Methyl 2-oxo-2,3-dihydro-1,3-benzothia­zole-3-acetate

The title compound, C₁₀H₉NO₃S, crystallizes with two mol­ecules in the asymmetric unit. The crystal packing is stabilized by van der Waals forces.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.040
• wR factor = 0.109
• Data-to-parameter ratio = 18.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    S2     -   C17     ..      11.48 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    N2     -   C17     ..       8.21 su

Alert level C
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C18
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C9
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C19
PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su ..       0.00

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           27.91
           From the CIF: _reflns_number_total               4931
           Count of symmetry unique reflns         2603
           Completeness (_total/calc)            189.44%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2328
           Fraction of Friedel pairs measured     0.894
           Are heavy atom types Z>Si present        yes

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Methyl 2-oxo-2,3-dihydro-1,3-benzothiazole-3-acetate

Crystal data

C10H9NO3S	F(000) = 464
Mr = 223.25	Dx = 1.432 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1967 reflections
a = 4.7858 (3) Å	θ = 2.0–28.0°
b = 12.4010 (7) Å	µ = 0.30 mm^−1
c = 17.5319 (10) Å	T = 296 K
β = 95.679 (5)°	Prism, pale yellow
V = 1035.39 (11) Å^3	0.53 × 0.35 × 0.17 mm
Z = 4

Data collection

Stoe IPDS-II diffractometer	4931 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	3875 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.070
Detector resolution: 6.67 pixels mm^-1	θmax = 27.9°, θmin = 2.0°
ω scans	h = −6→6
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −16→16
Tmin = 0.858, Tmax = 0.951	l = −22→22
17159 measured reflections

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)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.109	w = 1/[σ^2(Fo^2) + (0.0574P)^2 + 0.0745P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
4931 reflections	Δρmax = 0.39 e Å^−3
274 parameters	Δρmin = −0.39 e Å^−3
1 restraint	Absolute structure: Flack (1983), 2328 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.000 (1)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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
S1	0.65772 (14)	0.50016 (5)	0.17386 (4)	0.0637 (2)
O1	0.9706 (4)	0.38839 (19)	0.08544 (11)	0.0792 (7)
O2	0.4454 (4)	0.16603 (17)	0.07204 (12)	0.0771 (7)
O3	0.7311 (4)	0.02716 (14)	0.10153 (12)	0.0752 (6)
N1	0.7550 (4)	0.29566 (16)	0.17752 (11)	0.0542 (6)
C1	0.4998 (5)	0.42145 (19)	0.23975 (13)	0.0531 (7)
C2	0.3230 (5)	0.4537 (2)	0.29280 (15)	0.0641 (8)
C3	0.2183 (6)	0.3767 (3)	0.33842 (15)	0.0748 (9)
C4	0.2887 (6)	0.2690 (3)	0.33193 (15)	0.0721 (9)
C5	0.4684 (5)	0.2358 (2)	0.27873 (14)	0.0604 (8)
C6	0.5722 (4)	0.31255 (18)	0.23296 (12)	0.0506 (6)
C7	0.8235 (5)	0.3862 (2)	0.13763 (14)	0.0589 (8)
C8	0.8593 (5)	0.1912 (2)	0.15801 (15)	0.0577 (7)
C9	0.6504 (4)	0.12858 (19)	0.10609 (13)	0.0521 (7)
C10	0.5552 (8)	−0.0418 (3)	0.0493 (2)	0.0933 (13)
S2	0.45286 (19)	0.87879 (8)	0.45026 (6)	0.0924 (3)
O4	0.4169 (9)	0.9824 (2)	0.3156 (2)	0.1509 (18)
O5	0.3329 (5)	0.71516 (19)	0.21665 (11)	0.0801 (8)
O6	−0.0093 (5)	0.7643 (2)	0.12946 (11)	0.0833 (8)
N2	0.1212 (6)	0.8393 (2)	0.32702 (15)	0.0782 (9)
C11	0.2265 (5)	0.7692 (2)	0.44895 (15)	0.0653 (8)
C12	0.1941 (6)	0.6963 (3)	0.50762 (16)	0.0788 (12)
C13	0.0044 (7)	0.6150 (3)	0.4944 (2)	0.0825 (10)
C14	−0.1545 (6)	0.6056 (3)	0.42579 (18)	0.0754 (10)
C15	−0.1262 (6)	0.6769 (2)	0.36675 (16)	0.0689 (9)
C16	0.0664 (5)	0.7596 (2)	0.37872 (14)	0.0610 (8)
C17	0.3349 (9)	0.9095 (3)	0.3551 (3)	0.1025 (15)
C18	−0.0092 (8)	0.8432 (3)	0.2492 (2)	0.0920 (14)
C19	0.1289 (6)	0.7663 (2)	0.19779 (15)	0.0636 (8)
C20	0.1005 (8)	0.6966 (3)	0.07297 (18)	0.0879 (13)
H2	0.27570	0.52590	0.29760	0.0770*
H3	0.09790	0.39710	0.37430	0.0900*
H4	0.21510	0.21830	0.36350	0.0860*
H5	0.51650	0.16350	0.27440	0.0720*
H8A	0.90670	0.15040	0.20470	0.0690*
H8B	1.02970	0.20050	0.13300	0.0690*
H10A	0.36110	−0.02550	0.05330	0.1400*
H10B	0.59060	−0.11600	0.06260	0.1400*
H10C	0.59810	−0.02940	−0.00230	0.1400*
H12	0.29950	0.70300	0.55490	0.0950*
H13	−0.01700	0.56490	0.53290	0.0990*
H14	−0.28470	0.54990	0.41870	0.0900*
H15	−0.23430	0.66950	0.32000	0.0830*
H18A	0.00330	0.91600	0.22960	0.1110*
H18B	−0.20640	0.82490	0.24870	0.1110*
H20A	0.29380	0.71450	0.06920	0.1320*
H20B	−0.00540	0.70770	0.02420	0.1320*
H20C	0.08650	0.62240	0.08780	0.1320*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0710 (4)	0.0503 (3)	0.0689 (4)	0.0021 (3)	0.0027 (3)	0.0024 (3)
O1	0.0772 (12)	0.0878 (14)	0.0759 (12)	0.0009 (11)	0.0235 (10)	0.0067 (11)
O2	0.0589 (10)	0.0802 (13)	0.0866 (13)	0.0192 (9)	−0.0204 (9)	−0.0188 (10)
O3	0.0786 (11)	0.0541 (10)	0.0870 (12)	0.0116 (8)	−0.0216 (10)	−0.0124 (9)
N1	0.0544 (10)	0.0509 (10)	0.0567 (11)	0.0033 (8)	0.0026 (8)	−0.0059 (8)
C1	0.0520 (12)	0.0531 (12)	0.0521 (12)	0.0036 (9)	−0.0053 (9)	−0.0052 (9)
C2	0.0611 (13)	0.0697 (15)	0.0603 (14)	0.0095 (12)	−0.0004 (11)	−0.0133 (12)
C3	0.0621 (14)	0.104 (2)	0.0582 (14)	0.0073 (16)	0.0057 (11)	−0.0071 (16)
C4	0.0619 (14)	0.097 (2)	0.0561 (13)	−0.0073 (14)	−0.0002 (11)	0.0118 (14)
C5	0.0593 (13)	0.0610 (14)	0.0586 (13)	−0.0022 (10)	−0.0051 (11)	0.0033 (11)
C6	0.0460 (10)	0.0544 (12)	0.0491 (11)	0.0027 (9)	−0.0060 (9)	−0.0021 (9)
C7	0.0556 (12)	0.0607 (14)	0.0593 (13)	0.0004 (11)	−0.0002 (10)	0.0014 (12)
C8	0.0500 (11)	0.0568 (13)	0.0641 (13)	0.0095 (10)	−0.0053 (10)	−0.0099 (11)
C9	0.0469 (10)	0.0562 (12)	0.0528 (12)	0.0058 (9)	0.0037 (9)	−0.0073 (10)
C10	0.107 (3)	0.0651 (18)	0.102 (2)	−0.0024 (16)	−0.019 (2)	−0.0251 (16)
S2	0.0888 (5)	0.0844 (6)	0.1059 (6)	−0.0170 (4)	0.0191 (4)	−0.0384 (5)
O4	0.211 (4)	0.0722 (19)	0.181 (3)	−0.015 (2)	0.077 (3)	0.0095 (19)
O5	0.0798 (13)	0.0881 (14)	0.0704 (12)	0.0258 (11)	−0.0031 (10)	−0.0079 (10)
O6	0.0842 (13)	0.0983 (15)	0.0661 (11)	0.0235 (12)	0.0003 (10)	0.0142 (11)
N2	0.1027 (18)	0.0590 (13)	0.0744 (15)	0.0103 (12)	0.0166 (13)	−0.0042 (11)
C11	0.0561 (12)	0.0762 (17)	0.0642 (14)	0.0029 (12)	0.0097 (11)	−0.0222 (13)
C12	0.0710 (16)	0.111 (3)	0.0538 (14)	0.0062 (17)	0.0037 (12)	−0.0065 (16)
C13	0.0809 (17)	0.099 (2)	0.0693 (17)	−0.0022 (17)	0.0157 (14)	0.0047 (16)
C14	0.0697 (16)	0.081 (2)	0.0772 (18)	−0.0089 (14)	0.0153 (13)	−0.0090 (15)
C15	0.0669 (14)	0.0736 (17)	0.0647 (15)	0.0023 (13)	−0.0015 (12)	−0.0161 (14)
C16	0.0643 (13)	0.0628 (14)	0.0566 (13)	0.0126 (11)	0.0097 (10)	−0.0121 (12)
C17	0.127 (3)	0.0516 (17)	0.138 (3)	0.0049 (18)	0.058 (3)	−0.0074 (19)
C18	0.117 (3)	0.080 (2)	0.080 (2)	0.0407 (19)	0.0149 (18)	0.0111 (16)
C19	0.0702 (15)	0.0589 (14)	0.0619 (14)	0.0095 (12)	0.0074 (11)	0.0123 (12)
C20	0.096 (2)	0.104 (3)	0.0621 (16)	0.004 (2)	0.0006 (15)	−0.0055 (17)

Geometric parameters (Å, º)

S1—C1	1.741 (2)	C2—H2	0.9300
S1—C7	1.769 (3)	C3—H3	0.9300
S2—C11	1.737 (3)	C4—H4	0.9300
S2—C17	1.750 (5)	C5—H5	0.9300
O1—C7	1.209 (3)	C8—H8B	0.9700
O2—C9	1.191 (3)	C8—H8A	0.9700
O3—C10	1.458 (4)	C10—H10C	0.9600
O3—C9	1.320 (3)	C10—H10A	0.9600
O4—C17	1.227 (5)	C10—H10B	0.9600
O5—C19	1.184 (4)	C11—C12	1.390 (4)
O6—C19	1.310 (3)	C11—C16	1.389 (4)
O6—C20	1.437 (4)	C12—C13	1.361 (5)
N1—C8	1.442 (3)	C13—C14	1.363 (5)
N1—C6	1.386 (3)	C14—C15	1.378 (4)
N1—C7	1.379 (3)	C15—C16	1.381 (4)
N2—C16	1.384 (4)	C18—C19	1.509 (5)
N2—C17	1.395 (5)	C12—H12	0.9300
N2—C18	1.444 (4)	C13—H13	0.9300
C1—C2	1.377 (3)	C14—H14	0.9300
C1—C6	1.402 (3)	C15—H15	0.9300
C2—C3	1.372 (4)	C18—H18A	0.9700
C3—C4	1.385 (5)	C18—H18B	0.9700
C4—C5	1.392 (4)	C20—H20A	0.9600
C5—C6	1.370 (3)	C20—H20B	0.9600
C8—C9	1.500 (3)	C20—H20C	0.9600
S1···O5	3.212 (2)	C10···O1^xi	3.389 (4)
S1···N1	2.578 (2)	C10···O6^ix	3.394 (4)
S1···C2^i	3.675 (3)	C15···C19	3.494 (4)
S2···C16^i	3.621 (3)	C15···S2^iv	3.613 (3)
S2···N2	2.598 (3)	C16···O5	3.274 (3)
S2···C15^i	3.613 (3)	C16···S2^iv	3.621 (3)
S1···H10C^ii	3.1500	C17···O5	3.420 (5)
S1···H20C^i	3.0700	C19···C15	3.494 (4)
S2···H13^iii	3.1400	C20···C9^ii	3.568 (4)
O1···C10^ii	3.389 (4)	C2···H14^i	3.0000
O2···C6	3.360 (3)	C4···H12^xii	2.7800
O2···C7	3.412 (3)	C5···H12^xii	3.0400
O2···N1	2.767 (3)	C5···H8A^iv	3.0600
O2···C8^iv	3.328 (3)	C5···H8A	2.7800
O4···C5^v	3.223 (4)	C8···H5	2.7600
O5···C16	3.274 (3)	C13···H4^iii	3.0800
O5···C17	3.420 (5)	C14···H3	3.0300
O5···N2	2.744 (3)	C15···H2	3.0200
O5···S1	3.212 (2)	C15···H18B	2.7600
O6···C10^vi	3.394 (4)	C18···H15	2.7600
O1···H8B	2.4800	H2···C15	3.0200
O1···H10C^vii	2.8300	H2···O5	2.7700
O2···H10A	2.4300	H3···C14	3.0300
O2···H20B^viii	2.6200	H4···C13^xiii	3.0800
O2···H8B^iv	2.3900	H5···C8	2.7600
O2···H10C	2.8800	H5···H8A	2.3400
O3···H18A^ix	2.8400	H5···O4^x	2.4200
O4···H5^v	2.4200	H8A···C5	2.7800
O4···H18A	2.5100	H8A···H5	2.3400
O5···H2	2.7700	H8A···C5^i	3.0600
O5···H15^i	2.6700	H8B···O1	2.4800
O5···H18B^i	2.6000	H8B···O2^i	2.3900
O5···H20A	2.5700	H10A···O2	2.4300
O5···H20C	2.7000	H10B···O6^ix	2.6100
O6···H10B^vi	2.6100	H10B···H20A^x	2.5500
N1···S1	2.578 (2)	H10C···S1^xi	3.1500
N1···O2	2.767 (3)	H10C···O1^xiv	2.8300
N2···O5	2.744 (3)	H10C···O2	2.8800
N2···S2	2.598 (3)	H12···C4^xv	2.7800
C1···C7^iv	3.567 (3)	H12···C5^xv	3.0400
C2···C7^iv	3.540 (4)	H13···S2^xiii	3.1400
C2···S1^iv	3.675 (3)	H14···C2^iv	3.0000
C3···C6^iv	3.533 (3)	H15···O5^iv	2.6700
C5···C9	3.494 (3)	H15···C18	2.7600
C5···O4^x	3.223 (4)	H15···H18B	2.3100
C5···C8^iv	3.473 (3)	H18A···O3^vi	2.8400
C6···O2	3.360 (3)	H18A···O4	2.5100
C6···C3^i	3.533 (3)	H18B···O5^iv	2.6000
C7···C2^i	3.540 (4)	H18B···C15	2.7600
C7···C1^i	3.567 (3)	H18B···H15	2.3100
C7···O2	3.412 (3)	H20A···O5	2.5700
C8···C5^i	3.473 (3)	H20A···H10B^v	2.5500
C8···O2^i	3.328 (3)	H20B···O2^xvi	2.6200
C9···C20^xi	3.568 (4)	H20C···S1^iv	3.0700
C9···C5	3.494 (3)	H20C···O5	2.7000
C1—S1—C7	91.71 (11)	H10B—C10—H10C	109.00
C11—S2—C17	90.90 (16)	O3—C10—H10A	109.00
C9—O3—C10	116.3 (2)	O3—C10—H10B	109.00
C19—O6—C20	117.1 (3)	O3—C10—H10C	110.00
C6—N1—C7	115.51 (19)	H10A—C10—H10B	109.00
C7—N1—C8	120.4 (2)	S2—C11—C12	127.9 (2)
C6—N1—C8	124.0 (2)	S2—C11—C16	111.55 (19)
C16—N2—C18	123.4 (3)	C12—C11—C16	120.5 (2)
C16—N2—C17	113.2 (3)	C11—C12—C13	118.5 (3)
C17—N2—C18	123.1 (3)	C12—C13—C14	121.2 (3)
S1—C1—C2	128.41 (19)	C13—C14—C15	121.4 (3)
C2—C1—C6	120.7 (2)	C14—C15—C16	118.4 (3)
S1—C1—C6	110.89 (17)	N2—C16—C11	113.3 (2)
C1—C2—C3	118.4 (2)	N2—C16—C15	126.7 (2)
C2—C3—C4	121.2 (3)	C11—C16—C15	120.0 (2)
C3—C4—C5	120.8 (3)	S2—C17—O4	127.4 (4)
C4—C5—C6	118.1 (2)	S2—C17—N2	110.9 (3)
C1—C6—C5	120.8 (2)	O4—C17—N2	121.7 (4)
N1—C6—C1	112.54 (19)	N2—C18—C19	111.7 (3)
N1—C6—C5	126.6 (2)	O5—C19—O6	125.0 (3)
O1—C7—N1	126.0 (2)	O5—C19—C18	124.7 (3)
S1—C7—N1	109.31 (17)	O6—C19—C18	110.3 (3)
S1—C7—O1	124.7 (2)	C11—C12—H12	121.00
N1—C8—C9	112.55 (19)	C13—C12—H12	121.00
O2—C9—C8	124.7 (2)	C12—C13—H13	119.00
O3—C9—C8	110.39 (19)	C14—C13—H13	119.00
O2—C9—O3	124.9 (2)	C13—C14—H14	119.00
C3—C2—H2	121.00	C15—C14—H14	119.00
C1—C2—H2	121.00	C14—C15—H15	121.00
C4—C3—H3	119.00	C16—C15—H15	121.00
C2—C3—H3	119.00	N2—C18—H18A	109.00
C3—C4—H4	120.00	N2—C18—H18B	109.00
C5—C4—H4	120.00	C19—C18—H18A	109.00
C4—C5—H5	121.00	C19—C18—H18B	109.00
C6—C5—H5	121.00	H18A—C18—H18B	108.00
C9—C8—H8A	109.00	O6—C20—H20A	109.00
C9—C8—H8B	109.00	O6—C20—H20B	109.00
N1—C8—H8B	109.00	O6—C20—H20C	109.00
N1—C8—H8A	109.00	H20A—C20—H20B	109.00
H8A—C8—H8B	108.00	H20A—C20—H20C	109.00
H10A—C10—H10C	110.00	H20B—C20—H20C	109.00
C7—S1—C1—C2	−179.7 (2)	C16—N2—C17—O4	177.3 (4)
C7—S1—C1—C6	−0.40 (18)	C18—N2—C16—C11	176.9 (3)
C1—S1—C7—O1	178.4 (2)	C18—N2—C16—C15	−3.8 (5)
C1—S1—C7—N1	−0.86 (18)	S1—C1—C2—C3	178.8 (2)
C11—S2—C17—O4	−178.3 (4)	C2—C1—C6—N1	−179.1 (2)
C11—S2—C17—N2	2.7 (3)	S1—C1—C6—C5	−179.20 (18)
C17—S2—C11—C16	−1.1 (2)	C2—C1—C6—C5	0.2 (3)
C17—S2—C11—C12	179.1 (3)	C6—C1—C2—C3	−0.4 (4)
C10—O3—C9—O2	1.3 (4)	S1—C1—C6—N1	1.6 (2)
C10—O3—C9—C8	−176.6 (2)	C1—C2—C3—C4	0.3 (4)
C20—O6—C19—C18	178.5 (3)	C2—C3—C4—C5	0.0 (4)
C20—O6—C19—O5	−1.6 (4)	C3—C4—C5—C6	−0.3 (4)
C8—N1—C6—C1	−179.0 (2)	C4—C5—C6—C1	0.2 (3)
C6—N1—C8—C9	79.5 (3)	C4—C5—C6—N1	179.3 (2)
C7—N1—C8—C9	−97.0 (3)	N1—C8—C9—O2	14.1 (3)
C8—N1—C7—S1	178.75 (17)	N1—C8—C9—O3	−168.1 (2)
C7—N1—C6—C5	178.5 (2)	S2—C11—C12—C13	−179.6 (2)
C8—N1—C6—C5	1.8 (3)	C16—C11—C12—C13	0.6 (4)
C8—N1—C7—O1	−0.5 (4)	S2—C11—C16—N2	−0.7 (3)
C7—N1—C6—C1	−2.4 (3)	S2—C11—C16—C15	180.0 (2)
C6—N1—C7—S1	2.0 (2)	C12—C11—C16—C15	−0.2 (4)
C6—N1—C7—O1	−177.2 (2)	C12—C11—C16—N2	179.1 (3)
C18—N2—C17—S2	−177.7 (3)	C11—C12—C13—C14	−1.1 (5)
C16—N2—C17—S2	−3.6 (4)	C12—C13—C14—C15	1.1 (5)
C17—N2—C16—C11	2.8 (4)	C13—C14—C15—C16	−0.6 (5)
C17—N2—C16—C15	−177.9 (3)	C14—C15—C16—C11	0.2 (4)
C16—N2—C18—C19	−79.5 (4)	C14—C15—C16—N2	−179.0 (3)
C17—N2—C18—C19	94.0 (4)	N2—C18—C19—O6	174.2 (3)
C18—N2—C17—O4	3.2 (6)	N2—C18—C19—O5	−5.7 (4)

Symmetry codes: (i) x+1, y, z; (ii) −x+1, y+1/2, −z; (iii) −x, y+1/2, −z+1; (iv) x−1, y, z; (v) x, y+1, z; (vi) x−1, y+1, z; (vii) −x+2, y+1/2, −z; (viii) −x, y−1/2, −z; (ix) x+1, y−1, z; (x) x, y−1, z; (xi) −x+1, y−1/2, −z; (xii) −x+1, y−1/2, −z+1; (xiii) −x, y−1/2, −z+1; (xiv) −x+2, y−1/2, −z; (xv) −x+1, y+1/2, −z+1; (xvi) −x, y+1/2, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O4^x	0.93	2.42	3.223 (4)	144
C8—H8B···O1	0.97	2.48	2.831 (3)	101
C8—H8B···O2^i	0.97	2.39	3.328 (3)	163
C18—H18A···O4	0.97	2.51	2.833 (5)	100

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