Polymorphism of 3-(5-phenyl-1,3,4-oxa­diazol-2-yl)- and 3-[5-(pyridin-4-yl)-1,3,4-oxa­diazol-2-yl]-2H-chromen-2-ones

This study of 3-(5-phenyl-1,3,4-oxa­diazol-2-yl)-2H-chromen-2-one, C₁₇H₁₀N₂O₃, 1, and 3-[5-(pyridin-4-yl)-1,3,4-oxa­diazol-2-yl]-2H-chromen-2-one, C₁₆H₉N₃O₃, 2, was performed on the assumption of the potential anti­cancer activity of the compounds. Three poly­morphic structures for 1 and two poly­morphic structures for 2 have been studied thoroughly. The strongest inter­molecular inter­action is stacking of the `head-to-head' type in all the studied crystals. The poly­morphic structures of 1 differ with respect to the inter­molecular inter­actions between stacked columns. Two of the poly­morphs have a columnar or double columnar type of crystal organization, while the third poly­morphic structure can be classified as columnar-layered. The difference between the two structures of 2 is less pronounced. Both crystals can be considered as having very similar arrangements of neighbouring columns. The formation of poly­morphic modifications is caused by a subtle balance of very weak inter­molecular inter­actions and packing differences can be identified only using an analysis based on a study of the pairwise inter­action energies.

Computing details

For all structures, data collection: CrysAlis PRO (Rigaku OD, 2018); cell refinement: CrysAlis PRO (Rigaku OD, 2018); data reduction: CrysAlis PRO (Rigaku OD, 2018); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); software used to prepare material for publication: SHELXL2016 (Sheldrick, 2015b).

3-(5-Phenyl-1,3,4-oxadiazol-2-yl)-2H-chromen-2-one (1A)

Crystal data

C17H10N2O3	F(000) = 600
Mr = 290.27	Dx = 1.444 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 13.9075 (11) Å	Cell parameters from 945 reflections
b = 5.1543 (5) Å	θ = 3.4–20.7°
c = 18.8010 (16) Å	µ = 0.10 mm^−1
β = 97.772 (8)°	T = 293 K
V = 1335.3 (2) Å^3	Plate, colorless
Z = 4	0.20 × 0.15 × 0.04 mm

Data collection

Rigaku Xcalibur Sapphire3 diffractometer	2346 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1333 reflections with I > 2σ(I)
Detector resolution: 16.1827 pixels mm^-1	Rint = 0.069
ω scans	θmax = 25.0°, θmin = 3.4°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2018)	h = −16→16
Tmin = 0.004, Tmax = 1.000	k = −6→6
9965 measured reflections	l = −22→20

Refinement

Refinement on F^2	7 restraints
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.078	All H-atom parameters refined
wR(F^2) = 0.241	w = 1/[σ^2(Fo^2) + (0.1369P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.97	(Δ/σ)max < 0.001
2346 reflections	Δρmax = 0.39 e Å^−3
239 parameters	Δρmin = −0.17 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
O1	0.76161 (18)	0.9365 (5)	0.36464 (14)	0.0785 (8)
O2	0.8494 (2)	0.6267 (6)	0.42134 (17)	0.1013 (10)
O3	0.77974 (16)	0.3365 (4)	0.52195 (12)	0.0673 (7)
N1	0.6349 (2)	0.4322 (6)	0.54983 (18)	0.0793 (9)
N2	0.6746 (2)	0.2312 (6)	0.59440 (18)	0.0802 (10)
C1	0.6774 (2)	1.0762 (7)	0.34981 (18)	0.0649 (9)
C2	0.6745 (3)	1.2661 (8)	0.2993 (2)	0.0798 (11)
H2	0.725 (3)	1.271 (8)	0.273 (2)	0.103 (14)*
C3	0.5923 (3)	1.4062 (8)	0.2827 (2)	0.0809 (12)
H3	0.586 (3)	1.534 (9)	0.243 (2)	0.106 (14)*
C4	0.5128 (3)	1.3634 (8)	0.3170 (2)	0.0758 (11)
H4	0.460 (3)	1.457 (7)	0.3123 (18)	0.072 (11)*
C5	0.5145 (3)	1.1734 (7)	0.3685 (2)	0.0736 (11)
H5	0.455 (3)	1.141 (6)	0.3922 (19)	0.080 (10)*
C6	0.5976 (3)	1.0226 (6)	0.38567 (18)	0.0641 (9)
C7	0.6081 (3)	0.8218 (7)	0.43839 (19)	0.0683 (10)
H7	0.545 (3)	0.780 (7)	0.464 (2)	0.088 (11)*
C8	0.6922 (2)	0.6858 (6)	0.45400 (18)	0.0610 (8)
C9	0.7742 (3)	0.7406 (7)	0.41491 (19)	0.0690 (9)
C10	0.6995 (2)	0.4883 (7)	0.50841 (18)	0.0647 (9)
C11	0.7576 (3)	0.1808 (7)	0.57661 (19)	0.0659 (10)
C12	0.8293 (3)	−0.0100 (7)	0.6054 (2)	0.0666 (9)
C13	0.8079 (3)	−0.1747 (9)	0.6596 (2)	0.0835 (12)
H13	0.754 (3)	−0.151 (6)	0.6763 (17)	0.065 (10)*
C14	0.8752 (4)	−0.3637 (9)	0.6872 (3)	0.0892 (13)
H14	0.864 (4)	−0.469 (10)	0.725 (3)	0.128 (18)*
C15	0.9606 (3)	−0.3862 (8)	0.6591 (3)	0.0829 (12)
H15	1.007 (3)	−0.510 (8)	0.682 (2)	0.102 (14)*
C16	0.9801 (4)	−0.2253 (9)	0.6066 (3)	0.0905 (13)
H16	1.038 (3)	−0.244 (7)	0.587 (2)	0.085 (12)*
C17	0.9157 (3)	−0.0342 (8)	0.5799 (2)	0.0797 (11)
H17	0.929 (3)	0.090 (7)	0.539 (2)	0.088 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0735 (16)	0.0762 (17)	0.0913 (18)	0.0092 (13)	0.0311 (13)	0.0100 (14)
O2	0.0741 (16)	0.113 (2)	0.123 (2)	0.0253 (15)	0.0391 (16)	0.0243 (18)
O3	0.0607 (14)	0.0691 (15)	0.0733 (16)	0.0093 (12)	0.0137 (11)	−0.0006 (12)
N1	0.0653 (19)	0.083 (2)	0.092 (2)	0.0100 (17)	0.0189 (17)	0.0072 (18)
N2	0.070 (2)	0.079 (2)	0.094 (2)	−0.0001 (17)	0.0204 (17)	0.0036 (18)
C1	0.061 (2)	0.066 (2)	0.067 (2)	0.0077 (17)	0.0074 (16)	−0.0127 (18)
C2	0.085 (3)	0.077 (3)	0.082 (3)	0.002 (2)	0.028 (2)	0.002 (2)
C3	0.098 (3)	0.074 (3)	0.071 (3)	−0.001 (2)	0.009 (2)	0.001 (2)
C4	0.076 (3)	0.064 (2)	0.084 (3)	0.010 (2)	−0.001 (2)	−0.002 (2)
C5	0.062 (2)	0.076 (3)	0.085 (3)	0.0051 (19)	0.0137 (19)	0.002 (2)
C6	0.075 (2)	0.055 (2)	0.063 (2)	0.0030 (18)	0.0088 (17)	−0.0033 (16)
C7	0.0648 (16)	0.070 (2)	0.072 (2)	0.0077 (15)	0.0134 (16)	−0.0009 (18)
C8	0.0606 (15)	0.061 (2)	0.062 (2)	0.0047 (13)	0.0104 (13)	−0.0088 (16)
C9	0.0653 (17)	0.069 (2)	0.074 (2)	0.0044 (15)	0.0148 (15)	−0.0001 (18)
C10	0.059 (2)	0.067 (2)	0.068 (2)	0.0041 (18)	0.0080 (16)	−0.0074 (17)
C11	0.066 (2)	0.061 (2)	0.072 (2)	−0.0082 (18)	0.0097 (17)	−0.0063 (17)
C12	0.063 (2)	0.058 (2)	0.077 (2)	−0.0011 (17)	0.0010 (17)	−0.0018 (17)
C13	0.068 (3)	0.086 (3)	0.100 (3)	−0.003 (2)	0.022 (2)	−0.002 (2)
C14	0.098 (3)	0.075 (3)	0.093 (3)	−0.003 (3)	0.005 (3)	0.024 (2)
C15	0.082 (3)	0.066 (2)	0.096 (3)	0.006 (2)	−0.006 (2)	0.002 (2)
C16	0.084 (3)	0.081 (3)	0.108 (4)	0.017 (3)	0.018 (3)	0.006 (3)
C17	0.081 (3)	0.075 (3)	0.084 (3)	0.008 (2)	0.014 (2)	0.010 (2)

Geometric parameters (Å, º)

O1—C1	1.371 (4)	C6—C7	1.427 (5)
O1—C9	1.378 (4)	C7—C8	1.361 (5)
O2—C9	1.191 (4)	C7—H7	1.08 (4)
O3—C10	1.358 (4)	C8—C10	1.437 (5)
O3—C11	1.371 (4)	C8—C9	1.466 (5)
N1—C10	1.299 (4)	C11—C12	1.452 (5)
N1—N2	1.398 (4)	C12—C17	1.358 (5)
N2—C11	1.271 (4)	C12—C13	1.389 (6)
C1—C2	1.361 (5)	C13—C14	1.401 (6)
C1—C6	1.402 (5)	C13—H13	0.86 (3)
C2—C3	1.352 (6)	C14—C15	1.368 (6)
C2—H2	0.91 (5)	C14—H14	0.93 (5)
C3—C4	1.372 (6)	C15—C16	1.345 (6)
C3—H3	0.99 (4)	C15—H15	0.97 (4)
C4—C5	1.375 (5)	C16—C17	1.379 (6)
C4—H4	0.88 (4)	C16—H16	0.94 (4)
C5—C6	1.394 (5)	C17—H17	1.03 (4)
C5—H5	1.01 (4)
C1—O1—C9	123.4 (3)	O2—C9—O1	117.4 (3)
C10—O3—C11	102.5 (3)	O2—C9—C8	125.9 (3)
C10—N1—N2	106.0 (3)	O1—C9—C8	116.7 (3)
C11—N2—N1	107.0 (3)	N1—C10—O3	112.1 (3)
C2—C1—O1	117.6 (3)	N1—C10—C8	126.6 (3)
C2—C1—C6	121.8 (3)	O3—C10—C8	121.3 (3)
O1—C1—C6	120.6 (3)	N2—C11—O3	112.4 (3)
C3—C2—C1	119.3 (4)	N2—C11—C12	130.0 (4)
C3—C2—H2	124 (3)	O3—C11—C12	117.6 (3)
C1—C2—H2	116 (3)	C17—C12—C13	119.4 (4)
C2—C3—C4	121.1 (4)	C17—C12—C11	121.7 (4)
C2—C3—H3	121 (3)	C13—C12—C11	118.9 (4)
C4—C3—H3	118 (3)	C12—C13—C14	119.9 (4)
C3—C4—C5	120.5 (4)	C12—C13—H13	118 (2)
C3—C4—H4	126 (2)	C14—C13—H13	122 (2)
C5—C4—H4	114 (2)	C15—C14—C13	119.1 (4)
C4—C5—C6	119.7 (4)	C15—C14—H14	120 (3)
C4—C5—H5	119 (2)	C13—C14—H14	121 (3)
C6—C5—H5	121 (2)	C16—C15—C14	120.2 (4)
C5—C6—C1	117.7 (3)	C16—C15—H15	123 (3)
C5—C6—C7	124.7 (3)	C14—C15—H15	117 (3)
C1—C6—C7	117.6 (3)	C15—C16—C17	121.5 (5)
C8—C7—C6	121.9 (3)	C15—C16—H16	120 (2)
C8—C7—H7	121.8 (19)	C17—C16—H16	118 (2)
C6—C7—H7	116.3 (19)	C12—C17—C16	119.9 (4)
C7—C8—C10	119.6 (3)	C12—C17—H17	117 (2)
C7—C8—C9	119.8 (3)	C16—C17—H17	123 (2)
C10—C8—C9	120.6 (3)
C10—N1—N2—C11	−0.6 (4)	N2—N1—C10—O3	0.5 (4)
C9—O1—C1—C2	179.5 (3)	N2—N1—C10—C8	−179.1 (3)
C9—O1—C1—C6	−0.7 (5)	C11—O3—C10—N1	−0.2 (4)
O1—C1—C2—C3	179.3 (3)	C11—O3—C10—C8	179.4 (3)
C6—C1—C2—C3	−0.4 (6)	C7—C8—C10—N1	−5.1 (6)
C1—C2—C3—C4	1.3 (6)	C9—C8—C10—N1	175.3 (3)
C2—C3—C4—C5	−1.0 (6)	C7—C8—C10—O3	175.4 (3)
C3—C4—C5—C6	−0.3 (6)	C9—C8—C10—O3	−4.2 (5)
C4—C5—C6—C1	1.1 (5)	N1—N2—C11—O3	0.4 (4)
C4—C5—C6—C7	179.5 (3)	N1—N2—C11—C12	−180.0 (3)
C2—C1—C6—C5	−0.8 (5)	C10—O3—C11—N2	−0.1 (4)
O1—C1—C6—C5	179.4 (3)	C10—O3—C11—C12	−179.8 (3)
C2—C1—C6—C7	−179.3 (3)	N2—C11—C12—C17	−179.2 (4)
O1—C1—C6—C7	1.0 (5)	O3—C11—C12—C17	0.4 (5)
C5—C6—C7—C8	−178.3 (3)	N2—C11—C12—C13	2.0 (6)
C1—C6—C7—C8	0.1 (5)	O3—C11—C12—C13	−178.4 (3)
C6—C7—C8—C10	179.0 (3)	C17—C12—C13—C14	−0.1 (6)
C6—C7—C8—C9	−1.4 (5)	C11—C12—C13—C14	178.8 (4)
C1—O1—C9—O2	177.4 (3)	C12—C13—C14—C15	−1.4 (7)
C1—O1—C9—C8	−0.6 (5)	C13—C14—C15—C16	1.3 (7)
C7—C8—C9—O2	−176.2 (4)	C14—C15—C16—C17	0.2 (7)
C10—C8—C9—O2	3.4 (6)	C13—C12—C17—C16	1.6 (6)
C7—C8—C9—O1	1.6 (5)	C11—C12—C17—C16	−177.3 (3)
C10—C8—C9—O1	−178.8 (3)	C15—C16—C17—C12	−1.7 (7)

3-(5-Phenyl-1,3,4-oxadiazol-2-yl)-2H-chromen-2-one (1B)

Crystal data

C17H10N2O3	F(000) = 600
Mr = 290.27	Dx = 1.463 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 15.611 (5) Å	Cell parameters from 366 reflections
b = 3.8414 (9) Å	θ = 5.4–22.3°
c = 21.974 (7) Å	µ = 0.10 mm^−1
β = 90.74 (3)°	T = 293 K
V = 1317.6 (6) Å^3	Stick, colorless
Z = 4	0.30 × 0.05 × 0.04 mm

Data collection

Rigaku Xcalibur Sapphire3 diffractometer	2322 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1081 reflections with I > 2σ(I)
Detector resolution: 16.1827 pixels mm^-1	Rint = 0.117
ω scans	θmax = 25.0°, θmin = 3.2°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2018)	h = −16→18
Tmin = 0.135, Tmax = 1.000	k = −4→4
7763 measured reflections	l = −22→26

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.067	All H-atom parameters refined
wR(F^2) = 0.150	w = 1/[σ^2(Fo^2) + (0.0255P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.90	(Δ/σ)max < 0.001
2322 reflections	Δρmax = 0.18 e Å^−3
239 parameters	Δρmin = −0.24 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
O1	0.3572 (2)	0.5709 (6)	0.69352 (11)	0.0607 (8)
O2	0.4902 (2)	0.7312 (7)	0.71082 (12)	0.0737 (9)
O3	0.61618 (18)	0.5524 (6)	0.63231 (11)	0.0523 (7)
N1	0.5785 (2)	0.2576 (8)	0.55023 (14)	0.0598 (9)
N2	0.6674 (2)	0.3032 (8)	0.55050 (15)	0.0608 (9)
C1	0.2931 (3)	0.4297 (8)	0.65701 (17)	0.0509 (10)
C2	0.2117 (3)	0.4353 (10)	0.6799 (2)	0.0562 (11)
H2	0.200 (2)	0.515 (8)	0.7224 (17)	0.066 (11)*
C3	0.1463 (3)	0.2962 (10)	0.6439 (2)	0.0637 (12)
H3	0.091 (3)	0.297 (8)	0.6621 (16)	0.066 (12)*
C4	0.1634 (3)	0.1614 (10)	0.5872 (2)	0.0600 (11)
H4	0.114 (2)	0.061 (8)	0.5600 (16)	0.055 (10)*
C5	0.2450 (3)	0.1563 (10)	0.5651 (2)	0.0562 (11)
H5	0.254 (3)	0.076 (8)	0.5259 (17)	0.064 (12)*
C6	0.3129 (3)	0.2907 (8)	0.60069 (16)	0.0475 (10)
C7	0.3999 (3)	0.2915 (9)	0.58276 (18)	0.0489 (10)
H7	0.414 (2)	0.206 (8)	0.5423 (16)	0.058 (10)*
C8	0.4626 (3)	0.4269 (8)	0.61863 (16)	0.0464 (9)
C9	0.4408 (3)	0.5845 (9)	0.67627 (18)	0.0554 (11)
C10	0.5498 (3)	0.4098 (8)	0.59875 (17)	0.0473 (10)
C11	0.6864 (3)	0.4774 (8)	0.59857 (18)	0.0495 (10)
C12	0.7707 (3)	0.5818 (8)	0.62124 (19)	0.0535 (10)
C13	0.8415 (3)	0.5264 (10)	0.5849 (2)	0.0629 (12)
H13	0.839 (2)	0.437 (8)	0.5452 (16)	0.052 (11)*
C14	0.9227 (3)	0.6098 (11)	0.6064 (3)	0.0708 (13)
H14	0.967 (3)	0.581 (10)	0.575 (2)	0.103 (17)*
C15	0.9316 (4)	0.7524 (11)	0.6634 (3)	0.0710 (14)
H15	0.987 (3)	0.799 (9)	0.6761 (18)	0.069 (13)*
C16	0.8635 (3)	0.8131 (10)	0.6994 (2)	0.0669 (12)
H16	0.869 (3)	0.907 (10)	0.743 (2)	0.104 (16)*
C17	0.7818 (3)	0.7333 (10)	0.6778 (2)	0.0620 (12)
H17	0.738 (2)	0.769 (8)	0.7022 (15)	0.050 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.061 (2)	0.0764 (17)	0.0452 (16)	0.0058 (14)	0.0052 (15)	−0.0090 (13)
O2	0.071 (2)	0.098 (2)	0.0522 (17)	−0.0010 (16)	−0.0082 (17)	−0.0186 (16)
O3	0.0524 (19)	0.0598 (15)	0.0445 (15)	−0.0009 (12)	−0.0060 (14)	−0.0036 (12)
N1	0.054 (2)	0.072 (2)	0.053 (2)	−0.0013 (17)	−0.0006 (19)	−0.0099 (17)
N2	0.054 (3)	0.070 (2)	0.058 (2)	0.0015 (17)	−0.003 (2)	−0.0109 (18)
C1	0.060 (3)	0.048 (2)	0.045 (2)	0.0057 (19)	−0.003 (2)	0.0018 (18)
C2	0.057 (3)	0.065 (2)	0.046 (2)	0.009 (2)	0.010 (2)	0.006 (2)
C3	0.061 (3)	0.062 (2)	0.068 (3)	0.004 (2)	0.011 (3)	0.004 (2)
C4	0.055 (3)	0.064 (2)	0.062 (3)	−0.006 (2)	−0.003 (3)	−0.006 (2)
C5	0.059 (3)	0.060 (2)	0.049 (3)	−0.005 (2)	0.000 (2)	0.001 (2)
C6	0.052 (3)	0.046 (2)	0.044 (2)	0.0045 (17)	−0.001 (2)	0.0053 (18)
C7	0.056 (3)	0.048 (2)	0.042 (2)	0.0002 (18)	0.004 (2)	0.0021 (19)
C8	0.051 (3)	0.047 (2)	0.040 (2)	−0.0003 (17)	0.001 (2)	0.0040 (17)
C9	0.065 (3)	0.060 (2)	0.040 (2)	0.006 (2)	−0.005 (2)	0.000 (2)
C10	0.052 (3)	0.049 (2)	0.041 (2)	−0.0019 (17)	−0.004 (2)	0.0001 (18)
C11	0.052 (3)	0.048 (2)	0.048 (2)	−0.0013 (18)	0.000 (2)	−0.0024 (19)
C12	0.054 (3)	0.045 (2)	0.062 (3)	−0.0015 (17)	−0.004 (2)	0.0019 (19)
C13	0.065 (3)	0.067 (3)	0.056 (3)	0.000 (2)	0.003 (3)	−0.001 (2)
C14	0.060 (4)	0.071 (3)	0.081 (4)	0.002 (2)	0.003 (3)	0.005 (3)
C15	0.058 (4)	0.064 (3)	0.090 (4)	−0.009 (2)	−0.020 (3)	−0.003 (3)
C16	0.063 (4)	0.069 (3)	0.068 (3)	−0.005 (2)	−0.008 (3)	−0.005 (2)
C17	0.061 (3)	0.064 (3)	0.061 (3)	0.001 (2)	−0.002 (3)	−0.005 (2)

Geometric parameters (Å, º)

O1—C9	1.364 (5)	C6—C7	1.418 (5)
O1—C1	1.386 (5)	C7—C8	1.353 (5)
O2—C9	1.214 (5)	C7—H7	0.98 (3)
O3—C11	1.362 (4)	C8—C10	1.437 (5)
O3—C10	1.378 (4)	C8—C9	1.448 (5)
N1—C10	1.300 (4)	C11—C12	1.458 (5)
N1—N2	1.399 (4)	C12—C17	1.381 (5)
N2—C11	1.282 (4)	C12—C13	1.388 (6)
C1—C2	1.372 (6)	C13—C14	1.385 (6)
C1—C6	1.387 (5)	C13—H13	0.94 (3)
C2—C3	1.390 (6)	C14—C15	1.374 (7)
C2—H2	1.00 (3)	C14—H14	0.99 (5)
C3—C4	1.378 (6)	C15—C16	1.354 (6)
C3—H3	0.96 (4)	C15—H15	0.93 (4)
C4—C5	1.369 (6)	C16—C17	1.389 (6)
C4—H4	1.04 (4)	C16—H16	1.03 (4)
C5—C6	1.407 (5)	C17—H17	0.89 (3)
C5—H5	0.93 (3)
C9—O1—C1	122.7 (3)	O2—C9—O1	116.5 (4)
C11—O3—C10	103.3 (3)	O2—C9—C8	125.9 (4)
C10—N1—N2	107.0 (3)	O1—C9—C8	117.6 (4)
C11—N2—N1	106.7 (3)	N1—C10—O3	110.7 (4)
C2—C1—O1	116.6 (4)	N1—C10—C8	127.4 (4)
C2—C1—C6	123.5 (4)	O3—C10—C8	121.9 (3)
O1—C1—C6	119.9 (4)	N2—C11—O3	112.3 (4)
C1—C2—C3	117.6 (4)	N2—C11—C12	128.5 (4)
C1—C2—H2	122 (2)	O3—C11—C12	119.0 (3)
C3—C2—H2	120 (2)	C17—C12—C13	119.4 (4)
C4—C3—C2	120.5 (5)	C17—C12—C11	121.7 (4)
C4—C3—H3	124 (2)	C13—C12—C11	118.9 (4)
C2—C3—H3	115 (2)	C14—C13—C12	120.1 (5)
C5—C4—C3	121.2 (5)	C14—C13—H13	115 (2)
C5—C4—H4	118.2 (19)	C12—C13—H13	125 (2)
C3—C4—H4	121 (2)	C15—C14—C13	118.9 (5)
C4—C5—C6	119.7 (4)	C15—C14—H14	128 (3)
C4—C5—H5	119 (3)	C13—C14—H14	113 (3)
C6—C5—H5	121 (3)	C16—C15—C14	122.1 (5)
C1—C6—C5	117.5 (4)	C16—C15—H15	122 (3)
C1—C6—C7	118.2 (4)	C14—C15—H15	116 (3)
C5—C6—C7	124.3 (4)	C15—C16—C17	119.1 (5)
C8—C7—C6	121.8 (4)	C15—C16—H16	123 (3)
C8—C7—H7	119 (2)	C17—C16—H16	118 (3)
C6—C7—H7	119 (2)	C12—C17—C16	120.3 (5)
C7—C8—C10	119.1 (3)	C12—C17—H17	121 (2)
C7—C8—C9	119.6 (4)	C16—C17—H17	118 (2)
C10—C8—C9	121.3 (4)
C10—N1—N2—C11	0.1 (4)	N2—N1—C10—O3	−0.9 (4)
C9—O1—C1—C2	−179.5 (3)	N2—N1—C10—C8	−178.8 (3)
C9—O1—C1—C6	0.8 (5)	C11—O3—C10—N1	1.3 (4)
O1—C1—C2—C3	179.8 (3)	C11—O3—C10—C8	179.3 (3)
C6—C1—C2—C3	−0.6 (6)	C7—C8—C10—N1	−4.3 (6)
C1—C2—C3—C4	−0.6 (6)	C9—C8—C10—N1	175.4 (3)
C2—C3—C4—C5	0.9 (6)	C7—C8—C10—O3	177.9 (3)
C3—C4—C5—C6	0.0 (6)	C9—C8—C10—O3	−2.3 (5)
C2—C1—C6—C5	1.4 (5)	N1—N2—C11—O3	0.8 (4)
O1—C1—C6—C5	−179.0 (3)	N1—N2—C11—C12	177.4 (3)
C2—C1—C6—C7	−178.3 (3)	C10—O3—C11—N2	−1.3 (4)
O1—C1—C6—C7	1.3 (5)	C10—O3—C11—C12	−178.2 (3)
C4—C5—C6—C1	−1.1 (5)	N2—C11—C12—C17	−172.0 (4)
C4—C5—C6—C7	178.6 (3)	O3—C11—C12—C17	4.4 (5)
C1—C6—C7—C8	−0.8 (5)	N2—C11—C12—C13	7.9 (6)
C5—C6—C7—C8	179.5 (3)	O3—C11—C12—C13	−175.7 (3)
C6—C7—C8—C10	178.0 (3)	C17—C12—C13—C14	2.5 (6)
C6—C7—C8—C9	−1.7 (5)	C11—C12—C13—C14	−177.3 (4)
C1—O1—C9—O2	176.2 (3)	C12—C13—C14—C15	−1.0 (6)
C1—O1—C9—C8	−3.3 (5)	C13—C14—C15—C16	0.2 (7)
C7—C8—C9—O2	−175.7 (4)	C14—C15—C16—C17	−0.9 (7)
C10—C8—C9—O2	4.6 (6)	C13—C12—C17—C16	−3.3 (6)
C7—C8—C9—O1	3.7 (5)	C11—C12—C17—C16	176.6 (4)
C10—C8—C9—O1	−176.0 (3)	C15—C16—C17—C12	2.4 (6)

3-(5-Phenyl-1,3,4-oxadiazol-2-yl)-2H-chromen-2-one (1C)

Crystal data

C17H10N2O3	F(000) = 600
Mr = 290.27	Dx = 1.481 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 3.9158 (8) Å	Cell parameters from 566 reflections
b = 17.717 (3) Å	θ = 4.0–20.5°
c = 18.832 (3) Å	µ = 0.10 mm^−1
β = 94.670 (16)°	T = 293 K
V = 1302.1 (4) Å^3	Stick, colorless
Z = 4	0.30 × 0.05 × 0.04 mm

Data collection

Rigaku Xcalibur Sapphire3 diffractometer	2293 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1176 reflections with I > 2σ(I)
Detector resolution: 16.1827 pixels mm^-1	Rint = 0.113
ω scans	θmax = 25.0°, θmin = 3.5°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2018)	h = −4→4
Tmin = 0.169, Tmax = 1.000	k = −21→20
9086 measured reflections	l = −22→22

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.071	All H-atom parameters refined
wR(F^2) = 0.192	w = 1/[σ^2(Fo^2) + (0.0721P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.95	(Δ/σ)max < 0.001
2293 reflections	Δρmax = 0.20 e Å^−3
239 parameters	Δρmin = −0.26 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
O1	0.4135 (6)	0.46350 (15)	0.74455 (14)	0.0677 (8)
O2	0.3295 (8)	0.35074 (16)	0.69807 (16)	0.0822 (9)
O3	0.5322 (6)	0.31861 (13)	0.56545 (13)	0.0591 (7)
N1	0.8223 (8)	0.40721 (18)	0.51393 (18)	0.0680 (10)
N2	0.8019 (8)	0.34341 (19)	0.46962 (18)	0.0684 (10)
C1	0.5246 (9)	0.5372 (2)	0.7417 (2)	0.0572 (10)
C2	0.4804 (10)	0.5823 (3)	0.7995 (2)	0.0666 (11)
H2	0.376 (9)	0.565 (2)	0.840 (2)	0.068 (11)*
C3	0.5861 (11)	0.6569 (3)	0.7979 (3)	0.0709 (12)
H3	0.529 (8)	0.686 (2)	0.836 (2)	0.061 (11)*
C4	0.7348 (10)	0.6852 (3)	0.7395 (2)	0.0680 (11)
H4	0.815 (10)	0.736 (3)	0.740 (2)	0.095 (15)*
C5	0.7788 (9)	0.6396 (2)	0.6823 (2)	0.0595 (10)
H5	0.889 (8)	0.659 (2)	0.639 (2)	0.067 (11)*
C6	0.6744 (8)	0.5640 (2)	0.68265 (19)	0.0525 (9)
C7	0.7103 (9)	0.5130 (2)	0.6254 (2)	0.0544 (10)
H7	0.811 (8)	0.5285 (19)	0.5889 (19)	0.049 (10)*
C8	0.6056 (8)	0.4399 (2)	0.62857 (19)	0.0521 (9)
C9	0.4420 (10)	0.4130 (2)	0.6892 (2)	0.0604 (10)
C10	0.6590 (9)	0.3905 (2)	0.5686 (2)	0.0529 (9)
C11	0.6295 (8)	0.2934 (2)	0.5017 (2)	0.0562 (10)
C12	0.5312 (8)	0.2181 (2)	0.4767 (2)	0.0559 (10)
C13	0.5921 (10)	0.1977 (3)	0.4081 (2)	0.0631 (11)
H13	0.681 (9)	0.232 (2)	0.374 (2)	0.084 (13)*
C14	0.4956 (10)	0.1269 (3)	0.3825 (3)	0.0694 (12)
H14	0.553 (10)	0.115 (2)	0.334 (3)	0.089 (14)*
C15	0.3526 (11)	0.0765 (3)	0.4266 (3)	0.0761 (13)
H15	0.318 (11)	0.026 (3)	0.416 (3)	0.106 (16)*
C16	0.2963 (11)	0.0968 (3)	0.4957 (3)	0.0717 (12)
H16	0.203 (10)	0.061 (2)	0.529 (2)	0.085 (13)*
C17	0.3869 (9)	0.1679 (2)	0.5209 (2)	0.0631 (11)
H17	0.321 (8)	0.180 (2)	0.570 (2)	0.068 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0903 (18)	0.0551 (17)	0.0592 (17)	0.0011 (14)	0.0140 (14)	0.0090 (15)
O2	0.120 (2)	0.0509 (18)	0.079 (2)	−0.0079 (15)	0.0280 (18)	0.0108 (16)
O3	0.0725 (15)	0.0446 (16)	0.0610 (17)	−0.0036 (12)	0.0103 (13)	0.0020 (13)
N1	0.087 (2)	0.049 (2)	0.070 (2)	−0.0105 (16)	0.0225 (19)	−0.0029 (18)
N2	0.092 (2)	0.052 (2)	0.063 (2)	−0.0093 (17)	0.0211 (18)	−0.0050 (18)
C1	0.066 (2)	0.049 (2)	0.055 (2)	0.0071 (18)	−0.0011 (18)	0.000 (2)
C2	0.076 (3)	0.072 (3)	0.052 (3)	0.005 (2)	0.007 (2)	0.001 (2)
C3	0.080 (3)	0.071 (3)	0.062 (3)	0.008 (2)	0.006 (2)	−0.013 (3)
C4	0.079 (3)	0.057 (3)	0.067 (3)	0.000 (2)	0.003 (2)	−0.013 (2)
C5	0.070 (2)	0.054 (2)	0.056 (2)	−0.0019 (18)	0.008 (2)	0.002 (2)
C6	0.0535 (19)	0.052 (2)	0.051 (2)	−0.0022 (17)	0.0002 (17)	0.0021 (19)
C7	0.065 (2)	0.052 (3)	0.046 (2)	0.0008 (18)	0.0064 (19)	0.002 (2)
C8	0.057 (2)	0.046 (2)	0.053 (2)	0.0021 (17)	0.0000 (17)	0.0067 (19)
C9	0.077 (2)	0.049 (2)	0.056 (2)	0.006 (2)	0.011 (2)	0.006 (2)
C10	0.0556 (19)	0.044 (2)	0.059 (2)	−0.0006 (17)	0.0028 (17)	0.0036 (19)
C11	0.058 (2)	0.053 (3)	0.057 (3)	0.0040 (18)	0.0059 (18)	0.001 (2)
C12	0.060 (2)	0.047 (2)	0.060 (2)	0.0025 (17)	0.0040 (18)	−0.001 (2)
C13	0.074 (2)	0.057 (3)	0.059 (3)	0.005 (2)	0.009 (2)	−0.001 (2)
C14	0.080 (3)	0.066 (3)	0.061 (3)	0.005 (2)	0.006 (2)	−0.008 (3)
C15	0.084 (3)	0.052 (3)	0.092 (4)	0.000 (2)	0.001 (3)	−0.009 (3)
C16	0.084 (3)	0.055 (3)	0.077 (3)	−0.007 (2)	0.008 (2)	0.003 (3)
C17	0.069 (2)	0.056 (3)	0.065 (3)	−0.003 (2)	0.009 (2)	−0.002 (2)

Geometric parameters (Å, º)

O1—C1	1.380 (4)	C6—C7	1.422 (5)
O1—C9	1.385 (4)	C7—C8	1.361 (5)
O2—C9	1.205 (4)	C7—H7	0.87 (3)
O3—C11	1.363 (4)	C8—C9	1.436 (5)
O3—C10	1.367 (4)	C8—C10	1.457 (5)
N1—C10	1.290 (5)	C11—C12	1.457 (5)
N1—N2	1.403 (4)	C12—C17	1.370 (5)
N2—C11	1.293 (4)	C12—C13	1.381 (5)
C1—C2	1.371 (5)	C13—C14	1.386 (6)
C1—C6	1.383 (5)	C13—H13	0.97 (4)
C2—C3	1.385 (6)	C14—C15	1.370 (6)
C2—H2	0.95 (4)	C14—H14	0.98 (4)
C3—C4	1.380 (6)	C15—C16	1.384 (6)
C3—H3	0.92 (4)	C15—H15	0.92 (5)
C4—C5	1.369 (5)	C16—C17	1.382 (6)
C4—H4	0.96 (4)	C16—H16	0.99 (4)
C5—C6	1.401 (5)	C17—H17	1.00 (4)
C5—H5	1.02 (4)
C1—O1—C9	122.5 (3)	O2—C9—O1	115.7 (3)
C11—O3—C10	102.5 (3)	O2—C9—C8	127.3 (4)
C10—N1—N2	106.4 (3)	O1—C9—C8	116.9 (3)
C11—N2—N1	106.3 (3)	N1—C10—O3	112.4 (3)
C2—C1—O1	117.4 (4)	N1—C10—C8	126.3 (3)
C2—C1—C6	121.9 (4)	O3—C10—C8	121.3 (3)
O1—C1—C6	120.8 (4)	N2—C11—O3	112.4 (3)
C1—C2—C3	118.7 (4)	N2—C11—C12	127.6 (4)
C1—C2—H2	123 (2)	O3—C11—C12	119.9 (3)
C3—C2—H2	118 (2)	C17—C12—C13	120.7 (4)
C4—C3—C2	120.7 (5)	C17—C12—C11	120.6 (4)
C4—C3—H3	123 (2)	C13—C12—C11	118.7 (4)
C2—C3—H3	116 (2)	C12—C13—C14	120.0 (4)
C5—C4—C3	120.0 (4)	C12—C13—H13	123 (2)
C5—C4—H4	121 (3)	C14—C13—H13	117 (2)
C3—C4—H4	119 (3)	C15—C14—C13	119.5 (5)
C4—C5—C6	120.4 (4)	C15—C14—H14	124 (3)
C4—C5—H5	122 (2)	C13—C14—H14	116 (3)
C6—C5—H5	118 (2)	C14—C15—C16	120.3 (5)
C1—C6—C5	118.3 (4)	C14—C15—H15	124 (3)
C1—C6—C7	117.9 (4)	C16—C15—H15	115 (3)
C5—C6—C7	123.8 (4)	C17—C16—C15	120.3 (5)
C8—C7—C6	121.4 (4)	C17—C16—H16	118 (2)
C8—C7—H7	120 (2)	C15—C16—H16	122 (2)
C6—C7—H7	119 (2)	C12—C17—C16	119.2 (4)
C7—C8—C9	120.5 (4)	C12—C17—H17	125 (2)
C7—C8—C10	118.3 (3)	C16—C17—H17	115 (2)
C9—C8—C10	121.2 (3)
C10—N1—N2—C11	−0.4 (4)	N2—N1—C10—O3	1.1 (4)
C9—O1—C1—C2	179.4 (3)	N2—N1—C10—C8	−178.8 (3)
C9—O1—C1—C6	−0.6 (5)	C11—O3—C10—N1	−1.3 (4)
O1—C1—C2—C3	−179.3 (3)	C11—O3—C10—C8	178.6 (3)
C6—C1—C2—C3	0.7 (6)	C7—C8—C10—N1	5.9 (6)
C1—C2—C3—C4	−0.3 (6)	C9—C8—C10—N1	−175.1 (3)
C2—C3—C4—C5	0.1 (6)	C7—C8—C10—O3	−174.0 (3)
C3—C4—C5—C6	−0.2 (6)	C9—C8—C10—O3	5.1 (5)
C2—C1—C6—C5	−0.8 (5)	N1—N2—C11—O3	−0.4 (4)
O1—C1—C6—C5	179.2 (3)	N1—N2—C11—C12	178.4 (3)
C2—C1—C6—C7	179.8 (3)	C10—O3—C11—N2	1.0 (4)
O1—C1—C6—C7	−0.2 (5)	C10—O3—C11—C12	−177.9 (3)
C4—C5—C6—C1	0.5 (5)	N2—C11—C12—C17	171.4 (4)
C4—C5—C6—C7	179.9 (3)	O3—C11—C12—C17	−9.9 (5)
C1—C6—C7—C8	−0.9 (5)	N2—C11—C12—C13	−7.4 (6)
C5—C6—C7—C8	179.8 (3)	O3—C11—C12—C13	171.3 (3)
C6—C7—C8—C9	2.5 (5)	C17—C12—C13—C14	2.4 (6)
C6—C7—C8—C10	−178.4 (3)	C11—C12—C13—C14	−178.8 (3)
C1—O1—C9—O2	−178.8 (3)	C12—C13—C14—C15	−2.6 (6)
C1—O1—C9—C8	2.1 (5)	C13—C14—C15—C16	1.8 (6)
C7—C8—C9—O2	177.9 (4)	C14—C15—C16—C17	−0.7 (7)
C10—C8—C9—O2	−1.1 (6)	C13—C12—C17—C16	−1.3 (6)
C7—C8—C9—O1	−3.1 (5)	C11—C12—C17—C16	180.0 (3)
C10—C8—C9—O1	177.9 (3)	C15—C16—C17—C12	0.4 (6)

3-[5-(Pyridin-4-yl)-1,3,4-oxadiazol-2-yl]-2H-chromen-2-one (2A)

Crystal data

C16H9N3O3	F(000) = 300
Mr = 291.26	Dx = 1.523 Mg m^−3
Monoclinic, Pn	Mo Kα radiation, λ = 0.71073 Å
a = 3.7788 (9) Å	Cell parameters from 939 reflections
b = 9.9655 (17) Å	θ = 4.1–22.1°
c = 16.899 (3) Å	µ = 0.11 mm^−1
β = 93.466 (19)°	T = 293 K
V = 635.2 (2) Å^3	Stick, colorless
Z = 2	0.30 × 0.05 × 0.05 mm

Data collection

Rigaku Xcalibur Sapphire3 diffractometer	2204 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1512 reflections with I > 2σ(I)
Detector resolution: 16.1827 pixels mm^-1	Rint = 0.110
ω scans	θmax = 25.0°, θmin = 3.2°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2018)	h = −4→4
Tmin = 0.527, Tmax = 1.000	k = −11→11
7248 measured reflections	l = −20→20

Refinement

Refinement on F^2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.079	w = 1/[σ^2(Fo^2) + (0.0971P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.210	(Δ/σ)max < 0.001
S = 1.00	Δρmax = 0.25 e Å^−3
2204 reflections	Δρmin = −0.24 e Å^−3
235 parameters	Absolute structure: Flack x determined using 423 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
2 restraints	Absolute structure parameter: −0.4 (10)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
O1	0.7514 (13)	−0.0579 (6)	0.5152 (3)	0.0615 (14)
O2	0.7840 (19)	0.1020 (7)	0.4263 (4)	0.0807 (19)
O3	0.5099 (12)	0.3509 (5)	0.4541 (3)	0.0557 (14)
N1	0.2551 (18)	0.3788 (7)	0.5666 (4)	0.0664 (19)
N2	0.223 (2)	0.4985 (7)	0.5242 (4)	0.0681 (19)
N3	0.495 (2)	0.7525 (8)	0.2707 (5)	0.072 (2)
C1	0.6713 (19)	−0.1059 (8)	0.5884 (5)	0.0537 (18)
C2	0.7371 (19)	−0.2360 (8)	0.6062 (5)	0.058 (2)
H2	0.81 (2)	−0.296 (8)	0.578 (5)	0.06 (3)*
C3	0.666 (2)	−0.2873 (9)	0.6784 (6)	0.066 (2)
H3	0.69 (2)	−0.391 (9)	0.693 (5)	0.07 (2)*
C4	0.534 (2)	−0.2017 (9)	0.7362 (6)	0.066 (2)
H4	0.48 (2)	−0.245 (8)	0.790 (5)	0.08 (3)*
C5	0.462 (2)	−0.0703 (8)	0.7183 (5)	0.0600 (19)
H5	0.35 (2)	−0.010 (9)	0.753 (5)	0.07 (3)*
C6	0.5283 (19)	−0.0186 (7)	0.6438 (5)	0.0507 (17)
C7	0.4593 (19)	0.1144 (8)	0.6193 (4)	0.0533 (18)
H7	0.34 (2)	0.173 (8)	0.655 (4)	0.06 (2)*
C8	0.5229 (18)	0.1598 (7)	0.5462 (4)	0.0492 (16)
C9	0.694 (2)	0.0716 (8)	0.4909 (5)	0.061 (2)
C10	0.430 (2)	0.2950 (8)	0.5246 (5)	0.0573 (19)
C11	0.3753 (19)	0.4780 (8)	0.4582 (5)	0.0545 (19)
C12	0.4201 (18)	0.5719 (8)	0.3947 (4)	0.0545 (18)
C13	0.331 (2)	0.7062 (9)	0.4032 (6)	0.062 (2)
H13	0.26 (2)	0.738 (8)	0.454 (5)	0.06 (2)*
C14	0.375 (3)	0.7914 (10)	0.3395 (6)	0.072 (2)
H14	0.31 (3)	0.897 (10)	0.348 (6)	0.09 (3)*
C15	0.577 (2)	0.6252 (11)	0.2656 (6)	0.070 (2)
H15	0.64 (2)	0.609 (10)	0.212 (6)	0.08 (3)*
C16	0.543 (2)	0.5308 (9)	0.3236 (5)	0.061 (2)
H16	0.62 (2)	0.440 (8)	0.321 (5)	0.06 (2)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.058 (3)	0.065 (4)	0.063 (3)	0.003 (2)	0.011 (3)	−0.003 (3)
O2	0.106 (5)	0.075 (4)	0.064 (4)	0.011 (3)	0.031 (3)	0.004 (3)
O3	0.054 (3)	0.054 (3)	0.060 (3)	0.002 (2)	0.012 (2)	0.003 (2)
N1	0.069 (4)	0.056 (4)	0.076 (5)	0.006 (3)	0.018 (4)	−0.003 (3)
N2	0.075 (5)	0.068 (4)	0.063 (4)	0.006 (3)	0.018 (4)	0.000 (3)
N3	0.070 (5)	0.077 (5)	0.070 (5)	−0.009 (4)	0.009 (4)	0.007 (4)
C1	0.050 (4)	0.061 (5)	0.050 (4)	−0.001 (3)	0.006 (3)	−0.003 (3)
C2	0.049 (5)	0.057 (5)	0.069 (6)	0.006 (3)	0.005 (4)	−0.007 (4)
C3	0.060 (5)	0.062 (6)	0.074 (6)	−0.002 (4)	−0.004 (4)	0.000 (4)
C4	0.060 (5)	0.068 (6)	0.071 (6)	−0.009 (4)	0.007 (4)	0.011 (4)
C5	0.054 (4)	0.063 (5)	0.063 (5)	−0.001 (4)	0.005 (4)	0.000 (4)
C6	0.045 (4)	0.053 (4)	0.055 (4)	0.001 (3)	0.008 (3)	0.000 (3)
C7	0.047 (4)	0.059 (5)	0.055 (5)	0.006 (3)	0.005 (3)	−0.006 (4)
C8	0.046 (4)	0.049 (4)	0.053 (4)	0.000 (3)	0.012 (3)	0.000 (3)
C9	0.063 (5)	0.055 (5)	0.066 (6)	0.002 (4)	0.011 (4)	−0.007 (4)
C10	0.056 (4)	0.058 (5)	0.058 (5)	−0.006 (3)	0.008 (3)	0.003 (4)
C11	0.059 (5)	0.058 (4)	0.047 (4)	−0.002 (3)	0.004 (3)	0.002 (3)
C12	0.042 (4)	0.070 (5)	0.052 (5)	−0.010 (3)	0.005 (3)	0.004 (3)
C13	0.061 (5)	0.062 (5)	0.063 (6)	−0.004 (4)	0.011 (4)	0.003 (4)
C14	0.078 (6)	0.061 (6)	0.077 (6)	−0.004 (4)	0.002 (5)	0.010 (4)
C15	0.064 (5)	0.084 (7)	0.065 (6)	−0.007 (5)	0.017 (4)	−0.002 (5)
C16	0.059 (5)	0.058 (5)	0.068 (5)	0.003 (4)	0.007 (4)	0.002 (4)

Geometric parameters (Å, º)

O1—C9	1.368 (9)	C4—H4	1.04 (8)
O1—C1	1.377 (10)	C5—C6	1.397 (12)
O2—C9	1.202 (10)	C5—H5	0.95 (9)
O3—C10	1.366 (9)	C6—C7	1.408 (10)
O3—C11	1.368 (9)	C7—C8	1.352 (11)
N1—C10	1.301 (10)	C7—H7	0.98 (8)
N1—N2	1.393 (10)	C8—C10	1.434 (10)
N2—C11	1.302 (11)	C8—C9	1.462 (10)
N3—C15	1.309 (12)	C11—C12	1.441 (10)
N3—C14	1.331 (13)	C12—C16	1.378 (11)
C1—C2	1.350 (11)	C12—C13	1.390 (11)
C1—C6	1.409 (10)	C13—C14	1.388 (12)
C2—C3	1.365 (12)	C13—H13	0.96 (8)
C2—H2	0.83 (8)	C14—H14	1.09 (10)
C3—C4	1.411 (13)	C15—C16	1.370 (13)
C3—H3	1.07 (9)	C15—H15	0.96 (10)
C4—C5	1.367 (12)	C16—H16	0.95 (8)
C9—O1—C1	123.9 (6)	C7—C8—C9	119.5 (6)
C10—O3—C11	103.3 (6)	C10—C8—C9	120.9 (7)
C10—N1—N2	107.5 (7)	O2—C9—O1	117.5 (7)
C11—N2—N1	106.1 (7)	O2—C9—C8	126.1 (7)
C15—N3—C14	115.7 (8)	O1—C9—C8	116.3 (7)
C2—C1—O1	119.0 (7)	N1—C10—O3	111.1 (7)
C2—C1—C6	121.1 (7)	N1—C10—C8	126.1 (7)
O1—C1—C6	119.8 (6)	O3—C10—C8	122.7 (7)
C1—C2—C3	121.0 (8)	N2—C11—O3	111.9 (7)
C1—C2—H2	130 (6)	N2—C11—C12	127.9 (7)
C3—C2—H2	109 (6)	O3—C11—C12	120.2 (6)
C2—C3—C4	119.3 (8)	C16—C12—C13	118.2 (7)
C2—C3—H3	123 (4)	C16—C12—C11	121.2 (8)
C4—C3—H3	117 (4)	C13—C12—C11	120.6 (7)
C5—C4—C3	120.0 (9)	C14—C13—C12	117.9 (8)
C5—C4—H4	123 (5)	C14—C13—H13	123 (5)
C3—C4—H4	117 (5)	C12—C13—H13	119 (5)
C4—C5—C6	120.6 (8)	N3—C14—C13	124.2 (9)
C4—C5—H5	124 (5)	N3—C14—H14	119 (5)
C6—C5—H5	115 (5)	C13—C14—H14	117 (5)
C5—C6—C7	124.9 (7)	N3—C15—C16	125.8 (9)
C5—C6—C1	117.9 (6)	N3—C15—H15	107 (6)
C7—C6—C1	117.2 (7)	C16—C15—H15	127 (6)
C8—C7—C6	123.0 (7)	C15—C16—C12	118.1 (8)
C8—C7—H7	119 (4)	C15—C16—H16	125 (5)
C6—C7—H7	118 (4)	C12—C16—H16	116 (5)
C7—C8—C10	119.5 (7)
C10—N1—N2—C11	1.3 (10)	N2—N1—C10—O3	−1.8 (9)
C9—O1—C1—C2	179.7 (7)	N2—N1—C10—C8	179.9 (7)
C9—O1—C1—C6	−1.3 (11)	C11—O3—C10—N1	1.6 (8)
O1—C1—C2—C3	179.2 (7)	C11—O3—C10—C8	179.9 (7)
C6—C1—C2—C3	0.2 (12)	C7—C8—C10—N1	−6.9 (12)
C1—C2—C3—C4	−2.3 (12)	C9—C8—C10—N1	174.9 (8)
C2—C3—C4—C5	3.1 (13)	C7—C8—C10—O3	175.0 (7)
C3—C4—C5—C6	−1.8 (13)	C9—C8—C10—O3	−3.3 (12)
C4—C5—C6—C7	179.1 (7)	N1—N2—C11—O3	−0.3 (9)
C4—C5—C6—C1	−0.3 (12)	N1—N2—C11—C12	−178.5 (7)
C2—C1—C6—C5	1.1 (11)	C10—O3—C11—N2	−0.7 (9)
O1—C1—C6—C5	−177.9 (7)	C10—O3—C11—C12	177.6 (7)
C2—C1—C6—C7	−178.3 (7)	N2—C11—C12—C16	−170.9 (8)
O1—C1—C6—C7	2.8 (11)	O3—C11—C12—C16	11.1 (11)
C5—C6—C7—C8	−179.1 (8)	N2—C11—C12—C13	7.4 (13)
C1—C6—C7—C8	0.3 (11)	O3—C11—C12—C13	−170.6 (7)
C6—C7—C8—C10	177.1 (7)	C16—C12—C13—C14	−0.6 (11)
C6—C7—C8—C9	−4.6 (11)	C11—C12—C13—C14	−179.0 (8)
C1—O1—C9—O2	178.2 (8)	C15—N3—C14—C13	−0.9 (13)
C1—O1—C9—C8	−2.9 (10)	C12—C13—C14—N3	0.5 (13)
C7—C8—C9—O2	−175.4 (9)	C14—N3—C15—C16	1.5 (13)
C10—C8—C9—O2	2.9 (13)	N3—C15—C16—C12	−1.7 (14)
C7—C8—C9—O1	5.8 (10)	C13—C12—C16—C15	1.1 (11)
C10—C8—C9—O1	−175.9 (7)	C11—C12—C16—C15	179.5 (7)

3-[5-(Pyridin-4-yl)-1,3,4-oxadiazol-2-yl]-2H-chromen-2-one (2B)

Crystal data

C16H9N3O3	Dx = 1.524 Mg m^−3
Mr = 291.26	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21	Cell parameters from 921 reflections
a = 20.931 (2) Å	θ = 3.9–22.3°
b = 3.7708 (5) Å	µ = 0.11 mm^−1
c = 16.0887 (15) Å	T = 293 K
V = 1269.8 (2) Å^3	Stick, colorless
Z = 4	0.30 × 0.06 × 0.05 mm
F(000) = 600

Data collection

Rigaku Xcalibur Sapphire3 diffractometer	2162 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1539 reflections with I > 2σ(I)
Detector resolution: 16.1827 pixels mm^-1	Rint = 0.083
ω scans	θmax = 25.0°, θmin = 3.2°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2018)	h = −24→24
Tmin = 0.025, Tmax = 1.000	k = −3→4
8304 measured reflections	l = −17→19

Refinement

Refinement on F^2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.057	w = 1/[σ^2(Fo^2) + (0.049P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.133	(Δ/σ)max < 0.001
S = 0.96	Δρmax = 0.20 e Å^−3
2162 reflections	Δρmin = −0.12 e Å^−3
235 parameters	Absolute structure: Flack x determined using 482 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: 0.6 (10)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
O1	0.52761 (19)	0.1729 (11)	0.5149 (3)	0.0588 (11)
O2	0.4531 (2)	0.0329 (13)	0.4247 (3)	0.0752 (14)
O3	0.3275 (2)	0.2135 (10)	0.4532 (3)	0.0546 (11)
N1	0.3075 (3)	0.5030 (14)	0.5690 (3)	0.0631 (15)
N2	0.2503 (3)	0.4623 (14)	0.5262 (3)	0.0667 (15)
N3	0.1352 (3)	−0.0167 (14)	0.2676 (4)	0.0658 (14)
C1	0.5473 (3)	0.3023 (14)	0.5910 (4)	0.0521 (14)
C2	0.6114 (3)	0.2930 (18)	0.6082 (4)	0.0575 (17)
H2	0.640 (4)	0.223 (17)	0.570 (5)	0.08 (2)*
C3	0.6318 (3)	0.4245 (17)	0.6850 (5)	0.0636 (18)
H3	0.678 (3)	0.420 (15)	0.691 (4)	0.067 (18)*
C4	0.5889 (3)	0.5519 (19)	0.7419 (5)	0.0639 (18)
H4	0.601 (3)	0.627 (14)	0.795 (4)	0.060 (18)*
C5	0.5251 (3)	0.5615 (18)	0.7238 (4)	0.0575 (17)
H5	0.495 (3)	0.670 (14)	0.760 (4)	0.056 (17)*
C6	0.5029 (3)	0.4417 (16)	0.6475 (4)	0.0511 (15)
C7	0.4372 (3)	0.4472 (15)	0.6225 (4)	0.0506 (15)
H7	0.404 (3)	0.577 (12)	0.662 (3)	0.042 (14)*
C8	0.4184 (3)	0.3262 (15)	0.5471 (4)	0.0477 (14)
C9	0.4645 (3)	0.1692 (16)	0.4908 (4)	0.0567 (16)
C10	0.3515 (3)	0.3508 (15)	0.5256 (4)	0.0525 (14)
C11	0.2637 (3)	0.2938 (15)	0.4586 (4)	0.0540 (15)
C12	0.2199 (3)	0.1852 (14)	0.3929 (4)	0.0521 (15)
C13	0.1550 (3)	0.2134 (16)	0.4035 (4)	0.0573 (16)
H13	0.138 (3)	0.321 (13)	0.451 (4)	0.053 (16)*
C14	0.1147 (4)	0.1129 (17)	0.3402 (5)	0.0653 (18)
H14	0.072 (3)	0.111 (13)	0.349 (4)	0.047 (16)*
C15	0.1979 (3)	−0.0413 (18)	0.2591 (5)	0.0616 (17)
H15	0.211 (3)	−0.128 (17)	0.206 (4)	0.07 (2)*
C16	0.2419 (4)	0.0482 (16)	0.3185 (4)	0.0579 (17)
H16	0.285 (3)	0.038 (12)	0.311 (3)	0.040 (14)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.047 (3)	0.087 (3)	0.042 (3)	0.0030 (19)	−0.001 (2)	−0.007 (2)
O2	0.064 (3)	0.117 (4)	0.044 (3)	0.004 (3)	−0.004 (2)	−0.020 (3)
O3	0.051 (3)	0.074 (2)	0.039 (2)	0.0008 (19)	−0.004 (2)	−0.006 (2)
N1	0.048 (3)	0.090 (4)	0.052 (4)	0.003 (3)	−0.001 (3)	−0.018 (3)
N2	0.053 (3)	0.098 (4)	0.049 (4)	0.005 (3)	0.002 (3)	−0.014 (3)
N3	0.065 (4)	0.077 (3)	0.055 (4)	−0.004 (3)	−0.009 (3)	−0.003 (3)
C1	0.053 (4)	0.061 (4)	0.042 (4)	0.003 (3)	−0.001 (3)	0.001 (3)
C2	0.046 (4)	0.077 (4)	0.050 (5)	0.002 (3)	0.005 (3)	0.007 (3)
C3	0.046 (4)	0.082 (4)	0.063 (5)	−0.003 (3)	−0.008 (4)	0.011 (4)
C4	0.066 (5)	0.084 (5)	0.042 (4)	−0.009 (3)	−0.010 (4)	−0.001 (3)
C5	0.054 (4)	0.068 (4)	0.051 (4)	−0.002 (3)	0.002 (3)	−0.005 (3)
C6	0.049 (4)	0.064 (4)	0.041 (4)	−0.002 (3)	−0.002 (3)	0.002 (3)
C7	0.051 (4)	0.058 (4)	0.042 (4)	0.000 (3)	0.003 (3)	−0.001 (3)
C8	0.045 (4)	0.057 (3)	0.041 (4)	0.002 (2)	0.000 (3)	−0.001 (2)
C9	0.055 (4)	0.069 (4)	0.047 (4)	0.000 (3)	0.002 (3)	−0.002 (3)
C10	0.055 (4)	0.065 (3)	0.038 (4)	−0.003 (3)	−0.002 (3)	−0.001 (3)
C11	0.046 (4)	0.071 (4)	0.044 (4)	−0.002 (3)	−0.001 (3)	−0.004 (3)
C12	0.056 (4)	0.059 (3)	0.041 (4)	−0.003 (3)	−0.007 (3)	0.001 (3)
C13	0.052 (4)	0.070 (4)	0.049 (4)	0.000 (3)	0.001 (4)	−0.005 (3)
C14	0.051 (5)	0.075 (5)	0.070 (5)	−0.003 (3)	−0.009 (4)	−0.001 (3)
C15	0.067 (5)	0.074 (4)	0.045 (4)	−0.003 (3)	−0.003 (4)	−0.004 (3)
C16	0.048 (4)	0.078 (4)	0.048 (4)	−0.001 (3)	0.005 (3)	−0.007 (3)

Geometric parameters (Å, º)

O1—C9	1.376 (7)	C4—H4	0.94 (6)
O1—C1	1.381 (7)	C5—C6	1.389 (8)
O2—C9	1.206 (8)	C5—H5	0.95 (6)
O3—C10	1.370 (7)	C6—C7	1.433 (8)
O3—C11	1.372 (7)	C7—C8	1.354 (8)
N1—C10	1.290 (7)	C7—H7	1.05 (5)
N1—N2	1.390 (7)	C8—C10	1.446 (8)
N2—C11	1.290 (8)	C8—C9	1.450 (8)
N3—C15	1.323 (8)	C11—C12	1.458 (8)
N3—C14	1.337 (10)	C12—C13	1.374 (9)
C1—C2	1.370 (8)	C12—C16	1.383 (9)
C1—C6	1.402 (8)	C13—C14	1.375 (9)
C2—C3	1.397 (10)	C13—H13	0.94 (6)
C2—H2	0.91 (7)	C14—H14	0.90 (6)
C3—C4	1.370 (10)	C15—C16	1.369 (9)
C3—H3	0.97 (7)	C15—H15	0.95 (7)
C4—C5	1.366 (9)	C16—H16	0.92 (5)
C9—O1—C1	122.7 (5)	C7—C8—C9	120.2 (6)
C10—O3—C11	102.7 (5)	C10—C8—C9	121.4 (5)
C10—N1—N2	107.3 (5)	O2—C9—O1	116.3 (6)
C11—N2—N1	106.6 (5)	O2—C9—C8	126.4 (6)
C15—N3—C14	115.7 (6)	O1—C9—C8	117.3 (5)
C2—C1—O1	117.6 (6)	N1—C10—O3	111.5 (5)
C2—C1—C6	121.8 (6)	N1—C10—C8	126.2 (6)
O1—C1—C6	120.6 (5)	O3—C10—C8	122.3 (5)
C1—C2—C3	117.9 (6)	N2—C11—O3	111.9 (5)
C1—C2—H2	121 (5)	N2—C11—C12	127.8 (6)
C3—C2—H2	120 (5)	O3—C11—C12	120.3 (5)
C4—C3—C2	121.0 (6)	C13—C12—C16	117.8 (6)
C4—C3—H3	126 (4)	C13—C12—C11	120.7 (6)
C2—C3—H3	113 (4)	C16—C12—C11	121.6 (6)
C5—C4—C3	120.5 (7)	C12—C13—C14	119.6 (7)
C5—C4—H4	117 (4)	C12—C13—H13	121 (4)
C3—C4—H4	122 (4)	C14—C13—H13	119 (4)
C4—C5—C6	120.4 (7)	N3—C14—C13	123.4 (7)
C4—C5—H5	122 (4)	N3—C14—H14	116 (4)
C6—C5—H5	117 (4)	C13—C14—H14	120 (4)
C5—C6—C1	118.2 (6)	N3—C15—C16	125.4 (7)
C5—C6—C7	124.4 (6)	N3—C15—H15	114 (4)
C1—C6—C7	117.4 (5)	C16—C15—H15	121 (4)
C8—C7—C6	121.7 (6)	C15—C16—C12	118.1 (7)
C8—C7—H7	120 (3)	C15—C16—H16	124 (3)
C6—C7—H7	118 (3)	C12—C16—H16	118 (3)
C7—C8—C10	118.3 (6)
C10—N1—N2—C11	−1.3 (7)	N2—N1—C10—O3	1.5 (7)
C9—O1—C1—C2	−179.9 (5)	N2—N1—C10—C8	−179.5 (6)
C9—O1—C1—C6	−0.7 (8)	C11—O3—C10—N1	−1.2 (6)
O1—C1—C2—C3	179.8 (5)	C11—O3—C10—C8	179.8 (5)
C6—C1—C2—C3	0.7 (9)	C7—C8—C10—N1	5.6 (9)
C1—C2—C3—C4	1.3 (9)	C9—C8—C10—N1	−175.7 (6)
C2—C3—C4—C5	−1.7 (10)	C7—C8—C10—O3	−175.5 (5)
C3—C4—C5—C6	0.1 (10)	C9—C8—C10—O3	3.2 (9)
C4—C5—C6—C1	1.8 (9)	N1—N2—C11—O3	0.6 (7)
C4—C5—C6—C7	−178.9 (6)	N1—N2—C11—C12	179.7 (6)
C2—C1—C6—C5	−2.2 (8)	C10—O3—C11—N2	0.3 (6)
O1—C1—C6—C5	178.6 (5)	C10—O3—C11—C12	−178.9 (5)
C2—C1—C6—C7	178.4 (6)	N2—C11—C12—C13	−9.5 (10)
O1—C1—C6—C7	−0.7 (8)	O3—C11—C12—C13	169.6 (5)
C5—C6—C7—C8	−179.9 (6)	N2—C11—C12—C16	171.1 (6)
C1—C6—C7—C8	−0.6 (9)	O3—C11—C12—C16	−9.9 (9)
C6—C7—C8—C10	−178.2 (5)	C16—C12—C13—C14	−1.3 (9)
C6—C7—C8—C9	3.2 (9)	C11—C12—C13—C14	179.3 (6)
C1—O1—C9—O2	−176.4 (5)	C15—N3—C14—C13	−0.6 (10)
C1—O1—C9—C8	3.2 (8)	C12—C13—C14—N3	0.7 (10)
C7—C8—C9—O2	175.1 (6)	C14—N3—C15—C16	1.2 (10)
C10—C8—C9—O2	−3.5 (10)	N3—C15—C16—C12	−1.9 (10)
C7—C8—C9—O1	−4.4 (8)	C13—C12—C16—C15	1.8 (9)
C10—C8—C9—O1	177.0 (5)	C11—C12—C16—C15	−178.7 (5)