Methyl 5-nitro-2-(phenyl­amino)pyridine-4-carboxyl­ate

In the crystal structure of the title compound, C₁₃H₁₁N₃O₄, there are two independent mol­ecules in the asymmetric unit. In each case, the methyl­carboxyl­ate group is twisted by about 90° relative to the rest of the mol­ecule. The mol­ecules are packed in the crystal structure through N—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.041
• wR factor = 0.116
• Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............      24.99 Deg.

Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         47 Perc.
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N13    -   C19     ..       5.32 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C13
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        N23
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.10
PLAT480_ALERT_4_C Long H...A H-Bond Reported H21    ..  O11     ..       2.62 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C13 H11 N3 O4

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

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

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Computing details

Data collection: CAD-4-PC Software (Enraf–Nonius, 1992); cell refinement: CELDIM in CAD-4-PC Software; data reduction: XCAD4 (McArdle & Higgins, 1995); program(s) used to solve structure: OSCAIL (McArdle, 2005) and SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1993) and ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: OSCAIL.

Methyl 5-nitro-2-(phenylamino)pyridine-4-carboxylate

Crystal data

C13H11N3O4	Z = 4
Mr = 273.25	F(000) = 568
Triclinic, P1	Dx = 1.427 Mg m^−3
a = 9.990 (2) Å	Mo Kα radiation, λ = 0.71069 Å
b = 10.913 (3) Å	Cell parameters from 25 reflections
c = 12.6758 (19) Å	θ = 12–19°
α = 81.055 (17)°	µ = 0.11 mm^−1
β = 78.137 (16)°	T = 293 K
γ = 70.86 (2)°	Block, light yellow
V = 1271.8 (5) Å^3	0.50 × 0.40 × 0.30 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	2078 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.018
Graphite monochromator	θmax = 25.0°, θmin = 1.7°
ω–2θ scans	h = 0→11
Absorption correction: ψ scan (ABSCALC in OSCAIL; McArdle & Daly, 1999; North et al., 1968)	k = −12→12
Tmin = 0.948, Tmax = 0.968	l = −14→15
4900 measured reflections	3 standard reflections every 120 min
4452 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)] = 0.041	H-atom parameters constrained
wR(F^2) = 0.116	w = 1/[σ^2(Fo^2) + (0.0576P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.95	(Δ/σ)max = 0.021
4452 reflections	Δρmax = 0.19 e Å^−3
364 parameters	Δρmin = −0.17 e Å^−3
116 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0074 (14)

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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 4.0650 (0.0068) x + 4.6026 (0.0116) y + 8.2697 (0.0097) z = 3.2735 (0.0022)

* 0.0174 (0.0015) N11 * -0.0048 (0.0021) C11 * -0.0114 (0.0024) C12 * -0.0033 (0.0024) C13 * 0.0150 (0.0025) C14 * 0.0049 (0.0021) C15 * -0.0178 (0.0020) C16

Rms deviation of fitted atoms = 0.0122

- 5.0479 (0.0052) x + 2.4594 (0.0056) y + 8.5223 (0.0072) z = 2.9476 (0.0025)

Angle to previous plane (with approximate e.s.d.) = 11.93 (0.12)

* 0.0364 (0.0015) N11 * 0.0005 (0.0020) C17 * -0.0223 (0.0018) N12 * -0.0174 (0.0020) C18 * -0.0005 (0.0021) C19 * -0.0128 (0.0021) C110 * -0.0157 (0.0021) C111 * -0.0035 (0.0016) C112 * 0.0351 (0.0017) N13 0.0771 (0.0029) O13 0.0202 (0.0034) O14 0.9985 (0.0027) O11 - 1.2198 (0.0026) O12 - 1.3399 (0.0044) C113

Rms deviation of fitted atoms = 0.0205

- 4.6913 (0.0096) x + 1.9681 (0.0113) y + 9.1824 (0.0084) z = 4.9261 (0.0113)

Angle to previous plane (with approximate e.s.d.) = 4.98 (0.13)

* -0.0099 (0.0014) N21 * 0.0090 (0.0020) C21 * 0.0030 (0.0021) C22 * -0.0001 (0.0021) C23 * -0.0041 (0.0023) C24 * -0.0043 (0.0020) C25 * 0.0064 (0.0020) C26

Rms deviation of fitted atoms = 0.0061

- 6.1184 (0.0066) x + 2.1039 (0.0061) y + 7.1916 (0.0084) z = 3.6755 (0.0084)

Angle to previous plane (with approximate e.s.d.) = 11.92 (0.14)

* -0.0639 (0.0016) N21 * 0.0139 (0.0021) C27 * -0.0013 (0.0018) N22 * 0.0028 (0.0022) C28 * 0.0127 (0.0023) C29 * 0.0488 (0.0022) C210 * 0.0727 (0.0021) C211 * -0.0581 (0.0017) C212 * -0.0278 (0.0020) N23 0.1325 (0.0035) O23 - 0.2007 (0.0045) O24 0.8574 (0.0030) O21 - 1.3191 (0.0026) O22 - 1.6175 (0.0043) C213

Rms deviation of fitted atoms = 0.0425

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
O11	0.08162 (17)	0.46752 (18)	0.37646 (14)	0.0597 (5)
N21	0.2247 (2)	0.55210 (19)	0.53186 (15)	0.0496 (5)
H21	0.1646	0.5331	0.5025	0.064*
N11	−0.1946 (2)	0.25156 (19)	0.16230 (15)	0.0488 (5)
H11	−0.1499	0.1849	0.2013	0.063*
N22	0.3036 (2)	0.7224 (2)	0.55787 (15)	0.0516 (6)
O12	0.24138 (19)	0.40186 (19)	0.22975 (15)	0.0701 (6)
O22	0.1838 (2)	0.93528 (17)	0.21040 (14)	0.0650 (5)
O14	−0.0727 (3)	0.7773 (2)	0.08089 (19)	0.0969 (8)
O13	0.0670 (2)	0.6852 (2)	0.19687 (17)	0.0853 (7)
N12	−0.2027 (2)	0.46247 (19)	0.08975 (15)	0.0500 (5)
N13	−0.0189 (3)	0.6835 (2)	0.14154 (19)	0.0636 (6)
O21	−0.0380 (2)	1.00928 (19)	0.30268 (14)	0.0717 (6)
N23	0.2540 (3)	1.0500 (2)	0.4162 (2)	0.0794 (8)
O23	0.1810 (3)	1.1247 (2)	0.3545 (2)	0.1065 (9)
O24	0.3384 (4)	1.0803 (2)	0.4550 (2)	0.1475 (13)
C113	0.3565 (3)	0.3827 (4)	0.2894 (3)	0.0894 (11)
H13A	0.3469	0.4630	0.3167	0.125*
H13B	0.4472	0.3552	0.2423	0.125*
H13C	0.3520	0.3171	0.3488	0.125*
C16	−0.3703 (3)	0.3148 (2)	0.0365 (2)	0.0545 (7)
H16	−0.3429	0.3881	0.0063	0.071*
C26	0.4097 (3)	0.4549 (3)	0.64898 (19)	0.0549 (7)
H26	0.4309	0.5327	0.6437	0.071*
C19	−0.0578 (3)	0.5664 (2)	0.14810 (19)	0.0476 (6)
C210	0.1558 (3)	0.8766 (2)	0.39393 (19)	0.0474 (6)
C28	0.3073 (3)	0.8432 (3)	0.5263 (2)	0.0609 (8)
H28	0.3598	0.8764	0.5607	0.079*
C11	−0.3026 (2)	0.2321 (2)	0.11732 (18)	0.0444 (6)
C12	−0.3422 (3)	0.1230 (3)	0.1578 (2)	0.0686 (8)
H12	−0.2964	0.0657	0.2110	0.089*
C111	−0.0437 (3)	0.3503 (2)	0.21705 (19)	0.0469 (6)
H111	−0.0061	0.2741	0.2598	0.061*
C212	0.0870 (3)	0.9510 (2)	0.2988 (2)	0.0517 (7)
C110	0.0026 (2)	0.4550 (2)	0.21460 (18)	0.0434 (6)
C17	−0.1483 (2)	0.3567 (2)	0.15515 (18)	0.0428 (6)
C213	0.1345 (3)	0.9955 (3)	0.1094 (2)	0.0802 (10)
H23A	0.0536	0.9700	0.1026	0.112*
H23B	0.2107	0.9679	0.0500	0.112*
H23C	0.1067	1.0886	0.1087	0.112*
C23	0.3488 (4)	0.2245 (3)	0.6666 (2)	0.0779 (9)
H23	0.3281	0.1463	0.6728	0.101*
C24	0.4539 (3)	0.2324 (3)	0.7181 (2)	0.0779 (9)
H24	0.5041	0.1600	0.7590	0.101*
C14	−0.5187 (3)	0.1805 (3)	0.0423 (3)	0.0761 (9)
H14	−0.5920	0.1637	0.0179	0.099*
C211	0.1481 (2)	0.7538 (2)	0.42669 (19)	0.0480 (6)
H211	0.0917	0.7208	0.3960	0.062*
C112	0.1117 (3)	0.4448 (2)	0.2832 (2)	0.0476 (6)
C22	0.2742 (3)	0.3316 (3)	0.6058 (2)	0.0598 (7)
H22	0.2037	0.3255	0.5709	0.078*
C25	0.4834 (3)	0.3462 (3)	0.7088 (2)	0.0659 (8)
H25	0.5547	0.3513	0.7433	0.086*
C27	0.2262 (2)	0.6769 (2)	0.50743 (18)	0.0437 (6)
C21	0.3041 (2)	0.4476 (2)	0.59690 (18)	0.0456 (6)
C15	−0.4786 (3)	0.2881 (3)	0.0008 (2)	0.0651 (8)
H15	−0.5249	0.3448	−0.0525	0.085*
C18	−0.1571 (3)	0.5642 (2)	0.08795 (19)	0.0527 (7)
H18	−0.1946	0.6386	0.0433	0.069*
C13	−0.4497 (4)	0.0973 (3)	0.1203 (3)	0.0884 (11)
H13	−0.4753	0.0226	0.1483	0.115*
C29	0.2385 (3)	0.9216 (2)	0.4461 (2)	0.0535 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O11	0.0492 (11)	0.0863 (14)	0.0488 (11)	−0.0202 (9)	−0.0119 (9)	−0.0180 (10)
N21	0.0477 (13)	0.0548 (14)	0.0513 (13)	−0.0182 (10)	−0.0235 (10)	0.0060 (10)
N11	0.0546 (13)	0.0428 (12)	0.0516 (13)	−0.0104 (10)	−0.0264 (11)	0.0016 (10)
N22	0.0650 (14)	0.0503 (14)	0.0428 (12)	−0.0142 (11)	−0.0228 (11)	−0.0033 (10)
O12	0.0427 (11)	0.1039 (16)	0.0643 (12)	−0.0141 (10)	−0.0081 (10)	−0.0292 (11)
O22	0.0663 (12)	0.0661 (12)	0.0480 (11)	0.0009 (10)	−0.0178 (10)	0.0020 (9)
O14	0.139 (2)	0.0701 (15)	0.1004 (17)	−0.0513 (14)	−0.0586 (16)	0.0294 (13)
O13	0.1049 (17)	0.0816 (15)	0.0930 (16)	−0.0490 (13)	−0.0438 (14)	0.0036 (12)
N12	0.0563 (14)	0.0479 (13)	0.0477 (13)	−0.0143 (11)	−0.0218 (11)	0.0040 (10)
N13	0.0788 (17)	0.0636 (16)	0.0554 (15)	−0.0294 (14)	−0.0179 (13)	−0.0001 (12)
O21	0.0580 (12)	0.0760 (13)	0.0618 (13)	0.0088 (10)	−0.0234 (10)	0.0036 (10)
N23	0.117 (2)	0.0459 (15)	0.0875 (19)	−0.0184 (15)	−0.0579 (17)	−0.0034 (13)
O23	0.156 (2)	0.0534 (13)	0.130 (2)	−0.0294 (14)	−0.0943 (18)	0.0243 (13)
O24	0.233 (3)	0.0732 (16)	0.195 (3)	−0.0706 (19)	−0.154 (3)	0.0266 (17)
C113	0.0438 (17)	0.136 (3)	0.096 (2)	−0.0203 (18)	−0.0167 (17)	−0.041 (2)
C16	0.0614 (17)	0.0549 (16)	0.0526 (16)	−0.0189 (14)	−0.0231 (14)	−0.0008 (13)
C26	0.0531 (16)	0.0578 (17)	0.0510 (16)	−0.0144 (13)	−0.0173 (14)	0.0090 (13)
C19	0.0536 (16)	0.0476 (16)	0.0440 (15)	−0.0174 (12)	−0.0085 (13)	−0.0067 (12)
C210	0.0491 (15)	0.0448 (15)	0.0425 (14)	−0.0027 (12)	−0.0135 (12)	−0.0045 (12)
C28	0.079 (2)	0.0521 (18)	0.0596 (18)	−0.0159 (15)	−0.0317 (16)	−0.0105 (14)
C11	0.0452 (15)	0.0461 (15)	0.0418 (14)	−0.0105 (12)	−0.0105 (12)	−0.0071 (12)
C12	0.090 (2)	0.0588 (19)	0.0685 (19)	−0.0305 (17)	−0.0368 (17)	0.0093 (15)
C111	0.0492 (15)	0.0448 (14)	0.0439 (14)	−0.0039 (12)	−0.0181 (12)	−0.0047 (11)
C212	0.0590 (18)	0.0435 (15)	0.0496 (17)	−0.0055 (13)	−0.0194 (15)	−0.0045 (12)
C110	0.0420 (14)	0.0481 (15)	0.0393 (14)	−0.0100 (12)	−0.0075 (12)	−0.0090 (12)
C17	0.0441 (14)	0.0443 (15)	0.0364 (13)	−0.0053 (12)	−0.0103 (12)	−0.0068 (11)
C213	0.099 (2)	0.077 (2)	0.0460 (17)	0.0011 (18)	−0.0223 (17)	0.0030 (15)
C23	0.104 (3)	0.0462 (18)	0.079 (2)	−0.0214 (17)	−0.019 (2)	0.0088 (16)
C24	0.089 (2)	0.063 (2)	0.064 (2)	−0.0042 (18)	−0.0214 (18)	0.0141 (16)
C14	0.076 (2)	0.076 (2)	0.094 (2)	−0.0334 (18)	−0.0380 (19)	−0.0070 (19)
C211	0.0452 (15)	0.0522 (16)	0.0480 (15)	−0.0126 (12)	−0.0164 (13)	−0.0026 (12)
C112	0.0473 (17)	0.0481 (16)	0.0489 (17)	−0.0129 (13)	−0.0103 (13)	−0.0093 (13)
C22	0.0695 (19)	0.0517 (17)	0.0594 (18)	−0.0193 (14)	−0.0149 (15)	−0.0011 (14)
C25	0.0635 (19)	0.069 (2)	0.0570 (18)	−0.0088 (16)	−0.0209 (15)	0.0085 (15)
C27	0.0455 (14)	0.0448 (15)	0.0402 (14)	−0.0114 (11)	−0.0123 (12)	−0.0005 (11)
C21	0.0437 (15)	0.0473 (15)	0.0401 (14)	−0.0089 (12)	−0.0070 (12)	0.0011 (11)
C15	0.0661 (19)	0.0653 (19)	0.072 (2)	−0.0180 (15)	−0.0363 (16)	−0.0013 (15)
C18	0.0585 (17)	0.0497 (16)	0.0490 (16)	−0.0133 (13)	−0.0200 (14)	0.0058 (12)
C13	0.116 (3)	0.073 (2)	0.100 (3)	−0.058 (2)	−0.042 (2)	0.0162 (19)
C29	0.0710 (18)	0.0374 (15)	0.0527 (16)	−0.0073 (13)	−0.0251 (14)	−0.0069 (12)

Geometric parameters (Å, º)

O11—C112	1.202 (3)	C210—C211	1.362 (3)
N21—C27	1.353 (3)	C210—C29	1.398 (3)
N21—C21	1.412 (3)	C210—C212	1.501 (3)
N21—H21	0.860	C28—C29	1.367 (3)
N11—C17	1.355 (3)	C28—H28	0.930
N11—C11	1.406 (3)	C11—C12	1.369 (3)
N11—H11	0.860	C12—C13	1.380 (4)
N22—C28	1.327 (3)	C12—H12	0.930
N22—C27	1.345 (3)	C111—C110	1.361 (3)
O12—C112	1.303 (3)	C111—C17	1.409 (3)
O12—C113	1.445 (3)	C111—H111	0.930
O22—C212	1.314 (3)	C110—C112	1.495 (3)
O22—C213	1.449 (3)	C213—H23A	0.960
O14—N13	1.221 (3)	C213—H23B	0.960
O13—N13	1.221 (3)	C213—H23C	0.960
N12—C18	1.326 (3)	C23—C24	1.376 (4)
N12—C17	1.338 (3)	C23—C22	1.378 (4)
N13—C19	1.439 (3)	C23—H23	0.930
O21—C212	1.196 (3)	C24—C25	1.350 (4)
N23—O23	1.206 (3)	C24—H24	0.930
N23—O24	1.211 (3)	C14—C15	1.359 (4)
N23—C29	1.443 (3)	C14—C13	1.367 (4)
C113—H13A	0.960	C14—H14	0.930
C113—H13B	0.960	C211—C27	1.411 (3)
C113—H13C	0.960	C211—H211	0.930
C16—C15	1.381 (3)	C112—O11	1.202 (3)
C16—C11	1.385 (3)	C22—C21	1.377 (3)
C16—H16	0.930	C22—H22	0.930
C26—C25	1.379 (3)	C25—H25	0.930
C26—C21	1.383 (3)	C15—H15	0.930
C26—H26	0.930	C18—H18	0.930
C19—C18	1.378 (3)	C13—H13	0.930
C19—C110	1.401 (3)
C27—N21—C21	131.5 (2)	C19—C110—C112	124.5 (2)
C27—N21—H21	114.2	N12—C17—N11	119.3 (2)
C21—N21—H21	114.2	N12—C17—C111	122.3 (2)
C17—N11—C11	131.49 (19)	N11—C17—C111	118.5 (2)
C17—N11—H11	114.3	O22—C213—H23A	109.5
C11—N11—H11	114.3	O22—C213—H23B	109.5
C28—N22—C27	117.0 (2)	H23A—C213—H23B	109.5
C112—O12—C113	115.8 (2)	O22—C213—H23C	109.5
C212—O22—C213	116.9 (2)	H23A—C213—H23C	109.5
C18—N12—C17	117.0 (2)	H23B—C213—H23C	109.5
O13—N13—O14	122.5 (3)	C24—C23—C22	120.4 (3)
O13—N13—C19	118.6 (2)	C24—C23—H23	119.8
O14—N13—C19	118.9 (2)	C22—C23—H23	119.8
O23—N23—O24	121.8 (3)	C25—C24—C23	119.5 (3)
O23—N23—C29	119.1 (2)	C25—C24—H24	120.3
O24—N23—C29	119.0 (2)	C23—C24—H24	120.3
O12—C113—H13A	109.5	C15—C14—C13	119.1 (3)
O12—C113—H13B	109.5	C15—C14—H14	120.5
H13A—C113—H13B	109.5	C13—C14—H14	120.5
O12—C113—H13C	109.5	C210—C211—C27	119.7 (2)
H13A—C113—H13C	109.5	C210—C211—H211	120.2
H13B—C113—H13C	109.5	C27—C211—H211	120.2
C15—C16—C11	119.7 (3)	O11—C112—O12	125.5 (2)
C15—C16—H16	120.1	O11—C112—O12	125.5 (2)
C11—C16—H16	120.1	O11—C112—C110	123.7 (2)
C25—C26—C21	119.6 (3)	O11—C112—C110	123.7 (2)
C25—C26—H26	120.2	O12—C112—C110	110.7 (2)
C21—C26—H26	120.2	C21—C22—C23	119.9 (3)
C18—C19—C110	119.4 (2)	C21—C22—H22	120.0
C18—C19—N13	119.2 (2)	C23—C22—H22	120.0
C110—C19—N13	121.4 (2)	C24—C25—C26	121.2 (3)
C211—C210—C29	117.1 (2)	C24—C25—H25	119.4
C211—C210—C212	119.0 (2)	C26—C25—H25	119.4
C29—C210—C212	123.7 (2)	N22—C27—N21	119.7 (2)
N22—C28—C29	123.9 (2)	N22—C27—C211	122.4 (2)
N22—C28—H28	118.1	N21—C27—C211	117.9 (2)
C29—C28—H28	118.1	C22—C21—C26	119.3 (2)
C12—C11—C16	118.8 (2)	C22—C21—N21	116.5 (2)
C12—C11—N11	116.5 (2)	C26—C21—N21	124.1 (2)
C16—C11—N11	124.7 (2)	C14—C15—C16	121.2 (3)
C11—C12—C13	120.6 (3)	C14—C15—H15	119.4
C11—C12—H12	119.7	C16—C15—H15	119.4
C13—C12—H12	119.7	N12—C18—C19	124.1 (2)
C110—C111—C17	120.3 (2)	N12—C18—H18	118.0
C110—C111—H111	119.8	C19—C18—H18	118.0
C17—C111—H111	119.8	C14—C13—C12	120.6 (3)
O21—C212—O22	125.6 (2)	C14—C13—H13	119.7
O21—C212—C210	125.0 (3)	C12—C13—H13	119.7
O22—C212—C210	109.4 (2)	C28—C29—C210	120.0 (2)
C111—C110—C19	116.9 (2)	C28—C29—N23	119.0 (2)
C111—C110—C112	118.5 (2)	C210—C29—N23	121.1 (2)
O13—N13—C19—C18	178.5 (2)	C111—C110—C112—O11	−86.3 (3)
O14—N13—C19—C18	−1.6 (4)	C19—C110—C112—O11	92.8 (3)
O13—N13—C19—C110	−1.2 (4)	C111—C110—C112—O12	90.4 (3)
O14—N13—C19—C110	178.7 (2)	C19—C110—C112—O12	−90.6 (3)
C27—N22—C28—C29	−0.4 (4)	C24—C23—C22—C21	−0.3 (4)
C15—C16—C11—C12	2.0 (4)	C23—C24—C25—C26	0.3 (5)
C15—C16—C11—N11	−177.9 (2)	C21—C26—C25—C24	−0.4 (4)
C17—N11—C11—C12	−167.2 (3)	C28—N22—C27—N21	176.4 (2)
C17—N11—C11—C16	12.7 (4)	C28—N22—C27—C211	−1.9 (4)
C16—C11—C12—C13	−1.3 (4)	C21—N21—C27—N22	−7.4 (4)
N11—C11—C12—C13	178.6 (3)	C21—N21—C27—C211	170.9 (2)
C213—O22—C212—O21	1.0 (4)	C210—C211—C27—N22	3.3 (4)
C213—O22—C212—C210	177.1 (2)	C210—C211—C27—N21	−175.0 (2)
C211—C210—C212—O21	81.5 (3)	C23—C22—C21—C26	0.3 (4)
C29—C210—C212—O21	−104.1 (3)	C23—C22—C21—N21	179.0 (2)
C211—C210—C212—O22	−94.7 (3)	C25—C26—C21—C22	0.1 (4)
C29—C210—C212—O22	79.7 (3)	C25—C26—C21—N21	−178.5 (2)
C17—C111—C110—C19	−0.3 (3)	C27—N21—C21—C22	179.2 (2)
C17—C111—C110—C112	178.8 (2)	C27—N21—C21—C26	−2.1 (4)
C18—C19—C110—C111	−1.2 (3)	C13—C14—C15—C16	−0.3 (5)
N13—C19—C110—C111	178.5 (2)	C11—C16—C15—C14	−1.2 (4)
C18—C19—C110—C112	179.7 (2)	C17—N12—C18—C19	0.5 (4)
N13—C19—C110—C112	−0.6 (4)	C110—C19—C18—N12	1.2 (4)
C18—N12—C17—N11	178.1 (2)	N13—C19—C18—N12	−178.6 (2)
C18—N12—C17—C111	−2.1 (3)	C15—C14—C13—C12	1.0 (5)
C11—N11—C17—N12	−5.2 (4)	C11—C12—C13—C14	−0.2 (5)
C11—N11—C17—C111	175.0 (2)	N22—C28—C29—C210	1.4 (4)
C110—C111—C17—N12	2.1 (4)	N22—C28—C29—N23	−178.0 (3)
C110—C111—C17—N11	−178.1 (2)	C211—C210—C29—C28	0.0 (4)
C22—C23—C24—C25	0.0 (5)	C212—C210—C29—C28	−174.5 (2)
C29—C210—C211—C27	−2.2 (3)	C211—C210—C29—N23	179.4 (2)
C212—C210—C211—C27	172.6 (2)	C212—C210—C29—N23	4.9 (4)
C113—O12—C112—O11	−1.0 (4)	O23—N23—C29—C28	−171.7 (3)
C113—O12—C112—O11	−1.0 (4)	O24—N23—C29—C28	7.1 (4)
C113—O12—C112—C110	−177.5 (2)	O23—N23—C29—C210	8.9 (4)
C111—C110—C112—O11	−86.3 (3)	O24—N23—C29—C210	−172.3 (3)
C19—C110—C112—O11	92.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N21—H21···O11	0.86	2.25	3.060 (3)	158
N21—H21···O11^i	0.86	2.62	3.107 (3)	117
N11—H11···O21^ii	0.86	2.23	3.094 (3)	179

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