Structural characterization of some N-phenyl-4-oxo-4H-2-chromone carboxamides

N-phenyl-4-oxo-4H-2-chromone carboxamides were found to be inactive as MAO inhibitors in contrast with their N-phenyl-4-oxo-4H-3-chromone carboxamide isomers. In order to obtain a close insight into the docking mechanism for this family of compounds, the molecular and supramolecular structures of nine N-phenyl-4-oxo-4H-2-chromone carbox­amides were determined. It was found that, in most of the secondary structures, the N(amido) and the O(carboxyl) of the carboxamide residue participate in strong intramolecular interactions, with the O atom of the chromene ring and with the H(ortho)—C (phenyl), respectively. When the phenyl ring had accessible acceptors as substituents a third intramolecular hydrogen bond was also observed. As a consequence, rotations of the chromone and phenyl rings around the N—C(alpha) and C(alpha′)—C=O are constrained and the compounds were found to be more planar than would otherwise be expected. The deviation from planarity of the whole molecule can be quantified by the dihedral angles between mean planes of the aromatic rings and it was found that they were mainly affected by the degree of torsion of the phenyl ring with respect to the amide residue. The molecular conformations assumed by the secondary amides clearly contrast with that of a related tertiary amide that was also determined in this study. The unavailability of the N in this compound as a donor strongly influences the molecular isomerism and conformation. This analysis demonstrates that the molecules can be classified into four groups depending on the types of interactions formed as described above. If the secondary N(amido) of the carboximide is involved in two intramolecular interactions then this atom does not form any intermolecular contacts. In all other cases it does and the supramolecular structure formed is in most cases supplemented by weak C—H...O interactions.

Computing details

For all compounds, data collection: CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011); cell refinement: CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011); data reduction: CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011); program(s) used to solve structure: SHELXS (Sheldrick, 2008). Program(s) used to refine structure: OSCAIL (McArdle et al., 2004), SHELXS97 (Sheldrick, 2008) for (1), (2), (3), (4), (5), (6), (7); SHELXL (Sheldrick, 2008) & OSCAIL (McArdle, et al., 2004) for (8), (9). Molecular graphics: PLATON (Spek,2003) for (1), (2), (3), (4), (5), (6), (7); PLATON, (Spek, 2003) for (8), (9). Software used to prepare material for publication: OSCAIL (McArdle et al., 2004), SHELXS97 (Sheldrick, 2008) for (1), (2), (3), (4), (5), (6), (7); SHELXL (Sheldrick, 2008) & OSCAIL (McArdle, et al., 2004) for (8), (9).

(1) 4-oxo-N-(2-bromophenyl)-4H-chromene-2-carboxamide

Crystal data

C16H10BrNO3	F(000) = 688
Mr = 344.16	Dx = 1.726 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71075 Å
a = 5.466 (3) Å	Cell parameters from 3226 reflections
b = 17.381 (10) Å	θ = 2.8–27.5°
c = 13.948 (8) Å	µ = 3.11 mm^−1
β = 92.079 (11)°	T = 100 K
V = 1324.3 (13) Å^3	Needle, colourless
Z = 4	0.41 × 0.03 × 0.01 mm

Data collection

Rigaku Saturn724+ (2x2 bin mode) diffractometer	3006 independent reflections
Confocal monochromator	2790 reflections with I > 2σ(I)
Detector resolution: 28.5714 pixels mm^-1	Rint = 0.028
profile data from ω–scans	θmax = 27.5°, θmin = 2.9°
Absorption correction: multi-scan CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)	h = −7→6
Tmin = 0.362, Tmax = 0.970	k = −22→19
8859 measured reflections	l = −16→18

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.085	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0441P)^2 + 0.9945P] where P = (Fo^2 + 2Fc^2)/3
3006 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.63 e Å^−3
0 restraints	Δρmin = −0.56 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
Br12	0.26176 (4)	0.372219 (14)	0.093403 (16)	0.02194 (10)
O1	0.6905 (3)	0.32310 (9)	0.34702 (10)	0.0174 (3)
O2	0.2860 (3)	0.44462 (10)	0.46662 (11)	0.0233 (4)
O4	1.0428 (3)	0.31106 (10)	0.61106 (11)	0.0232 (4)
N2	0.3134 (4)	0.41089 (12)	0.30775 (13)	0.0180 (4)
H2	0.4018	0.3830	0.2693	0.022*
C2	0.6115 (4)	0.36306 (13)	0.42413 (16)	0.0174 (5)
C3	0.7194 (4)	0.36093 (13)	0.51201 (16)	0.0184 (5)
H3	0.6534	0.3906	0.5621	0.022*
C4	0.9357 (4)	0.31395 (13)	0.53217 (15)	0.0181 (5)
C4A	1.0161 (4)	0.26908 (13)	0.44891 (15)	0.0174 (4)
C5	1.2206 (4)	0.22019 (13)	0.45639 (16)	0.0192 (5)
H5	1.3057	0.2140	0.5165	0.023*
C6	1.2992 (4)	0.18095 (14)	0.37693 (17)	0.0212 (5)
H6	1.4386	0.1484	0.3822	0.025*
C7	1.1721 (5)	0.18953 (14)	0.28865 (17)	0.0219 (5)
H7	1.2273	0.1628	0.2341	0.026*
C8	0.9676 (4)	0.23610 (14)	0.27935 (16)	0.0199 (5)
H8	0.8802	0.2409	0.2196	0.024*
C8A	0.8933 (4)	0.27580 (13)	0.36018 (15)	0.0162 (4)
C21	0.3869 (4)	0.41074 (13)	0.40220 (15)	0.0179 (4)
C211	0.1130 (4)	0.45024 (13)	0.26411 (15)	0.0175 (4)
C212	0.0607 (4)	0.43882 (13)	0.16572 (16)	0.0189 (5)
C213	−0.1343 (5)	0.47547 (14)	0.11821 (17)	0.0221 (5)
H213	−0.1677	0.4663	0.0519	0.027*
C214	−0.2799 (5)	0.52563 (14)	0.16856 (17)	0.0228 (5)
H214	−0.4132	0.5513	0.1368	0.027*
C215	−0.2294 (5)	0.53819 (14)	0.26620 (17)	0.0218 (5)
H215	−0.3283	0.5729	0.3004	0.026*
C216	−0.0368 (4)	0.50069 (14)	0.31404 (17)	0.0207 (5)
H216	−0.0065	0.5092	0.3807	0.025*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br12	0.02153 (15)	0.02328 (15)	0.02084 (14)	0.00238 (9)	−0.00158 (9)	−0.00366 (8)
O1	0.0182 (8)	0.0191 (8)	0.0149 (7)	0.0016 (7)	−0.0002 (6)	−0.0010 (6)
O2	0.0237 (9)	0.0256 (9)	0.0206 (8)	0.0025 (8)	0.0024 (7)	−0.0020 (7)
O4	0.0272 (9)	0.0265 (9)	0.0157 (7)	0.0025 (8)	−0.0037 (6)	−0.0001 (6)
N2	0.0170 (10)	0.0197 (10)	0.0173 (9)	0.0025 (8)	0.0009 (7)	−0.0015 (7)
C2	0.0178 (12)	0.0157 (11)	0.0188 (10)	−0.0014 (9)	0.0017 (9)	0.0003 (8)
C3	0.0199 (12)	0.0187 (11)	0.0167 (10)	0.0000 (9)	0.0007 (9)	−0.0012 (8)
C4	0.0215 (12)	0.0169 (11)	0.0161 (10)	−0.0037 (9)	0.0019 (8)	0.0011 (8)
C4A	0.0204 (12)	0.0148 (11)	0.0169 (10)	−0.0025 (9)	0.0004 (8)	0.0020 (8)
C5	0.0186 (12)	0.0191 (11)	0.0196 (10)	−0.0016 (9)	−0.0032 (8)	0.0015 (8)
C6	0.0174 (12)	0.0188 (11)	0.0273 (11)	0.0001 (10)	0.0009 (9)	−0.0001 (9)
C7	0.0236 (12)	0.0205 (12)	0.0220 (11)	−0.0029 (10)	0.0045 (9)	−0.0038 (9)
C8	0.0215 (12)	0.0196 (11)	0.0184 (10)	−0.0045 (10)	−0.0019 (9)	−0.0006 (8)
C8A	0.0159 (11)	0.0136 (10)	0.0188 (10)	−0.0015 (9)	−0.0008 (8)	0.0008 (8)
C21	0.0187 (11)	0.0146 (10)	0.0203 (10)	−0.0038 (9)	−0.0010 (8)	0.0019 (8)
C211	0.0158 (11)	0.0159 (11)	0.0207 (10)	−0.0028 (9)	−0.0004 (8)	0.0017 (8)
C212	0.0183 (12)	0.0161 (11)	0.0226 (10)	−0.0019 (9)	0.0030 (9)	−0.0010 (8)
C213	0.0221 (12)	0.0221 (12)	0.0219 (11)	−0.0020 (10)	−0.0029 (9)	0.0034 (9)
C214	0.0189 (12)	0.0199 (12)	0.0294 (12)	0.0019 (10)	−0.0021 (9)	0.0036 (9)
C215	0.0197 (12)	0.0196 (12)	0.0262 (11)	0.0007 (10)	0.0024 (9)	−0.0004 (9)
C216	0.0195 (12)	0.0196 (12)	0.0230 (11)	−0.0020 (10)	−0.0003 (9)	0.0001 (9)

Geometric parameters (Å, º)

Br12—C212	1.909 (2)	C6—C7	1.400 (3)
O1—C2	1.363 (3)	C6—H6	0.9500
O1—C8A	1.387 (3)	C7—C8	1.382 (4)
O2—C21	1.223 (3)	C7—H7	0.9500
O4—C4	1.229 (3)	C8—C8A	1.395 (3)
N2—C21	1.363 (3)	C8—H8	0.9500
N2—C211	1.411 (3)	C211—C216	1.402 (3)
N2—H2	0.8803	C211—C212	1.406 (3)
C2—C3	1.341 (3)	C212—C213	1.389 (3)
C2—C21	1.503 (3)	C213—C214	1.388 (3)
C3—C4	1.456 (3)	C213—H213	0.9500
C3—H3	0.9500	C214—C215	1.397 (3)
C4—C4A	1.479 (3)	C214—H214	0.9500
C4A—C8A	1.391 (3)	C215—C216	1.388 (3)
C4A—C5	1.405 (3)	C215—H215	0.9500
C5—C6	1.383 (3)	C216—H216	0.9500
C5—H5	0.9500
C2—O1—C8A	118.16 (17)	C7—C8—H8	120.9
C21—N2—C211	128.0 (2)	C8A—C8—H8	120.9
C21—N2—H2	116.0	O1—C8A—C4A	121.68 (19)
C211—N2—H2	116.0	O1—C8A—C8	116.18 (19)
C3—C2—O1	124.4 (2)	C4A—C8A—C8	122.1 (2)
C3—C2—C21	122.0 (2)	O2—C21—N2	125.7 (2)
O1—C2—C21	113.57 (19)	O2—C21—C2	120.2 (2)
C2—C3—C4	121.3 (2)	N2—C21—C2	114.1 (2)
C2—C3—H3	119.4	C216—C211—C212	118.1 (2)
C4—C3—H3	119.4	C216—C211—N2	123.2 (2)
O4—C4—C3	123.6 (2)	C212—C211—N2	118.7 (2)
O4—C4—C4A	122.4 (2)	C213—C212—C211	121.8 (2)
C3—C4—C4A	113.99 (19)	C213—C212—Br12	118.19 (17)
C8A—C4A—C5	118.3 (2)	C211—C212—Br12	120.05 (18)
C8A—C4A—C4	120.4 (2)	C214—C213—C212	119.4 (2)
C5—C4A—C4	121.3 (2)	C214—C213—H213	120.3
C6—C5—C4A	120.5 (2)	C212—C213—H213	120.3
C6—C5—H5	119.7	C213—C214—C215	119.6 (2)
C4A—C5—H5	119.7	C213—C214—H214	120.2
C5—C6—C7	119.6 (2)	C215—C214—H214	120.2
C5—C6—H6	120.2	C216—C215—C214	121.0 (2)
C7—C6—H6	120.2	C216—C215—H215	119.5
C8—C7—C6	121.3 (2)	C214—C215—H215	119.5
C8—C7—H7	119.4	C215—C216—C211	120.1 (2)
C6—C7—H7	119.4	C215—C216—H216	120.0
C7—C8—C8A	118.2 (2)	C211—C216—H216	120.0
C8A—O1—C2—C3	1.3 (3)	C7—C8—C8A—O1	178.7 (2)
C8A—O1—C2—C21	−178.46 (18)	C7—C8—C8A—C4A	−0.8 (3)
O1—C2—C3—C4	−0.2 (4)	C211—N2—C21—O2	1.3 (4)
C21—C2—C3—C4	179.5 (2)	C211—N2—C21—C2	−179.2 (2)
C2—C3—C4—O4	178.9 (2)	C3—C2—C21—O2	−5.5 (4)
C2—C3—C4—C4A	−1.5 (3)	O1—C2—C21—O2	174.3 (2)
O4—C4—C4A—C8A	−178.2 (2)	C3—C2—C21—N2	175.1 (2)
C3—C4—C4A—C8A	2.1 (3)	O1—C2—C21—N2	−5.2 (3)
O4—C4—C4A—C5	0.3 (3)	C21—N2—C211—C216	4.0 (4)
C3—C4—C4A—C5	−179.4 (2)	C21—N2—C211—C212	−176.3 (2)
C8A—C4A—C5—C6	1.1 (3)	C216—C211—C212—C213	−0.5 (3)
C4—C4A—C5—C6	−177.4 (2)	N2—C211—C212—C213	179.8 (2)
C4A—C5—C6—C7	−0.6 (4)	C216—C211—C212—Br12	178.88 (17)
C5—C6—C7—C8	−0.5 (4)	N2—C211—C212—Br12	−0.8 (3)
C6—C7—C8—C8A	1.2 (4)	C211—C212—C213—C214	0.9 (4)
C2—O1—C8A—C4A	−0.5 (3)	Br12—C212—C213—C214	−178.48 (18)
C2—O1—C8A—C8	−179.95 (19)	C212—C213—C214—C215	−0.4 (4)
C5—C4A—C8A—O1	−179.8 (2)	C213—C214—C215—C216	−0.6 (4)
C4—C4A—C8A—O1	−1.2 (3)	C214—C215—C216—C211	1.0 (4)
C5—C4A—C8A—C8	−0.3 (3)	C212—C211—C216—C215	−0.5 (3)
C4—C4A—C8A—C8	178.2 (2)	N2—C211—C216—C215	179.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.88	2.15	2.607 (3)	112
N2—H2···Br12	0.88	2.55	3.067 (2)	118
C216—H216···O2	0.95	2.26	2.884 (3)	122
C7—H7···O4^i	0.95	2.52	3.257 (3)	135
C8—H8···O4^ii	0.95	2.51	3.344 (3)	146

Symmetry codes: (i) x+1/2, −y+1/2, z−1/2; (ii) x−1/2, −y+1/2, z−1/2.

(2) 4-oxo-N-(3-bromophenyl)-4H-chromene-2-carboxamide

Crystal data

C16H10BrNO3	Dx = 1.703 Mg m^−3
Mr = 344.16	Mo Kα radiation, λ = 0.71075 Å
Orthorhombic, Pca21	Cell parameters from 3388 reflections
a = 23.047 (8) Å	θ = 3.1–27.5°
b = 4.8246 (15) Å	µ = 3.07 mm^−1
c = 12.075 (4) Å	T = 100 K
V = 1342.7 (8) Å^3	Plate, colourless
Z = 4	0.16 × 0.09 × 0.03 mm
F(000) = 688

Data collection

Rigaku Saturn724+ (2x2 bin mode) diffractometer	2239 independent reflections
Confocal monochromator	2187 reflections with I > 2σ(I)
Detector resolution: 28.5714 pixels mm^-1	Rint = 0.022
profile data from ω–scans	θmax = 27.5°, θmin = 3.8°
Absorption correction: multi-scan CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)	h = −29→24
Tmin = 0.639, Tmax = 0.914	k = −6→3
4354 measured reflections	l = −15→8

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)] = 0.023	H-atom parameters constrained
wR(F^2) = 0.063	w = 1/[σ^2(Fo^2) + (0.047P)^2 + 0.0382P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.003
2239 reflections	Δρmax = 0.43 e Å^−3
190 parameters	Δρmin = −0.31 e Å^−3
1 restraint	Absolute structure: Flack, 1983
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.020 (9)

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
Br13	0.523997 (9)	0.48848 (4)	0.75594 (6)	0.02123 (8)
O1	0.25259 (7)	0.2171 (3)	0.46952 (12)	0.0157 (3)
O2	0.32440 (7)	0.7469 (3)	0.32571 (14)	0.0214 (3)
O4	0.16750 (7)	0.1198 (3)	0.17515 (14)	0.0206 (3)
N2	0.34760 (9)	0.5228 (3)	0.48768 (19)	0.0161 (4)
H2	0.3340	0.4007	0.5352	0.019*
C2	0.26585 (9)	0.3703 (4)	0.37912 (18)	0.0150 (4)
C3	0.23848 (9)	0.3499 (4)	0.28137 (18)	0.0165 (4)
H3	0.2498	0.4670	0.2219	0.020*
C4	0.19187 (8)	0.1521 (4)	0.26497 (19)	0.0150 (4)
C4A	0.17654 (11)	−0.0068 (3)	0.3642 (2)	0.0144 (5)
C5	0.13081 (9)	−0.2005 (4)	0.36346 (19)	0.0181 (4)
H5	0.1089	−0.2286	0.2977	0.022*
C6	0.11761 (10)	−0.3498 (4)	0.4576 (2)	0.0192 (4)
H6	0.0868	−0.4806	0.4567	0.023*
C7	0.14986 (10)	−0.3077 (4)	0.55479 (19)	0.0198 (4)
H7	0.1408	−0.4119	0.6193	0.024*
C8	0.19443 (10)	−0.1174 (4)	0.55795 (18)	0.0180 (4)
H8	0.2158	−0.0873	0.6242	0.022*
C8A	0.20752 (11)	0.0300 (4)	0.4616 (2)	0.0145 (4)
C21	0.31573 (9)	0.5678 (4)	0.39571 (19)	0.0158 (4)
C211	0.40077 (9)	0.6520 (4)	0.51556 (17)	0.0152 (4)
C212	0.43113 (10)	0.5379 (4)	0.6048 (2)	0.0158 (4)
H212	0.4155	0.3860	0.6449	0.019*
C213	0.48420 (9)	0.6492 (4)	0.63359 (18)	0.0177 (4)
C214	0.50899 (10)	0.8670 (4)	0.57701 (19)	0.0192 (4)
H214	0.5459	0.9378	0.5975	0.023*
C215	0.47820 (10)	0.9794 (4)	0.4891 (3)	0.0189 (6)
H215	0.4943	1.1311	0.4495	0.023*
C216	0.42444 (9)	0.8763 (4)	0.45741 (19)	0.0172 (4)
H216	0.4040	0.9568	0.3971	0.021*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br13	0.01956 (13)	0.02661 (12)	0.01750 (14)	0.00389 (7)	−0.00492 (11)	−0.00170 (10)
O1	0.0151 (7)	0.0173 (6)	0.0145 (7)	−0.0020 (6)	0.0004 (6)	0.0036 (5)
O2	0.0235 (8)	0.0215 (7)	0.0191 (8)	−0.0050 (6)	−0.0010 (6)	0.0074 (6)
O4	0.0215 (9)	0.0253 (8)	0.0148 (7)	−0.0015 (6)	−0.0038 (6)	0.0041 (6)
N2	0.0158 (10)	0.0175 (8)	0.0149 (10)	−0.0019 (6)	0.0008 (8)	0.0025 (6)
C2	0.0157 (11)	0.0129 (8)	0.0164 (11)	0.0013 (7)	0.0028 (8)	0.0020 (8)
C3	0.0169 (10)	0.0161 (8)	0.0166 (11)	0.0016 (7)	0.0007 (8)	0.0044 (8)
C4	0.0139 (9)	0.0178 (7)	0.0134 (10)	0.0040 (6)	0.0009 (8)	0.0001 (9)
C4A	0.0142 (11)	0.0155 (9)	0.0135 (11)	0.0027 (7)	0.0001 (9)	0.0004 (6)
C5	0.0154 (10)	0.0190 (9)	0.0198 (11)	0.0012 (8)	0.0004 (9)	−0.0014 (8)
C6	0.0148 (10)	0.0199 (9)	0.0229 (11)	−0.0015 (8)	0.0020 (9)	0.0014 (9)
C7	0.0198 (11)	0.0202 (9)	0.0194 (11)	0.0014 (8)	0.0025 (9)	0.0055 (9)
C8	0.0188 (11)	0.0214 (10)	0.0136 (10)	0.0011 (8)	−0.0007 (8)	0.0039 (8)
C8A	0.0145 (11)	0.0141 (8)	0.0149 (11)	0.0017 (7)	0.0015 (10)	0.0000 (7)
C21	0.0140 (11)	0.0169 (8)	0.0164 (11)	0.0019 (8)	0.0006 (8)	0.0001 (8)
C211	0.0141 (10)	0.0152 (8)	0.0163 (10)	0.0026 (7)	0.0007 (8)	−0.0045 (8)
C212	0.0172 (11)	0.0171 (8)	0.0131 (11)	0.0017 (8)	0.0023 (9)	−0.0015 (7)
C213	0.0185 (11)	0.0209 (9)	0.0135 (10)	0.0045 (8)	−0.0007 (8)	−0.0034 (8)
C214	0.0148 (10)	0.0197 (9)	0.0231 (11)	−0.0007 (8)	−0.0005 (9)	−0.0072 (9)
C215	0.0212 (13)	0.0159 (10)	0.0195 (15)	−0.0014 (7)	0.0036 (9)	−0.0012 (8)
C216	0.0190 (11)	0.0165 (9)	0.0161 (10)	0.0011 (8)	0.0027 (8)	−0.0002 (8)

Geometric parameters (Å, º)

Br13—C213	1.904 (2)	C6—C7	1.404 (3)
O1—C2	1.353 (2)	C6—H6	0.9500
O1—C8A	1.380 (3)	C7—C8	1.378 (3)
O2—C21	1.225 (3)	C7—H7	0.9500
O4—C4	1.231 (3)	C8—C8A	1.397 (3)
N2—C21	1.349 (3)	C8—H8	0.9500
N2—C211	1.415 (3)	C211—C212	1.397 (3)
N2—H2	0.8800	C211—C216	1.401 (3)
C2—C3	1.342 (3)	C212—C213	1.380 (3)
C2—C21	1.507 (3)	C212—H212	0.9500
C3—C4	1.451 (3)	C213—C214	1.377 (3)
C3—H3	0.9500	C214—C215	1.388 (4)
C4—C4A	1.465 (3)	C214—H214	0.9500
C4A—C8A	1.387 (4)	C215—C216	1.389 (3)
C4A—C5	1.409 (3)	C215—H215	0.9500
C5—C6	1.380 (3)	C216—H216	0.9500
C5—H5	0.9500
C2—O1—C8A	118.12 (18)	C7—C8—H8	120.7
C21—N2—C211	126.60 (19)	C8A—C8—H8	120.7
C21—N2—H2	116.7	O1—C8A—C4A	122.0 (2)
C211—N2—H2	116.7	O1—C8A—C8	116.0 (2)
C3—C2—O1	124.30 (18)	C4A—C8A—C8	122.0 (2)
C3—C2—C21	121.46 (19)	O2—C21—N2	126.3 (2)
O1—C2—C21	114.23 (19)	O2—C21—C2	118.6 (2)
C2—C3—C4	121.09 (19)	N2—C21—C2	115.03 (19)
C2—C3—H3	119.5	C212—C211—C216	119.7 (2)
C4—C3—H3	119.5	C212—C211—N2	116.31 (18)
O4—C4—C3	122.78 (19)	C216—C211—N2	123.94 (19)
O4—C4—C4A	122.95 (19)	C213—C212—C211	119.0 (2)
C3—C4—C4A	114.27 (19)	C213—C212—H212	120.5
C8A—C4A—C5	118.4 (2)	C211—C212—H212	120.5
C8A—C4A—C4	120.1 (2)	C214—C213—C212	122.6 (2)
C5—C4A—C4	121.5 (2)	C214—C213—Br13	119.72 (17)
C6—C5—C4A	120.4 (2)	C212—C213—Br13	117.64 (17)
C6—C5—H5	119.8	C213—C214—C215	117.8 (2)
C4A—C5—H5	119.8	C213—C214—H214	121.1
C5—C6—C7	119.8 (2)	C215—C214—H214	121.1
C5—C6—H6	120.1	C214—C215—C216	121.8 (2)
C7—C6—H6	120.1	C214—C215—H215	119.1
C8—C7—C6	120.9 (2)	C216—C215—H215	119.1
C8—C7—H7	119.5	C215—C216—C211	119.1 (2)
C6—C7—H7	119.5	C215—C216—H216	120.5
C7—C8—C8A	118.5 (2)	C211—C216—H216	120.5
C8A—O1—C2—C3	−0.9 (3)	C7—C8—C8A—O1	−179.87 (19)
C8A—O1—C2—C21	−179.82 (17)	C7—C8—C8A—C4A	1.0 (3)
O1—C2—C3—C4	−1.1 (3)	C211—N2—C21—O2	−7.5 (4)
C21—C2—C3—C4	177.75 (17)	C211—N2—C21—C2	171.04 (18)
C2—C3—C4—O4	−176.8 (2)	C3—C2—C21—O2	13.4 (3)
C2—C3—C4—C4A	2.8 (3)	O1—C2—C21—O2	−167.63 (18)
O4—C4—C4A—C8A	176.9 (2)	C3—C2—C21—N2	−165.3 (2)
C3—C4—C4A—C8A	−2.8 (3)	O1—C2—C21—N2	13.7 (3)
O4—C4—C4A—C5	−2.6 (3)	C21—N2—C211—C212	−168.9 (2)
C3—C4—C4A—C5	177.71 (18)	C21—N2—C211—C216	9.0 (3)
C8A—C4A—C5—C6	−0.2 (3)	C216—C211—C212—C213	−0.1 (3)
C4—C4A—C5—C6	179.30 (19)	N2—C211—C212—C213	177.88 (18)
C4A—C5—C6—C7	0.2 (3)	C211—C212—C213—C214	−0.9 (3)
C5—C6—C7—C8	0.5 (3)	C211—C212—C213—Br13	179.78 (15)
C6—C7—C8—C8A	−1.0 (3)	C212—C213—C214—C215	1.2 (3)
C2—O1—C8A—C4A	0.9 (3)	Br13—C213—C214—C215	−179.39 (18)
C2—O1—C8A—C8	−178.26 (18)	C213—C214—C215—C216	−0.7 (4)
C5—C4A—C8A—O1	−179.45 (19)	C214—C215—C216—C211	−0.2 (3)
C4—C4A—C8A—O1	1.0 (3)	C212—C211—C216—C215	0.7 (3)
C5—C4A—C8A—C8	−0.3 (3)	N2—C211—C216—C215	−177.2 (2)
C4—C4A—C8A—C8	−179.88 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.88	2.22	2.649 (3)	110
N2—H2···O4^i	0.88	2.17	3.004 (3)	159
C216—H216···O2	0.95	2.27	2.870 (3)	121
C212—H212···O4^i	0.95	2.33	3.156 (3)	145

Symmetry code: (i) −x+1/2, y, z+1/2.

(3)

Crystal data

C16H10BrNO3	Z = 2
Mr = 344.16	F(000) = 344
Triclinic, P1	Dx = 1.762 Mg m^−3
a = 5.722 (5) Å	Mo Kα radiation, λ = 0.71075 Å
b = 7.968 (7) Å	Cell parameters from 1452 reflections
c = 14.558 (13) Å	θ = 2.6–31.2°
α = 96.004 (13)°	µ = 3.18 mm^−1
β = 99.996 (15)°	T = 100 K
γ = 92.558 (15)°	Plate, colourless
V = 648.7 (10) Å^3	0.19 × 0.08 × 0.03 mm

Data collection

Rigaku Saturn724+ (2x2 bin mode) diffractometer	2780 independent reflections
Confocal monochromator	2592 reflections with I > 2σ(I)
Detector resolution: 28.5714 pixels mm^-1	Rint = 0.044
profile data from ω–scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)	h = −6→7
Tmin = 0.584, Tmax = 0.911	k = −9→10
6313 measured reflections	l = −18→18

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.151	H-atom parameters constrained
S = 1.16	w = 1/[σ^2(Fo^2) + (0.0715P)^2 + 2.0177P] where P = (Fo^2 + 2Fc^2)/3
2780 reflections	(Δ/σ)max = 0.001
190 parameters	Δρmax = 0.81 e Å^−3
0 restraints	Δρmin = −0.97 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
Br14	1.37110 (8)	0.86145 (5)	0.90039 (3)	0.02077 (18)
O1	0.3326 (6)	0.7829 (4)	0.3227 (2)	0.0169 (6)
O2	0.6866 (6)	0.8991 (4)	0.4534 (2)	0.0188 (7)
O4	−0.2543 (6)	0.5159 (4)	0.3709 (2)	0.0179 (6)
N2	0.5704 (6)	0.7368 (5)	0.5608 (3)	0.0165 (7)
H2	0.4421	0.6798	0.5760	0.020*
C2	0.3184 (8)	0.7368 (5)	0.4089 (3)	0.0141 (8)
C3	0.1261 (8)	0.6525 (5)	0.4278 (3)	0.0178 (9)
H3	0.1257	0.6261	0.4899	0.021*
C4	−0.0806 (7)	0.6011 (5)	0.3555 (3)	0.0137 (8)
C4A	−0.0657 (8)	0.6549 (5)	0.2637 (3)	0.0169 (9)
C5	−0.2509 (9)	0.6196 (5)	0.1859 (3)	0.0203 (9)
H5	−0.3936	0.5605	0.1929	0.024*
C6	−0.2291 (9)	0.6692 (6)	0.0997 (3)	0.0226 (10)
H6	−0.3553	0.6438	0.0475	0.027*
C7	−0.0194 (9)	0.7573 (6)	0.0895 (3)	0.0216 (9)
H7	−0.0054	0.7925	0.0302	0.026*
C8	0.1676 (9)	0.7941 (6)	0.1642 (3)	0.0216 (9)
H8	0.3101	0.8527	0.1567	0.026*
C8A	0.1412 (8)	0.7427 (5)	0.2508 (3)	0.0152 (8)
C21	0.5460 (8)	0.7997 (5)	0.4767 (3)	0.0152 (8)
C213	0.9153 (8)	0.7342 (6)	0.7981 (3)	0.0184 (9)
H213	0.8981	0.6883	0.8545	0.022*
C211	0.7605 (8)	0.7759 (5)	0.6377 (3)	0.0160 (8)
C212	0.7349 (8)	0.7086 (6)	0.7210 (3)	0.0191 (9)
H212	0.5926	0.6452	0.7242	0.023*
C214	1.1227 (8)	0.8278 (6)	0.7928 (3)	0.0181 (9)
C215	1.1514 (8)	0.8974 (6)	0.7115 (3)	0.0191 (9)
H215	1.2937	0.9618	0.7092	0.023*
C216	0.9699 (8)	0.8718 (5)	0.6335 (3)	0.0176 (9)
H216	0.9873	0.9190	0.5776	0.021*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br14	0.0174 (3)	0.0245 (3)	0.0185 (3)	−0.00504 (17)	−0.00055 (17)	0.00269 (17)
O1	0.0161 (16)	0.0199 (15)	0.0145 (15)	−0.0039 (12)	0.0015 (12)	0.0047 (11)
O2	0.0194 (17)	0.0178 (15)	0.0186 (16)	−0.0056 (12)	0.0027 (12)	0.0033 (12)
O4	0.0144 (15)	0.0185 (15)	0.0203 (16)	−0.0036 (11)	0.0007 (12)	0.0055 (12)
N2	0.0127 (18)	0.0173 (17)	0.0188 (18)	−0.0057 (13)	−0.0004 (14)	0.0068 (14)
C2	0.017 (2)	0.0129 (18)	0.0131 (19)	−0.0016 (15)	0.0029 (16)	0.0043 (14)
C3	0.018 (2)	0.017 (2)	0.017 (2)	−0.0020 (16)	0.0018 (16)	0.0022 (16)
C4	0.011 (2)	0.0114 (18)	0.020 (2)	0.0012 (14)	0.0044 (16)	0.0046 (15)
C4A	0.020 (2)	0.016 (2)	0.016 (2)	−0.0009 (16)	0.0026 (16)	0.0041 (15)
C5	0.022 (2)	0.017 (2)	0.021 (2)	−0.0066 (17)	−0.0007 (18)	0.0042 (16)
C6	0.022 (2)	0.024 (2)	0.021 (2)	−0.0016 (18)	0.0008 (18)	0.0058 (18)
C7	0.023 (2)	0.024 (2)	0.018 (2)	0.0015 (18)	0.0020 (18)	0.0040 (17)
C8	0.021 (2)	0.021 (2)	0.025 (2)	−0.0010 (17)	0.0075 (18)	0.0069 (18)
C8A	0.014 (2)	0.0145 (19)	0.016 (2)	0.0004 (15)	0.0002 (16)	0.0026 (15)
C21	0.014 (2)	0.0131 (18)	0.019 (2)	0.0010 (15)	0.0032 (16)	0.0044 (15)
C213	0.016 (2)	0.020 (2)	0.018 (2)	−0.0053 (16)	0.0023 (16)	0.0019 (16)
C211	0.015 (2)	0.0148 (19)	0.017 (2)	−0.0026 (15)	0.0008 (16)	0.0020 (15)
C212	0.018 (2)	0.017 (2)	0.022 (2)	−0.0052 (16)	0.0061 (17)	0.0041 (16)
C214	0.016 (2)	0.018 (2)	0.018 (2)	−0.0041 (16)	−0.0004 (16)	0.0013 (16)
C215	0.014 (2)	0.020 (2)	0.023 (2)	−0.0040 (16)	0.0039 (17)	−0.0009 (17)
C216	0.023 (2)	0.0141 (19)	0.015 (2)	−0.0041 (16)	0.0027 (17)	0.0026 (15)

Geometric parameters (Å, º)

Br14—C214	1.911 (5)	C6—C7	1.401 (7)
O1—C2	1.358 (5)	C6—H6	0.9500
O1—C8A	1.378 (5)	C7—C8	1.383 (7)
O2—C21	1.218 (5)	C7—H7	0.9500
O4—C4	1.244 (5)	C8—C8A	1.397 (6)
N2—C21	1.358 (6)	C8—H8	0.9500
N2—C211	1.417 (5)	C213—C212	1.378 (6)
N2—H2	0.92	C213—C214	1.392 (6)
C2—C3	1.347 (6)	C213—H213	0.9500
C2—C21	1.521 (6)	C211—C212	1.403 (6)
C3—C4	1.452 (6)	C211—C216	1.406 (6)
C3—H3	0.9500	C212—H212	0.9500
C4—C4A	1.461 (6)	C214—C215	1.390 (6)
C4A—C8A	1.399 (6)	C215—C216	1.390 (6)
C4A—C5	1.405 (6)	C215—H215	0.9500
C5—C6	1.379 (7)	C216—H216	0.9500
C5—H5	0.9500
C2—O1—C8A	118.7 (3)	C7—C8—H8	120.9
C21—N2—C211	126.7 (4)	C8A—C8—H8	120.9
C21—N2—H2	119.0	O1—C8A—C8	115.8 (4)
C211—N2—H2	113.2	O1—C8A—C4A	122.1 (4)
C3—C2—O1	123.3 (4)	C8—C8A—C4A	122.1 (4)
C3—C2—C21	127.7 (4)	O2—C21—N2	125.9 (4)
O1—C2—C21	109.0 (3)	O2—C21—C2	119.8 (4)
C2—C3—C4	121.6 (4)	N2—C21—C2	114.3 (4)
C2—C3—H3	119.2	C212—C213—C214	119.4 (4)
C4—C3—H3	119.2	C212—C213—H213	120.3
O4—C4—C3	122.2 (4)	C214—C213—H213	120.3
O4—C4—C4A	123.1 (4)	C212—C211—C216	119.7 (4)
C3—C4—C4A	114.6 (4)	C212—C211—N2	116.3 (4)
C8A—C4A—C5	117.8 (4)	C216—C211—N2	123.9 (4)
C8A—C4A—C4	119.6 (4)	C213—C212—C211	120.3 (4)
C5—C4A—C4	122.6 (4)	C213—C212—H212	119.8
C6—C5—C4A	121.1 (4)	C211—C212—H212	119.8
C6—C5—H5	119.4	C215—C214—C213	121.5 (4)
C4A—C5—H5	119.4	C215—C214—Br14	119.8 (3)
C5—C6—C7	119.5 (4)	C213—C214—Br14	118.8 (3)
C5—C6—H6	120.3	C216—C215—C214	119.3 (4)
C7—C6—H6	120.3	C216—C215—H215	120.3
C8—C7—C6	121.3 (4)	C214—C215—H215	120.3
C8—C7—H7	119.4	C215—C216—C211	119.8 (4)
C6—C7—H7	119.4	C215—C216—H216	120.1
C7—C8—C8A	118.2 (4)	C211—C216—H216	120.1
C8A—O1—C2—C3	0.3 (6)	C5—C4A—C8A—C8	−0.3 (7)
C8A—O1—C2—C21	−178.1 (3)	C4—C4A—C8A—C8	178.6 (4)
O1—C2—C3—C4	1.4 (7)	C211—N2—C21—O2	1.0 (7)
C21—C2—C3—C4	179.6 (4)	C211—N2—C21—C2	−178.5 (4)
C2—C3—C4—O4	176.3 (4)	C3—C2—C21—O2	−167.1 (4)
C2—C3—C4—C4A	−2.8 (6)	O1—C2—C21—O2	11.3 (6)
O4—C4—C4A—C8A	−176.6 (4)	C3—C2—C21—N2	12.4 (6)
C3—C4—C4A—C8A	2.5 (6)	O1—C2—C21—N2	−169.2 (4)
O4—C4—C4A—C5	2.3 (7)	C21—N2—C211—C212	173.6 (4)
C3—C4—C4A—C5	−178.7 (4)	C21—N2—C211—C216	−8.4 (7)
C8A—C4A—C5—C6	0.3 (7)	C214—C213—C212—C211	0.2 (7)
C4—C4A—C5—C6	−178.6 (4)	C216—C211—C212—C213	−0.9 (7)
C4A—C5—C6—C7	−0.4 (7)	N2—C211—C212—C213	177.2 (4)
C5—C6—C7—C8	0.7 (7)	C212—C213—C214—C215	0.5 (7)
C6—C7—C8—C8A	−0.8 (7)	C212—C213—C214—Br14	−179.8 (3)
C2—O1—C8A—C8	179.9 (4)	C213—C214—C215—C216	−0.5 (7)
C2—O1—C8A—C4A	−0.6 (6)	Br14—C214—C215—C216	179.8 (3)
C7—C8—C8A—O1	−179.9 (4)	C214—C215—C216—C211	−0.2 (7)
C7—C8—C8A—C4A	0.6 (7)	C212—C211—C216—C215	0.9 (7)
C5—C4A—C8A—O1	−179.8 (4)	N2—C211—C216—C215	−177.1 (4)
C4—C4A—C8A—O1	−0.9 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C216—H216···O2	0.95	2.26	2.869 (6)	121
N2—H2···O4^i	0.92	2.14	3.005 (5)	157
C3—H3···O4^i	0.95	2.44	3.330 (6)	156
C212—H212···O4^i	0.95	2.41	3.215 (6)	143
C216—H216···O2^ii	0.95	2.44	3.134 (6)	129

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+2, −y+2, −z+1.

(4) 4-oxo-N-(2-nitrophenyl)-4H-chromene-2-carboxamide

Crystal data

C16H10N2O5	F(000) = 640
Mr = 310.26	Dx = 1.571 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71075 Å
a = 12.3425 (10) Å	Cell parameters from 2942 reflections
b = 5.885 (4) Å	θ = 2.6–27.4°
c = 18.316 (15) Å	µ = 0.12 mm^−1
β = 99.543 (13)°	T = 100 K
V = 1312.0 (14) Å^3	Needle, yellow
Z = 4	0.12 × 0.02 × 0.01 mm

Data collection

Rigaku Saturn724+ (2x2 bin mode) diffractometer	2301 independent reflections
Confocal monochromator	1919 reflections with I > 2σ(I)
Detector resolution: 28.5714 pixels mm^-1	Rint = 0.066
profile data from ω–scans	θmax = 25.0°, θmin = 3.0°
Absorption correction: multi-scan CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)	h = −14→14
Tmin = 0.986, Tmax = 0.999	k = −6→7
17589 measured reflections	l = −21→21

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)] = 0.067	H-atom parameters constrained
wR(F^2) = 0.177	w = 1/[σ^2(Fo^2) + (0.0938P)^2 + 0.3435P] where P = (Fo^2 + 2Fc^2)/3
S = 1.16	(Δ/σ)max < 0.001
2301 reflections	Δρmax = 0.28 e Å^−3
209 parameters	Δρmin = −0.26 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.003 (2)

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
O1	0.28568 (15)	0.6881 (3)	0.58689 (10)	0.0237 (5)
O4	0.22045 (16)	1.0182 (4)	0.38729 (11)	0.0287 (5)
O2	0.08647 (16)	0.3009 (4)	0.50359 (11)	0.0281 (5)
O21	0.32799 (17)	0.3896 (4)	0.74380 (11)	0.0315 (6)
O22	0.36832 (17)	0.1007 (4)	0.81642 (12)	0.0342 (6)
N2	0.18532 (19)	0.3317 (4)	0.62186 (13)	0.0246 (6)
H2	0.2322	0.4222	0.6493	0.029*
N21	0.30819 (19)	0.1969 (4)	0.76523 (13)	0.0252 (6)
C21	0.1527 (2)	0.3985 (5)	0.54998 (15)	0.0234 (7)
C2	0.2083 (2)	0.6112 (5)	0.53048 (16)	0.0240 (7)
C3	0.1839 (2)	0.7130 (5)	0.46431 (16)	0.0252 (7)
H3	0.1290	0.6494	0.4275	0.030*
C4	0.2405 (2)	0.9203 (5)	0.44784 (16)	0.0240 (7)
C4A	0.3241 (2)	1.0012 (5)	0.50929 (15)	0.0232 (7)
C5	0.3863 (2)	1.1974 (5)	0.50316 (16)	0.0246 (7)
H5	0.3746	1.2823	0.4584	0.030*
C6	0.4642 (2)	1.2683 (5)	0.56159 (17)	0.0273 (7)
H6	0.5047	1.4036	0.5574	0.033*
C7	0.4837 (2)	1.1407 (5)	0.62705 (17)	0.0277 (7)
H7	0.5387	1.1886	0.6666	0.033*
C8	0.4244 (2)	0.9479 (5)	0.63481 (16)	0.0249 (7)
H8	0.4375	0.8611	0.6791	0.030*
C8A	0.3442 (2)	0.8830 (5)	0.57547 (16)	0.0228 (7)
C211	0.1536 (2)	0.1372 (5)	0.65744 (16)	0.0237 (7)
C212	0.2111 (2)	0.0730 (5)	0.72724 (16)	0.0254 (7)
C213	0.1823 (2)	−0.1206 (5)	0.76322 (16)	0.0262 (7)
H213	0.2232	−0.1626	0.8098	0.031*
C214	0.0948 (2)	−0.2510 (5)	0.73137 (17)	0.0289 (7)
H214	0.0738	−0.3812	0.7564	0.035*
C215	0.0370 (2)	−0.1912 (5)	0.66223 (16)	0.0279 (7)
H215	−0.0230	−0.2822	0.6399	0.034*
C216	0.0662 (2)	0.0007 (5)	0.62540 (16)	0.0248 (7)
H216	0.0262	0.0388	0.5781	0.030*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0238 (10)	0.0264 (12)	0.0214 (11)	−0.0034 (8)	0.0054 (8)	−0.0014 (8)
O4	0.0299 (11)	0.0343 (13)	0.0228 (11)	0.0005 (9)	0.0072 (9)	0.0047 (9)
O2	0.0274 (11)	0.0334 (13)	0.0231 (11)	−0.0048 (9)	0.0031 (9)	−0.0011 (9)
O21	0.0338 (12)	0.0330 (13)	0.0278 (12)	−0.0053 (10)	0.0057 (9)	0.0003 (10)
O22	0.0316 (12)	0.0399 (14)	0.0288 (12)	0.0024 (10)	−0.0020 (9)	0.0034 (10)
N2	0.0229 (12)	0.0287 (14)	0.0226 (13)	−0.0013 (10)	0.0053 (10)	−0.0021 (11)
N21	0.0254 (13)	0.0292 (15)	0.0219 (13)	−0.0007 (11)	0.0060 (10)	−0.0021 (11)
C21	0.0215 (14)	0.0275 (17)	0.0231 (15)	0.0030 (12)	0.0095 (12)	0.0011 (12)
C2	0.0223 (14)	0.0276 (17)	0.0236 (16)	0.0014 (12)	0.0079 (12)	−0.0028 (12)
C3	0.0258 (15)	0.0289 (17)	0.0223 (16)	−0.0006 (12)	0.0085 (12)	−0.0002 (13)
C4	0.0243 (14)	0.0254 (16)	0.0251 (16)	0.0019 (12)	0.0121 (12)	−0.0010 (13)
C4A	0.0237 (15)	0.0269 (17)	0.0211 (15)	0.0029 (12)	0.0098 (11)	−0.0008 (12)
C5	0.0240 (14)	0.0286 (17)	0.0224 (15)	0.0019 (12)	0.0069 (11)	0.0026 (13)
C6	0.0230 (15)	0.0298 (17)	0.0307 (17)	−0.0039 (13)	0.0087 (12)	0.0010 (13)
C7	0.0222 (14)	0.0340 (18)	0.0274 (16)	−0.0013 (13)	0.0061 (12)	−0.0016 (14)
C8	0.0235 (14)	0.0322 (17)	0.0196 (14)	0.0025 (12)	0.0050 (11)	0.0024 (12)
C8A	0.0196 (13)	0.0238 (16)	0.0275 (16)	−0.0004 (12)	0.0113 (11)	−0.0014 (12)
C211	0.0234 (14)	0.0287 (17)	0.0215 (15)	0.0002 (12)	0.0112 (11)	−0.0008 (12)
C212	0.0188 (14)	0.0333 (17)	0.0258 (16)	−0.0008 (12)	0.0083 (12)	−0.0019 (13)
C213	0.0270 (15)	0.0301 (17)	0.0230 (16)	0.0024 (13)	0.0084 (12)	−0.0006 (13)
C214	0.0299 (16)	0.0302 (17)	0.0297 (17)	0.0008 (13)	0.0136 (13)	0.0048 (13)
C215	0.0267 (15)	0.0315 (18)	0.0280 (17)	0.0012 (13)	0.0115 (12)	−0.0017 (14)
C216	0.0234 (14)	0.0288 (17)	0.0236 (15)	−0.0003 (12)	0.0079 (11)	−0.0016 (13)

Geometric parameters (Å, º)

O1—C2	1.363 (3)	C5—H5	0.9500
O1—C8A	1.389 (3)	C6—C7	1.401 (4)
O4—C4	1.238 (4)	C6—H6	0.9500
O2—C21	1.221 (3)	C7—C8	1.370 (4)
O21—N21	1.237 (3)	C7—H7	0.9500
O22—N21	1.233 (3)	C8—C8A	1.397 (4)
N2—C21	1.369 (4)	C8—H8	0.9500
N2—C211	1.404 (4)	C211—C216	1.394 (4)
N2—H2	0.8800	C211—C212	1.407 (4)
N21—C212	1.475 (4)	C212—C213	1.392 (4)
C21—C2	1.499 (4)	C213—C214	1.373 (4)
C2—C3	1.341 (4)	C213—H213	0.9500
C3—C4	1.462 (4)	C214—C215	1.392 (4)
C3—H3	0.9500	C214—H214	0.9500
C4—C4A	1.475 (4)	C215—C216	1.393 (4)
C4A—C8A	1.384 (4)	C215—H215	0.9500
C4A—C5	1.401 (4)	C216—H216	0.9500
C5—C6	1.380 (4)
C2—O1—C8A	118.4 (2)	C8—C7—C6	120.9 (3)
C21—N2—C211	128.3 (2)	C8—C7—H7	119.5
C21—N2—H2	115.8	C6—C7—H7	119.5
C211—N2—H2	115.8	C7—C8—C8A	117.9 (3)
O22—N21—O21	122.4 (2)	C7—C8—H8	121.1
O22—N21—C212	118.1 (2)	C8A—C8—H8	121.1
O21—N21—C212	119.4 (2)	C4A—C8A—O1	121.7 (3)
O2—C21—N2	126.2 (3)	C4A—C8A—C8	123.0 (3)
O2—C21—C2	120.5 (3)	O1—C8A—C8	115.3 (3)
N2—C21—C2	113.3 (2)	C216—C211—N2	122.0 (3)
C3—C2—O1	124.1 (3)	C216—C211—C212	117.8 (3)
C3—C2—C21	123.1 (3)	N2—C211—C212	120.2 (3)
O1—C2—C21	112.8 (2)	C213—C212—C211	121.3 (3)
C2—C3—C4	121.1 (3)	C213—C212—N21	115.6 (3)
C2—C3—H3	119.5	C211—C212—N21	123.0 (3)
C4—C3—H3	119.5	C214—C213—C212	120.1 (3)
O4—C4—C3	122.8 (3)	C214—C213—H213	120.0
O4—C4—C4A	123.0 (3)	C212—C213—H213	120.0
C3—C4—C4A	114.2 (3)	C213—C214—C215	119.6 (3)
C8A—C4A—C5	117.6 (3)	C213—C214—H214	120.2
C8A—C4A—C4	120.5 (3)	C215—C214—H214	120.2
C5—C4A—C4	121.9 (3)	C214—C215—C216	120.7 (3)
C6—C5—C4A	120.5 (3)	C214—C215—H215	119.6
C6—C5—H5	119.7	C216—C215—H215	119.6
C4A—C5—H5	119.7	C215—C216—C211	120.5 (3)
C5—C6—C7	120.0 (3)	C215—C216—H216	119.8
C5—C6—H6	120.0	C211—C216—H216	119.8
C7—C6—H6	120.0
C211—N2—C21—O2	2.0 (5)	C5—C4A—C8A—C8	−1.5 (4)
C211—N2—C21—C2	−177.2 (2)	C4—C4A—C8A—C8	178.2 (3)
C8A—O1—C2—C3	−0.6 (4)	C2—O1—C8A—C4A	1.3 (4)
C8A—O1—C2—C21	179.2 (2)	C2—O1—C8A—C8	−178.1 (2)
O2—C21—C2—C3	4.6 (4)	C7—C8—C8A—C4A	1.6 (4)
N2—C21—C2—C3	−176.2 (3)	C7—C8—C8A—O1	−179.1 (2)
O2—C21—C2—O1	−175.3 (2)	C21—N2—C211—C216	−11.6 (4)
N2—C21—C2—O1	4.0 (3)	C21—N2—C211—C212	167.7 (3)
O1—C2—C3—C4	−0.1 (4)	C216—C211—C212—C213	0.2 (4)
C21—C2—C3—C4	−179.9 (3)	N2—C211—C212—C213	−179.1 (3)
C2—C3—C4—O4	179.7 (3)	C216—C211—C212—N21	177.0 (2)
C2—C3—C4—C4A	0.2 (4)	N2—C211—C212—N21	−2.4 (4)
O4—C4—C4A—C8A	−179.0 (3)	O22—N21—C212—C213	14.0 (4)
C3—C4—C4A—C8A	0.4 (4)	O21—N21—C212—C213	−167.7 (2)
O4—C4—C4A—C5	0.6 (4)	O22—N21—C212—C211	−162.9 (3)
C3—C4—C4A—C5	180.0 (2)	O21—N21—C212—C211	15.4 (4)
C8A—C4A—C5—C6	−0.1 (4)	C211—C212—C213—C214	−1.3 (4)
C4—C4A—C5—C6	−179.8 (3)	N21—C212—C213—C214	−178.3 (2)
C4A—C5—C6—C7	1.6 (4)	C212—C213—C214—C215	1.5 (4)
C5—C6—C7—C8	−1.5 (5)	C213—C214—C215—C216	−0.7 (4)
C6—C7—C8—C8A	0.0 (4)	C214—C215—C216—C211	−0.4 (4)
C5—C4A—C8A—O1	179.2 (2)	N2—C211—C216—C215	179.9 (2)
C4—C4A—C8A—O1	−1.1 (4)	C212—C211—C216—C215	0.6 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.88	2.11	2.571 (3)	112
N2—H2···O21	0.88	1.94	2.627 (3)	134
C216—H216···O2	0.95	2.26	2.889 (4)	123
C213—H213···O4^i	0.95	2.53	3.241 (4)	132
C214—H214···Cg(C211)^ii	0.95	2.93	3.694 (4)	138

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, −y−3/2, z+1/2.

(5) 4-oxo-N-(2-methoxyphenyl)-4H-chromene-2-carboxamide

Crystal data

C17H13NO4	Dx = 1.400 Mg m^−3
Mr = 295.28	Mo Kα radiation, λ = 0.71075 Å
Orthorhombic, P212121	Cell parameters from 3020 reflections
a = 4.7199 (12) Å	θ = 2.5–27.5°
b = 15.345 (5) Å	µ = 0.10 mm^−1
c = 19.338 (6) Å	T = 100 K
V = 1400.6 (7) Å^3	Needle, colourless
Z = 4	0.55 × 0.03 × 0.03 mm
F(000) = 616

Data collection

Rigaku Saturn724+ (2x2 bin mode) diffractometer	1884 independent reflections
Confocal monochromator	1827 reflections with I > 2σ(I)
Detector resolution: 28.5714 pixels mm^-1	Rint = 0.027
profile data from ω–scans	θmax = 27.5°, θmin = 3.4°
Absorption correction: multi-scan CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)	h = −6→5
Tmin = 0.947, Tmax = 0.997	k = −7→19
8860 measured reflections	l = −23→25

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)] = 0.039	H-atom parameters constrained
wR(F^2) = 0.095	w = 1/[σ^2(Fo^2) + (0.0446P)^2 + 0.4148P] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max < 0.001
1884 reflections	Δρmax = 0.16 e Å^−3
200 parameters	Δρmin = −0.18 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.011 (2)

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
O1	0.7078 (3)	0.50953 (9)	0.74107 (7)	0.0220 (3)
O2	0.2885 (4)	0.69785 (9)	0.72435 (8)	0.0276 (4)
O4	1.0136 (4)	0.63868 (10)	0.91115 (8)	0.0332 (4)
O212	0.1110 (4)	0.43648 (9)	0.59294 (8)	0.0291 (4)
N2	0.3010 (4)	0.57077 (11)	0.66184 (8)	0.0223 (4)
H2	0.3882	0.5202	0.6592	0.027*
C2	0.6131 (5)	0.58987 (12)	0.75943 (11)	0.0214 (4)
C3	0.7068 (5)	0.63515 (13)	0.81414 (10)	0.0237 (4)
H3	0.6289	0.6910	0.8236	0.028*
C4	0.9261 (5)	0.60010 (13)	0.85925 (11)	0.0241 (4)
C4A	1.0318 (5)	0.51391 (13)	0.83821 (10)	0.0222 (4)
C5	1.2500 (5)	0.47176 (14)	0.87455 (11)	0.0253 (5)
H5	1.3325	0.4993	0.9137	0.030*
C6	1.3461 (5)	0.39082 (14)	0.85408 (11)	0.0269 (5)
H6	1.4944	0.3630	0.8789	0.032*
C7	1.2238 (5)	0.34992 (14)	0.79658 (11)	0.0277 (5)
H7	1.2895	0.2940	0.7828	0.033*
C8	1.0089 (5)	0.38973 (13)	0.75964 (11)	0.0239 (4)
H8	0.9254	0.3617	0.7209	0.029*
C8A	0.9179 (5)	0.47191 (13)	0.78061 (10)	0.0217 (4)
C21	0.3850 (5)	0.62501 (12)	0.71321 (10)	0.0209 (4)
C211	0.0883 (5)	0.58679 (13)	0.61199 (10)	0.0209 (4)
C212	−0.0122 (5)	0.51401 (13)	0.57523 (10)	0.0236 (4)
C213	−0.2221 (5)	0.52462 (14)	0.52549 (10)	0.0255 (5)
H213	−0.2926	0.4756	0.5009	0.031*
C214	−0.3280 (5)	0.60757 (14)	0.51206 (11)	0.0272 (5)
H214	−0.4707	0.6150	0.4779	0.033*
C215	−0.2283 (5)	0.67946 (14)	0.54783 (11)	0.0256 (5)
H215	−0.3026	0.7357	0.5383	0.031*
C216	−0.0187 (5)	0.66905 (13)	0.59780 (10)	0.0228 (4)
H216	0.0511	0.7183	0.6222	0.027*
C217	0.0184 (7)	0.35984 (15)	0.55655 (12)	0.0385 (6)
H21A	0.1137	0.3085	0.5757	0.058*
H21B	0.0656	0.3655	0.5074	0.058*
H21C	−0.1870	0.3534	0.5617	0.058*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0229 (7)	0.0207 (6)	0.0225 (7)	0.0011 (6)	−0.0018 (6)	0.0008 (5)
O2	0.0286 (8)	0.0235 (7)	0.0307 (8)	0.0029 (7)	−0.0044 (7)	−0.0032 (6)
O4	0.0422 (10)	0.0297 (8)	0.0276 (8)	−0.0005 (8)	−0.0114 (9)	−0.0032 (6)
O212	0.0385 (9)	0.0216 (7)	0.0272 (7)	−0.0003 (7)	−0.0040 (8)	−0.0006 (6)
N2	0.0239 (9)	0.0206 (8)	0.0224 (8)	0.0005 (7)	−0.0018 (8)	0.0011 (6)
C2	0.0210 (10)	0.0205 (9)	0.0227 (9)	−0.0011 (8)	0.0015 (9)	0.0021 (7)
C3	0.0259 (10)	0.0214 (9)	0.0240 (9)	−0.0009 (9)	−0.0004 (10)	0.0020 (8)
C4	0.0258 (11)	0.0230 (9)	0.0235 (10)	−0.0046 (9)	0.0000 (9)	0.0025 (8)
C4A	0.0208 (10)	0.0219 (9)	0.0239 (9)	−0.0032 (8)	0.0018 (9)	0.0044 (8)
C5	0.0226 (11)	0.0288 (10)	0.0245 (10)	−0.0029 (9)	0.0001 (9)	0.0071 (8)
C6	0.0220 (11)	0.0299 (10)	0.0288 (10)	−0.0002 (9)	0.0010 (9)	0.0093 (8)
C7	0.0277 (11)	0.0265 (10)	0.0289 (11)	0.0027 (9)	0.0039 (10)	0.0032 (8)
C8	0.0241 (10)	0.0242 (9)	0.0234 (9)	−0.0010 (9)	0.0019 (9)	0.0029 (8)
C8A	0.0191 (10)	0.0245 (9)	0.0216 (9)	0.0000 (9)	0.0016 (8)	0.0057 (8)
C21	0.0209 (10)	0.0197 (9)	0.0220 (9)	−0.0025 (8)	0.0020 (9)	0.0024 (7)
C211	0.0192 (9)	0.0244 (9)	0.0190 (9)	−0.0003 (8)	0.0013 (8)	0.0023 (7)
C212	0.0248 (11)	0.0250 (9)	0.0211 (9)	−0.0013 (9)	0.0043 (9)	0.0006 (8)
C213	0.0252 (11)	0.0304 (10)	0.0209 (9)	−0.0050 (10)	0.0033 (9)	−0.0040 (8)
C214	0.0231 (11)	0.0372 (11)	0.0214 (9)	−0.0001 (10)	−0.0010 (9)	−0.0008 (8)
C215	0.0231 (11)	0.0299 (10)	0.0238 (10)	0.0014 (9)	0.0006 (9)	0.0035 (8)
C216	0.0226 (10)	0.0245 (9)	0.0213 (9)	−0.0002 (9)	0.0011 (9)	0.0009 (7)
C217	0.0565 (17)	0.0246 (11)	0.0343 (12)	−0.0076 (12)	−0.0020 (14)	−0.0049 (9)

Geometric parameters (Å, º)

O1—C2	1.359 (2)	C6—H6	0.9500
O1—C8A	1.379 (2)	C7—C8	1.383 (3)
O2—C21	1.226 (2)	C7—H7	0.9500
O4—C4	1.236 (3)	C8—C8A	1.392 (3)
O212—C212	1.368 (3)	C8—H8	0.9500
O212—C217	1.438 (3)	C211—C216	1.387 (3)
N2—C21	1.355 (3)	C211—C212	1.406 (3)
N2—C211	1.413 (3)	C212—C213	1.390 (3)
N2—H2	0.8797	C213—C214	1.392 (3)
C2—C3	1.341 (3)	C213—H213	0.9500
C2—C21	1.500 (3)	C214—C215	1.385 (3)
C3—C4	1.457 (3)	C214—H214	0.9500
C3—H3	0.9500	C215—C216	1.392 (3)
C4—C4A	1.471 (3)	C215—H215	0.9500
C4A—C8A	1.395 (3)	C216—H216	0.9500
C4A—C5	1.405 (3)	C217—H21A	0.9800
C5—C6	1.380 (3)	C217—H21B	0.9800
C5—H5	0.9500	C217—H21C	0.9800
C6—C7	1.401 (3)
C2—O1—C8A	118.14 (16)	O1—C8A—C4A	121.77 (18)
C212—O212—C217	117.36 (18)	C8—C8A—C4A	122.2 (2)
C21—N2—C211	126.93 (17)	O2—C21—N2	125.5 (2)
C21—N2—H2	116.6	O2—C21—C2	119.32 (18)
C211—N2—H2	116.5	N2—C21—C2	115.21 (17)
C3—C2—O1	124.61 (19)	C216—C211—C212	119.99 (19)
C3—C2—C21	121.38 (19)	C216—C211—N2	123.50 (19)
O1—C2—C21	114.01 (17)	C212—C211—N2	116.51 (18)
C2—C3—C4	121.03 (19)	O212—C212—C213	125.31 (19)
C2—C3—H3	119.5	O212—C212—C211	114.88 (18)
C4—C3—H3	119.5	C213—C212—C211	119.81 (19)
O4—C4—C3	123.1 (2)	C212—C213—C214	119.48 (19)
O4—C4—C4A	122.8 (2)	C212—C213—H213	120.3
C3—C4—C4A	114.03 (18)	C214—C213—H213	120.3
C8A—C4A—C5	117.99 (19)	C215—C214—C213	120.9 (2)
C8A—C4A—C4	120.39 (19)	C215—C214—H214	119.6
C5—C4A—C4	121.62 (19)	C213—C214—H214	119.6
C6—C5—C4A	120.8 (2)	C214—C215—C216	119.8 (2)
C6—C5—H5	119.6	C214—C215—H215	120.1
C4A—C5—H5	119.6	C216—C215—H215	120.1
C5—C6—C7	119.7 (2)	C211—C216—C215	120.03 (19)
C5—C6—H6	120.2	C211—C216—H216	120.0
C7—C6—H6	120.2	C215—C216—H216	120.0
C8—C7—C6	120.9 (2)	O212—C217—H21A	109.5
C8—C7—H7	119.5	O212—C217—H21B	109.5
C6—C7—H7	119.5	H21A—C217—H21B	109.5
C7—C8—C8A	118.4 (2)	O212—C217—H21C	109.5
C7—C8—H8	120.8	H21A—C217—H21C	109.5
C8A—C8—H8	120.8	H21B—C217—H21C	109.5
O1—C8A—C8	116.07 (19)
C8A—O1—C2—C3	−0.9 (3)	C4—C4A—C8A—C8	−179.0 (2)
C8A—O1—C2—C21	179.99 (16)	C211—N2—C21—O2	−0.4 (3)
O1—C2—C3—C4	0.3 (3)	C211—N2—C21—C2	178.93 (18)
C21—C2—C3—C4	179.28 (19)	C3—C2—C21—O2	2.4 (3)
C2—C3—C4—O4	−178.2 (2)	O1—C2—C21—O2	−178.51 (19)
C2—C3—C4—C4A	0.9 (3)	C3—C2—C21—N2	−177.0 (2)
O4—C4—C4A—C8A	177.6 (2)	O1—C2—C21—N2	2.1 (3)
C3—C4—C4A—C8A	−1.5 (3)	C21—N2—C211—C216	16.5 (3)
O4—C4—C4A—C5	−3.0 (3)	C21—N2—C211—C212	−164.3 (2)
C3—C4—C4A—C5	177.89 (19)	C217—O212—C212—C213	0.8 (3)
C8A—C4A—C5—C6	−0.7 (3)	C217—O212—C212—C211	−179.4 (2)
C4—C4A—C5—C6	179.9 (2)	C216—C211—C212—O212	179.19 (19)
C4A—C5—C6—C7	−0.3 (3)	N2—C211—C212—O212	0.0 (3)
C5—C6—C7—C8	0.4 (3)	C216—C211—C212—C213	−1.0 (3)
C6—C7—C8—C8A	0.5 (3)	N2—C211—C212—C213	179.81 (18)
C2—O1—C8A—C8	−179.76 (18)	O212—C212—C213—C214	−179.5 (2)
C2—O1—C8A—C4A	0.3 (3)	C211—C212—C213—C214	0.8 (3)
C7—C8—C8A—O1	178.55 (18)	C212—C213—C214—C215	−0.3 (3)
C7—C8—C8A—C4A	−1.5 (3)	C213—C214—C215—C216	0.2 (3)
C5—C4A—C8A—O1	−178.47 (18)	C212—C211—C216—C215	0.9 (3)
C4—C4A—C8A—O1	1.0 (3)	N2—C211—C216—C215	179.96 (19)
C5—C4A—C8A—C8	1.6 (3)	C214—C215—C216—C211	−0.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.88	2.19	2.630 (2)	110
N2—H2···O212	0.88	2.24	2.612 (2)	105
C7—H7···O2^i	0.95	2.48	3.302 (3)	145
C216—H216···O2	0.95	2.29	2.879 (3)	119

Symmetry code: (i) −x+2, y−1/2, −z+3/2.

(6) 4-oxo-N-(3-methoxyphenyl)-4H-chromene-2-carboxamide

Crystal data

C17H13NO4	Dx = 1.531 Mg m^−3
Mr = 295.28	Synchrotron radiation, λ = 0.68890 Å
Orthorhombic, Pna21	Cell parameters from 1964 reflections
a = 12.82 (3) Å	θ = 1.5–26.7°
b = 26.29 (6) Å	µ = 0.11 mm^−1
c = 3.802 (9) Å	T = 100 K
V = 1281 (5) Å^3	Lath, colourless
Z = 4	0.02 × 0.01 × 0.01 mm
F(000) = 616

Data collection

CrystalLogic diffractometer	785 reflections with I > 2σ(I)
Double crystal silicon monochromator	Rint = 0.197
Detector resolution: 28.5714 pixels mm^-1	θmax = 26.7°, θmin = 1.5°
profile data from ω–scans	h = −16→16
9122 measured reflections	k = −17→34
1693 independent reflections	l = −4→4

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)] = 0.103	H-atom parameters constrained
wR(F^2) = 0.334	w = 1/[σ^2(Fo^2) + (0.197P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max < 0.001
1693 reflections	Δρmax = 0.47 e Å^−3
200 parameters	Δρmin = −0.74 e Å^−3
1 restraint	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0 (10)

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
O1	0.3171 (3)	0.72092 (19)	0.144 (2)	0.047 (2)
O2	0.4509 (3)	0.62497 (18)	0.586 (2)	0.0512 (19)
O4	0.5846 (4)	0.7995 (2)	0.322 (3)	0.058 (2)
O213	0.3052 (3)	0.4565 (2)	0.748 (3)	0.054 (2)
N2	0.2795 (4)	0.6326 (2)	0.426 (2)	0.047 (2)
H2	0.2355	0.6530	0.3179	0.056*
C2	0.3987 (5)	0.7008 (3)	0.322 (3)	0.040 (2)
C3	0.4888 (5)	0.7246 (3)	0.376 (3)	0.054 (3)
H3	0.5449	0.7068	0.4832	0.065*
C4	0.5026 (5)	0.7762 (3)	0.276 (4)	0.048 (3)
C4A	0.4114 (5)	0.7996 (3)	0.105 (4)	0.052 (3)
C5	0.4077 (5)	0.8500 (3)	0.008 (3)	0.047 (2)
H5	0.4668	0.8710	0.0476	0.056*
C6	0.3225 (5)	0.8701 (3)	−0.143 (3)	0.049 (3)
H6	0.3213	0.9051	−0.2065	0.059*
C7	0.2359 (5)	0.8395 (3)	−0.204 (4)	0.049 (3)
H7	0.1769	0.8533	−0.3210	0.059*
C8	0.2345 (5)	0.7912 (3)	−0.101 (3)	0.050 (3)
H8	0.1731	0.7713	−0.1264	0.060*
C8A	0.3242 (5)	0.7704 (3)	0.044 (3)	0.042 (2)
C21	0.3803 (5)	0.6489 (3)	0.454 (3)	0.048 (3)
C211	0.2395 (5)	0.5871 (3)	0.554 (3)	0.045 (3)
C212	0.2998 (5)	0.5439 (3)	0.582 (4)	0.052 (3)
H212	0.3716	0.5444	0.5201	0.062*
C213	0.2537 (5)	0.5007 (3)	0.702 (3)	0.046 (3)
C214	0.1496 (5)	0.4998 (3)	0.803 (4)	0.054 (3)
H214	0.1197	0.4695	0.8939	0.065*
C215	0.0912 (5)	0.5425 (3)	0.771 (4)	0.054 (3)
H215	0.0200	0.5422	0.8406	0.064*
C216	0.1348 (5)	0.5862 (3)	0.637 (3)	0.043 (3)
H216	0.0931	0.6157	0.6019	0.052*
C217	0.4061 (5)	0.4521 (3)	0.591 (4)	0.056 (3)
H21A	0.4017	0.4610	0.3416	0.084*
H21B	0.4311	0.4171	0.6156	0.084*
H21C	0.4546	0.4753	0.7099	0.084*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.031 (2)	0.025 (3)	0.085 (6)	0.0014 (19)	−0.002 (3)	0.003 (3)
O2	0.033 (2)	0.037 (3)	0.083 (6)	0.003 (2)	−0.008 (3)	0.003 (4)
O4	0.035 (2)	0.045 (3)	0.092 (7)	−0.005 (2)	0.004 (4)	−0.007 (4)
O213	0.037 (2)	0.037 (3)	0.089 (6)	0.003 (2)	0.003 (4)	0.008 (4)
N2	0.036 (3)	0.032 (4)	0.072 (6)	0.002 (3)	−0.005 (4)	0.009 (4)
C2	0.039 (3)	0.025 (4)	0.057 (7)	0.006 (3)	−0.007 (4)	0.005 (4)
C3	0.036 (3)	0.036 (5)	0.090 (10)	0.004 (3)	−0.002 (5)	0.002 (5)
C4	0.030 (3)	0.032 (4)	0.082 (8)	−0.002 (3)	−0.003 (5)	−0.005 (5)
C4A	0.031 (3)	0.037 (4)	0.087 (9)	0.003 (3)	0.008 (5)	−0.003 (5)
C5	0.035 (3)	0.049 (5)	0.057 (7)	−0.005 (3)	0.007 (4)	−0.003 (5)
C6	0.038 (3)	0.030 (4)	0.080 (9)	−0.001 (3)	−0.002 (5)	−0.010 (5)
C7	0.031 (3)	0.041 (5)	0.075 (8)	0.001 (3)	−0.004 (5)	0.004 (5)
C8	0.035 (3)	0.034 (4)	0.080 (9)	0.001 (3)	0.002 (4)	0.013 (5)
C8A	0.031 (3)	0.033 (4)	0.061 (7)	−0.001 (3)	0.002 (4)	−0.002 (5)
C21	0.036 (3)	0.032 (4)	0.075 (8)	0.002 (3)	−0.002 (4)	−0.012 (5)
C211	0.040 (3)	0.021 (4)	0.073 (8)	0.000 (3)	−0.008 (4)	−0.006 (5)
C212	0.038 (3)	0.029 (4)	0.088 (9)	0.008 (3)	−0.004 (5)	0.000 (5)
C213	0.037 (3)	0.028 (4)	0.072 (8)	0.000 (3)	0.003 (4)	0.001 (4)
C214	0.036 (3)	0.046 (5)	0.080 (9)	−0.002 (3)	0.001 (5)	0.020 (6)
C215	0.039 (3)	0.033 (4)	0.089 (9)	−0.002 (3)	0.016 (5)	−0.006 (5)
C216	0.036 (3)	0.028 (4)	0.067 (8)	0.008 (3)	0.011 (4)	0.004 (4)
C217	0.041 (3)	0.046 (5)	0.082 (9)	0.003 (3)	0.005 (5)	0.010 (6)

Geometric parameters (Å, º)

O1—C2	1.355 (9)	C6—H6	0.9500
O1—C8A	1.358 (10)	C7—C8	1.327 (11)
O2—C21	1.211 (10)	C7—H7	0.9500
O4—C4	1.228 (8)	C8—C8A	1.388 (11)
O213—C213	1.348 (9)	C8—H8	0.9500
O213—C217	1.427 (10)	C211—C212	1.377 (10)
N2—C21	1.366 (9)	C211—C216	1.379 (10)
N2—C211	1.389 (10)	C212—C213	1.360 (12)
N2—H2	0.8806	C212—H212	0.9500
C2—C3	1.329 (10)	C213—C214	1.389 (11)
C2—C21	1.472 (12)	C214—C215	1.354 (11)
C3—C4	1.422 (12)	C214—H214	0.9500
C3—H3	0.9500	C215—C216	1.377 (11)
C4—C4A	1.471 (12)	C215—H215	0.9500
C4A—C5	1.376 (12)	C216—H216	0.9500
C4A—C8A	1.376 (10)	C217—H21A	0.9800
C5—C6	1.342 (12)	C217—H21B	0.9800
C5—H5	0.9500	C217—H21C	0.9800
C6—C7	1.392 (10)
C2—O1—C8A	117.6 (6)	O1—C8A—C8	115.7 (6)
C213—O213—C217	117.3 (7)	C4A—C8A—C8	121.3 (8)
C21—N2—C211	126.3 (7)	O2—C21—N2	125.2 (8)
C21—N2—H2	116.8	O2—C21—C2	120.2 (7)
C211—N2—H2	116.8	N2—C21—C2	114.6 (7)
C3—C2—O1	124.3 (8)	C212—C211—C216	121.0 (7)
C3—C2—C21	121.5 (8)	C212—C211—N2	122.0 (7)
O1—C2—C21	114.1 (6)	C216—C211—N2	116.9 (6)
C2—C3—C4	121.1 (8)	C213—C212—C211	118.2 (7)
C2—C3—H3	119.5	C213—C212—H212	120.9
C4—C3—H3	119.5	C211—C212—H212	120.9
O4—C4—C3	122.9 (8)	O213—C213—C212	123.5 (7)
O4—C4—C4A	122.3 (8)	O213—C213—C214	114.9 (7)
C3—C4—C4A	114.7 (6)	C212—C213—C214	121.6 (7)
C5—C4A—C8A	117.6 (8)	C215—C214—C213	119.6 (8)
C5—C4A—C4	123.2 (7)	C215—C214—H214	120.2
C8A—C4A—C4	119.1 (8)	C213—C214—H214	120.2
C6—C5—C4A	121.5 (7)	C214—C215—C216	120.0 (7)
C6—C5—H5	119.2	C214—C215—H215	120.0
C4A—C5—H5	119.2	C216—C215—H215	120.0
C5—C6—C7	119.5 (8)	C215—C216—C211	119.6 (7)
C5—C6—H6	120.3	C215—C216—H216	120.2
C7—C6—H6	120.3	C211—C216—H216	120.2
C8—C7—C6	121.0 (9)	O213—C217—H21A	109.5
C8—C7—H7	119.5	O213—C217—H21B	109.5
C6—C7—H7	119.5	H21A—C217—H21B	109.5
C7—C8—C8A	118.8 (7)	O213—C217—H21C	109.5
C7—C8—H8	120.6	H21A—C217—H21C	109.5
C8A—C8—H8	120.6	H21B—C217—H21C	109.5
O1—C8A—C4A	122.8 (7)
C8A—O1—C2—C3	−6.8 (15)	C7—C8—C8A—C4A	4.7 (18)
C8A—O1—C2—C21	173.7 (9)	C211—N2—C21—O2	2.4 (18)
O1—C2—C3—C4	6.3 (18)	C211—N2—C21—C2	−174.8 (10)
C21—C2—C3—C4	−174.3 (11)	C3—C2—C21—O2	−7.0 (17)
C2—C3—C4—O4	179.9 (13)	O1—C2—C21—O2	172.5 (10)
C2—C3—C4—C4A	−1.3 (17)	C3—C2—C21—N2	170.4 (10)
O4—C4—C4A—C5	−4.9 (19)	O1—C2—C21—N2	−10.1 (14)
C3—C4—C4A—C5	176.2 (11)	C21—N2—C211—C212	−29.8 (17)
O4—C4—C4A—C8A	176.2 (12)	C21—N2—C211—C216	153.0 (11)
C3—C4—C4A—C8A	−2.7 (17)	C216—C211—C212—C213	−1.3 (18)
C8A—C4A—C5—C6	0.0 (17)	N2—C211—C212—C213	−178.4 (11)
C4—C4A—C5—C6	−179.0 (12)	C217—O213—C213—C212	−14.2 (17)
C4A—C5—C6—C7	−0.4 (17)	C217—O213—C213—C214	168.9 (11)
C5—C6—C7—C8	3.2 (18)	C211—C212—C213—O213	−178.5 (11)
C6—C7—C8—C8A	−5.2 (18)	C211—C212—C213—C214	−2 (2)
C2—O1—C8A—C4A	2.4 (14)	O213—C213—C214—C215	179.3 (12)
C2—O1—C8A—C8	−172.7 (10)	C212—C213—C214—C215	2 (2)
C5—C4A—C8A—O1	−176.8 (10)	C213—C214—C215—C216	0 (2)
C4—C4A—C8A—O1	2.2 (17)	C214—C215—C216—C211	−3.5 (19)
C5—C4A—C8A—C8	−2.1 (17)	C212—C211—C216—C215	4.0 (17)
C4—C4A—C8A—C8	177.0 (11)	N2—C211—C216—C215	−178.8 (11)
C7—C8—C8A—O1	179.8 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.88	2.17	2.603 (10)	110
C212—H212···O2	0.95	2.36	2.879 (10)	114
N2—H2···O4^i	0.88	2.30	3.096 (9)	150
C216—H216···O4^i	0.95	2.47	3.298 (12)	145

Symmetry code: (i) x−1/2, −y+3/2, z.

(7)

Crystal data

C18H15NO3	Dx = 1.349 Mg m^−3
Mr = 293.31	Mo Kα radiation, λ = 0.71075 Å
Orthorhombic, Pbca	Cell parameters from 8087 reflections
a = 21.094 (9) Å	θ = 2.3–27.5°
b = 16.297 (7) Å	µ = 0.09 mm^−1
c = 8.402 (3) Å	T = 100 K
V = 2888 (2) Å^3	Needle, colourless
Z = 8	0.42 × 0.03 × 0.02 mm
F(000) = 1232

Data collection

Rigaku Saturn724+ (2x2 bin mode) diffractometer	3292 independent reflections
Radiation source: fine-focus sealed tube	3016 reflections with I > 2σ(I)
Confocal monochromator	Rint = 0.047
Detector resolution: 28.5714 pixels mm^-1	θmax = 27.5°, θmin = 3.2°
profile data from ω–scans	h = −22→27
Absorption correction: multi-scan CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)	k = −21→17
Tmin = 0.962, Tmax = 0.998	l = −10→9
15138 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)] = 0.067	H-atom parameters constrained
wR(F^2) = 0.135	w = 1/[σ^2(Fo^2) + (0.0317P)^2 + 2.9914P] where P = (Fo^2 + 2Fc^2)/3
S = 1.22	(Δ/σ)max = 0.001
3292 reflections	Δρmax = 0.24 e Å^−3
202 parameters	Δρmin = −0.27 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0030 (5)

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
O1	0.55375 (7)	0.66144 (9)	0.60195 (16)	0.0192 (3)
O2	0.62167 (7)	0.67264 (9)	0.98491 (17)	0.0227 (4)
O4	0.42329 (7)	0.52040 (10)	0.84134 (19)	0.0262 (4)
N2	0.64975 (8)	0.73701 (10)	0.7539 (2)	0.0183 (4)
H2	0.6360	0.7459	0.6463	0.022*
C2	0.55920 (10)	0.64433 (12)	0.7602 (2)	0.0175 (4)
C3	0.51890 (10)	0.59682 (13)	0.8425 (3)	0.0198 (4)
H3	0.5269	0.5864	0.9519	0.024*
C4	0.46314 (10)	0.56096 (12)	0.7674 (3)	0.0198 (4)
C4A	0.45796 (9)	0.57841 (12)	0.5962 (2)	0.0186 (4)
C5	0.40836 (10)	0.54582 (13)	0.5041 (3)	0.0210 (4)
H5	0.3772	0.5122	0.5532	0.025*
C6	0.40436 (10)	0.56207 (14)	0.3439 (3)	0.0236 (5)
H6	0.3705	0.5400	0.2829	0.028*
C7	0.45054 (10)	0.61135 (13)	0.2706 (3)	0.0224 (5)
H7	0.4476	0.6227	0.1599	0.027*
C8	0.50023 (10)	0.64347 (13)	0.3577 (3)	0.0206 (4)
H8	0.5318	0.6762	0.3078	0.025*
C8A	0.50320 (9)	0.62698 (12)	0.5200 (2)	0.0180 (4)
C21	0.61389 (10)	0.68602 (12)	0.8420 (2)	0.0188 (4)
C211	0.69852 (9)	0.78711 (12)	0.8247 (2)	0.0177 (4)
C212	0.75124 (9)	0.75153 (13)	0.8986 (2)	0.0181 (4)
C213	0.79617 (9)	0.80408 (13)	0.9700 (2)	0.0189 (4)
C214	0.78806 (10)	0.88859 (13)	0.9618 (3)	0.0215 (5)
H214	0.8182	0.9237	1.0113	0.026*
C215	0.73638 (10)	0.92271 (13)	0.8821 (3)	0.0215 (5)
H215	0.7322	0.9806	0.8746	0.026*
C216	0.69118 (10)	0.87202 (13)	0.8138 (3)	0.0205 (4)
H216	0.6556	0.8948	0.7603	0.025*
C217	0.76132 (10)	0.65978 (13)	0.8988 (3)	0.0221 (5)
H21A	0.7505	0.6376	1.0037	0.033*
H21B	0.8058	0.6477	0.8751	0.033*
H21C	0.7342	0.6345	0.8178	0.033*
C218	0.85363 (10)	0.76855 (14)	1.0529 (3)	0.0249 (5)
H21D	0.8780	0.8129	1.1023	0.037*
H21E	0.8802	0.7399	0.9751	0.037*
H21F	0.8399	0.7298	1.1351	0.037*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0172 (7)	0.0257 (7)	0.0146 (7)	−0.0032 (6)	−0.0015 (6)	−0.0003 (6)
O2	0.0269 (8)	0.0257 (8)	0.0156 (7)	−0.0033 (6)	−0.0033 (6)	0.0000 (6)
O4	0.0219 (8)	0.0302 (8)	0.0264 (9)	−0.0036 (7)	0.0041 (7)	0.0032 (7)
N2	0.0169 (8)	0.0217 (8)	0.0165 (8)	−0.0017 (7)	−0.0032 (7)	0.0003 (7)
C2	0.0176 (10)	0.0208 (9)	0.0139 (10)	0.0010 (8)	−0.0010 (8)	−0.0014 (8)
C3	0.0189 (10)	0.0234 (10)	0.0171 (10)	0.0004 (8)	0.0013 (8)	0.0009 (8)
C4	0.0169 (10)	0.0196 (9)	0.0230 (11)	0.0017 (8)	0.0036 (8)	−0.0006 (8)
C4A	0.0151 (9)	0.0199 (10)	0.0207 (11)	0.0015 (8)	0.0012 (8)	−0.0012 (8)
C5	0.0145 (9)	0.0205 (10)	0.0280 (12)	0.0009 (8)	−0.0003 (9)	−0.0012 (9)
C6	0.0159 (10)	0.0269 (11)	0.0280 (12)	0.0023 (8)	−0.0053 (9)	−0.0056 (9)
C7	0.0198 (10)	0.0284 (11)	0.0189 (11)	0.0048 (9)	−0.0030 (9)	−0.0013 (9)
C8	0.0185 (10)	0.0244 (10)	0.0188 (11)	−0.0001 (8)	0.0001 (8)	−0.0005 (8)
C8A	0.0136 (9)	0.0215 (10)	0.0187 (10)	0.0004 (8)	−0.0020 (8)	−0.0034 (8)
C21	0.0181 (10)	0.0206 (10)	0.0176 (11)	0.0009 (8)	−0.0010 (8)	−0.0010 (8)
C211	0.0162 (10)	0.0228 (10)	0.0140 (10)	−0.0016 (8)	0.0006 (8)	−0.0012 (8)
C212	0.0169 (9)	0.0224 (10)	0.0148 (10)	0.0002 (8)	0.0025 (8)	0.0023 (8)
C213	0.0152 (10)	0.0247 (10)	0.0168 (10)	0.0001 (8)	0.0013 (8)	0.0005 (8)
C214	0.0189 (10)	0.0237 (10)	0.0220 (11)	−0.0021 (8)	−0.0004 (9)	−0.0022 (8)
C215	0.0208 (11)	0.0190 (10)	0.0249 (11)	−0.0012 (8)	0.0008 (9)	−0.0005 (8)
C216	0.0181 (10)	0.0236 (10)	0.0198 (10)	0.0021 (8)	−0.0013 (9)	0.0007 (8)
C217	0.0213 (11)	0.0216 (10)	0.0233 (11)	0.0020 (8)	−0.0015 (9)	0.0027 (8)
C218	0.0187 (10)	0.0305 (12)	0.0257 (12)	0.0006 (9)	−0.0035 (9)	−0.0003 (9)

Geometric parameters (Å, º)

O1—C2	1.363 (2)	C8—C8A	1.391 (3)
O1—C8A	1.388 (2)	C8—H8	0.9500
O2—C21	1.231 (3)	C211—C216	1.396 (3)
O4—C4	1.237 (3)	C211—C212	1.399 (3)
N2—C21	1.345 (3)	C212—C213	1.411 (3)
N2—C211	1.442 (3)	C212—C217	1.510 (3)
N2—H2	0.96	C213—C214	1.390 (3)
C2—C3	1.342 (3)	C213—C218	1.513 (3)
C2—C21	1.505 (3)	C214—C215	1.395 (3)
C3—C4	1.457 (3)	C214—H214	0.9500
C3—H3	0.9500	C215—C216	1.386 (3)
C4—C4A	1.470 (3)	C215—H215	0.9500
C4A—C8A	1.395 (3)	C216—H216	0.9500
C4A—C5	1.406 (3)	C217—H21A	0.9800
C5—C6	1.375 (3)	C217—H21B	0.9800
C5—H5	0.9500	C217—H21C	0.9800
C6—C7	1.405 (3)	C218—H21D	0.9800
C6—H6	0.9500	C218—H21E	0.9800
C7—C8	1.382 (3)	C218—H21F	0.9800
C7—H7	0.9500
C2—O1—C8A	117.75 (16)	O2—C21—C2	117.88 (19)
C21—N2—C211	121.60 (17)	N2—C21—C2	117.29 (18)
C21—N2—H2	116.2	C216—C211—C212	121.88 (19)
C211—N2—H2	121.2	C216—C211—N2	117.08 (18)
C3—C2—O1	124.55 (19)	C212—C211—N2	121.03 (18)
C3—C2—C21	120.71 (19)	C211—C212—C213	118.09 (19)
O1—C2—C21	114.70 (17)	C211—C212—C217	121.51 (18)
C2—C3—C4	121.3 (2)	C213—C212—C217	120.38 (18)
C2—C3—H3	119.3	C214—C213—C212	119.84 (19)
C4—C3—H3	119.3	C214—C213—C218	120.05 (19)
O4—C4—C3	123.1 (2)	C212—C213—C218	120.10 (19)
O4—C4—C4A	123.0 (2)	C213—C214—C215	121.0 (2)
C3—C4—C4A	113.96 (18)	C213—C214—H214	119.5
C8A—C4A—C5	118.08 (19)	C215—C214—H214	119.5
C8A—C4A—C4	120.51 (19)	C216—C215—C214	119.92 (19)
C5—C4A—C4	121.40 (19)	C216—C215—H215	120.0
C6—C5—C4A	120.8 (2)	C214—C215—H215	120.0
C6—C5—H5	119.6	C215—C216—C211	119.2 (2)
C4A—C5—H5	119.6	C215—C216—H216	120.4
C5—C6—C7	119.8 (2)	C211—C216—H216	120.4
C5—C6—H6	120.1	C212—C217—H21A	109.5
C7—C6—H6	120.1	C212—C217—H21B	109.5
C8—C7—C6	120.7 (2)	H21A—C217—H21B	109.5
C8—C7—H7	119.7	C212—C217—H21C	109.5
C6—C7—H7	119.7	H21A—C217—H21C	109.5
C7—C8—C8A	118.7 (2)	H21B—C217—H21C	109.5
C7—C8—H8	120.6	C213—C218—H21D	109.5
C8A—C8—H8	120.6	C213—C218—H21E	109.5
O1—C8A—C8	116.26 (18)	H21D—C218—H21E	109.5
O1—C8A—C4A	121.83 (18)	C213—C218—H21F	109.5
C8—C8A—C4A	121.91 (19)	H21D—C218—H21F	109.5
O2—C21—N2	124.81 (19)	H21E—C218—H21F	109.5
C8A—O1—C2—C3	−0.4 (3)	C211—N2—C21—O2	−5.5 (3)
C8A—O1—C2—C21	−178.11 (16)	C211—N2—C21—C2	172.70 (17)
O1—C2—C3—C4	−2.2 (3)	C3—C2—C21—O2	2.6 (3)
C21—C2—C3—C4	175.44 (18)	O1—C2—C21—O2	−179.52 (18)
C2—C3—C4—O4	−176.2 (2)	C3—C2—C21—N2	−175.67 (19)
C2—C3—C4—C4A	2.9 (3)	O1—C2—C21—N2	2.2 (3)
O4—C4—C4A—C8A	177.7 (2)	C21—N2—C211—C216	−117.3 (2)
C3—C4—C4A—C8A	−1.4 (3)	C21—N2—C211—C212	63.7 (3)
O4—C4—C4A—C5	−3.4 (3)	C216—C211—C212—C213	3.1 (3)
C3—C4—C4A—C5	177.49 (18)	N2—C211—C212—C213	−177.96 (18)
C8A—C4A—C5—C6	−0.6 (3)	C216—C211—C212—C217	−175.2 (2)
C4—C4A—C5—C6	−179.45 (19)	N2—C211—C212—C217	3.7 (3)
C4A—C5—C6—C7	0.4 (3)	C211—C212—C213—C214	−1.7 (3)
C5—C6—C7—C8	0.3 (3)	C217—C212—C213—C214	176.64 (19)
C6—C7—C8—C8A	−0.9 (3)	C211—C212—C213—C218	179.36 (19)
C2—O1—C8A—C8	−177.94 (18)	C217—C212—C213—C218	−2.3 (3)
C2—O1—C8A—C4A	2.0 (3)	C212—C213—C214—C215	−0.8 (3)
C7—C8—C8A—O1	−179.38 (18)	C218—C213—C214—C215	178.2 (2)
C7—C8—C8A—C4A	0.7 (3)	C213—C214—C215—C216	2.0 (3)
C5—C4A—C8A—O1	−179.90 (17)	C214—C215—C216—C211	−0.6 (3)
C4—C4A—C8A—O1	−1.0 (3)	C212—C211—C216—C215	−1.9 (3)
C5—C4A—C8A—C8	0.0 (3)	N2—C211—C216—C215	179.08 (18)
C4—C4A—C8A—C8	178.89 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.96	2.25	2.692 (2)	107
N2—H2···O2^i	0.96	1.92	2.762 (2)	145

Symmetry code: (i) x, −y+3/2, z−1/2.

(8) N-(4-methylphenyl)-7-Methoxy-4-oxo-4H-chromone-2-carboxamide

Crystal data

C18H15NO4	F(000) = 648
Mr = 309.31	Dx = 1.423 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71075 Å
a = 14.327 (4) Å	Cell parameters from 3906 reflections
b = 8.468 (2) Å	θ = 2.8–31.4°
c = 12.708 (3) Å	µ = 0.10 mm^−1
β = 110.514 (3)°	T = 100 K
V = 1444.0 (6) Å^3	Plate, yellow
Z = 4	0.18 × 0.15 × 0.03 mm

Data collection

Rigaku Saturn724+ (2x2 bin mode) diffractometer	3291 independent reflections
Confocal monochromator	2921 reflections with I > 2σ(I)
Detector resolution: 28.5714 pixels mm^-1	Rint = 0.024
profile data from ω–scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)	h = −18→18
Tmin = 0.982, Tmax = 0.997	k = −9→10
8914 measured reflections	l = −16→16

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.103	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0488P)^2 + 0.4926P] where P = (Fo^2 + 2Fc^2)/3
3291 reflections	(Δ/σ)max < 0.001
210 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.19 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
O1	0.40257 (6)	0.19553 (11)	0.42610 (7)	0.0165 (2)
O2	0.16539 (7)	0.08301 (12)	0.24327 (8)	0.0224 (2)
O4	0.40905 (7)	0.43035 (12)	0.14664 (7)	0.0197 (2)
O7	0.72190 (7)	0.36580 (12)	0.64640 (7)	0.0206 (2)
N2	0.24454 (8)	0.03740 (13)	0.43181 (9)	0.0154 (2)
H2	0.2997	0.0582	0.4884	0.019*
C2	0.32380 (9)	0.19573 (15)	0.32845 (10)	0.0151 (3)
C3	0.32109 (9)	0.27374 (15)	0.23514 (10)	0.0156 (3)
H3	0.2622	0.2708	0.1705	0.019*
C4	0.40671 (9)	0.36220 (16)	0.23174 (10)	0.0152 (3)
C4A	0.49084 (9)	0.36311 (16)	0.33789 (10)	0.0150 (3)
C5	0.57817 (10)	0.44658 (16)	0.35037 (11)	0.0177 (3)
H5	0.5836	0.5018	0.2877	0.021*
C6	0.65641 (10)	0.45088 (16)	0.45090 (11)	0.0178 (3)
H6	0.7150	0.5090	0.4578	0.021*
C7	0.64881 (9)	0.36796 (16)	0.54390 (10)	0.0162 (3)
C8	0.56334 (10)	0.28260 (16)	0.53404 (10)	0.0168 (3)
H8	0.5581	0.2261	0.5963	0.020*
C8A	0.48593 (9)	0.28173 (15)	0.43147 (10)	0.0152 (3)
C21	0.23635 (9)	0.09862 (15)	0.33097 (10)	0.0154 (3)
C31	0.81371 (10)	0.44425 (17)	0.65695 (11)	0.0193 (3)
H31A	0.8608	0.4323	0.7339	0.029*
H31B	0.8008	0.5567	0.6397	0.029*
H31C	0.8421	0.3972	0.6044	0.029*
C211	0.17248 (9)	−0.05758 (15)	0.45520 (10)	0.0147 (3)
C212	0.20314 (9)	−0.14008 (16)	0.55653 (10)	0.0161 (3)
H212	0.2703	−0.1327	0.6061	0.019*
C213	0.13593 (10)	−0.23293 (16)	0.58538 (10)	0.0174 (3)
H213	0.1582	−0.2902	0.6540	0.021*
C214	0.03628 (10)	−0.24384 (16)	0.51556 (11)	0.0172 (3)
C215	0.00717 (10)	−0.16224 (16)	0.41412 (11)	0.0177 (3)
H215	−0.0601	−0.1696	0.3647	0.021*
C216	0.07336 (10)	−0.07041 (16)	0.38288 (11)	0.0170 (3)
H216	0.0515	−0.0166	0.3128	0.020*
C217	−0.03773 (10)	−0.33647 (17)	0.55035 (11)	0.0210 (3)
H21A	−0.0900	−0.3778	0.4834	0.031*
H21B	−0.0677	−0.2675	0.5917	0.031*
H21C	−0.0037	−0.4245	0.5986	0.031*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0133 (4)	0.0201 (5)	0.0153 (4)	−0.0033 (4)	0.0039 (3)	0.0015 (3)
O2	0.0183 (5)	0.0282 (6)	0.0172 (5)	−0.0056 (4)	0.0018 (4)	0.0022 (4)
O4	0.0190 (5)	0.0243 (5)	0.0166 (4)	0.0015 (4)	0.0072 (4)	0.0050 (4)
O7	0.0154 (5)	0.0277 (6)	0.0172 (4)	−0.0070 (4)	0.0037 (4)	0.0004 (4)
N2	0.0127 (5)	0.0166 (6)	0.0154 (5)	−0.0027 (4)	0.0030 (4)	−0.0008 (4)
C2	0.0136 (6)	0.0147 (6)	0.0164 (6)	0.0021 (5)	0.0047 (5)	−0.0028 (5)
C3	0.0147 (6)	0.0160 (7)	0.0155 (6)	0.0023 (5)	0.0048 (5)	−0.0009 (5)
C4	0.0155 (6)	0.0153 (7)	0.0160 (6)	0.0043 (5)	0.0071 (5)	0.0003 (5)
C4A	0.0148 (6)	0.0150 (6)	0.0160 (6)	0.0015 (5)	0.0065 (5)	0.0001 (5)
C5	0.0187 (6)	0.0170 (7)	0.0193 (6)	0.0003 (5)	0.0092 (5)	0.0034 (5)
C6	0.0155 (6)	0.0172 (7)	0.0217 (6)	−0.0030 (5)	0.0077 (5)	0.0016 (5)
C7	0.0151 (6)	0.0175 (7)	0.0155 (6)	0.0006 (5)	0.0046 (5)	−0.0009 (5)
C8	0.0172 (6)	0.0178 (7)	0.0163 (6)	−0.0010 (5)	0.0069 (5)	0.0016 (5)
C8A	0.0145 (6)	0.0143 (6)	0.0187 (6)	−0.0014 (5)	0.0080 (5)	−0.0009 (5)
C21	0.0163 (6)	0.0136 (6)	0.0165 (6)	0.0009 (5)	0.0061 (5)	−0.0009 (5)
C31	0.0145 (6)	0.0223 (7)	0.0205 (6)	−0.0056 (5)	0.0056 (5)	−0.0023 (5)
C211	0.0152 (6)	0.0124 (6)	0.0175 (6)	−0.0017 (5)	0.0069 (5)	−0.0024 (5)
C212	0.0152 (6)	0.0160 (7)	0.0155 (6)	−0.0008 (5)	0.0036 (5)	−0.0020 (5)
C213	0.0217 (7)	0.0145 (7)	0.0164 (6)	−0.0003 (5)	0.0071 (5)	0.0004 (5)
C214	0.0191 (6)	0.0133 (7)	0.0216 (6)	−0.0014 (5)	0.0100 (5)	−0.0036 (5)
C215	0.0138 (6)	0.0178 (7)	0.0207 (6)	−0.0004 (5)	0.0050 (5)	−0.0015 (5)
C216	0.0163 (6)	0.0168 (7)	0.0169 (6)	0.0000 (5)	0.0045 (5)	0.0005 (5)
C217	0.0217 (7)	0.0186 (7)	0.0254 (7)	−0.0025 (6)	0.0118 (6)	0.0002 (5)

Geometric parameters (Å, º)

O1—C2	1.3535 (15)	C7—C8	1.3893 (19)
O1—C8A	1.3808 (15)	C8—C8A	1.3842 (17)
O2—C21	1.2242 (15)	C8—H8	0.9500
O4—C4	1.2366 (16)	C31—H31A	0.9800
O7—C7	1.3555 (15)	C31—H31B	0.9800
O7—C31	1.4374 (16)	C31—H31C	0.9800
N2—C21	1.3488 (16)	C211—C212	1.3938 (18)
N2—C211	1.4200 (17)	C211—C216	1.3993 (18)
N2—H2	0.8796	C212—C213	1.3883 (19)
C2—C3	1.3460 (18)	C212—H212	0.9500
C2—C21	1.5084 (18)	C213—C214	1.3951 (18)
C3—C4	1.4508 (18)	C213—H213	0.9500
C3—H3	0.9500	C214—C215	1.3915 (19)
C4—C4A	1.4605 (17)	C214—C217	1.5046 (19)
C4A—C5	1.3968 (18)	C215—C216	1.3877 (19)
C4A—C8A	1.3973 (18)	C215—H215	0.9500
C5—C6	1.3735 (18)	C216—H216	0.9500
C5—H5	0.9500	C217—H21A	0.9800
C6—C7	1.4113 (18)	C217—H21B	0.9800
C6—H6	0.9500	C217—H21C	0.9800
C2—O1—C8A	118.25 (10)	O2—C21—C2	118.07 (11)
C7—O7—C31	117.19 (10)	N2—C21—C2	115.67 (11)
C21—N2—C211	126.08 (11)	O7—C31—H31A	109.5
C21—N2—H2	117.0	O7—C31—H31B	109.5
C211—N2—H2	116.9	H31A—C31—H31B	109.5
C3—C2—O1	124.45 (12)	O7—C31—H31C	109.5
C3—C2—C21	121.23 (11)	H31A—C31—H31C	109.5
O1—C2—C21	114.32 (11)	H31B—C31—H31C	109.5
C2—C3—C4	121.06 (11)	C212—C211—C216	119.12 (12)
C2—C3—H3	119.5	C212—C211—N2	117.41 (11)
C4—C3—H3	119.5	C216—C211—N2	123.46 (12)
O4—C4—C3	123.32 (11)	C213—C212—C211	120.31 (12)
O4—C4—C4A	122.60 (12)	C213—C212—H212	119.8
C3—C4—C4A	114.08 (11)	C211—C212—H212	119.8
C5—C4A—C8A	117.60 (11)	C212—C213—C214	121.30 (12)
C5—C4A—C4	121.60 (11)	C212—C213—H213	119.4
C8A—C4A—C4	120.79 (12)	C214—C213—H213	119.4
C6—C5—C4A	121.71 (12)	C215—C214—C213	117.65 (12)
C6—C5—H5	119.1	C215—C214—C217	121.18 (12)
C4A—C5—H5	119.1	C213—C214—C217	121.14 (12)
C5—C6—C7	119.24 (12)	C216—C215—C214	122.02 (12)
C5—C6—H6	120.4	C216—C215—H215	119.0
C7—C6—H6	120.4	C214—C215—H215	119.0
O7—C7—C8	116.06 (11)	C215—C216—C211	119.57 (12)
O7—C7—C6	123.44 (12)	C215—C216—H216	120.2
C8—C7—C6	120.50 (12)	C211—C216—H216	120.2
C8A—C8—C7	118.53 (12)	C214—C217—H21A	109.5
C8A—C8—H8	120.7	C214—C217—H21B	109.5
C7—C8—H8	120.7	H21A—C217—H21B	109.5
O1—C8A—C8	116.29 (11)	C214—C217—H21C	109.5
O1—C8A—C4A	121.29 (11)	H21A—C217—H21C	109.5
C8—C8A—C4A	122.42 (12)	H21B—C217—H21C	109.5
O2—C21—N2	126.26 (12)
C8A—O1—C2—C3	0.46 (18)	C5—C4A—C8A—O1	−179.60 (12)
C8A—O1—C2—C21	−179.86 (10)	C4—C4A—C8A—O1	1.33 (19)
O1—C2—C3—C4	2.0 (2)	C5—C4A—C8A—C8	0.44 (19)
C21—C2—C3—C4	−177.67 (11)	C4—C4A—C8A—C8	−178.63 (12)
C2—C3—C4—O4	177.01 (13)	C211—N2—C21—O2	0.3 (2)
C2—C3—C4—C4A	−2.58 (18)	C211—N2—C21—C2	−179.96 (11)
O4—C4—C4A—C5	2.4 (2)	C3—C2—C21—O2	5.29 (19)
C3—C4—C4A—C5	−178.05 (12)	O1—C2—C21—O2	−174.40 (11)
O4—C4—C4A—C8A	−178.61 (12)	C3—C2—C21—N2	−174.43 (12)
C3—C4—C4A—C8A	0.98 (17)	O1—C2—C21—N2	5.88 (16)
C8A—C4A—C5—C6	−0.7 (2)	C21—N2—C211—C212	165.18 (12)
C4—C4A—C5—C6	178.33 (12)	C21—N2—C211—C216	−15.6 (2)
C4A—C5—C6—C7	0.5 (2)	C216—C211—C212—C213	−0.37 (19)
C31—O7—C7—C8	175.91 (12)	N2—C211—C212—C213	178.90 (11)
C31—O7—C7—C6	−4.19 (18)	C211—C212—C213—C214	−1.3 (2)
C5—C6—C7—O7	−179.75 (12)	C212—C213—C214—C215	1.98 (19)
C5—C6—C7—C8	0.1 (2)	C212—C213—C214—C217	−176.18 (12)
O7—C7—C8—C8A	179.47 (12)	C213—C214—C215—C216	−1.1 (2)
C6—C7—C8—C8A	−0.4 (2)	C217—C214—C215—C216	177.04 (12)
C2—O1—C8A—C8	177.85 (11)	C214—C215—C216—C211	−0.5 (2)
C2—O1—C8A—C4A	−2.12 (17)	C212—C211—C216—C215	1.21 (19)
C7—C8—C8A—O1	−179.83 (12)	N2—C211—C216—C215	−178.01 (12)
C7—C8—C8A—C4A	0.1 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.88	2.23	2.6532 (15)	109
C216—H216···O2	0.95	2.27	2.8659 (17)	120
N2—H2···O4^i	0.88	2.07	2.9279 (14)	164
C212—H212···O4^i	0.95	2.54	3.2864 (17)	136
C5—H5···Cg1^ii	0.95	2.83	3.7025 (18)	154
C31—H31C···Cg3^iii	0.98	2.61	3.5002 (18)	151

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) −x+1, −y, −z+1.

(9) N-methyl-4-oxo-N-phenyl-4H-chromene-2-carboxamide

Crystal data

C17H13NO3	Z = 2
Mr = 279.28	F(000) = 292
Triclinic, P1	Dx = 1.398 Mg m^−3
a = 7.4724 (5) Å	Mo Kα radiation, λ = 0.71075 Å
b = 9.3647 (4) Å	Cell parameters from 5555 reflections
c = 10.5398 (5) Å	θ = 3.0–27.5°
α = 88.283 (13)°	µ = 0.10 mm^−1
β = 71.173 (1)°	T = 120 K
γ = 72.420 (1)°	Block, colourless
V = 663.59 (4) Å^3	0.76 × 0.45 × 0.22 mm

Data collection

Rigaku RAXIS conversion diffractometer	3024 independent reflections
Graphite Monochromator monochromator	2425 reflections with I > 2σ(I)
Detector resolution: 10.0000 pixels mm^-1	Rint = 0.021
profile data from ω–scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)	h = −9→9
Tmin = 0.930, Tmax = 0.979	k = −12→12
6707 measured reflections	l = −13→13

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.113	H-atom parameters constrained
S = 1.14	w = 1/[σ^2(Fo^2) + (0.060P)^2 + 0.0624P] where P = (Fo^2 + 2Fc^2)/3
3024 reflections	(Δ/σ)max < 0.001
191 parameters	Δρmax = 0.25 e Å^−3
0 restraints	Δρmin = −0.21 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
O1	0.53271 (12)	0.57756 (9)	0.66982 (8)	0.0208 (2)
O2	0.27146 (13)	0.47080 (10)	0.97601 (9)	0.0259 (2)
O4	0.92266 (13)	0.15759 (10)	0.64684 (10)	0.0312 (2)
N2	0.23881 (15)	0.70696 (11)	0.90829 (10)	0.0219 (2)
C2	0.51650 (18)	0.49146 (13)	0.77590 (12)	0.0197 (3)
C3	0.64093 (18)	0.35334 (13)	0.77233 (12)	0.0222 (3)
H3	0.6208	0.2992	0.8507	0.027*
C4	0.80615 (18)	0.28409 (13)	0.65165 (13)	0.0226 (3)
C4A	0.81897 (17)	0.37708 (13)	0.53622 (12)	0.0215 (3)
C5	0.96635 (18)	0.32814 (15)	0.41015 (13)	0.0263 (3)
H5	1.0608	0.2310	0.3973	0.032*
C6	0.97510 (19)	0.41974 (16)	0.30514 (13)	0.0294 (3)
H6	1.0750	0.3856	0.2202	0.035*
C7	0.8366 (2)	0.56321 (15)	0.32371 (13)	0.0282 (3)
H7	0.8435	0.6261	0.2510	0.034*
C8	0.69028 (18)	0.61442 (14)	0.44601 (12)	0.0237 (3)
H8	0.5965	0.7119	0.4585	0.028*
C8A	0.68312 (17)	0.51989 (13)	0.55086 (12)	0.0202 (3)
C21	0.33380 (18)	0.55760 (13)	0.89686 (12)	0.0202 (3)
C22	0.04060 (18)	0.76355 (14)	1.01040 (13)	0.0267 (3)
H22A	−0.0355	0.8572	0.9835	0.040*
H22B	0.0545	0.7826	1.0971	0.040*
H22C	−0.0292	0.6886	1.0186	0.040*
C211	0.32976 (17)	0.81684 (12)	0.84241 (12)	0.0202 (3)
C212	0.25129 (18)	0.90638 (13)	0.75428 (12)	0.0228 (3)
H212	0.1367	0.8969	0.7390	0.027*
C213	0.34090 (19)	1.00976 (14)	0.68861 (13)	0.0267 (3)
H213	0.2882	1.0710	0.6276	0.032*
C214	0.5078 (2)	1.02407 (14)	0.71180 (14)	0.0284 (3)
H214	0.5706	1.0937	0.6653	0.034*
C215	0.58231 (19)	0.93700 (14)	0.80260 (13)	0.0270 (3)
H215	0.6946	0.9486	0.8198	0.032*
C216	0.49348 (18)	0.83254 (13)	0.86883 (12)	0.0229 (3)
H216	0.5443	0.7727	0.9313	0.027*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0240 (5)	0.0192 (4)	0.0167 (4)	−0.0060 (3)	−0.0041 (3)	0.0030 (3)
O2	0.0298 (5)	0.0244 (4)	0.0226 (5)	−0.0109 (4)	−0.0054 (4)	0.0069 (4)
O4	0.0268 (5)	0.0240 (5)	0.0374 (6)	−0.0006 (4)	−0.0103 (4)	0.0020 (4)
N2	0.0211 (5)	0.0207 (5)	0.0201 (5)	−0.0063 (4)	−0.0020 (4)	0.0024 (4)
C2	0.0245 (6)	0.0192 (6)	0.0177 (6)	−0.0102 (5)	−0.0072 (5)	0.0039 (4)
C3	0.0250 (6)	0.0222 (6)	0.0209 (6)	−0.0077 (5)	−0.0094 (5)	0.0038 (5)
C4	0.0209 (6)	0.0216 (6)	0.0273 (7)	−0.0064 (5)	−0.0103 (5)	0.0007 (5)
C4A	0.0203 (6)	0.0249 (6)	0.0215 (6)	−0.0095 (5)	−0.0072 (5)	−0.0007 (5)
C5	0.0199 (6)	0.0320 (7)	0.0256 (7)	−0.0075 (5)	−0.0056 (5)	−0.0047 (5)
C6	0.0246 (7)	0.0446 (8)	0.0199 (6)	−0.0162 (6)	−0.0028 (5)	−0.0031 (5)
C7	0.0305 (7)	0.0393 (8)	0.0213 (6)	−0.0202 (6)	−0.0088 (5)	0.0070 (5)
C8	0.0253 (7)	0.0263 (6)	0.0227 (6)	−0.0117 (5)	−0.0088 (5)	0.0048 (5)
C8A	0.0209 (6)	0.0235 (6)	0.0169 (6)	−0.0095 (5)	−0.0044 (5)	−0.0011 (5)
C21	0.0233 (6)	0.0211 (6)	0.0179 (6)	−0.0082 (5)	−0.0079 (5)	0.0033 (4)
C22	0.0219 (6)	0.0275 (6)	0.0239 (6)	−0.0053 (5)	−0.0008 (5)	0.0013 (5)
C211	0.0202 (6)	0.0158 (5)	0.0195 (6)	−0.0036 (4)	−0.0013 (5)	−0.0012 (4)
C212	0.0211 (6)	0.0195 (6)	0.0260 (6)	−0.0042 (5)	−0.0073 (5)	0.0003 (5)
C213	0.0290 (7)	0.0197 (6)	0.0287 (7)	−0.0049 (5)	−0.0090 (5)	0.0059 (5)
C214	0.0294 (7)	0.0205 (6)	0.0337 (7)	−0.0107 (5)	−0.0058 (6)	0.0036 (5)
C215	0.0237 (7)	0.0266 (6)	0.0308 (7)	−0.0092 (5)	−0.0078 (5)	−0.0004 (5)
C216	0.0238 (6)	0.0215 (6)	0.0208 (6)	−0.0044 (5)	−0.0064 (5)	0.0008 (5)

Geometric parameters (Å, º)

O1—C2	1.3537 (13)	C7—C8	1.3774 (18)
O1—C8A	1.3753 (14)	C7—H7	0.9500
O2—C21	1.2291 (14)	C8—C8A	1.3927 (16)
O4—C4	1.2313 (15)	C8—H8	0.9500
N2—C21	1.3528 (15)	C22—H22A	0.9800
N2—C211	1.4414 (14)	C22—H22B	0.9800
N2—C22	1.4710 (15)	C22—H22C	0.9800
C2—C3	1.3389 (17)	C211—C212	1.3848 (16)
C2—C21	1.5119 (17)	C211—C216	1.3881 (17)
C3—C4	1.4542 (17)	C212—C213	1.3845 (16)
C3—H3	0.9500	C212—H212	0.9500
C4—C4A	1.4695 (17)	C213—C214	1.3900 (19)
C4A—C8A	1.3907 (17)	C213—H213	0.9500
C4A—C5	1.4055 (17)	C214—C215	1.3834 (19)
C5—C6	1.3767 (19)	C214—H214	0.9500
C5—H5	0.9500	C215—C216	1.3918 (17)
C6—C7	1.400 (2)	C215—H215	0.9500
C6—H6	0.9500	C216—H216	0.9500
C2—O1—C8A	118.55 (9)	O1—C8A—C8	115.40 (11)
C21—N2—C211	124.34 (10)	C4A—C8A—C8	122.26 (11)
C21—N2—C22	117.72 (10)	O2—C21—N2	123.00 (11)
C211—N2—C22	117.22 (9)	O2—C21—C2	117.89 (10)
C3—C2—O1	123.62 (11)	N2—C21—C2	118.95 (10)
C3—C2—C21	121.65 (10)	N2—C22—H22A	109.5
O1—C2—C21	114.50 (10)	N2—C22—H22B	109.5
C2—C3—C4	121.71 (11)	H22A—C22—H22B	109.5
C2—C3—H3	119.1	N2—C22—H22C	109.5
C4—C3—H3	119.1	H22A—C22—H22C	109.5
O4—C4—C3	122.57 (11)	H22B—C22—H22C	109.5
O4—C4—C4A	123.30 (12)	C212—C211—C216	120.83 (11)
C3—C4—C4A	114.12 (10)	C212—C211—N2	119.43 (11)
C8A—C4A—C5	117.94 (11)	C216—C211—N2	119.73 (11)
C8A—C4A—C4	119.62 (11)	C213—C212—C211	119.57 (12)
C5—C4A—C4	122.44 (11)	C213—C212—H212	120.2
C6—C5—C4A	120.62 (12)	C211—C212—H212	120.2
C6—C5—H5	119.7	C212—C213—C214	120.12 (12)
C4A—C5—H5	119.7	C212—C213—H213	119.9
C5—C6—C7	119.90 (12)	C214—C213—H213	119.9
C5—C6—H6	120.0	C215—C214—C213	120.00 (11)
C7—C6—H6	120.0	C215—C214—H214	120.0
C8—C7—C6	120.88 (12)	C213—C214—H214	120.0
C8—C7—H7	119.6	C214—C215—C216	120.26 (12)
C6—C7—H7	119.6	C214—C215—H215	119.9
C7—C8—C8A	118.41 (12)	C216—C215—H215	119.9
C7—C8—H8	120.8	C211—C216—C215	119.17 (11)
C8A—C8—H8	120.8	C211—C216—H216	120.4
O1—C8A—C4A	122.34 (10)	C215—C216—H216	120.4
C8A—O1—C2—C3	1.01 (17)	C7—C8—C8A—C4A	0.51 (18)
C8A—O1—C2—C21	−173.54 (9)	C211—N2—C21—O2	162.39 (12)
O1—C2—C3—C4	−0.03 (19)	C22—N2—C21—O2	−7.61 (18)
C21—C2—C3—C4	174.14 (11)	C211—N2—C21—C2	−22.40 (17)
C2—C3—C4—O4	179.56 (12)	C22—N2—C21—C2	167.60 (11)
C2—C3—C4—C4A	−1.50 (17)	C3—C2—C21—O2	−19.26 (18)
O4—C4—C4A—C8A	−178.96 (12)	O1—C2—C21—O2	155.41 (11)
C3—C4—C4A—C8A	2.10 (16)	C3—C2—C21—N2	165.29 (11)
O4—C4—C4A—C5	0.16 (19)	O1—C2—C21—N2	−20.04 (16)
C3—C4—C4A—C5	−178.77 (11)	C21—N2—C211—C212	120.54 (13)
C8A—C4A—C5—C6	0.20 (18)	C22—N2—C211—C212	−69.42 (15)
C4—C4A—C5—C6	−178.95 (11)	C21—N2—C211—C216	−60.01 (16)
C4A—C5—C6—C7	0.17 (19)	C22—N2—C211—C216	110.03 (13)
C5—C6—C7—C8	−0.20 (19)	C216—C211—C212—C213	1.96 (17)
C6—C7—C8—C8A	−0.13 (19)	N2—C211—C212—C213	−178.60 (11)
C2—O1—C8A—C4A	−0.32 (17)	C211—C212—C213—C214	−0.42 (19)
C2—O1—C8A—C8	179.76 (10)	C212—C213—C214—C215	−1.26 (19)
C5—C4A—C8A—O1	179.54 (10)	C213—C214—C215—C216	1.41 (19)
C4—C4A—C8A—O1	−1.29 (17)	C212—C211—C216—C215	−1.80 (17)
C5—C4A—C8A—C8	−0.55 (18)	N2—C211—C216—C215	178.76 (11)
C4—C4A—C8A—C8	178.62 (11)	C214—C215—C216—C211	0.11 (18)
C7—C8—C8A—O1	−179.57 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C213—H213···O4^i	0.95	2.54	3.1803 (18)	125

Symmetry code: (i) x−1, y+1, z.