Ethyl 3-methyl-6-oxo-5-[3-(tri­fluoro­methyl)­phenyl]-1,6-di­hydro-1-pyridazine­acetate

The title compound, C₁₆H₁₅F₃N₂O₃, is composed of a 3-(tri­fluoro­methyl)­phenyl ring and a pyridazinone ring, which are approximately coplanar, and an ethyl acetate group on the pyridazinone ring. In the crystal structure, centrosymmetric­ally related mol­ecules form dimers through non-classical intermolecular C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.059
• wR factor = 0.185
• Data-to-parameter ratio = 12.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C15

Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         46 Perc.
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.33 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.72 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C8
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C14
PLAT301_ALERT_3_C Main Residue  Disorder .........................      16.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT410_ALERT_2_C Short Intra H...H Contact  H3     ..  H7      ..       1.97 Ang.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      18.10 Deg.
              C15' -O3   -C15     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      26.70 Deg.
              F3   -C12  -F2"     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      42.00 Deg.
              F2"  -C12  -F2'     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      30.80 Deg.
              F1"  -C12  -F1'     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      20.80 Deg.
              F1   -C12  -F1'     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      44.00 Deg.
              F3   -C12  -F3'     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      33.20 Deg.
              F3'  -C12  -F3"     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      34.80 Deg.
              F2'  -C12  -F2      1.555   1.555   1.555

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  13 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

Ethyl 3-methyl-6-oxo-5-[3-(trifluoromethyl)phenyl]-1,6-dihydro-1-pyridazineacetate

Crystal data

C16H15F3N2O3	F(000) = 704
Mr = 340.30	Dx = 1.386 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.4846 (14) Å	Cell parameters from 1728 reflections
b = 8.1059 (15) Å	θ = 2.6–21.2°
c = 27.139 (5) Å	µ = 0.12 mm^−1
β = 97.867 (4)°	T = 294 K
V = 1631.0 (5) Å^3	Block, colorless
Z = 4	0.32 × 0.28 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer	3339 independent reflections
Radiation source: fine-focus sealed tube	1552 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
φ and ω scans	θmax = 26.4°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→9
Tmin = 0.952, Tmax = 0.988	k = −9→10
8917 measured reflections	l = −33→33

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.185	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0757P)^2 + 0.5612P] where P = (Fo^2 + 2Fc^2)/3
3339 reflections	(Δ/σ)max = 0.001
260 parameters	Δρmax = 0.27 e Å^−3
24 restraints	Δρmin = −0.30 e Å^−3

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)
N1	0.7811 (3)	0.4311 (3)	0.07656 (9)	0.0558 (7)
N2	0.7152 (3)	0.5876 (3)	0.07755 (9)	0.0563 (7)
O1	0.8815 (3)	0.2028 (3)	0.04244 (8)	0.0777 (7)
O2	0.5275 (3)	0.2105 (3)	0.10549 (9)	0.0785 (7)
O3	0.7340 (3)	0.1201 (3)	0.16680 (9)	0.0845 (8)
C1	0.8200 (4)	0.3442 (4)	0.03555 (12)	0.0541 (8)
C2	0.7811 (3)	0.4299 (3)	−0.01170 (10)	0.0454 (7)
C3	0.7186 (3)	0.5870 (4)	−0.00972 (11)	0.0508 (7)
H3	0.6956	0.6469	−0.0391	0.061*
C4	0.6872 (4)	0.6629 (3)	0.03496 (12)	0.0522 (8)
C5	0.6176 (5)	0.8374 (4)	0.03451 (14)	0.0741 (10)
H5A	0.5764	0.8611	0.0657	0.111*
H5B	0.5195	0.8499	0.0080	0.111*
H5C	0.7128	0.9123	0.0295	0.111*
C6	0.8064 (3)	0.3500 (4)	−0.05958 (11)	0.0492 (7)
C7	0.7556 (4)	0.4326 (4)	−0.10428 (12)	0.0626 (9)
H7	0.7063	0.5378	−0.1037	0.075*
C8	0.7766 (4)	0.3625 (5)	−0.14932 (13)	0.0682 (9)
C9	0.8483 (5)	0.2063 (5)	−0.15140 (15)	0.0836 (11)
H9	0.8621	0.1582	−0.1818	0.100*
C10	0.8985 (5)	0.1240 (5)	−0.10791 (16)	0.0900 (12)
H10	0.9472	0.0187	−0.1089	0.108*
C11	0.8791 (4)	0.1923 (4)	−0.06253 (13)	0.0689 (9)
H11	0.9148	0.1329	−0.0335	0.083*
C12	0.7222 (7)	0.4563 (6)	−0.19511 (16)	0.1055 (15)
C13	0.8133 (5)	0.3498 (4)	0.12451 (11)	0.0669 (9)
H13A	0.8125	0.4313	0.1507	0.080*
H13B	0.9314	0.2985	0.1284	0.080*
C14	0.6720 (5)	0.2203 (4)	0.12970 (11)	0.0600 (8)
F1	0.7232 (17)	0.379 (2)	−0.2376 (5)	0.133 (3)	0.452 (3)
F2	0.5314 (9)	0.4860 (11)	−0.1985 (3)	0.121 (3)	0.452 (3)
F3	0.7851 (12)	0.6087 (9)	−0.1944 (3)	0.120 (2)	0.452 (3)
C15	0.617 (3)	−0.022 (3)	0.1748 (8)	0.083 (5)	0.48 (4)
H15A	0.6335	−0.1117	0.1523	0.100*	0.48 (4)
H15B	0.4908	0.0099	0.1705	0.100*	0.48 (4)
C16	0.682 (5)	−0.069 (4)	0.2284 (9)	0.151 (11)	0.48 (4)
H16A	0.6035	−0.1518	0.2389	0.227*	0.48 (4)
H16B	0.6803	0.0267	0.2492	0.227*	0.48 (4)
H16C	0.8024	−0.1114	0.2309	0.227*	0.48 (4)
F1'	0.662 (2)	0.362 (3)	−0.2359 (7)	0.133 (3)	0.297 (6)
F2'	0.593 (2)	0.5724 (16)	−0.1971 (5)	0.121 (3)	0.297 (6)
F3'	0.8632 (14)	0.5372 (18)	−0.2138 (4)	0.120 (2)	0.297 (6)
C15'	0.598 (2)	0.015 (2)	0.1861 (12)	0.107 (8)	0.52 (4)
H15C	0.5056	−0.0185	0.1594	0.129*	0.52 (4)
H15D	0.5414	0.0738	0.2110	0.129*	0.52 (4)
C16'	0.703 (3)	−0.132 (2)	0.2086 (10)	0.122 (7)	0.52 (4)
H16D	0.6243	−0.2030	0.2239	0.183*	0.52 (4)
H16E	0.7992	−0.0947	0.2332	0.183*	0.52 (4)
H16F	0.7527	−0.1909	0.1830	0.183*	0.52 (4)
F3"	0.8715 (16)	0.4422 (19)	−0.2218 (5)	0.120 (2)	0.251 (5)
F2"	0.711 (3)	0.6181 (13)	−0.1877 (6)	0.121 (3)	0.251 (5)
F1"	0.5906 (18)	0.400 (2)	−0.2254 (5)	0.133 (3)	0.251 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0691 (16)	0.0412 (15)	0.0562 (17)	−0.0025 (12)	0.0056 (12)	0.0068 (13)
N2	0.0645 (16)	0.0383 (15)	0.0652 (18)	−0.0056 (12)	0.0061 (12)	0.0004 (13)
O1	0.1078 (18)	0.0442 (14)	0.0800 (17)	0.0224 (13)	0.0083 (13)	0.0164 (11)
O2	0.0752 (16)	0.0777 (17)	0.0785 (17)	−0.0015 (13)	−0.0036 (13)	0.0199 (13)
O3	0.0885 (17)	0.0854 (18)	0.0757 (16)	−0.0125 (14)	−0.0028 (13)	0.0362 (14)
C1	0.0553 (18)	0.0410 (18)	0.065 (2)	0.0015 (14)	0.0039 (15)	0.0104 (16)
C2	0.0410 (14)	0.0375 (16)	0.0577 (19)	0.0001 (12)	0.0067 (12)	0.0078 (14)
C3	0.0500 (16)	0.0416 (17)	0.061 (2)	−0.0007 (13)	0.0076 (14)	0.0108 (15)
C4	0.0505 (17)	0.0389 (16)	0.067 (2)	−0.0020 (13)	0.0078 (14)	0.0043 (16)
C5	0.088 (2)	0.0376 (18)	0.097 (3)	0.0062 (17)	0.014 (2)	−0.0015 (17)
C6	0.0411 (15)	0.0454 (17)	0.062 (2)	0.0026 (13)	0.0110 (13)	0.0032 (15)
C7	0.067 (2)	0.058 (2)	0.063 (2)	0.0021 (16)	0.0085 (16)	0.0046 (17)
C8	0.067 (2)	0.079 (3)	0.058 (2)	−0.0042 (19)	0.0076 (16)	−0.003 (2)
C9	0.082 (3)	0.096 (3)	0.075 (3)	0.003 (2)	0.018 (2)	−0.026 (2)
C10	0.105 (3)	0.075 (3)	0.092 (3)	0.028 (2)	0.018 (2)	−0.012 (2)
C11	0.075 (2)	0.059 (2)	0.074 (2)	0.0166 (18)	0.0122 (18)	0.0021 (18)
C12	0.129 (4)	0.122 (4)	0.065 (3)	0.003 (3)	0.012 (3)	0.000 (3)
C13	0.088 (2)	0.058 (2)	0.051 (2)	−0.0068 (18)	−0.0035 (16)	0.0097 (16)
C14	0.077 (2)	0.053 (2)	0.0503 (19)	0.0086 (18)	0.0103 (17)	0.0098 (16)
F1	0.171 (9)	0.163 (4)	0.063 (3)	0.006 (7)	0.009 (5)	−0.021 (3)
F2	0.148 (6)	0.134 (7)	0.075 (3)	0.033 (5)	−0.013 (4)	0.020 (5)
F3	0.167 (6)	0.106 (6)	0.086 (4)	−0.021 (5)	0.017 (3)	0.029 (4)
C15	0.101 (10)	0.078 (8)	0.072 (9)	−0.025 (7)	0.015 (6)	0.036 (8)
C16	0.183 (18)	0.153 (19)	0.116 (14)	−0.067 (18)	0.016 (12)	0.054 (13)
F1'	0.171 (9)	0.163 (4)	0.063 (3)	0.006 (7)	0.009 (5)	−0.021 (3)
F2'	0.148 (6)	0.134 (7)	0.075 (3)	0.033 (5)	−0.013 (4)	0.020 (5)
F3'	0.167 (6)	0.106 (6)	0.086 (4)	−0.021 (5)	0.017 (3)	0.029 (4)
C15'	0.104 (10)	0.128 (14)	0.089 (13)	−0.035 (9)	0.008 (8)	0.034 (9)
C16'	0.126 (10)	0.084 (9)	0.148 (16)	−0.008 (8)	−0.007 (12)	0.055 (10)
F3"	0.167 (6)	0.106 (6)	0.086 (4)	−0.021 (5)	0.017 (3)	0.029 (4)
F2"	0.148 (6)	0.134 (7)	0.075 (3)	0.033 (5)	−0.013 (4)	0.020 (5)
F1"	0.171 (9)	0.163 (4)	0.063 (3)	0.006 (7)	0.009 (5)	−0.021 (3)

Geometric parameters (Å, º)

N1—N2	1.363 (3)	C10—H10	0.9300
N1—C1	1.381 (4)	C11—H11	0.9300
N1—C13	1.449 (4)	C12—F1"	1.278 (9)
N2—C4	1.299 (4)	C12—F1	1.313 (8)
O1—C1	1.240 (3)	C12—F3	1.321 (7)
O2—C14	1.189 (4)	C12—F2"	1.332 (10)
O3—C14	1.327 (4)	C12—F2'	1.346 (9)
O3—C15'	1.474 (9)	C12—F1'	1.373 (9)
O3—C15	1.480 (9)	C12—F3'	1.396 (8)
C1—C2	1.452 (4)	C12—F3"	1.418 (9)
C2—C3	1.360 (4)	C12—F2	1.438 (7)
C2—C6	1.487 (4)	C13—C14	1.510 (4)
C3—C4	1.408 (4)	C13—H13A	0.9700
C3—H3	0.9300	C13—H13B	0.9700
C4—C5	1.506 (4)	C15—C16	1.517 (10)
C5—H5A	0.9600	C15—H15A	0.9700
C5—H5B	0.9600	C15—H15B	0.9700
C5—H5C	0.9600	C16—H16A	0.9600
C6—C7	1.392 (4)	C16—H16B	0.9600
C6—C11	1.396 (4)	C16—H16C	0.9600
C7—C8	1.376 (4)	C15'—C16'	1.511 (10)
C7—H7	0.9300	C15'—H15C	0.9700
C8—C9	1.379 (5)	C15'—H15D	0.9700
C8—C12	1.466 (5)	C16'—H16D	0.9600
C9—C10	1.363 (5)	C16'—H16E	0.9600
C9—H9	0.9300	C16'—H16F	0.9600
C10—C11	1.376 (5)
N2—N1—C1	127.4 (2)	F1"—C12—F3'	119.2 (9)
N2—N1—C13	114.9 (3)	F1—C12—F3'	79.0 (9)
C1—N1—C13	117.7 (3)	F3—C12—F3'	44.0 (7)
C4—N2—N1	115.8 (3)	F2"—C12—F3'	70.1 (8)
C14—O3—C15'	115.7 (9)	F2'—C12—F3'	103.4 (8)
C14—O3—C15	115.8 (9)	F1'—C12—F3'	98.7 (9)
C15'—O3—C15	18.1 (17)	F1"—C12—F3"	103.5 (8)
O1—C1—N1	117.7 (3)	F1—C12—F3"	54.0 (8)
O1—C1—C2	126.9 (3)	F3—C12—F3"	77.2 (8)
N1—C1—C2	115.4 (3)	F2"—C12—F3"	103.2 (9)
C3—C2—C1	116.2 (3)	F2'—C12—F3"	130.4 (9)
C3—C2—C6	121.9 (3)	F1'—C12—F3"	74.8 (8)
C1—C2—C6	121.9 (3)	F3'—C12—F3"	33.2 (6)
C2—C3—C4	122.8 (3)	F1"—C12—F2	49.3 (8)
C2—C3—H3	118.6	F1—C12—F2	98.6 (7)
C4—C3—H3	118.6	F3—C12—F2	101.2 (6)
N2—C4—C3	122.4 (3)	F2"—C12—F2	76.2 (9)
N2—C4—C5	117.5 (3)	F2'—C12—F2	34.8 (7)
C3—C4—C5	120.1 (3)	F1'—C12—F2	80.1 (9)
C4—C5—H5A	109.5	F3'—C12—F2	133.8 (8)
C4—C5—H5B	109.5	F3"—C12—F2	145.7 (7)
H5A—C5—H5B	109.5	F1"—C12—C8	117.4 (9)
C4—C5—H5C	109.5	F1—C12—C8	117.5 (11)
H5A—C5—H5C	109.5	F3—C12—C8	114.5 (5)
H5B—C5—H5C	109.5	F2"—C12—C8	113.5 (8)
C7—C6—C11	116.9 (3)	F2'—C12—C8	120.8 (7)
C7—C6—C2	120.0 (3)	F1'—C12—C8	114.6 (14)
C11—C6—C2	123.1 (3)	F3'—C12—C8	114.6 (6)
C8—C7—C6	121.6 (3)	F3"—C12—C8	104.2 (6)
C8—C7—H7	119.2	F2—C12—C8	107.4 (5)
C6—C7—H7	119.2	N1—C13—C14	111.6 (3)
C7—C8—C9	120.5 (3)	N1—C13—H13A	109.3
C7—C8—C12	119.1 (4)	C14—C13—H13A	109.3
C9—C8—C12	120.4 (4)	N1—C13—H13B	109.3
C10—C9—C8	118.5 (4)	C14—C13—H13B	109.3
C10—C9—H9	120.8	H13A—C13—H13B	108.0
C8—C9—H9	120.8	O2—C14—O3	125.1 (3)
C9—C10—C11	121.8 (4)	O2—C14—C13	126.2 (3)
C9—C10—H10	119.1	O3—C14—C13	108.7 (3)
C11—C10—H10	119.1	O3—C15—C16	102.6 (10)
C10—C11—C6	120.6 (3)	O3—C15—H15A	111.2
C10—C11—H11	119.7	C16—C15—H15A	111.2
C6—C11—H11	119.7	O3—C15—H15B	111.2
F1"—C12—F1	50.3 (8)	C16—C15—H15B	111.2
F1"—C12—F3	125.9 (10)	H15A—C15—H15B	109.2
F1—C12—F3	114.5 (9)	O3—C15'—C16'	104.5 (10)
F1"—C12—F2"	113.0 (9)	O3—C15'—H15C	110.8
F1—C12—F2"	127.7 (12)	C16'—C15'—H15C	110.8
F3—C12—F2"	26.7 (8)	O3—C15'—H15D	110.8
F1"—C12—F2'	74.8 (9)	C16'—C15'—H15D	110.8
F1—C12—F2'	112.9 (12)	H15C—C15'—H15D	108.9
F3—C12—F2'	66.4 (8)	C15'—C16'—H16D	109.5
F2"—C12—F2'	42.0 (8)	C15'—C16'—H16E	109.5
F1"—C12—F1'	30.8 (9)	H16D—C16'—H16E	109.5
F1—C12—F1'	20.8 (11)	C15'—C16'—H16F	109.5
F3—C12—F1'	127.8 (13)	H16D—C16'—H16F	109.5
F2"—C12—F1'	130.8 (15)	H16E—C16'—H16F	109.5
F2'—C12—F1'	101.7 (11)
C1—N1—N2—C4	−0.4 (4)	C7—C8—C12—F1"	−114.7 (10)
C13—N1—N2—C4	179.4 (2)	C9—C8—C12—F1"	65.5 (10)
N2—N1—C1—O1	179.1 (3)	C7—C8—C12—F1	−171.9 (7)
C13—N1—C1—O1	−0.6 (4)	C9—C8—C12—F1	8.3 (8)
N2—N1—C1—C2	−1.7 (4)	C7—C8—C12—F3	49.4 (7)
C13—N1—C1—C2	178.6 (2)	C9—C8—C12—F3	−130.4 (6)
O1—C1—C2—C3	−178.2 (3)	C7—C8—C12—F2"	20.1 (11)
N1—C1—C2—C3	2.7 (4)	C9—C8—C12—F2"	−159.7 (10)
O1—C1—C2—C6	2.4 (4)	C7—C8—C12—F2'	−26.7 (11)
N1—C1—C2—C6	−176.7 (2)	C9—C8—C12—F2'	153.5 (10)
C1—C2—C3—C4	−1.9 (4)	C7—C8—C12—F1'	−148.9 (9)
C6—C2—C3—C4	177.5 (2)	C9—C8—C12—F1'	31.3 (10)
N1—N2—C4—C3	1.4 (4)	C7—C8—C12—F3'	98.0 (9)
N1—N2—C4—C5	−178.9 (2)	C9—C8—C12—F3'	−81.8 (9)
C2—C3—C4—N2	−0.3 (4)	C7—C8—C12—F3"	131.6 (8)
C2—C3—C4—C5	−179.9 (3)	C9—C8—C12—F3"	−48.2 (8)
C3—C2—C6—C7	−3.8 (4)	C7—C8—C12—F2	−62.1 (6)
C1—C2—C6—C7	175.5 (3)	C9—C8—C12—F2	118.1 (5)
C3—C2—C6—C11	176.5 (3)	N2—N1—C13—C14	105.9 (3)
C1—C2—C6—C11	−4.1 (4)	C1—N1—C13—C14	−74.3 (4)
C11—C6—C7—C8	−0.2 (4)	C15'—O3—C14—O2	−14.7 (15)
C2—C6—C7—C8	−179.9 (3)	C15—O3—C14—O2	5.4 (14)
C6—C7—C8—C9	0.4 (5)	C15'—O3—C14—C13	163.9 (14)
C6—C7—C8—C12	−179.4 (3)	C15—O3—C14—C13	−176.0 (13)
C7—C8—C9—C10	−0.3 (5)	N1—C13—C14—O2	−19.0 (5)
C12—C8—C9—C10	179.5 (4)	N1—C13—C14—O3	162.4 (3)
C8—C9—C10—C11	0.1 (6)	C14—O3—C15—C16	−159 (2)
C9—C10—C11—C6	0.0 (6)	C15'—O3—C15—C16	−64 (5)
C7—C6—C11—C10	0.0 (5)	C14—O3—C15'—C16'	155 (2)
C2—C6—C11—C10	179.6 (3)	C15—O3—C15'—C16'	60 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2^i	0.93	2.56	3.395 (4)	150
C11—H11···O1	0.93	2.19	2.847 (4)	127

Symmetry code: (i) −x+1, −y+1, −z.