0.2707 (3)	0.0361 (14)
C8	0.7123 (6)	0.9912 (12)	0.2147 (5)	0.068 (2)
H8	0.7151	0.9391	0.1627	0.082*
C9	0.6031 (7)	1.0101 (13)	0.2341 (6)	0.082 (3)
H9	0.5334	0.9671	0.1963	0.099*
C10	0.5972 (7)	1.0921 (11)	0.3092 (5)	0.068 (2)
H10	0.5236	1.1058	0.3222	0.082*
C11	0.6992 (6)	1.1530 (12)	0.3644 (4)	0.061 (2)
H11	0.6953	1.2099	0.4150	0.073*
C12	0.8082 (6)	1.1312 (10)	0.3458 (4)	0.0487 (18)
H12	0.8774	1.1731	0.3844	0.058*
C13	1.1584 (9)	1.0611 (13)	0.5007 (5)	0.0903 (19)
H13A	1.2321	0.9916	0.5112	0.108*
H13B	1.1139	1.0223	0.5412	0.108*
C14	1.1865 (9)	1.2542 (12)	0.5121 (5)	0.0903 (19)
H14A	1.2327	1.2758	0.5700	0.135*
H14B	1.1131	1.3220	0.5012	0.135*
H14C	1.2319	1.2909	0.4727	0.135*
C15	0.6961 (5)	0.3395 (11)	0.7237 (4)	0.0439 (15)
C16	0.7388 (5)	0.3452 (9)	0.8174 (3)	0.0344 (13)
C17	0.7792 (5)	0.4971 (9)	0.8604 (3)	0.0357 (15)
C18	0.7812 (6)	0.6817 (9)	0.8237 (4)	0.0521 (18)
H18A	0.7917	0.6727	0.7666	0.078*
H18B	0.8464	0.7493	0.8591	0.078*
H18C	0.7067	0.7416	0.8217	0.078*
C19	0.8580 (5)	0.3378 (9)	0.9935 (3)	0.0321 (12)
C20	0.7360 (5)	0.1734 (9)	0.8683 (3)	0.0348 (14)
H20	0.7563	0.0727	0.8354	0.042*
C21	0.6142 (5)	0.1359 (8)	0.8834 (4)	0.0353 (14)
C22	0.5791 (6)	0.2147 (11)	0.9516 (4)	0.0538 (19)
H22	0.6327	0.2868	0.9907	0.065*
C23	0.4647 (7)	0.1858 (12)	0.9613 (5)	0.068 (2)
H23	0.4422	0.2400	1.0069	0.081*
C24	0.3844 (6)	0.0800 (11)	0.9059 (5)	0.060 (2)
H24	0.3081	0.0615	0.9137	0.072*
C25	0.4170 (6)	0.0002 (11)	0.8378 (5)	0.064 (2)
H25	0.3630	−0.0728	0.7995	0.077*
C26	0.5312 (5)	0.0299 (10)	0.8273 (4)	0.0513 (17)
H26	0.5525	−0.0231	0.7810	0.062*
C27	0.6171 (9)	0.1544 (15)	0.6029 (5)	0.101 (2)
H27A	0.6819	0.1510	0.5746	0.121*
H27B	0.5658	0.2561	0.5806	0.121*
C28	0.5477 (9)	−0.0128 (14)	0.5861 (5)	0.101 (2)
H28A	0.5136	−0.0255	0.5254	0.151*
H28B	0.4845	−0.0094	0.6150	0.151*
H28C	0.5996	−0.1132	0.6068	0.151*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.047 (3)	0.025 (3)	0.036 (3)	0.000 (3)	0.006 (2)	0.005 (2)
N2	0.055 (3)	0.028 (3)	0.038 (3)	−0.002 (3)	0.016 (2)	−0.002 (3)
N3	0.048 (3)	0.030 (3)	0.037 (3)	−0.002 (3)	0.011 (2)	0.000 (2)
N4	0.032 (3)	0.026 (3)	0.039 (3)	0.000 (2)	−0.002 (2)	−0.002 (2)
O1	0.060 (3)	0.051 (3)	0.037 (2)	−0.002 (2)	−0.005 (2)	−0.015 (2)
O2	0.101 (4)	0.056 (4)	0.047 (3)	0.009 (3)	−0.004 (3)	0.001 (3)
O3	0.060 (3)	0.035 (2)	0.032 (2)	0.006 (2)	0.0160 (19)	0.001 (2)
O4	0.078 (3)	0.057 (3)	0.030 (2)	−0.017 (3)	0.000 (2)	−0.007 (2)
O5	0.076 (3)	0.058 (3)	0.045 (2)	0.006 (3)	0.009 (2)	0.020 (3)
O6	0.060 (3)	0.037 (2)	0.031 (2)	−0.004 (2)	0.0070 (18)	−0.001 (2)
C1	0.051 (4)	0.039 (4)	0.037 (3)	0.003 (3)	0.003 (3)	0.004 (4)
C2	0.040 (3)	0.025 (3)	0.036 (3)	0.002 (3)	0.007 (2)	0.000 (3)
C3	0.040 (3)	0.034 (4)	0.032 (3)	−0.001 (3)	0.006 (2)	0.007 (3)
C4	0.069 (4)	0.029 (4)	0.046 (4)	0.012 (3)	0.009 (3)	0.002 (3)
C5	0.041 (3)	0.018 (3)	0.040 (3)	−0.002 (3)	0.017 (2)	−0.001 (3)
C6	0.048 (3)	0.026 (3)	0.033 (3)	0.005 (3)	0.013 (2)	0.000 (3)
C7	0.046 (3)	0.025 (3)	0.037 (3)	0.002 (3)	0.010 (3)	0.002 (3)
C8	0.043 (4)	0.068 (6)	0.093 (5)	0.004 (4)	0.015 (4)	−0.038 (5)
C9	0.053 (5)	0.078 (7)	0.112 (7)	−0.008 (5)	0.015 (5)	−0.047 (6)
C10	0.058 (5)	0.052 (5)	0.101 (6)	−0.009 (4)	0.033 (5)	−0.003 (5)
C11	0.064 (5)	0.066 (5)	0.059 (4)	0.004 (4)	0.027 (4)	−0.013 (4)
C12	0.047 (4)	0.055 (5)	0.044 (3)	0.010 (3)	0.012 (3)	−0.004 (3)
C13	0.100 (4)	0.079 (4)	0.068 (3)	−0.005 (4)	−0.020 (3)	−0.021 (3)
C14	0.100 (4)	0.079 (4)	0.068 (3)	−0.005 (4)	−0.020 (3)	−0.021 (3)
C15	0.036 (3)	0.051 (4)	0.046 (3)	0.007 (4)	0.013 (3)	0.008 (4)
C16	0.035 (3)	0.033 (4)	0.038 (3)	0.001 (3)	0.013 (2)	0.002 (3)
C17	0.035 (3)	0.035 (4)	0.039 (3)	0.004 (3)	0.013 (3)	0.007 (3)
C18	0.059 (4)	0.032 (4)	0.061 (4)	0.000 (4)	0.008 (3)	0.015 (3)
C19	0.035 (3)	0.028 (3)	0.034 (3)	0.000 (3)	0.012 (2)	0.000 (3)
C20	0.037 (3)	0.035 (4)	0.031 (3)	0.003 (3)	0.005 (2)	−0.001 (3)
C21	0.042 (3)	0.022 (3)	0.043 (3)	0.000 (3)	0.013 (3)	0.007 (3)
C22	0.042 (4)	0.067 (5)	0.058 (4)	−0.007 (4)	0.022 (3)	−0.014 (4)
C23	0.062 (5)	0.073 (6)	0.081 (5)	0.006 (5)	0.041 (4)	0.007 (5)
C24	0.039 (4)	0.056 (5)	0.089 (5)	−0.002 (4)	0.027 (4)	0.019 (4)
C25	0.050 (4)	0.067 (6)	0.074 (5)	−0.021 (4)	0.011 (4)	0.001 (5)
C26	0.051 (4)	0.048 (4)	0.056 (4)	−0.017 (4)	0.014 (3)	−0.008 (4)
C27	0.126 (5)	0.101 (5)	0.062 (3)	−0.028 (4)	0.001 (3)	−0.017 (4)
C28	0.126 (5)	0.101 (5)	0.062 (3)	−0.028 (4)	0.001 (3)	−0.017 (4)

Geometric parameters (Å, º)

N1—C5	1.377 (8)	C10—H10	0.9300
N1—C3	1.386 (7)	C11—C12	1.372 (9)
N1—H1	0.8600	C11—H11	0.9300
N2—C5	1.336 (8)	C12—H12	0.9300
N2—C6	1.463 (7)	C13—C14	1.472 (11)
N2—H2	0.8600	C13—H13A	0.9700
N3—C19	1.355 (8)	C13—H13B	0.9700
N3—C17	1.385 (7)	C14—H14A	0.9600
N3—H3	0.8600	C14—H14B	0.9600
N4—C19	1.336 (8)	C14—H14C	0.9600
N4—C20	1.466 (7)	C15—C16	1.462 (8)
N4—H4	0.8600	C16—C17	1.343 (9)
O1—C1	1.320 (9)	C16—C20	1.522 (9)
O1—C13	1.459 (8)	C17—C18	1.497 (9)
O2—C1	1.215 (8)	C18—H18A	0.9600
O3—C5	1.235 (6)	C18—H18B	0.9600
O4—C15	1.330 (10)	C18—H18C	0.9600
O4—C27	1.450 (8)	C20—C21	1.509 (8)
O5—C15	1.230 (8)	C20—H20	0.9800
O6—C19	1.255 (6)	C21—C26	1.380 (8)
C1—C2	1.464 (8)	C21—C22	1.394 (8)
C2—C3	1.351 (9)	C22—C23	1.383 (9)
C2—C6	1.532 (9)	C22—H22	0.9300
C3—C4	1.491 (9)	C23—C24	1.358 (11)
C4—H4A	0.9600	C23—H23	0.9300
C4—H4B	0.9600	C24—C25	1.380 (10)
C4—H4C	0.9600	C24—H24	0.9300
C6—C7	1.530 (8)	C25—C26	1.386 (9)
C6—H6	0.9800	C25—H25	0.9300
C7—C8	1.375 (8)	C26—H26	0.9300
C7—C12	1.384 (8)	C27—C28	1.464 (10)
C8—C9	1.380 (10)	C27—H27A	0.9700
C8—H8	0.9300	C27—H27B	0.9700
C9—C10	1.370 (10)	C28—H28A	0.9600
C9—H9	0.9300	C28—H28B	0.9600
C10—C11	1.356 (10)	C28—H28C	0.9600
C5—N1—C3	123.5 (5)	H13A—C13—H13B	108.4
C5—N1—H1	118.2	C13—C14—H14A	109.5
C3—N1—H1	118.2	C13—C14—H14B	109.5
C5—N2—C6	124.0 (5)	H14A—C14—H14B	109.5
C5—N2—H2	118.0	C13—C14—H14C	109.5
C6—N2—H2	118.0	H14A—C14—H14C	109.5
C19—N3—C17	123.3 (5)	H14B—C14—H14C	109.5
C19—N3—H3	118.3	O5—C15—O4	121.9 (5)
C17—N3—H3	118.3	O5—C15—C16	126.0 (7)
C19—N4—C20	123.1 (5)	O4—C15—C16	112.1 (6)
C19—N4—H4	118.5	C17—C16—C15	122.5 (6)
C20—N4—H4	118.5	C17—C16—C20	118.6 (5)
C1—O1—C13	115.7 (6)	C15—C16—C20	118.9 (6)
C15—O4—C27	116.6 (6)	C16—C17—N3	120.0 (6)
O2—C1—O1	122.5 (6)	C16—C17—C18	127.2 (5)
O2—C1—C2	125.4 (7)	N3—C17—C18	112.8 (6)
O1—C1—C2	112.0 (6)	C17—C18—H18A	109.5
C3—C2—C1	122.6 (6)	C17—C18—H18B	109.5
C3—C2—C6	119.2 (5)	H18A—C18—H18B	109.5
C1—C2—C6	118.1 (6)	C17—C18—H18C	109.5
C2—C3—N1	119.1 (6)	H18A—C18—H18C	109.5
C2—C3—C4	127.4 (5)	H18B—C18—H18C	109.5
N1—C3—C4	113.5 (5)	O6—C19—N4	123.3 (6)
C3—C4—H4A	109.5	O6—C19—N3	120.3 (6)
C3—C4—H4B	109.5	N4—C19—N3	116.4 (4)
H4A—C4—H4B	109.5	N4—C20—C21	111.0 (4)
C3—C4—H4C	109.5	N4—C20—C16	109.0 (5)
H4A—C4—H4C	109.5	C21—C20—C16	113.0 (5)
H4B—C4—H4C	109.5	N4—C20—H20	107.9
O3—C5—N2	123.7 (6)	C21—C20—H20	107.9
O3—C5—N1	120.3 (6)	C16—C20—H20	107.9
N2—C5—N1	116.0 (4)	C26—C21—C22	117.6 (6)
N2—C6—C7	112.1 (5)	C26—C21—C20	121.1 (5)
N2—C6—C2	108.8 (5)	C22—C21—C20	121.2 (5)
C7—C6—C2	111.1 (5)	C23—C22—C21	120.1 (7)
N2—C6—H6	108.3	C23—C22—H22	119.9
C7—C6—H6	108.3	C21—C22—H22	119.9
C2—C6—H6	108.3	C24—C23—C22	121.5 (7)
C8—C7—C12	117.5 (6)	C24—C23—H23	119.2
C8—C7—C6	122.0 (5)	C22—C23—H23	119.2
C12—C7—C6	120.5 (5)	C23—C24—C25	119.5 (6)
C7—C8—C9	121.2 (7)	C23—C24—H24	120.2
C7—C8—H8	119.4	C25—C24—H24	120.2
C9—C8—H8	119.4	C24—C25—C26	119.3 (7)
C10—C9—C8	120.0 (7)	C24—C25—H25	120.4
C10—C9—H9	120.0	C26—C25—H25	120.4
C8—C9—H9	120.0	C21—C26—C25	122.0 (6)
C11—C10—C9	119.7 (7)	C21—C26—H26	119.0
C11—C10—H10	120.1	C25—C26—H26	119.0
C9—C10—H10	120.1	O4—C27—C28	108.9 (8)
C10—C11—C12	120.3 (7)	O4—C27—H27A	109.9
C10—C11—H11	119.8	C28—C27—H27A	109.9
C12—C11—H11	119.8	O4—C27—H27B	109.9
C11—C12—C7	121.3 (6)	C28—C27—H27B	109.9
C11—C12—H12	119.3	H27A—C27—H27B	108.3
C7—C12—H12	119.3	C27—C28—H28A	109.5
O1—C13—C14	108.3 (8)	C27—C28—H28B	109.5
O1—C13—H13A	110.0	H28A—C28—H28B	109.5
C14—C13—H13A	110.0	C27—C28—H28C	109.5
O1—C13—H13B	110.0	H28A—C28—H28C	109.5
C14—C13—H13B	110.0	H28B—C28—H28C	109.5
C13—O1—C1—O2	2.5 (10)	C27—O4—C15—O5	0.1 (9)
C13—O1—C1—C2	−178.7 (6)	C27—O4—C15—C16	177.3 (6)
O2—C1—C2—C3	−13.8 (10)	O5—C15—C16—C17	−6.0 (9)
O1—C1—C2—C3	167.3 (5)	O4—C15—C16—C17	177.0 (5)
O2—C1—C2—C6	169.0 (6)	O5—C15—C16—C20	173.3 (6)
O1—C1—C2—C6	−9.8 (8)	O4—C15—C16—C20	−3.8 (7)
C1—C2—C3—N1	−172.0 (5)	C15—C16—C17—N3	−175.4 (5)
C6—C2—C3—N1	5.1 (8)	C20—C16—C17—N3	5.4 (8)
C1—C2—C3—C4	8.0 (10)	C15—C16—C17—C18	4.0 (9)
C6—C2—C3—C4	−174.9 (6)	C20—C16—C17—C18	−175.3 (6)
C5—N1—C3—C2	16.4 (8)	C19—N3—C17—C16	14.0 (8)
C5—N1—C3—C4	−163.6 (5)	C19—N3—C17—C18	−165.4 (5)
C6—N2—C5—O3	165.3 (5)	C20—N4—C19—O6	160.9 (5)
C6—N2—C5—N1	−16.2 (7)	C20—N4—C19—N3	−19.5 (7)
C3—N1—C5—O3	167.2 (5)	C17—N3—C19—O6	172.3 (5)
C3—N1—C5—N2	−11.4 (7)	C17—N3—C19—N4	−7.4 (7)
C5—N2—C6—C7	−89.5 (7)	C19—N4—C20—C21	−89.9 (6)
C5—N2—C6—C2	33.7 (7)	C19—N4—C20—C16	35.2 (7)
C3—C2—C6—N2	−27.0 (8)	C17—C16—C20—N4	−26.9 (7)
C1—C2—C6—N2	150.2 (5)	C15—C16—C20—N4	153.8 (5)
C3—C2—C6—C7	96.8 (6)	C17—C16—C20—C21	97.0 (6)
C1—C2—C6—C7	−85.9 (6)	C15—C16—C20—C21	−82.2 (6)
N2—C6—C7—C8	26.1 (9)	N4—C20—C21—C26	−145.0 (6)
C2—C6—C7—C8	−95.9 (7)	C16—C20—C21—C26	92.2 (7)
N2—C6—C7—C12	−155.7 (6)	N4—C20—C21—C22	38.6 (8)
C2—C6—C7—C12	82.3 (7)	C16—C20—C21—C22	−84.2 (7)
C12—C7—C8—C9	−2.5 (12)	C26—C21—C22—C23	0.0 (10)
C6—C7—C8—C9	175.8 (8)	C20—C21—C22—C23	176.5 (6)
C7—C8—C9—C10	2.2 (14)	C21—C22—C23—C24	0.5 (12)
C8—C9—C10—C11	−0.5 (14)	C22—C23—C24—C25	−0.4 (12)
C9—C10—C11—C12	−0.7 (13)	C23—C24—C25—C26	−0.2 (12)
C10—C11—C12—C7	0.4 (12)	C22—C21—C26—C25	−0.6 (10)
C8—C7—C12—C11	1.2 (11)	C20—C21—C26—C25	−177.1 (6)
C6—C7—C12—C11	−177.1 (7)	C24—C25—C26—C21	0.7 (11)
C1—O1—C13—C14	169.7 (8)	C15—O4—C27—C28	−158.3 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O6^i	0.86	2.17	2.993 (7)	161
N2—H2···O6^ii	0.86	2.07	2.907 (7)	166
N3—H3···O3^iii	0.86	2.07	2.927 (7)	172
N4—H4···O3^iv	0.86	2.15	2.947 (7)	154

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