A comparison of the structures of some 2- and 3-substituted chromone derivatives: a structural study on the importance of the secondary carboxamide backbone for the inhibitory activity of MAO-B

The structures of 2- and 3-substituted tertiary carboxamides and analogous pyrrolidine structures are compared.

Key indicators

Structure: 1

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.056
• wR factor = 0.133
• Data-to-parameter ratio = 16.0

Structure: 3

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.069
• wR factor = 0.152
• Data-to-parameter ratio = 20.2

Structure: 4

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.048
• wR factor = 0.102
• Data-to-parameter ratio = 20.7

checkCIF/PLATON results

No syntax errors found



Datablock: 1


Alert level C
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      7.372 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         18 Report

Alert level G
PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety .....        C32 Check
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ...          2 Report
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         14 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   3 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: 3


Alert level C
STRVA01_ALERT_4_C           Flack test results are meaningless.
           From the CIF: _refine_ls_abs_structure_Flack   -0.100
           From the CIF: _refine_ls_abs_structure_Flack_su    0.600
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0050 Ang.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.840 Check
PLAT915_ALERT_3_C Low Friedel Pair Coverage ......................         82 %
PLAT934_ALERT_3_C Number of (Iobs-Icalc)/SigmaW > 10 Outliers ....          1 Check

Alert level G
PLAT032_ALERT_4_G Std. Uncertainty on Flack Parameter Value High .      0.600 Report
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        118 Note
PLAT916_ALERT_2_G Hooft y and Flack x Parameter values differ by .       0.30 Check

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   5 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: 4


Alert level C
STRVA01_ALERT_2_C           Chirality of atom sites is inverted?
           From the CIF: _refine_ls_abs_structure_Flack    1.200
           From the CIF: _refine_ls_abs_structure_Flack_su    0.500
PLAT915_ALERT_3_C Low Friedel Pair Coverage ......................         84 %

Alert level G
PLAT032_ALERT_4_G Std. Uncertainty on Flack Parameter Value High .      0.500 Report
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT111_ALERT_2_G ADDSYM Detects (Pseudo) Centre of Symmetry .....         83 %Fit
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ...          1 Report
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         79 Note
PLAT916_ALERT_2_G Hooft y and Flack x Parameter values differ by .       0.10 Check

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   6 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

For all compounds, data collection: CrystalClear-SM Expert (Rigaku, 2012); cell refinement: CrystalClear-SM Expert (Rigaku, 2012); data reduction: CrystalClear-SM Expert (Rigaku, 2012). Program(s) used to solve structure: SHELXS (Sheldrick, 2015), PLATON (Spek, 2009), Flipper 25 (Oszlányi & Sütő, 2004) and Olex2 (Dolomanov et al., 2009 for (1); SHELXS (Sheldrick, 2015), PLATON (Spek, 2009), Flipper 25 (Oszlányi & Sütő, 2004) and Olex2 (Dolomanov et al., 2009). for (3); SHELXS (Sheldrick, 2015), PLATON (Spek, 2009), Flipper 25 (Oszlányi & Sütő, 2004) and Olex2 (Dolomanov et al., 2009) for (4). For all compounds, program(s) used to refine structure: OSCAIL (McArdle et al., 2004), ShelXle (Hübschle et al., 2011) and SHELXL2014/17 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: OSCAIL (McArdle et al., 2004), SHELXL2014/17 (Sheldrick, 2015) and PLATON (Spek, 2009).

(1) N-Methyl-4-oxo-N-phenyl-4H-chromene-3-carboxamide

Crystal data

C17H13NO3	Z = 4
Mr = 279.28	F(000) = 584
Monoclinic, P21/c	Dx = 1.383 Mg m^−3
a = 6.716 (4) Å	Mo Kα radiation, λ = 0.71075 Å
b = 6.809 (4) Å	µ = 0.10 mm^−1
c = 29.425 (17) Å	T = 100 K
β = 94.784 (7)°	Rod, colourless
V = 1340.9 (14) Å^3	0.25 × 0.07 × 0.06 mm

Data collection

Rigaku Saturn724+ diffractometer	3032 independent reflections
Radiation source: Rotating Anode	2304 reflections with I > 2σ(I)
Confocal monochromator	Rint = 0.043
Detector resolution: 28.5714 pixels mm^-1	θmax = 27.4°, θmin = 3.0°
profile data from ω–scans	h = −8→8
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2012)	k = −8→8
Tmin = 0.572, Tmax = 1.000	l = −17→38
6206 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.056	H-atom parameters constrained
wR(F^2) = 0.133	w = 1/[σ^2(Fo^2) + (0.0336P)^2 + 1.136P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
3032 reflections	Δρmax = 0.30 e Å^−3
190 parameters	Δρmin = −0.25 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	0.6806 (2)	0.7176 (2)	0.54188 (5)	0.0226 (3)
O3	0.6513 (2)	0.4530 (2)	0.66760 (5)	0.0351 (4)
O4	0.1517 (2)	0.5956 (2)	0.59524 (5)	0.0219 (3)
N3	0.4090 (3)	0.6598 (2)	0.68645 (5)	0.0204 (4)
C2	0.6722 (3)	0.6736 (3)	0.58634 (7)	0.0206 (4)
H2	0.7952	0.6604	0.6045	0.025*
C3	0.5026 (3)	0.6467 (3)	0.60699 (6)	0.0181 (4)
C4	0.3091 (3)	0.6483 (3)	0.58017 (6)	0.0176 (4)
C4A	0.3200 (3)	0.7089 (3)	0.53230 (6)	0.0175 (4)
C5	0.1473 (3)	0.7317 (3)	0.50257 (7)	0.0225 (4)
H5	0.0196	0.7139	0.5136	0.027*
C6	0.1615 (3)	0.7800 (3)	0.45738 (7)	0.0262 (5)
H6	0.0437	0.7970	0.4376	0.031*
C7	0.3497 (3)	0.8040 (3)	0.44074 (7)	0.0250 (5)
H7	0.3586	0.8342	0.4095	0.030*
C8	0.5213 (3)	0.7842 (3)	0.46923 (7)	0.0228 (4)
H8	0.6488	0.8018	0.4581	0.027*
C8A	0.5041 (3)	0.7376 (3)	0.51492 (6)	0.0184 (4)
C31	0.5272 (3)	0.5798 (3)	0.65592 (7)	0.0218 (4)
C32	0.4238 (4)	0.5723 (3)	0.73235 (7)	0.0329 (6)
H32A	0.3328	0.6409	0.7513	0.049*
H32B	0.3872	0.4331	0.7302	0.049*
H32C	0.5612	0.5848	0.7461	0.049*
C311	0.2721 (3)	0.8175 (3)	0.67737 (6)	0.0180 (4)
C312	0.0764 (3)	0.7959 (4)	0.68895 (7)	0.0296 (5)
H312	0.0338	0.6752	0.7011	0.036*
C313	−0.0547 (4)	0.9506 (5)	0.68268 (8)	0.0428 (7)
H313	−0.1879	0.9361	0.6908	0.051*
C314	0.0046 (4)	1.1271 (4)	0.66470 (8)	0.0450 (8)
H314	−0.0873	1.2330	0.6605	0.054*
C315	0.1985 (4)	1.1481 (3)	0.65283 (8)	0.0352 (6)
H315	0.2394	1.2679	0.6399	0.042*
C316	0.3337 (3)	0.9941 (3)	0.65974 (6)	0.0225 (4)
H316	0.4679	1.0098	0.6524	0.027*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0171 (7)	0.0268 (8)	0.0242 (7)	0.0015 (6)	0.0046 (6)	−0.0019 (6)
O3	0.0367 (10)	0.0375 (9)	0.0303 (8)	0.0219 (8)	−0.0014 (7)	0.0022 (7)
O4	0.0176 (7)	0.0269 (8)	0.0215 (7)	−0.0015 (6)	0.0035 (5)	0.0009 (6)
N3	0.0232 (9)	0.0203 (8)	0.0178 (8)	0.0059 (7)	0.0024 (7)	0.0032 (6)
C2	0.0162 (10)	0.0218 (10)	0.0236 (10)	0.0045 (8)	−0.0001 (8)	−0.0030 (8)
C3	0.0151 (10)	0.0187 (9)	0.0206 (9)	0.0021 (8)	0.0018 (7)	−0.0025 (7)
C4	0.0164 (10)	0.0161 (9)	0.0203 (9)	0.0013 (8)	0.0024 (7)	−0.0019 (7)
C4A	0.0180 (10)	0.0153 (9)	0.0195 (9)	0.0008 (8)	0.0032 (7)	−0.0026 (7)
C5	0.0181 (10)	0.0257 (11)	0.0238 (10)	−0.0004 (9)	0.0025 (8)	−0.0009 (8)
C6	0.0254 (11)	0.0299 (12)	0.0227 (10)	0.0018 (10)	−0.0019 (8)	0.0010 (8)
C7	0.0343 (12)	0.0213 (10)	0.0202 (9)	−0.0002 (9)	0.0063 (9)	0.0007 (8)
C8	0.0254 (11)	0.0181 (10)	0.0263 (10)	0.0004 (9)	0.0101 (8)	−0.0027 (8)
C8A	0.0178 (10)	0.0148 (9)	0.0227 (9)	0.0012 (8)	0.0024 (8)	−0.0029 (7)
C31	0.0190 (10)	0.0226 (10)	0.0235 (10)	0.0049 (9)	−0.0005 (8)	0.0002 (8)
C32	0.0523 (16)	0.0281 (12)	0.0183 (10)	0.0063 (11)	0.0021 (10)	0.0045 (8)
C311	0.0160 (10)	0.0215 (10)	0.0162 (8)	0.0055 (8)	−0.0006 (7)	−0.0028 (7)
C312	0.0219 (11)	0.0415 (13)	0.0257 (10)	0.0011 (10)	0.0035 (9)	−0.0075 (9)
C313	0.0223 (12)	0.071 (2)	0.0347 (13)	0.0161 (13)	−0.0016 (10)	−0.0213 (13)
C314	0.0448 (16)	0.0515 (17)	0.0355 (13)	0.0353 (14)	−0.0166 (12)	−0.0195 (12)
C315	0.0542 (16)	0.0229 (11)	0.0257 (11)	0.0127 (11)	−0.0121 (11)	−0.0039 (9)
C316	0.0254 (11)	0.0232 (10)	0.0181 (9)	0.0021 (9)	−0.0023 (8)	−0.0017 (8)

Geometric parameters (Å, º)

O1—C2	1.348 (2)	C7—C8	1.374 (3)
O1—C8A	1.377 (2)	C7—H7	0.9500
O3—C31	1.229 (2)	C8—C8A	1.395 (3)
O4—C4	1.233 (2)	C8—H8	0.9500
N3—C31	1.361 (3)	C32—H32A	0.9800
N3—C311	1.425 (3)	C32—H32B	0.9800
N3—C32	1.472 (3)	C32—H32C	0.9800
C2—C3	1.347 (3)	C311—C316	1.386 (3)
C2—H2	0.9500	C311—C312	1.393 (3)
C3—C4	1.464 (3)	C312—C313	1.375 (3)
C3—C31	1.506 (3)	C312—H312	0.9500
C4—C4A	1.476 (3)	C313—C314	1.385 (4)
C4A—C8A	1.391 (3)	C313—H313	0.9500
C4A—C5	1.402 (3)	C314—C315	1.384 (4)
C5—C6	1.381 (3)	C314—H314	0.9500
C5—H5	0.9500	C315—C316	1.391 (3)
C6—C7	1.403 (3)	C315—H315	0.9500
C6—H6	0.9500	C316—H316	0.9500
C2—O1—C8A	118.54 (16)	O1—C8A—C8	116.18 (18)
C31—N3—C311	125.50 (16)	C4A—C8A—C8	122.26 (19)
C31—N3—C32	116.47 (17)	O3—C31—N3	121.05 (18)
C311—N3—C32	118.03 (17)	O3—C31—C3	119.82 (18)
C3—C2—O1	124.97 (19)	N3—C31—C3	119.13 (17)
C3—C2—H2	117.5	N3—C32—H32A	109.5
O1—C2—H2	117.5	N3—C32—H32B	109.5
C2—C3—C4	120.15 (18)	H32A—C32—H32B	109.5
C2—C3—C31	116.29 (18)	N3—C32—H32C	109.5
C4—C3—C31	122.62 (17)	H32A—C32—H32C	109.5
O4—C4—C3	123.61 (18)	H32B—C32—H32C	109.5
O4—C4—C4A	122.49 (18)	C316—C311—C312	120.02 (19)
C3—C4—C4A	113.82 (17)	C316—C311—N3	121.05 (18)
C8A—C4A—C5	118.01 (18)	C312—C311—N3	118.83 (19)
C8A—C4A—C4	120.47 (17)	C313—C312—C311	119.6 (2)
C5—C4A—C4	121.47 (18)	C313—C312—H312	120.2
C6—C5—C4A	120.51 (19)	C311—C312—H312	120.2
C6—C5—H5	119.7	C312—C313—C314	121.0 (2)
C4A—C5—H5	119.7	C312—C313—H313	119.5
C5—C6—C7	120.01 (19)	C314—C313—H313	119.5
C5—C6—H6	120.0	C315—C314—C313	119.5 (2)
C7—C6—H6	120.0	C315—C314—H314	120.2
C8—C7—C6	120.68 (19)	C313—C314—H314	120.2
C8—C7—H7	119.7	C314—C315—C316	120.1 (2)
C6—C7—H7	119.7	C314—C315—H315	119.9
C7—C8—C8A	118.51 (19)	C316—C315—H315	119.9
C7—C8—H8	120.7	C311—C316—C315	119.8 (2)
C8A—C8—H8	120.7	C311—C316—H316	120.1
O1—C8A—C4A	121.54 (17)	C315—C316—H316	120.1
C8A—O1—C2—C3	0.1 (3)	C7—C8—C8A—O1	179.39 (17)
O1—C2—C3—C4	5.2 (3)	C7—C8—C8A—C4A	0.7 (3)
O1—C2—C3—C31	174.45 (18)	C311—N3—C31—O3	174.8 (2)
C2—C3—C4—O4	168.55 (19)	C32—N3—C31—O3	−6.1 (3)
C31—C3—C4—O4	0.0 (3)	C311—N3—C31—C3	−6.0 (3)
C2—C3—C4—C4A	−8.3 (3)	C32—N3—C31—C3	173.13 (19)
C31—C3—C4—C4A	−176.85 (17)	C2—C3—C31—O3	−42.0 (3)
O4—C4—C4A—C8A	−169.94 (18)	C4—C3—C31—O3	126.9 (2)
C3—C4—C4A—C8A	7.0 (3)	C2—C3—C31—N3	138.8 (2)
O4—C4—C4A—C5	7.5 (3)	C4—C3—C31—N3	−52.3 (3)
C3—C4—C4A—C5	−175.54 (18)	C31—N3—C311—C316	−54.2 (3)
C8A—C4A—C5—C6	0.5 (3)	C32—N3—C311—C316	126.7 (2)
C4—C4A—C5—C6	−177.09 (19)	C31—N3—C311—C312	129.5 (2)
C4A—C5—C6—C7	0.9 (3)	C32—N3—C311—C312	−49.6 (3)
C5—C6—C7—C8	−1.4 (3)	C316—C311—C312—C313	0.1 (3)
C6—C7—C8—C8A	0.7 (3)	N3—C311—C312—C313	176.53 (19)
C2—O1—C8A—C4A	−1.6 (3)	C311—C312—C313—C314	0.5 (3)
C2—O1—C8A—C8	179.71 (17)	C312—C313—C314—C315	0.1 (4)
C5—C4A—C8A—O1	−179.89 (17)	C313—C314—C315—C316	−1.2 (3)
C4—C4A—C8A—O1	−2.3 (3)	C312—C311—C316—C315	−1.3 (3)
C5—C4A—C8A—C8	−1.2 (3)	N3—C311—C316—C315	−177.58 (18)
C4—C4A—C8A—C8	176.34 (18)	C314—C315—C316—C311	1.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O4^i	0.95	2.47	3.253 (3)	140
C5—H5···O1^ii	0.95	2.49	3.432 (3)	172
C314—H314···O3^iii	0.95	2.33	3.255 (3)	164

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

(3) 3-(Pyrrolidine-1-carbonyl)-4H-chromen-4-one

Crystal data

C14H13NO3	Dx = 1.437 Mg m^−3
Mr = 243.25	Mo Kα radiation, λ = 0.71075 Å
Orthorhombic, P212121	Cell parameters from 4253 reflections
a = 7.430 (3) Å	θ = 2.3–31.2°
b = 11.963 (6) Å	µ = 0.10 mm^−1
c = 12.648 (6) Å	T = 100 K
V = 1124.2 (9) Å^3	Lath, colourless
Z = 4	0.22 × 0.07 × 0.03 mm
F(000) = 512

Data collection

Rigaku Saturn724+ diffractometer	3294 independent reflections
Radiation source: Rotating Anode	3066 reflections with I > 2σ(I)
Confocal monochromator	Rint = 0.031
Detector resolution: 28.5714 pixels mm^-1	θmax = 31.3°, θmin = 2.3°
profile data from ω–scans	h = −8→10
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2012)	k = −17→15
Tmin = 0.978, Tmax = 0.997	l = −18→18
7547 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.069	w = 1/[σ^2(Fo^2) + (0.0459P)^2 + 1.1472P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.152	(Δ/σ)max < 0.001
S = 1.07	Δρmax = 0.51 e Å^−3
3294 reflections	Δρmin = −0.44 e Å^−3
163 parameters	Absolute structure: Flack x determined using 946 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013)
0 restraints	Absolute structure parameter: −0.1 (6)

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.8069 (3)	0.5658 (2)	0.58566 (17)	0.0247 (5)
O3	0.6707 (4)	0.8949 (2)	0.5280 (2)	0.0362 (6)
O4	0.5779 (3)	0.66383 (19)	0.30612 (18)	0.0255 (5)
N311	0.7972 (4)	0.8846 (2)	0.3665 (2)	0.0292 (6)
C2	0.7960 (5)	0.6739 (3)	0.5573 (2)	0.0254 (7)
H2	0.8374	0.7277	0.6068	0.030*
C3	0.7316 (4)	0.7126 (3)	0.4646 (2)	0.0224 (6)
C4	0.6548 (4)	0.6348 (3)	0.3885 (2)	0.0215 (6)
C4A	0.6710 (4)	0.5165 (3)	0.4186 (2)	0.0212 (6)
C5	0.6124 (4)	0.4305 (3)	0.3517 (2)	0.0236 (6)
H5	0.5596	0.4485	0.2855	0.028*
C6	0.6304 (5)	0.3197 (3)	0.3812 (3)	0.0263 (7)
H6	0.5910	0.2620	0.3351	0.032*
C7	0.7069 (5)	0.2928 (3)	0.4790 (3)	0.0271 (7)
H7	0.7185	0.2166	0.4992	0.033*
C8	0.7659 (5)	0.3762 (3)	0.5466 (3)	0.0259 (6)
H8	0.8178	0.3581	0.6131	0.031*
C8A	0.7474 (4)	0.4865 (3)	0.5153 (2)	0.0223 (6)
C31	0.7301 (5)	0.8378 (3)	0.4541 (3)	0.0259 (6)
C312	0.8921 (6)	0.8294 (3)	0.2780 (3)	0.0318 (8)
H31A	0.8245	0.7634	0.2523	0.038*
H31B	1.0147	0.8057	0.2991	0.038*
C313	0.8989 (7)	0.9193 (3)	0.1957 (4)	0.0430 (10)
H31C	0.7881	0.9192	0.1522	0.052*
H31D	1.0043	0.9093	0.1487	0.052*
C314	0.9147 (8)	1.0274 (4)	0.2587 (3)	0.0477 (12)
H31E	0.8685	1.0916	0.2175	0.057*
H31F	1.0414	1.0421	0.2784	0.057*
C315	0.7994 (5)	1.0074 (3)	0.3571 (3)	0.0360 (8)
H31G	0.8542	1.0424	0.4203	0.043*
H31H	0.6763	1.0374	0.3474	0.043*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0315 (12)	0.0273 (11)	0.0153 (9)	−0.0027 (10)	−0.0022 (9)	−0.0007 (8)
O3	0.0401 (14)	0.0323 (13)	0.0362 (14)	0.0008 (11)	0.0038 (12)	−0.0126 (11)
O4	0.0296 (12)	0.0265 (11)	0.0202 (10)	0.0029 (10)	−0.0052 (9)	0.0009 (9)
N311	0.0379 (16)	0.0207 (12)	0.0288 (14)	−0.0021 (12)	−0.0007 (13)	−0.0022 (11)
C2	0.0289 (16)	0.0275 (15)	0.0196 (14)	−0.0026 (13)	−0.0011 (13)	−0.0041 (12)
C3	0.0221 (14)	0.0245 (14)	0.0208 (14)	0.0004 (12)	0.0003 (12)	−0.0033 (11)
C4	0.0209 (13)	0.0247 (14)	0.0188 (13)	0.0017 (11)	0.0018 (11)	−0.0011 (11)
C4A	0.0195 (13)	0.0259 (14)	0.0180 (13)	−0.0005 (12)	0.0013 (11)	0.0002 (11)
C5	0.0246 (14)	0.0289 (15)	0.0174 (13)	−0.0008 (12)	0.0003 (12)	−0.0013 (11)
C6	0.0300 (17)	0.0246 (15)	0.0243 (15)	−0.0042 (12)	0.0012 (13)	−0.0017 (12)
C7	0.0325 (17)	0.0236 (14)	0.0252 (15)	−0.0005 (13)	0.0028 (14)	0.0053 (12)
C8	0.0274 (15)	0.0310 (16)	0.0193 (14)	0.0007 (13)	−0.0019 (13)	0.0044 (12)
C8A	0.0205 (14)	0.0292 (15)	0.0171 (13)	−0.0013 (12)	0.0008 (11)	−0.0012 (11)
C31	0.0267 (15)	0.0261 (15)	0.0250 (14)	−0.0003 (13)	−0.0040 (13)	−0.0043 (12)
C312	0.045 (2)	0.0271 (16)	0.0229 (15)	−0.0047 (16)	0.0005 (15)	0.0001 (13)
C313	0.047 (2)	0.042 (2)	0.040 (2)	0.0007 (19)	0.010 (2)	0.0069 (17)
C314	0.076 (3)	0.036 (2)	0.030 (2)	−0.019 (2)	−0.009 (2)	0.0046 (16)
C315	0.042 (2)	0.0226 (15)	0.044 (2)	−0.0042 (15)	−0.0086 (17)	0.0010 (14)

Geometric parameters (Å, º)

O1—C2	1.345 (4)	C6—H6	0.9500
O1—C8A	1.374 (4)	C7—C8	1.386 (5)
O3—C31	1.239 (4)	C7—H7	0.9500
O4—C4	1.238 (4)	C8—C8A	1.384 (4)
N311—C31	1.337 (4)	C8—H8	0.9500
N311—C315	1.474 (4)	C312—C313	1.498 (5)
N311—C312	1.480 (5)	C312—H31A	0.9900
C2—C3	1.348 (4)	C312—H31B	0.9900
C2—H2	0.9500	C313—C314	1.524 (6)
C3—C4	1.455 (4)	C313—H31C	0.9900
C3—C31	1.504 (4)	C313—H31D	0.9900
C4—C4A	1.471 (4)	C314—C315	1.529 (6)
C4A—C8A	1.396 (4)	C314—H31E	0.9900
C4A—C5	1.401 (4)	C314—H31F	0.9900
C5—C6	1.383 (5)	C315—H31G	0.9900
C5—H5	0.9500	C315—H31H	0.9900
C6—C7	1.399 (5)
C2—O1—C8A	118.2 (2)	O1—C8A—C4A	121.4 (3)
C31—N311—C315	119.2 (3)	C8—C8A—C4A	122.4 (3)
C31—N311—C312	128.2 (3)	O3—C31—N311	121.8 (3)
C315—N311—C312	112.2 (3)	O3—C31—C3	119.0 (3)
O1—C2—C3	125.7 (3)	N311—C31—C3	119.2 (3)
O1—C2—H2	117.2	N311—C312—C313	102.8 (3)
C3—C2—H2	117.2	N311—C312—H31A	111.2
C2—C3—C4	119.7 (3)	C313—C312—H31A	111.2
C2—C3—C31	114.9 (3)	N311—C312—H31B	111.2
C4—C3—C31	125.1 (3)	C313—C312—H31B	111.2
O4—C4—C3	124.0 (3)	H31A—C312—H31B	109.1
O4—C4—C4A	121.7 (3)	C312—C313—C314	104.4 (3)
C3—C4—C4A	114.3 (3)	C312—C313—H31C	110.9
C8A—C4A—C5	117.8 (3)	C314—C313—H31C	110.9
C8A—C4A—C4	120.5 (3)	C312—C313—H31D	110.9
C5—C4A—C4	121.7 (3)	C314—C313—H31D	110.9
C6—C5—C4A	120.7 (3)	H31C—C313—H31D	108.9
C6—C5—H5	119.7	C313—C314—C315	104.5 (3)
C4A—C5—H5	119.7	C313—C314—H31E	110.9
C5—C6—C7	119.9 (3)	C315—C314—H31E	110.9
C5—C6—H6	120.0	C313—C314—H31F	110.9
C7—C6—H6	120.0	C315—C314—H31F	110.9
C8—C7—C6	120.6 (3)	H31E—C314—H31F	108.9
C8—C7—H7	119.7	N311—C315—C314	103.2 (3)
C6—C7—H7	119.7	N311—C315—H31G	111.1
C8A—C8—C7	118.6 (3)	C314—C315—H31G	111.1
C8A—C8—H8	120.7	N311—C315—H31H	111.1
C7—C8—H8	120.7	C314—C315—H31H	111.1
O1—C8A—C8	116.2 (3)	H31G—C315—H31H	109.1
C8A—O1—C2—C3	−0.2 (5)	C5—C4A—C8A—O1	−179.5 (3)
O1—C2—C3—C4	4.3 (5)	C4—C4A—C8A—O1	1.0 (4)
O1—C2—C3—C31	178.5 (3)	C5—C4A—C8A—C8	−0.3 (5)
C2—C3—C4—O4	173.1 (3)	C4—C4A—C8A—C8	−179.8 (3)
C31—C3—C4—O4	−0.4 (5)	C315—N311—C31—O3	−0.5 (5)
C2—C3—C4—C4A	−5.3 (4)	C312—N311—C31—O3	171.9 (3)
C31—C3—C4—C4A	−178.8 (3)	C315—N311—C31—C3	−178.7 (3)
O4—C4—C4A—C8A	−175.6 (3)	C312—N311—C31—C3	−6.3 (5)
C3—C4—C4A—C8A	2.8 (4)	C2—C3—C31—O3	−46.6 (4)
O4—C4—C4A—C5	4.9 (5)	C4—C3—C31—O3	127.2 (4)
C3—C4—C4A—C5	−176.7 (3)	C2—C3—C31—N311	131.6 (3)
C8A—C4A—C5—C6	−0.1 (5)	C4—C3—C31—N311	−54.6 (5)
C4—C4A—C5—C6	179.4 (3)	C31—N311—C312—C313	168.7 (4)
C4A—C5—C6—C7	0.4 (5)	C315—N311—C312—C313	−18.4 (4)
C5—C6—C7—C8	−0.4 (5)	N311—C312—C313—C314	32.8 (5)
C6—C7—C8—C8A	0.0 (5)	C312—C313—C314—C315	−36.0 (5)
C2—O1—C8A—C8	178.2 (3)	C31—N311—C315—C314	169.9 (3)
C2—O1—C8A—C4A	−2.5 (4)	C312—N311—C315—C314	−3.6 (4)
C7—C8—C8A—O1	179.6 (3)	C313—C314—C315—N311	24.0 (4)
C7—C8—C8A—C4A	0.3 (5)

Hydrogen-bond geometry (Å, º)

Cg is the centroid of the benzene ring C4A/C5–C8/C8A

D—H···A	D—H	H···A	D···A	D—H···A
C312—H31A···O4	0.99	2.29	3.082 (5)	136
C2—H2···O4^i	0.95	2.47	3.338 (4)	152
C6—H6···O4^ii	0.95	2.48	3.389 (4)	161
C8—H8···O4^iii	0.95	2.57	3.514 (4)	170
C314—H31E···O3^iv	0.99	2.42	3.128 (5)	128
C313—H31D···Cg^v	0.99	2.59	3.570 (6)	170

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

(4) 2-(Pyrrolidine-1-carbonyl)-4H-chromen-4-one

Crystal data

C14H13NO3	Dx = 1.411 Mg m^−3
Mr = 243.25	Mo Kα radiation, λ = 0.71075 Å
Orthorhombic, Aba2	Cell parameters from 3760 reflections
a = 15.337 (6) Å	θ = 2.3–31.2°
b = 21.940 (8) Å	µ = 0.10 mm^−1
c = 6.808 (3) Å	T = 100 K
V = 2290.8 (16) Å^3	Needle, colourless
Z = 8	0.50 × 0.04 × 0.02 mm
F(000) = 1024

Data collection

Rigaku Saturn724+ diffractometer	3374 independent reflections
Radiation source: Rotating Anode	3079 reflections with I > 2σ(I)
Confocal monochromator	Rint = 0.034
Detector resolution: 28.5714 pixels mm^-1	θmax = 31.3°, θmin = 2.3°
profile data from ω–scans	h = −21→17
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2012)	k = −29→31
Tmin = 0.952, Tmax = 0.998	l = −9→8
9598 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.048	w = 1/[σ^2(Fo^2) + (0.0386P)^2 + 1.0329P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.102	(Δ/σ)max < 0.001
S = 1.11	Δρmax = 0.32 e Å^−3
3374 reflections	Δρmin = −0.21 e Å^−3
163 parameters	Absolute structure: Flack x determined using 1043 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: 1.2 (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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.60596 (8)	0.22901 (6)	0.4803 (2)	0.0186 (3)
O2	0.42149 (9)	0.32316 (7)	0.4657 (3)	0.0254 (4)
O4	0.42290 (10)	0.09521 (7)	0.4038 (3)	0.0244 (4)
C2	0.52132 (12)	0.24216 (9)	0.4484 (3)	0.0176 (4)
C3	0.45851 (13)	0.19980 (9)	0.4233 (3)	0.0193 (4)
H3	0.3999	0.2124	0.4038	0.023*
C4	0.47910 (13)	0.13519 (9)	0.4255 (3)	0.0191 (4)
C4A	0.57164 (13)	0.12141 (9)	0.4559 (3)	0.0182 (4)
C5	0.60362 (13)	0.06129 (9)	0.4609 (4)	0.0207 (4)
H5	0.5647	0.0281	0.4423	0.025*
C6	0.69058 (14)	0.05020 (9)	0.4923 (4)	0.0227 (5)
H6	0.7113	0.0094	0.4973	0.027*
C7	0.74912 (15)	0.09874 (9)	0.5172 (4)	0.0220 (4)
H7	0.8093	0.0906	0.5375	0.026*
C8	0.71978 (14)	0.15805 (9)	0.5122 (3)	0.0203 (4)
H8	0.7592	0.1911	0.5286	0.024*
C8A	0.63128 (13)	0.16867 (9)	0.4826 (3)	0.0174 (4)
C21	0.49892 (13)	0.30951 (9)	0.4482 (3)	0.0186 (4)
N211	0.56212 (11)	0.35131 (7)	0.4300 (3)	0.0185 (4)
C212	0.53740 (13)	0.41656 (8)	0.4348 (4)	0.0203 (4)
H21G	0.5017	0.4259	0.5522	0.024*
H21H	0.5043	0.4280	0.3156	0.024*
C213	0.62437 (14)	0.44949 (9)	0.4428 (4)	0.0233 (5)
H21E	0.6442	0.4548	0.5801	0.028*
H21F	0.6207	0.4899	0.3789	0.028*
C214	0.68522 (14)	0.40700 (10)	0.3296 (4)	0.0231 (5)
H21C	0.6780	0.4123	0.1861	0.028*
H21D	0.7469	0.4146	0.3648	0.028*
C215	0.65665 (13)	0.34367 (9)	0.3941 (4)	0.0208 (4)
H21A	0.6676	0.3132	0.2896	0.025*
H21B	0.6874	0.3309	0.5152	0.025*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0133 (6)	0.0152 (6)	0.0271 (8)	−0.0003 (5)	−0.0021 (6)	0.0001 (7)
O2	0.0154 (7)	0.0248 (7)	0.0360 (10)	0.0030 (5)	−0.0001 (7)	0.0003 (8)
O4	0.0199 (8)	0.0242 (7)	0.0289 (10)	−0.0073 (6)	0.0007 (7)	−0.0016 (7)
C2	0.0166 (9)	0.0184 (8)	0.0177 (10)	0.0008 (7)	0.0000 (8)	−0.0008 (9)
C3	0.0155 (9)	0.0211 (9)	0.0213 (11)	−0.0005 (7)	0.0013 (8)	0.0010 (10)
C4	0.0191 (10)	0.0209 (9)	0.0173 (11)	−0.0035 (7)	0.0021 (8)	−0.0006 (9)
C4A	0.0188 (9)	0.0181 (8)	0.0177 (11)	−0.0024 (7)	0.0028 (8)	0.0002 (9)
C5	0.0212 (10)	0.0175 (8)	0.0235 (11)	−0.0027 (7)	0.0028 (9)	0.0009 (9)
C6	0.0245 (11)	0.0167 (9)	0.0267 (12)	0.0018 (7)	0.0039 (9)	0.0013 (10)
C7	0.0185 (10)	0.0230 (10)	0.0244 (12)	0.0018 (8)	0.0010 (9)	0.0030 (10)
C8	0.0179 (10)	0.0197 (9)	0.0233 (11)	−0.0014 (7)	−0.0008 (8)	0.0002 (9)
C8A	0.0172 (9)	0.0161 (8)	0.0189 (10)	0.0002 (7)	−0.0004 (8)	0.0009 (8)
C21	0.0174 (9)	0.0199 (9)	0.0185 (11)	0.0022 (7)	−0.0011 (8)	−0.0006 (9)
N211	0.0160 (8)	0.0163 (7)	0.0231 (10)	0.0013 (6)	−0.0010 (7)	−0.0011 (8)
C212	0.0216 (10)	0.0167 (9)	0.0225 (11)	0.0034 (7)	−0.0021 (9)	0.0005 (9)
C213	0.0242 (10)	0.0165 (9)	0.0291 (13)	−0.0021 (7)	−0.0011 (9)	0.0011 (10)
C214	0.0190 (11)	0.0238 (11)	0.0263 (12)	−0.0028 (8)	−0.0009 (9)	0.0022 (10)
C215	0.0143 (9)	0.0185 (9)	0.0295 (12)	0.0004 (7)	−0.0004 (8)	0.0008 (9)

Geometric parameters (Å, º)

O1—C2	1.347 (2)	C8—C8A	1.392 (3)
O1—C8A	1.380 (2)	C8—H8	0.9500
O2—C21	1.230 (2)	C21—N211	1.340 (3)
O4—C4	1.239 (2)	N211—C215	1.480 (3)
C2—C3	1.349 (3)	N211—C212	1.481 (2)
C2—C21	1.517 (3)	C212—C213	1.518 (3)
C3—C4	1.452 (3)	C212—H21G	0.9900
C3—H3	0.9500	C212—H21H	0.9900
C4—C4A	1.466 (3)	C213—C214	1.528 (3)
C4A—C8A	1.395 (3)	C213—H21E	0.9900
C4A—C5	1.408 (3)	C213—H21F	0.9900
C5—C6	1.373 (3)	C214—C215	1.522 (3)
C5—H5	0.9500	C214—H21C	0.9900
C6—C7	1.403 (3)	C214—H21D	0.9900
C6—H6	0.9500	C215—H21A	0.9900
C7—C8	1.377 (3)	C215—H21B	0.9900
C7—H7	0.9500
C2—O1—C8A	118.59 (15)	O2—C21—C2	117.10 (17)
O1—C2—C3	124.10 (18)	N211—C21—C2	120.19 (17)
O1—C2—C21	115.27 (16)	C21—N211—C215	130.26 (16)
C3—C2—C21	120.60 (17)	C21—N211—C212	118.31 (16)
C2—C3—C4	121.05 (19)	C215—N211—C212	111.34 (15)
C2—C3—H3	119.5	N211—C212—C213	103.65 (16)
C4—C3—H3	119.5	N211—C212—H21G	111.0
O4—C4—C3	122.60 (19)	C213—C212—H21G	111.0
O4—C4—C4A	122.99 (19)	N211—C212—H21H	111.0
C3—C4—C4A	114.41 (17)	C213—C212—H21H	111.0
C8A—C4A—C5	117.71 (18)	H21G—C212—H21H	109.0
C8A—C4A—C4	120.01 (18)	C212—C213—C214	103.19 (17)
C5—C4A—C4	122.28 (17)	C212—C213—H21E	111.1
C6—C5—C4A	120.57 (18)	C214—C213—H21E	111.1
C6—C5—H5	119.7	C212—C213—H21F	111.1
C4A—C5—H5	119.7	C214—C213—H21F	111.1
C5—C6—C7	120.39 (19)	H21E—C213—H21F	109.1
C5—C6—H6	119.8	C215—C214—C213	103.63 (19)
C7—C6—H6	119.8	C215—C214—H21C	111.0
C8—C7—C6	120.3 (2)	C213—C214—H21C	111.0
C8—C7—H7	119.8	C215—C214—H21D	111.0
C6—C7—H7	119.8	C213—C214—H21D	111.0
C7—C8—C8A	118.71 (19)	H21C—C214—H21D	109.0
C7—C8—H8	120.6	N211—C215—C214	103.08 (17)
C8A—C8—H8	120.6	N211—C215—H21A	111.1
O1—C8A—C8	115.90 (17)	C214—C215—H21A	111.1
O1—C8A—C4A	121.82 (17)	N211—C215—H21B	111.1
C8—C8A—C4A	122.28 (18)	C214—C215—H21B	111.1
O2—C21—N211	122.71 (18)	H21A—C215—H21B	109.1
C8A—O1—C2—C3	1.8 (3)	C5—C4A—C8A—O1	−179.9 (2)
C8A—O1—C2—C21	179.99 (19)	C4—C4A—C8A—O1	−0.3 (3)
O1—C2—C3—C4	−1.2 (4)	C5—C4A—C8A—C8	0.4 (3)
C21—C2—C3—C4	−179.3 (2)	C4—C4A—C8A—C8	180.0 (2)
C2—C3—C4—O4	179.6 (2)	O1—C2—C21—O2	−163.5 (2)
C2—C3—C4—C4A	−0.2 (3)	C3—C2—C21—O2	14.8 (3)
O4—C4—C4A—C8A	−178.9 (2)	O1—C2—C21—N211	16.3 (3)
C3—C4—C4A—C8A	0.9 (3)	C3—C2—C21—N211	−165.4 (2)
O4—C4—C4A—C5	0.6 (4)	O2—C21—N211—C215	−175.3 (2)
C3—C4—C4A—C5	−179.5 (2)	C2—C21—N211—C215	5.0 (4)
C8A—C4A—C5—C6	0.4 (4)	O2—C21—N211—C212	1.1 (3)
C4—C4A—C5—C6	−179.1 (2)	C2—C21—N211—C212	−178.7 (2)
C4A—C5—C6—C7	−0.9 (4)	C21—N211—C212—C213	171.5 (2)
C5—C6—C7—C8	0.6 (4)	C215—N211—C212—C213	−11.5 (3)
C6—C7—C8—C8A	0.1 (3)	N211—C212—C213—C214	31.0 (2)
C2—O1—C8A—C8	178.7 (2)	C212—C213—C214—C215	−39.4 (2)
C2—O1—C8A—C4A	−1.0 (3)	C21—N211—C215—C214	163.8 (2)
C7—C8—C8A—O1	179.6 (2)	C212—N211—C215—C214	−12.8 (3)
C7—C8—C8A—C4A	−0.7 (3)	C213—C214—C215—N211	31.8 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O2^i	0.95	2.55	3.137 (3)	121
C214—H21C···O4^ii	0.99	2.47	3.340 (3)	146

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