Influence of ortho-substituent on the molecular and crystal structures of 2-(N-aryl­imino)­coumarin-3-carboxamide: isotypic and polymorphic structures

During a comprehensive study of a series of 2-(N-aryl­imino)­coumarin-3-carboxamides with the aryl group substituted in the ortho-position by either a halogen atom, a methyl group or a meth­oxy group, the existence of three groups of isotypic crystal structures has been revealed. The similarity of crystal structures belonging to the same groups was confirmed by the analysis based on the comparison of pairwise interactions energies obtained from quantum chemical calculations. Group I includes unsubstituted, methyl-substituted and polymorphic modification 1 of fluoro-substituted 2-(N-arylimino)coumarin-3-carboxamide. Structures of polymorphic modification 2 of fluoro-substituted derivative, chloro-substituted and polymorphic modification 1 of bromo-substituted 2-(N-arylimino)coumarin-3-carboxamide may represent group II. Group III contains structures of polymorphic modification 2 of bromo-substituted derivative, iodine- and methoxy-substituted 2-(N-arylimino)coumarin-3-carboxamides. Structures of the same type group have extremely close parameters of the unit cell as well as those of molecular and crystal structures. But they are not identical. Polymorphic modifications of fluoro- and bromo-substituted 2-(N-aryl­imino)­coumarin-3-carboxamides belong to different crystal types mainly due to different arrangement of basic structural motifs separated out using quantum chemical calculations.

Computing details

Program(s) used to solve structure: SHELXT 2014/5 (Sheldrick, 2014) for (1h), 1me, 1f_2, 1cl, 1br1, (1i), 1ome. For all structures, program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2016).

(1h)

Crystal data

C16H12N2O2	Z = 2
Mr = 264.28	F(000) = 276
Triclinic, P1	Dx = 1.388 Mg m^−3
a = 4.8281 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.5805 (13) Å	Cell parameters from 524 reflections
c = 15.436 (2) Å	θ = 4.0–23.4°
α = 96.790 (13)°	µ = 0.09 mm^−1
β = 95.002 (15)°	T = 293 K
γ = 91.404 (15)°	Stick, colorless
V = 632.16 (19) Å^3	0.50 × 0.08 × 0.03 mm

Data collection

Xcalibur, Sapphire3 diffractometer	2219 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1143 reflections with I > 2σ(I)
Detector resolution: 16.1827 pixels mm^-1	Rint = 0.064
ω scans	θmax = 25.0°, θmin = 3.4°
Absorption correction: multi-scan CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −5→5
Tmin = 0.257, Tmax = 1.000	k = −10→9
4959 measured reflections	l = −18→17

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)] = 0.068	w = 1/[σ^2(Fo^2) + (0.0628P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.184	(Δ/σ)max < 0.001
S = 1.00	Δρmax = 0.23 e Å^−3
2219 reflections	Δρmin = −0.21 e Å^−3
182 parameters	Extinction correction: SHELXL-2016/6 (Sheldrick 2016), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.015 (6)

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	0.2757 (4)	0.3562 (2)	0.76143 (12)	0.0555 (6)
O2	0.7423 (4)	0.3298 (3)	0.49995 (14)	0.0703 (7)
N1	0.5844 (5)	0.5525 (3)	0.74705 (16)	0.0576 (7)
N2	0.8788 (5)	0.5255 (3)	0.60645 (17)	0.0624 (8)
H2NA	1.001957	0.561643	0.576327	0.075*
H2NB	0.857303	0.570756	0.658067	0.075*
C1	0.1326 (6)	0.2176 (3)	0.7303 (2)	0.0501 (8)
C2	−0.0531 (7)	0.1623 (4)	0.7825 (2)	0.0606 (9)
H2	−0.077785	0.217241	0.836765	0.073*
C3	−0.2032 (7)	0.0242 (4)	0.7538 (2)	0.0691 (10)
H3	−0.333835	−0.012776	0.787936	0.083*
C4	−0.1593 (7)	−0.0593 (4)	0.6740 (2)	0.0684 (10)
H4	−0.259551	−0.152828	0.654922	0.082*
C5	0.0313 (6)	−0.0046 (3)	0.6231 (2)	0.0579 (9)
H5	0.061921	−0.062342	0.570133	0.070*
C6	0.1798 (6)	0.1365 (3)	0.6499 (2)	0.0486 (7)
C7	0.3776 (6)	0.2042 (3)	0.60100 (19)	0.0515 (8)
H7	0.411534	0.152205	0.546798	0.062*
C8	0.5167 (6)	0.3396 (3)	0.62988 (19)	0.0479 (8)
C9	0.4638 (6)	0.4233 (3)	0.71439 (19)	0.0486 (8)
C10	0.7223 (6)	0.4002 (4)	0.5734 (2)	0.0544 (8)
C11	0.5232 (7)	0.6270 (4)	0.8300 (2)	0.0615 (9)
C12	0.3274 (9)	0.7368 (5)	0.8366 (3)	0.0914 (13)
H12	0.219408	0.758001	0.786721	0.110*
C13	0.2872 (12)	0.8178 (5)	0.9173 (4)	0.1176 (18)
H13	0.152601	0.893387	0.920653	0.141*
C14	0.4372 (13)	0.7899 (6)	0.9905 (3)	0.112 (2)
H14	0.408325	0.844684	1.044413	0.134*
C15	0.6331 (13)	0.6792 (7)	0.9837 (3)	0.134 (2)
H15	0.738461	0.657005	1.033813	0.160*
C16	0.6781 (10)	0.5987 (6)	0.9030 (3)	0.1096 (15)
H16	0.815775	0.524934	0.899346	0.131*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0605 (13)	0.0586 (13)	0.0461 (13)	−0.0101 (10)	0.0124 (10)	−0.0019 (10)
O2	0.0782 (16)	0.0780 (16)	0.0520 (15)	−0.0100 (12)	0.0166 (12)	−0.0083 (11)
N1	0.0692 (18)	0.0560 (16)	0.0447 (16)	−0.0111 (13)	0.0107 (13)	−0.0066 (12)
N2	0.0705 (18)	0.0665 (18)	0.0499 (17)	−0.0087 (14)	0.0161 (14)	0.0001 (13)
C1	0.0464 (18)	0.0497 (19)	0.054 (2)	−0.0009 (14)	−0.0012 (15)	0.0082 (14)
C2	0.065 (2)	0.060 (2)	0.056 (2)	−0.0047 (16)	0.0073 (17)	0.0050 (16)
C3	0.068 (2)	0.063 (2)	0.079 (3)	−0.0042 (17)	0.014 (2)	0.0148 (18)
C4	0.069 (2)	0.050 (2)	0.084 (3)	−0.0040 (16)	0.006 (2)	0.0007 (18)
C5	0.065 (2)	0.051 (2)	0.055 (2)	0.0013 (15)	0.0039 (17)	−0.0028 (15)
C6	0.0494 (18)	0.0439 (18)	0.0510 (18)	0.0043 (14)	0.0012 (14)	0.0021 (13)
C7	0.0535 (19)	0.060 (2)	0.0393 (17)	0.0049 (15)	0.0058 (14)	−0.0024 (14)
C8	0.0507 (19)	0.0513 (19)	0.0415 (16)	0.0031 (14)	0.0067 (14)	0.0023 (13)
C9	0.0483 (18)	0.0522 (19)	0.0462 (17)	0.0009 (14)	0.0062 (14)	0.0082 (14)
C10	0.058 (2)	0.054 (2)	0.049 (2)	0.0043 (15)	0.0031 (16)	0.0020 (15)
C11	0.069 (2)	0.063 (2)	0.050 (2)	−0.0156 (17)	0.0126 (17)	−0.0011 (16)
C12	0.105 (3)	0.096 (3)	0.072 (3)	0.015 (2)	0.018 (2)	−0.007 (2)
C13	0.158 (5)	0.101 (3)	0.096 (4)	0.010 (3)	0.060 (4)	−0.021 (3)
C14	0.159 (5)	0.100 (4)	0.069 (3)	−0.056 (3)	0.054 (3)	−0.036 (3)
C15	0.174 (6)	0.159 (5)	0.055 (3)	−0.005 (4)	−0.010 (3)	−0.025 (3)
C16	0.130 (4)	0.129 (4)	0.062 (3)	0.025 (3)	−0.001 (3)	−0.013 (3)

Geometric parameters (Å, º)

O1—C9	1.368 (3)	C5—H5	0.9300
O1—C1	1.375 (3)	C6—C7	1.422 (4)
O2—C10	1.233 (3)	C7—C8	1.337 (4)
N1—C9	1.268 (3)	C7—H7	0.9300
N1—C11	1.420 (4)	C8—C9	1.459 (4)
N2—C10	1.323 (4)	C8—C10	1.500 (4)
N2—H2NA	0.8600	C11—C16	1.347 (5)
N2—H2NB	0.8600	C11—C12	1.353 (5)
C1—C2	1.369 (4)	C12—C13	1.384 (5)
C1—C6	1.388 (4)	C12—H12	0.9300
C2—C3	1.380 (4)	C13—C14	1.337 (7)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.385 (5)	C14—C15	1.358 (7)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.370 (4)	C15—C16	1.388 (6)
C4—H4	0.9300	C15—H15	0.9300
C5—C6	1.392 (4)	C16—H16	0.9300
C9—O1—C1	122.2 (2)	C7—C8—C10	118.3 (3)
C9—N1—C11	120.9 (3)	C9—C8—C10	122.3 (3)
C10—N2—H2NA	120.0	N1—C9—O1	118.4 (3)
C10—N2—H2NB	120.0	N1—C9—C8	124.0 (3)
H2NA—N2—H2NB	120.0	O1—C9—C8	117.6 (3)
C2—C1—O1	117.1 (3)	O2—C10—N2	123.3 (3)
C2—C1—C6	121.9 (3)	O2—C10—C8	119.0 (3)
O1—C1—C6	121.0 (3)	N2—C10—C8	117.7 (3)
C1—C2—C3	119.3 (3)	C16—C11—C12	118.9 (4)
C1—C2—H2	120.4	C16—C11—N1	119.8 (3)
C3—C2—H2	120.4	C12—C11—N1	121.1 (3)
C2—C3—C4	120.0 (3)	C11—C12—C13	120.2 (4)
C2—C3—H3	120.0	C11—C12—H12	119.9
C4—C3—H3	120.0	C13—C12—H12	119.9
C5—C4—C3	120.2 (3)	C14—C13—C12	121.6 (5)
C5—C4—H4	119.9	C14—C13—H13	119.2
C3—C4—H4	119.9	C12—C13—H13	119.2
C4—C5—C6	120.7 (3)	C13—C14—C15	118.0 (4)
C4—C5—H5	119.7	C13—C14—H14	121.0
C6—C5—H5	119.7	C15—C14—H14	121.0
C1—C6—C5	117.9 (3)	C14—C15—C16	120.9 (5)
C1—C6—C7	117.3 (3)	C14—C15—H15	119.5
C5—C6—C7	124.8 (3)	C16—C15—H15	119.5
C8—C7—C6	122.5 (3)	C11—C16—C15	120.3 (5)
C8—C7—H7	118.7	C11—C16—H16	119.8
C6—C7—H7	118.7	C15—C16—H16	119.8
C7—C8—C9	119.4 (3)
C9—O1—C1—C2	−179.2 (2)	C1—O1—C9—C8	−2.1 (4)
C9—O1—C1—C6	2.0 (4)	C7—C8—C9—N1	−179.7 (3)
O1—C1—C2—C3	179.5 (3)	C10—C8—C9—N1	0.1 (5)
C6—C1—C2—C3	−1.7 (5)	C7—C8—C9—O1	1.4 (4)
C1—C2—C3—C4	1.9 (5)	C10—C8—C9—O1	−178.8 (2)
C2—C3—C4—C5	−0.5 (5)	C7—C8—C10—O2	5.1 (4)
C3—C4—C5—C6	−1.1 (5)	C9—C8—C10—O2	−174.7 (3)
C2—C1—C6—C5	0.1 (5)	C7—C8—C10—N2	−173.2 (3)
O1—C1—C6—C5	178.8 (2)	C9—C8—C10—N2	6.9 (4)
C2—C1—C6—C7	−179.8 (3)	C9—N1—C11—C16	92.6 (4)
O1—C1—C6—C7	−1.1 (4)	C9—N1—C11—C12	−93.2 (4)
C4—C5—C6—C1	1.3 (5)	C16—C11—C12—C13	−0.3 (6)
C4—C5—C6—C7	−178.8 (3)	N1—C11—C12—C13	−174.5 (4)
C1—C6—C7—C8	0.4 (4)	C11—C12—C13—C14	−0.4 (7)
C5—C6—C7—C8	−179.5 (3)	C12—C13—C14—C15	0.2 (8)
C6—C7—C8—C9	−0.6 (5)	C13—C14—C15—C16	0.7 (8)
C6—C7—C8—C10	179.6 (3)	C12—C11—C16—C15	1.2 (7)
C11—N1—C9—O1	−0.8 (5)	N1—C11—C16—C15	175.4 (4)
C11—N1—C9—C8	−179.7 (3)	C14—C15—C16—C11	−1.4 (8)
C1—O1—C9—N1	178.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2NB···N1	0.86	2.00	2.687 (3)	136
N2—H2NA···O2^i	0.86	2.06	2.912 (3)	172

Symmetry code: (i) −x+2, −y+1, −z+1.

(1me)

Crystal data

C17H14N2O2	Z = 2
Mr = 278.30	F(000) = 292
Triclinic, P1	Dx = 1.371 Mg m^−3
a = 4.8956 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.6425 (15) Å	Cell parameters from 339 reflections
c = 14.958 (2) Å	θ = 4.0–22.1°
α = 103.662 (13)°	µ = 0.09 mm^−1
β = 94.580 (12)°	T = 293 K
γ = 98.382 (12)°	Stick, yellow
V = 674.00 (18) Å^3	0.20 × 0.05 × 0.03 mm

Data collection

Xcalibur, Sapphire3 diffractometer	2366 independent reflections
Radiation source: Enhance (Mo) X-ray Source	967 reflections with I > 2σ(I)
Detector resolution: 16.1827 pixels mm^-1	Rint = 0.074
ω scans	θmax = 25.0°, θmin = 2.9°
Absorption correction: multi-scan CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −5→5
Tmin = 0.013, Tmax = 1.000	k = −10→11
4150 measured reflections	l = −17→17

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.080	H-atom parameters constrained
wR(F^2) = 0.211	w = 1/[σ^2(Fo^2) + (0.0652P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.92	(Δ/σ)max < 0.001
2366 reflections	Δρmax = 0.28 e Å^−3
191 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	0.2223 (5)	0.3819 (3)	0.75520 (18)	0.0645 (9)
O2	0.7729 (6)	0.3193 (3)	0.5020 (2)	0.0808 (11)
N1	0.5159 (7)	0.5774 (4)	0.7379 (2)	0.0609 (10)
N2	0.8232 (8)	0.5409 (4)	0.5964 (2)	0.0831 (13)
H2NA	0.948253	0.575758	0.566638	0.100*
H2NB	0.772303	0.596106	0.643943	0.100*
C1	0.0965 (8)	0.2394 (4)	0.7259 (3)	0.0522 (10)
C2	−0.0982 (9)	0.1928 (4)	0.7770 (3)	0.0634 (12)
H2	−0.138878	0.254938	0.830105	0.076*
C3	−0.2343 (9)	0.0509 (5)	0.7482 (3)	0.0703 (13)
H3	−0.371591	0.018223	0.781528	0.084*
C4	−0.1695 (10)	−0.0433 (5)	0.6708 (3)	0.0714 (13)
H4	−0.262713	−0.138407	0.651655	0.086*
C5	0.0368 (9)	0.0067 (5)	0.6220 (3)	0.0653 (12)
H5	0.085584	−0.056282	0.570725	0.078*
C6	0.1712 (8)	0.1498 (4)	0.6490 (3)	0.0523 (10)
C7	0.3782 (8)	0.2111 (4)	0.5993 (3)	0.0569 (11)
H7	0.429557	0.152021	0.546906	0.068*
C8	0.4979 (8)	0.3500 (4)	0.6264 (3)	0.0529 (10)
C9	0.4168 (8)	0.4446 (4)	0.7085 (3)	0.0542 (10)
C10	0.7100 (8)	0.4038 (4)	0.5692 (3)	0.0570 (11)
C11	0.4295 (8)	0.6661 (4)	0.8181 (3)	0.0571 (11)
C12	0.2564 (8)	0.7621 (5)	0.8056 (3)	0.0658 (12)
H12	0.190340	0.764277	0.745949	0.079*
C13	0.1804 (10)	0.8552 (5)	0.8812 (4)	0.0766 (14)
H13	0.061632	0.919133	0.872501	0.092*
C14	0.2808 (10)	0.8532 (5)	0.9695 (3)	0.0750 (14)
H14	0.229855	0.915041	1.020840	0.090*
C15	0.4566 (9)	0.7590 (4)	0.9805 (3)	0.0666 (12)
H15	0.525811	0.759163	1.040269	0.080*
C16	0.5355 (8)	0.6640 (4)	0.9071 (3)	0.0603 (11)
C17	0.7259 (9)	0.5606 (5)	0.9209 (3)	0.0762 (14)
H17A	0.624446	0.463396	0.902530	0.114*
H17B	0.799250	0.582948	0.985096	0.114*
H17C	0.876154	0.569174	0.883983	0.114*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0618 (18)	0.0594 (19)	0.0710 (18)	−0.0022 (15)	0.0256 (15)	0.0154 (15)
O2	0.092 (2)	0.073 (2)	0.077 (2)	0.0078 (18)	0.0417 (18)	0.0106 (16)
N1	0.058 (2)	0.052 (2)	0.070 (2)	0.0004 (19)	0.0191 (18)	0.0114 (18)
N2	0.090 (3)	0.062 (3)	0.086 (3)	−0.013 (2)	0.043 (2)	0.002 (2)
C1	0.045 (2)	0.052 (2)	0.057 (2)	0.000 (2)	0.0090 (19)	0.014 (2)
C2	0.065 (3)	0.054 (3)	0.070 (3)	0.000 (2)	0.013 (2)	0.019 (2)
C3	0.059 (3)	0.070 (3)	0.088 (3)	0.002 (2)	0.018 (2)	0.033 (3)
C4	0.077 (3)	0.055 (3)	0.079 (3)	−0.003 (2)	0.005 (3)	0.019 (2)
C5	0.068 (3)	0.061 (3)	0.069 (3)	0.010 (2)	0.007 (2)	0.020 (2)
C6	0.049 (2)	0.047 (2)	0.062 (2)	0.005 (2)	0.007 (2)	0.0184 (19)
C7	0.056 (3)	0.060 (3)	0.053 (2)	0.010 (2)	0.007 (2)	0.010 (2)
C8	0.048 (2)	0.058 (3)	0.055 (2)	0.008 (2)	0.0086 (19)	0.0181 (19)
C9	0.051 (2)	0.049 (2)	0.059 (2)	−0.002 (2)	0.0096 (19)	0.014 (2)
C10	0.056 (3)	0.054 (3)	0.062 (2)	0.004 (2)	0.012 (2)	0.017 (2)
C11	0.051 (2)	0.053 (3)	0.070 (3)	0.002 (2)	0.021 (2)	0.019 (2)
C12	0.054 (3)	0.067 (3)	0.076 (3)	0.005 (2)	0.015 (2)	0.018 (2)
C13	0.071 (3)	0.068 (3)	0.098 (4)	0.019 (3)	0.021 (3)	0.026 (3)
C14	0.078 (3)	0.059 (3)	0.085 (3)	0.006 (3)	0.032 (3)	0.007 (3)
C15	0.067 (3)	0.054 (3)	0.076 (3)	0.005 (2)	0.022 (2)	0.012 (2)
C16	0.053 (3)	0.049 (3)	0.082 (3)	0.009 (2)	0.022 (2)	0.018 (2)
C17	0.069 (3)	0.072 (3)	0.091 (3)	0.011 (3)	0.021 (3)	0.024 (3)

Geometric parameters (Å, º)

O1—C1	1.373 (4)	C7—C8	1.334 (5)
O1—C9	1.377 (4)	C7—H7	0.9300
O2—C10	1.226 (4)	C8—C9	1.467 (5)
N1—C9	1.260 (4)	C8—C10	1.508 (5)
N1—C11	1.433 (4)	C11—C12	1.377 (6)
N2—C10	1.311 (5)	C11—C16	1.395 (6)
N2—H2NA	0.8600	C12—C13	1.382 (5)
N2—H2NB	0.8600	C12—H12	0.9300
C1—C2	1.359 (5)	C13—C14	1.378 (6)
C1—C6	1.376 (5)	C13—H13	0.9300
C2—C3	1.383 (5)	C14—C15	1.367 (6)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.383 (5)	C15—C16	1.375 (5)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.388 (6)	C16—C17	1.498 (6)
C4—H4	0.9300	C17—H17A	0.9600
C5—C6	1.389 (5)	C17—H17B	0.9600
C5—H5	0.9300	C17—H17C	0.9600
C6—C7	1.443 (5)
C1—O1—C9	123.0 (3)	N1—C9—C8	123.6 (3)
C9—N1—C11	121.8 (3)	O1—C9—C8	117.0 (4)
C10—N2—H2NA	120.0	O2—C10—N2	123.3 (4)
C10—N2—H2NB	120.0	O2—C10—C8	119.8 (4)
H2NA—N2—H2NB	120.0	N2—C10—C8	116.8 (3)
C2—C1—O1	116.9 (3)	C12—C11—C16	120.5 (4)
C2—C1—C6	122.7 (4)	C12—C11—N1	118.4 (4)
O1—C1—C6	120.4 (3)	C16—C11—N1	120.9 (4)
C1—C2—C3	118.5 (4)	C11—C12—C13	120.3 (5)
C1—C2—H2	120.7	C11—C12—H12	119.9
C3—C2—H2	120.7	C13—C12—H12	119.9
C2—C3—C4	121.1 (4)	C14—C13—C12	119.9 (4)
C2—C3—H3	119.5	C14—C13—H13	120.1
C4—C3—H3	119.5	C12—C13—H13	120.1
C3—C4—C5	118.9 (4)	C15—C14—C13	119.0 (4)
C3—C4—H4	120.6	C15—C14—H14	120.5
C5—C4—H4	120.6	C13—C14—H14	120.5
C4—C5—C6	120.6 (4)	C14—C15—C16	122.9 (5)
C4—C5—H5	119.7	C14—C15—H15	118.6
C6—C5—H5	119.7	C16—C15—H15	118.6
C1—C6—C5	118.2 (4)	C15—C16—C11	117.5 (4)
C1—C6—C7	118.1 (4)	C15—C16—C17	121.9 (4)
C5—C6—C7	123.7 (3)	C11—C16—C17	120.6 (4)
C8—C7—C6	121.9 (3)	C16—C17—H17A	109.5
C8—C7—H7	119.0	C16—C17—H17B	109.5
C6—C7—H7	119.0	H17A—C17—H17B	109.5
C7—C8—C9	119.6 (3)	C16—C17—H17C	109.5
C7—C8—C10	117.8 (3)	H17A—C17—H17C	109.5
C9—C8—C10	122.7 (4)	H17B—C17—H17C	109.5
N1—C9—O1	119.4 (3)
C9—O1—C1—C2	−178.0 (4)	C7—C8—C9—N1	−178.8 (4)
C9—O1—C1—C6	3.0 (6)	C10—C8—C9—N1	0.1 (6)
O1—C1—C2—C3	178.4 (4)	C7—C8—C9—O1	1.6 (6)
C6—C1—C2—C3	−2.6 (7)	C10—C8—C9—O1	−179.5 (4)
C1—C2—C3—C4	1.8 (7)	C7—C8—C10—O2	−2.2 (6)
C2—C3—C4—C5	0.3 (7)	C9—C8—C10—O2	178.9 (4)
C3—C4—C5—C6	−1.7 (7)	C7—C8—C10—N2	179.3 (4)
C2—C1—C6—C5	1.3 (6)	C9—C8—C10—N2	0.4 (6)
O1—C1—C6—C5	−179.7 (4)	C9—N1—C11—C12	−105.6 (5)
C2—C1—C6—C7	179.3 (4)	C9—N1—C11—C16	79.6 (5)
O1—C1—C6—C7	−1.7 (6)	C16—C11—C12—C13	−1.6 (6)
C4—C5—C6—C1	0.9 (7)	N1—C11—C12—C13	−176.4 (4)
C4—C5—C6—C7	−177.0 (4)	C11—C12—C13—C14	0.8 (7)
C1—C6—C7—C8	0.6 (6)	C12—C13—C14—C15	0.4 (7)
C5—C6—C7—C8	178.4 (4)	C13—C14—C15—C16	−0.9 (7)
C6—C7—C8—C9	−0.5 (6)	C14—C15—C16—C11	0.1 (6)
C6—C7—C8—C10	−179.5 (4)	C14—C15—C16—C17	−179.3 (4)
C11—N1—C9—O1	−0.8 (6)	C12—C11—C16—C15	1.1 (6)
C11—N1—C9—C8	179.6 (4)	N1—C11—C16—C15	175.8 (3)
C1—O1—C9—N1	177.5 (4)	C12—C11—C16—C17	−179.4 (4)
C1—O1—C9—C8	−2.9 (6)	N1—C11—C16—C17	−4.7 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2NB···N1	0.86	1.98	2.679 (4)	138
N2—H2NA···O2^i	0.86	2.06	2.919 (4)	173

Symmetry code: (i) −x+2, −y+1, −z+1.

(1f_1)

Crystal data

C16H11FN2O2	Z = 2
Mr = 282.27	F(000) = 292
Triclinic, P1	Dx = 1.465 Mg m^−3
a = 4.6371 (13) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.957 (3) Å	Cell parameters from 274 reflections
c = 15.788 (6) Å	θ = 3.8–20.8°
α = 99.88 (3)°	µ = 0.11 mm^−1
β = 96.61 (3)°	T = 293 K
γ = 93.21 (3)°	Stick, colorless
V = 639.8 (4) Å^3	0.30 × 0.04 × 0.02 mm

Data collection

Xcalibur, Sapphire3 diffractometer	2841 independent reflections
Radiation source: Enhance (Mo) X-ray Source	651 reflections with I > 2σ(I)
Detector resolution: 16.1827 pixels mm^-1	Rint = 0.129
ω scans	θmax = 25.0°, θmin = 3.2°
Absorption correction: multi-scan CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −5→5
Tmin = 0.092, Tmax = 1.000	k = −10→10
2841 measured reflections	l = −18→18

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.077	H-atom parameters constrained
wR(F^2) = 0.185	w = 1/[σ^2(Fo^2) + (0.0697P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.68	(Δ/σ)max = 0.002
2841 reflections	Δρmax = 0.23 e Å^−3
191 parameters	Δρmin = −0.21 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.

Refinement. Refined as a 2-component twin.

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

	x	y	z	Uiso*/Ueq
F1	0.8245 (13)	0.4894 (9)	0.8971 (4)	0.117 (3)
O1	0.2888 (14)	0.3557 (8)	0.7581 (4)	0.061 (2)
O2	0.7525 (15)	0.3285 (9)	0.5002 (4)	0.075 (2)
N1	0.5782 (16)	0.5592 (11)	0.7451 (5)	0.061 (3)
N2	0.8865 (15)	0.5302 (10)	0.6053 (5)	0.068 (3)
H2A	1.005135	0.565731	0.574276	0.082*
H2B	0.870294	0.579060	0.656177	0.082*
C1	0.148 (2)	0.2177 (13)	0.7277 (7)	0.051 (3)
C2	−0.045 (2)	0.1591 (13)	0.7786 (6)	0.066 (3)
H2	−0.071000	0.215075	0.832135	0.079*
C3	−0.194 (2)	0.0198 (14)	0.7498 (8)	0.068 (3)
H3	−0.320256	−0.020127	0.783314	0.082*
C4	−0.152 (2)	−0.0597 (13)	0.6699 (7)	0.067 (3)
H4	−0.258692	−0.152569	0.649471	0.081*
C5	0.044 (2)	−0.0074 (13)	0.6176 (7)	0.065 (3)
H5	0.073067	−0.065204	0.564902	0.078*
C6	0.1906 (19)	0.1344 (13)	0.6482 (7)	0.054 (3)
C7	0.3885 (19)	0.2034 (13)	0.6026 (6)	0.060 (3)
H7	0.429008	0.149482	0.550051	0.072*
C8	0.522 (2)	0.3435 (13)	0.6310 (7)	0.049 (3)
C9	0.481 (2)	0.4260 (14)	0.7142 (7)	0.056 (3)
C10	0.724 (2)	0.3965 (13)	0.5738 (7)	0.053 (3)
C11	0.516 (2)	0.6334 (12)	0.8268 (7)	0.044 (3)
C12	0.324 (2)	0.7486 (13)	0.8302 (9)	0.073 (4)
H12	0.224961	0.771976	0.780051	0.088*
C13	0.288 (2)	0.8244 (14)	0.9097 (9)	0.083 (4)
H13	0.163858	0.902843	0.912260	0.099*
C14	0.421 (3)	0.7943 (14)	0.9882 (8)	0.084 (4)
H14	0.388058	0.848556	1.041480	0.101*
C15	0.607 (2)	0.6774 (16)	0.9811 (8)	0.082 (4)
H15	0.704314	0.649360	1.030114	0.099*
C16	0.641 (2)	0.6075 (13)	0.9027 (9)	0.064 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.115 (5)	0.122 (7)	0.112 (5)	0.010 (6)	0.014 (5)	0.020 (5)
O1	0.060 (5)	0.050 (5)	0.068 (5)	−0.018 (4)	0.014 (4)	−0.004 (4)
O2	0.085 (5)	0.081 (6)	0.064 (4)	−0.010 (4)	0.041 (4)	0.007 (4)
N1	0.051 (5)	0.070 (7)	0.055 (6)	−0.023 (5)	0.012 (5)	−0.006 (5)
N2	0.052 (6)	0.084 (8)	0.066 (6)	−0.008 (6)	0.027 (5)	−0.003 (5)
C1	0.037 (7)	0.054 (9)	0.063 (9)	0.013 (7)	0.000 (6)	0.016 (7)
C2	0.060 (7)	0.060 (9)	0.071 (8)	−0.015 (7)	0.009 (6)	−0.004 (7)
C3	0.057 (7)	0.077 (10)	0.068 (8)	−0.014 (7)	0.010 (7)	0.009 (7)
C4	0.057 (7)	0.058 (9)	0.083 (9)	−0.009 (6)	0.002 (7)	0.009 (7)
C5	0.046 (7)	0.071 (10)	0.072 (8)	−0.014 (6)	0.009 (6)	0.001 (7)
C6	0.031 (6)	0.055 (9)	0.074 (9)	−0.020 (6)	0.015 (6)	0.007 (7)
C7	0.040 (7)	0.070 (10)	0.071 (8)	0.032 (7)	0.004 (6)	0.009 (7)
C8	0.052 (7)	0.051 (8)	0.049 (7)	0.000 (6)	0.019 (6)	0.013 (6)
C9	0.035 (7)	0.065 (9)	0.063 (8)	−0.008 (6)	0.009 (6)	0.004 (7)
C10	0.047 (6)	0.062 (9)	0.054 (7)	0.002 (6)	0.009 (6)	0.018 (6)
C11	0.044 (6)	0.061 (8)	0.023 (6)	−0.021 (6)	0.012 (5)	−0.002 (6)
C12	0.050 (7)	0.048 (8)	0.119 (11)	0.002 (7)	0.033 (8)	−0.004 (8)
C13	0.076 (9)	0.081 (10)	0.081 (8)	−0.003 (7)	0.014 (9)	−0.010 (9)
C14	0.082 (10)	0.067 (10)	0.088 (10)	−0.043 (8)	0.034 (9)	−0.033 (8)
C15	0.085 (9)	0.095 (11)	0.059 (9)	−0.029 (9)	0.027 (7)	−0.011 (8)
C16	0.067 (9)	0.048 (8)	0.077 (9)	0.002 (6)	0.034 (8)	−0.006 (7)

Geometric parameters (Å, º)

F1—C16	1.393 (11)	C5—C6	1.389 (12)
O1—C1	1.348 (11)	C5—H5	0.9300
O1—C9	1.377 (10)	C6—C7	1.409 (12)
O2—C10	1.242 (10)	C7—C8	1.347 (13)
N1—C9	1.247 (12)	C7—H7	0.9300
N1—C11	1.415 (11)	C8—C9	1.432 (12)
N2—C10	1.362 (12)	C8—C10	1.486 (11)
N2—H2A	0.8600	C11—C16	1.331 (12)
N2—H2B	0.8600	C11—C12	1.400 (11)
C1—C6	1.387 (11)	C12—C13	1.355 (14)
C1—C2	1.407 (12)	C12—H12	0.9300
C2—C3	1.371 (13)	C13—C14	1.395 (14)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.378 (13)	C14—C15	1.391 (13)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.408 (11)	C15—C16	1.318 (13)
C4—H4	0.9300	C15—H15	0.9300
C1—O1—C9	124.0 (8)	C7—C8—C10	115.5 (10)
C9—N1—C11	121.5 (8)	C9—C8—C10	124.5 (11)
C10—N2—H2A	120.0	N1—C9—O1	118.4 (9)
C10—N2—H2B	120.0	N1—C9—C8	125.6 (11)
H2A—N2—H2B	120.0	O1—C9—C8	115.6 (10)
O1—C1—C6	121.3 (10)	O2—C10—N2	118.5 (10)
O1—C1—C2	118.5 (10)	O2—C10—C8	124.7 (11)
C6—C1—C2	120.3 (11)	N2—C10—C8	116.8 (10)
C3—C2—C1	120.3 (10)	C16—C11—C12	116.3 (10)
C3—C2—H2	119.9	C16—C11—N1	124.6 (11)
C1—C2—H2	119.9	C12—C11—N1	119.0 (11)
C2—C3—C4	118.5 (10)	C13—C12—C11	117.0 (13)
C2—C3—H3	120.8	C13—C12—H12	121.5
C4—C3—H3	120.8	C11—C12—H12	121.5
C3—C4—C5	123.3 (11)	C12—C13—C14	125.2 (13)
C3—C4—H4	118.4	C12—C13—H13	117.4
C5—C4—H4	118.4	C14—C13—H13	117.4
C6—C5—C4	117.0 (10)	C15—C14—C13	115.3 (12)
C6—C5—H5	121.5	C15—C14—H14	122.4
C4—C5—H5	121.5	C13—C14—H14	122.4
C1—C6—C5	120.7 (10)	C16—C15—C14	118.0 (13)
C1—C6—C7	115.7 (10)	C16—C15—H15	121.0
C5—C6—C7	123.7 (10)	C14—C15—H15	121.0
C8—C7—C6	123.5 (10)	C15—C16—C11	128.2 (12)
C8—C7—H7	118.3	C15—C16—F1	117.0 (14)
C6—C7—H7	118.3	C11—C16—F1	114.8 (11)
C7—C8—C9	119.8 (10)
C9—O1—C1—C6	0.7 (13)	C7—C8—C9—N1	−175.4 (11)
C9—O1—C1—C2	−179.4 (9)	C10—C8—C9—N1	9.3 (17)
O1—C1—C2—C3	179.5 (10)	C7—C8—C9—O1	−3.1 (13)
C6—C1—C2—C3	−0.6 (15)	C10—C8—C9—O1	−178.5 (9)
C1—C2—C3—C4	−0.6 (15)	C7—C8—C10—O2	7.6 (15)
C2—C3—C4—C5	2.2 (16)	C9—C8—C10—O2	−176.9 (11)
C3—C4—C5—C6	−2.6 (15)	C7—C8—C10—N2	−173.0 (9)
O1—C1—C6—C5	−179.9 (9)	C9—C8—C10—N2	2.5 (15)
C2—C1—C6—C5	0.3 (15)	C9—N1—C11—C16	76.2 (13)
O1—C1—C6—C7	0.0 (15)	C9—N1—C11—C12	−107.6 (11)
C2—C1—C6—C7	−179.8 (9)	C16—C11—C12—C13	1.4 (12)
C4—C5—C6—C1	1.3 (14)	N1—C11—C12—C13	−175.1 (9)
C4—C5—C6—C7	−178.7 (10)	C11—C12—C13—C14	−1.7 (15)
C1—C6—C7—C8	−2.5 (15)	C12—C13—C14—C15	0.8 (16)
C5—C6—C7—C8	177.4 (10)	C13—C14—C15—C16	0.3 (14)
C6—C7—C8—C9	4.1 (14)	C14—C15—C16—C11	−0.5 (15)
C6—C7—C8—C10	179.9 (10)	C14—C15—C16—F1	−179.1 (9)
C11—N1—C9—O1	5.5 (16)	C12—C11—C16—C15	−0.3 (14)
C11—N1—C9—C8	177.6 (10)	N1—C11—C16—C15	175.9 (10)
C1—O1—C9—N1	173.7 (10)	C12—C11—C16—F1	178.2 (8)
C1—O1—C9—C8	0.8 (12)	N1—C11—C16—F1	−5.5 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···N1	0.86	2.08	2.748 (10)	134
N2—H2A···O2^i	0.86	2.03	2.882 (9)	172

Symmetry code: (i) −x+2, −y+1, −z+1.

(1f_2)

Crystal data

C16H11FN2O2	F(000) = 584
Mr = 282.27	Dx = 1.475 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 4.6995 (14) Å	Cell parameters from 283 reflections
b = 30.579 (8) Å	θ = 4.0–25.9°
c = 8.853 (3) Å	µ = 0.11 mm^−1
β = 92.70 (2)°	T = 293 K
V = 1270.8 (7) Å^3	Stick, colorless
Z = 4	0.30 × 0.04 × 0.02 mm

Data collection

Xcalibur, Sapphire3 diffractometer	2243 independent reflections
Radiation source: Enhance (Mo) X-ray Source	889 reflections with I > 2σ(I)
Detector resolution: 16.1827 pixels mm^-1	Rint = 0.146
ω scans	θmax = 25.0°, θmin = 3.1°
Absorption correction: multi-scan CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −5→5
Tmin = 0.512, Tmax = 1.000	k = −35→36
8424 measured reflections	l = −10→10

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.071	H-atom parameters constrained
wR(F^2) = 0.167	w = 1/[σ^2(Fo^2) + (0.0341P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.90	(Δ/σ)max < 0.001
2243 reflections	Δρmax = 0.21 e Å^−3
190 parameters	Δρmin = −0.19 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
F1	0.3187 (7)	0.29819 (9)	0.6230 (4)	0.0889 (11)
O1	0.8208 (6)	0.36971 (9)	0.7199 (4)	0.0502 (9)
O2	0.2508 (7)	0.49972 (10)	0.6722 (4)	0.0639 (10)
N1	0.5125 (8)	0.37600 (11)	0.5146 (4)	0.0506 (11)
N2	0.1554 (8)	0.44622 (12)	0.5029 (4)	0.0566 (11)
H2NA	0.019688	0.460887	0.458352	0.068*
H2NB	0.197128	0.420570	0.470786	0.068*
C1	0.9515 (10)	0.38595 (14)	0.8500 (5)	0.0457 (12)
C2	1.1618 (9)	0.36019 (14)	0.9180 (5)	0.0494 (13)
H2	1.209492	0.333372	0.876530	0.059*
C3	1.3000 (10)	0.37521 (16)	1.0492 (5)	0.0529 (13)
H3	1.443110	0.358304	1.095979	0.063*
C4	1.2298 (10)	0.41470 (16)	1.1119 (5)	0.0570 (14)
H4	1.325310	0.424540	1.199862	0.068*
C5	1.0151 (10)	0.43960 (15)	1.0425 (5)	0.0528 (13)
H5	0.963920	0.465957	1.086007	0.063*
C6	0.8727 (9)	0.42583 (14)	0.9072 (5)	0.0437 (12)
C7	0.6530 (9)	0.45002 (15)	0.8261 (5)	0.0483 (13)
H7	0.596580	0.476884	0.863860	0.058*
C8	0.5274 (9)	0.43503 (13)	0.6981 (5)	0.0404 (11)
C9	0.6135 (10)	0.39264 (14)	0.6371 (6)	0.0450 (12)
C10	0.3008 (10)	0.46320 (16)	0.6212 (5)	0.0484 (12)
C11	0.6129 (10)	0.33560 (15)	0.4625 (5)	0.0480 (12)
C12	0.8104 (10)	0.33415 (17)	0.3499 (5)	0.0602 (14)
H12	0.885776	0.359915	0.312877	0.072*
C13	0.8938 (12)	0.29405 (19)	0.2935 (6)	0.0716 (17)
H13	1.027950	0.292992	0.219654	0.086*
C14	0.7806 (12)	0.25620 (19)	0.3454 (6)	0.0735 (17)
H14	0.833744	0.229579	0.304488	0.088*
C15	0.5890 (12)	0.25702 (17)	0.4574 (6)	0.0715 (16)
H15	0.513725	0.231296	0.494833	0.086*
C16	0.5122 (11)	0.29687 (15)	0.5123 (6)	0.0580 (14)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.100 (3)	0.083 (2)	0.084 (3)	0.0010 (18)	0.011 (2)	0.0071 (18)
O1	0.054 (2)	0.0490 (19)	0.046 (2)	0.0065 (16)	−0.0133 (17)	−0.0072 (16)
O2	0.072 (3)	0.044 (2)	0.074 (3)	0.0138 (17)	−0.018 (2)	−0.0130 (18)
N1	0.052 (3)	0.047 (2)	0.050 (3)	0.005 (2)	−0.016 (2)	−0.013 (2)
N2	0.063 (3)	0.043 (2)	0.062 (3)	0.013 (2)	−0.015 (2)	−0.002 (2)
C1	0.051 (3)	0.047 (3)	0.038 (3)	−0.004 (2)	−0.002 (2)	−0.001 (2)
C2	0.053 (3)	0.047 (3)	0.047 (3)	0.004 (2)	−0.012 (3)	−0.001 (2)
C3	0.053 (3)	0.060 (3)	0.045 (3)	0.004 (3)	−0.012 (3)	0.007 (3)
C4	0.058 (4)	0.073 (4)	0.039 (3)	−0.005 (3)	−0.016 (3)	0.002 (3)
C5	0.056 (3)	0.053 (3)	0.048 (3)	−0.002 (3)	−0.003 (3)	−0.003 (3)
C6	0.038 (3)	0.049 (3)	0.043 (3)	−0.001 (2)	−0.006 (2)	−0.003 (2)
C7	0.050 (3)	0.044 (3)	0.051 (3)	0.000 (2)	0.005 (3)	−0.006 (2)
C8	0.040 (3)	0.041 (3)	0.040 (3)	−0.003 (2)	−0.004 (2)	0.000 (2)
C9	0.042 (3)	0.039 (3)	0.054 (3)	0.002 (2)	0.000 (3)	−0.004 (2)
C10	0.045 (3)	0.058 (3)	0.042 (3)	0.006 (3)	0.001 (2)	0.002 (3)
C11	0.053 (3)	0.046 (3)	0.043 (3)	0.004 (2)	−0.013 (3)	−0.008 (2)
C12	0.058 (3)	0.067 (4)	0.054 (4)	0.006 (3)	−0.009 (3)	−0.014 (3)
C13	0.072 (4)	0.081 (4)	0.061 (4)	0.016 (3)	−0.001 (3)	−0.013 (3)
C14	0.089 (5)	0.063 (4)	0.067 (4)	0.028 (3)	−0.017 (4)	−0.023 (3)
C15	0.088 (4)	0.048 (3)	0.076 (4)	0.005 (3)	−0.021 (4)	−0.002 (3)
C16	0.067 (4)	0.055 (3)	0.052 (4)	0.003 (3)	−0.001 (3)	−0.005 (3)

Geometric parameters (Å, º)

F1—C16	1.369 (5)	C5—C6	1.408 (6)
O1—C1	1.373 (5)	C6—C7	1.435 (6)
O1—C9	1.382 (5)	C7—C8	1.334 (6)
O2—C10	1.231 (5)	C8—C9	1.469 (5)
N1—C9	1.270 (5)	C8—C10	1.507 (6)
N1—C11	1.408 (5)	C11—C16	1.356 (6)
N2—C10	1.329 (6)	C11—C12	1.394 (5)
C1—C6	1.378 (5)	C12—C13	1.388 (6)
C1—C2	1.380 (6)	C13—C14	1.363 (6)
C2—C3	1.383 (6)	C14—C15	1.370 (7)
C3—C4	1.376 (6)	C15—C16	1.367 (6)
C4—C5	1.385 (6)
C1—O1—C9	122.5 (4)	N1—C9—O1	118.4 (4)
C9—N1—C11	120.9 (4)	N1—C9—C8	124.7 (5)
O1—C1—C6	120.8 (5)	O1—C9—C8	116.9 (4)
O1—C1—C2	116.3 (4)	O2—C10—N2	122.9 (5)
C6—C1—C2	123.0 (5)	O2—C10—C8	119.7 (5)
C1—C2—C3	118.4 (4)	N2—C10—C8	117.3 (4)
C4—C3—C2	121.3 (5)	C16—C11—C12	117.3 (4)
C3—C4—C5	119.1 (5)	C16—C11—N1	122.2 (4)
C4—C5—C6	121.4 (5)	C12—C11—N1	120.4 (4)
C1—C6—C5	116.9 (5)	C13—C12—C11	119.6 (5)
C1—C6—C7	118.2 (5)	C14—C13—C12	120.5 (5)
C5—C6—C7	125.0 (4)	C13—C14—C15	120.6 (5)
C8—C7—C6	121.8 (4)	C16—C15—C14	117.8 (5)
C7—C8—C9	119.8 (5)	C11—C16—C15	124.1 (5)
C7—C8—C10	117.5 (4)	C11—C16—F1	117.4 (4)
C9—C8—C10	122.7 (4)	C15—C16—F1	118.4 (4)
C9—O1—C1—C6	2.3 (6)	C7—C8—C9—N1	−178.2 (4)
C9—O1—C1—C2	−177.7 (4)	C10—C8—C9—N1	1.4 (7)
O1—C1—C2—C3	179.9 (4)	C7—C8—C9—O1	1.4 (6)
C6—C1—C2—C3	−0.2 (7)	C10—C8—C9—O1	−179.0 (4)
C1—C2—C3—C4	0.4 (7)	C7—C8—C10—O2	4.4 (6)
C2—C3—C4—C5	0.5 (7)	C9—C8—C10—O2	−175.2 (4)
C3—C4—C5—C6	−1.6 (7)	C7—C8—C10—N2	−173.1 (4)
O1—C1—C6—C5	179.0 (4)	C9—C8—C10—N2	7.3 (6)
C2—C1—C6—C5	−0.9 (6)	C9—N1—C11—C16	83.8 (6)
O1—C1—C6—C7	−0.7 (6)	C9—N1—C11—C12	−100.0 (5)
C2—C1—C6—C7	179.4 (4)	C16—C11—C12—C13	0.3 (7)
C4—C5—C6—C1	1.8 (6)	N1—C11—C12—C13	−176.1 (5)
C4—C5—C6—C7	−178.5 (4)	C11—C12—C13—C14	1.1 (8)
C1—C6—C7—C8	−0.5 (6)	C12—C13—C14—C15	−2.0 (9)
C5—C6—C7—C8	179.8 (4)	C13—C14—C15—C16	1.3 (9)
C6—C7—C8—C9	0.1 (6)	C12—C11—C16—C15	−1.0 (8)
C6—C7—C8—C10	−179.5 (4)	N1—C11—C16—C15	175.3 (5)
C11—N1—C9—O1	−1.2 (6)	C12—C11—C16—F1	179.9 (4)
C11—N1—C9—C8	178.4 (4)	N1—C11—C16—F1	−3.8 (7)
C1—O1—C9—N1	177.0 (4)	C14—C15—C16—C11	0.2 (9)
C1—O1—C9—C8	−2.6 (6)	C14—C15—C16—F1	179.3 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2NB···N1	0.86	2.04	2.724 (5)	136
N2—H2NA···O2^i	0.86	2.07	2.916 (5)	170

Symmetry code: (i) −x, −y+1, −z+1.

(1cl)

Crystal data

C16H11ClN2O2	F(000) = 616
Mr = 298.72	Dx = 1.496 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 4.3746 (9) Å	Cell parameters from 578 reflections
b = 30.823 (5) Å	θ = 3.9–20.5°
c = 9.855 (3) Å	µ = 0.29 mm^−1
β = 93.225 (17)°	T = 293 K
V = 1326.7 (5) Å^3	Stick, colorless
Z = 4	0.30 × 0.05 × 0.05 mm

Data collection

Xcalibur, Sapphire3 diffractometer	2320 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1067 reflections with I > 2σ(I)
Detector resolution: 16.1827 pixels mm^-1	Rint = 0.124
ω scans	θmax = 25.0°, θmin = 3.4°
Absorption correction: multi-scan CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −5→4
Tmin = 0.174, Tmax = 1.000	k = −36→36
8350 measured reflections	l = −11→8

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.073	H-atom parameters constrained
wR(F^2) = 0.197	w = 1/[σ^2(Fo^2) + (0.0654P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.95	(Δ/σ)max = 0.012
2320 reflections	Δρmax = 0.27 e Å^−3
190 parameters	Δρmin = −0.25 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
Cl1	0.1732 (3)	0.65365 (5)	0.63880 (17)	0.0862 (6)
O1	0.2352 (7)	0.63234 (9)	0.2215 (3)	0.0584 (9)
O2	0.7695 (8)	0.50059 (10)	0.3356 (4)	0.0790 (11)
N1	0.5614 (9)	0.63210 (11)	0.4090 (5)	0.0633 (12)
N2	0.8536 (9)	0.55605 (12)	0.4783 (5)	0.0737 (13)
H2NA	0.973587	0.540865	0.531624	0.088*
H2NB	0.817367	0.582716	0.497412	0.088*
C1	0.1079 (10)	0.61332 (14)	0.1057 (5)	0.0518 (12)
C2	−0.0938 (10)	0.63792 (14)	0.0263 (5)	0.0564 (13)
H2	−0.142617	0.666025	0.051792	0.068*
C3	−0.2221 (11)	0.62012 (15)	−0.0916 (6)	0.0662 (15)
H3	−0.362674	0.636057	−0.145546	0.079*
C4	−0.1429 (11)	0.57845 (16)	−0.1306 (6)	0.0637 (14)
H4	−0.227099	0.566765	−0.211251	0.076*
C5	0.0591 (11)	0.55469 (15)	−0.0501 (6)	0.0622 (14)
H5	0.110756	0.526780	−0.076333	0.075*
C6	0.1887 (9)	0.57174 (13)	0.0708 (5)	0.0507 (12)
C7	0.3897 (10)	0.54853 (13)	0.1648 (5)	0.0564 (13)
H7	0.432947	0.519691	0.145812	0.068*
C8	0.5178 (10)	0.56585 (13)	0.2777 (5)	0.0510 (12)
C9	0.4428 (11)	0.61133 (14)	0.3079 (6)	0.0556 (13)
C10	0.7256 (11)	0.53850 (15)	0.3677 (6)	0.0619 (13)
C11	0.4987 (11)	0.67728 (14)	0.4258 (5)	0.0578 (13)
C12	0.6346 (12)	0.70819 (15)	0.3422 (6)	0.0714 (15)
H12	0.758450	0.699754	0.273265	0.086*
C13	0.5760 (12)	0.75178 (16)	0.3671 (7)	0.0766 (17)
H13	0.659160	0.772697	0.312012	0.092*
C14	0.3997 (12)	0.76481 (17)	0.4701 (7)	0.0757 (17)
H14	0.367044	0.794221	0.484619	0.091*
C15	0.2710 (11)	0.73462 (17)	0.5521 (6)	0.0722 (16)
H15	0.146330	0.743308	0.620512	0.087*
C16	0.3301 (11)	0.69076 (15)	0.5311 (6)	0.0663 (14)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0998 (11)	0.0784 (10)	0.0797 (13)	−0.0085 (7)	−0.0016 (8)	0.0000 (8)
O1	0.069 (2)	0.0390 (17)	0.065 (3)	0.0105 (14)	−0.0097 (17)	−0.0024 (15)
O2	0.112 (3)	0.045 (2)	0.078 (3)	0.0213 (18)	−0.019 (2)	−0.0036 (17)
N1	0.084 (3)	0.040 (2)	0.064 (3)	0.0086 (19)	−0.012 (2)	−0.003 (2)
N2	0.105 (3)	0.049 (2)	0.065 (4)	0.014 (2)	−0.016 (3)	−0.004 (2)
C1	0.063 (3)	0.043 (3)	0.050 (4)	−0.006 (2)	−0.001 (2)	−0.008 (2)
C2	0.066 (3)	0.040 (3)	0.063 (4)	0.002 (2)	0.001 (2)	0.003 (2)
C3	0.071 (3)	0.057 (3)	0.069 (4)	−0.003 (2)	−0.011 (3)	0.008 (3)
C4	0.071 (3)	0.059 (3)	0.061 (4)	−0.010 (2)	0.000 (3)	−0.006 (3)
C5	0.072 (3)	0.046 (3)	0.068 (4)	−0.002 (2)	−0.003 (3)	−0.009 (2)
C6	0.054 (3)	0.038 (2)	0.060 (4)	−0.001 (2)	0.003 (2)	−0.002 (2)
C7	0.061 (3)	0.037 (2)	0.072 (4)	0.004 (2)	0.009 (3)	−0.002 (2)
C8	0.061 (3)	0.040 (2)	0.052 (4)	0.003 (2)	0.003 (2)	−0.001 (2)
C9	0.067 (3)	0.040 (2)	0.060 (4)	0.003 (2)	0.003 (3)	0.000 (2)
C10	0.080 (3)	0.048 (3)	0.057 (4)	0.009 (2)	−0.003 (3)	0.002 (2)
C11	0.077 (3)	0.049 (3)	0.044 (3)	0.012 (2)	−0.019 (3)	−0.009 (2)
C12	0.091 (4)	0.046 (3)	0.075 (4)	−0.001 (2)	−0.011 (3)	0.001 (3)
C13	0.094 (4)	0.050 (3)	0.083 (5)	0.004 (3)	−0.013 (3)	−0.001 (3)
C14	0.080 (4)	0.050 (3)	0.095 (5)	0.004 (3)	−0.020 (3)	−0.015 (3)
C15	0.079 (4)	0.059 (3)	0.077 (5)	0.005 (3)	−0.008 (3)	−0.026 (3)
C16	0.081 (3)	0.056 (3)	0.060 (4)	−0.006 (2)	−0.016 (3)	−0.003 (3)

Geometric parameters (Å, º)

Cl1—C16	1.728 (5)	C5—C6	1.393 (7)
O1—C1	1.372 (5)	C6—C7	1.432 (6)
O1—C9	1.372 (5)	C7—C8	1.329 (6)
O2—C10	1.229 (5)	C8—C9	1.474 (6)
N1—C9	1.270 (6)	C8—C10	1.494 (6)
N1—C11	1.431 (5)	C11—C16	1.371 (7)
N2—C10	1.314 (6)	C11—C12	1.412 (7)
C1—C2	1.374 (6)	C12—C13	1.392 (6)
C1—C6	1.378 (5)	C13—C14	1.369 (8)
C2—C3	1.376 (7)	C14—C15	1.374 (7)
C3—C4	1.390 (6)	C15—C16	1.394 (6)
C4—C5	1.367 (7)
C1—O1—C9	122.5 (4)	N1—C9—O1	118.4 (4)
C9—N1—C11	120.6 (4)	N1—C9—C8	123.5 (4)
O1—C1—C2	117.1 (4)	O1—C9—C8	118.1 (4)
O1—C1—C6	120.5 (4)	O2—C10—N2	122.7 (4)
C2—C1—C6	122.4 (4)	O2—C10—C8	118.9 (5)
C1—C2—C3	118.7 (4)	N2—C10—C8	118.5 (4)
C2—C3—C4	120.4 (5)	C16—C11—C12	119.9 (4)
C5—C4—C3	119.9 (5)	C16—C11—N1	119.8 (5)
C4—C5—C6	120.9 (4)	C12—C11—N1	120.0 (5)
C1—C6—C5	117.8 (4)	C13—C12—C11	117.4 (5)
C1—C6—C7	117.4 (4)	C14—C13—C12	122.0 (6)
C5—C6—C7	124.8 (4)	C13—C14—C15	120.3 (5)
C8—C7—C6	123.7 (4)	C14—C15—C16	119.0 (5)
C7—C8—C9	117.6 (4)	C11—C16—C15	121.2 (5)
C7—C8—C10	118.9 (4)	C11—C16—Cl1	120.9 (4)
C9—C8—C10	123.5 (5)	C15—C16—Cl1	117.9 (5)
C9—O1—C1—C2	−179.0 (4)	C7—C8—C9—N1	−176.6 (5)
C9—O1—C1—C6	−0.7 (7)	C10—C8—C9—N1	4.1 (8)
O1—C1—C2—C3	179.0 (4)	C7—C8—C9—O1	3.0 (7)
C6—C1—C2—C3	0.7 (7)	C10—C8—C9—O1	−176.3 (4)
C1—C2—C3—C4	−1.5 (8)	C7—C8—C10—O2	−0.8 (7)
C2—C3—C4—C5	1.3 (8)	C9—C8—C10—O2	178.5 (4)
C3—C4—C5—C6	−0.3 (8)	C7—C8—C10—N2	179.3 (5)
O1—C1—C6—C5	−178.0 (4)	C9—C8—C10—N2	−1.4 (7)
C2—C1—C6—C5	0.2 (7)	C9—N1—C11—C16	112.0 (6)
O1—C1—C6—C7	4.7 (6)	C9—N1—C11—C12	−74.1 (6)
C2—C1—C6—C7	−177.1 (4)	C16—C11—C12—C13	−3.4 (7)
C4—C5—C6—C1	−0.4 (7)	N1—C11—C12—C13	−177.3 (4)
C4—C5—C6—C7	176.6 (5)	C11—C12—C13—C14	1.5 (8)
C1—C6—C7—C8	−5.0 (7)	C12—C13—C14—C15	−0.8 (9)
C5—C6—C7—C8	178.0 (5)	C13—C14—C15—C16	1.8 (8)
C6—C7—C8—C9	1.1 (7)	C12—C11—C16—C15	4.6 (7)
C6—C7—C8—C10	−179.6 (4)	N1—C11—C16—C15	178.5 (4)
C11—N1—C9—O1	−5.0 (7)	C12—C11—C16—Cl1	−177.6 (4)
C11—N1—C9—C8	174.5 (4)	N1—C11—C16—Cl1	−3.7 (6)
C1—O1—C9—N1	176.4 (4)	C14—C15—C16—C11	−3.8 (7)
C1—O1—C9—C8	−3.2 (7)	C14—C15—C16—Cl1	178.3 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2NB···N1	0.86	2.05	2.738 (5)	136
N2—H2NA···O2^i	0.86	2.11	2.965 (5)	174

Symmetry code: (i) −x+2, −y+1, −z+1.

(1br1)

Crystal data

C16H11BrN2O2	F(000) = 688
Mr = 343.18	Dx = 1.691 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 4.1661 (2) Å	Cell parameters from 1628 reflections
b = 31.0277 (16) Å	θ = 3.9–23.6°
c = 10.4434 (6) Å	µ = 3.05 mm^−1
β = 92.933 (4)°	T = 293 K
V = 1348.19 (12) Å^3	Block, yellow
Z = 4	0.30 × 0.10 × 0.08 mm

Data collection

Xcalibur, Sapphire3 diffractometer	2355 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1938 reflections with I > 2σ(I)
Detector resolution: 16.1827 pixels mm^-1	Rint = 0.058
ω scans	θmax = 25.0°, θmin = 3.3°
Absorption correction: multi-scan CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −4→4
Tmin = 0.622, Tmax = 1.000	k = −36→35
8677 measured reflections	l = −12→12

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.119	w = 1/[σ^2(Fo^2) + (0.0601P)^2 + 0.0494P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.001
2355 reflections	Δρmax = 0.48 e Å^−3
190 parameters	Δρmin = −0.43 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
Br1	0.20573 (9)	0.65376 (2)	0.63591 (4)	0.0600 (2)
O1	0.2559 (5)	0.63198 (7)	0.2135 (2)	0.0428 (5)
O2	0.7797 (7)	0.50028 (8)	0.3382 (3)	0.0691 (8)
N1	0.5749 (7)	0.63206 (8)	0.3964 (3)	0.0453 (7)
N2	0.8450 (8)	0.55520 (9)	0.4756 (3)	0.0642 (9)
H2NA	0.960898	0.540057	0.529209	0.077*
H2NB	0.804022	0.581710	0.492492	0.077*
C1	0.1381 (7)	0.61340 (10)	0.1020 (3)	0.0394 (7)
C2	−0.0510 (8)	0.63780 (11)	0.0204 (3)	0.0442 (8)
H2	−0.098628	0.666165	0.041048	0.053*
C3	−0.1702 (8)	0.62026 (12)	−0.0924 (4)	0.0520 (9)
H3	−0.304264	0.636616	−0.147231	0.062*
C4	−0.0939 (10)	0.57842 (13)	−0.1259 (4)	0.0567 (10)
H4	−0.170022	0.566960	−0.203965	0.068*
C5	0.0941 (8)	0.55436 (12)	−0.0430 (4)	0.0517 (9)
H5	0.143953	0.526213	−0.065263	0.062*
C6	0.2140 (8)	0.57055 (10)	0.0742 (3)	0.0410 (8)
C7	0.4065 (7)	0.54751 (10)	0.1688 (3)	0.0450 (8)
H7	0.450253	0.518579	0.154272	0.054*
C8	0.5254 (8)	0.56552 (10)	0.2764 (3)	0.0420 (8)
C9	0.4605 (7)	0.61139 (10)	0.3020 (3)	0.0388 (7)
C10	0.7307 (9)	0.53789 (11)	0.3683 (4)	0.0494 (9)
C11	0.5172 (8)	0.67669 (10)	0.4099 (3)	0.0405 (7)
C12	0.6377 (9)	0.70642 (11)	0.3259 (3)	0.0490 (9)
H12	0.747892	0.696778	0.256177	0.059*
C13	0.5974 (9)	0.74995 (11)	0.3438 (4)	0.0520 (9)
H13	0.681185	0.769415	0.286601	0.062*
C14	0.4344 (9)	0.76476 (11)	0.4456 (4)	0.0548 (10)
H14	0.404915	0.794201	0.456748	0.066*
C15	0.3144 (8)	0.73604 (11)	0.5311 (4)	0.0507 (9)
H15	0.201688	0.745940	0.599831	0.061*
C16	0.3619 (8)	0.69248 (10)	0.5145 (3)	0.0428 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0640 (3)	0.0674 (3)	0.0482 (3)	−0.00823 (17)	−0.0008 (2)	0.00545 (16)
O1	0.0514 (13)	0.0331 (12)	0.0433 (14)	0.0072 (10)	−0.0039 (11)	−0.0039 (10)
O2	0.091 (2)	0.0369 (15)	0.078 (2)	0.0216 (12)	−0.0120 (16)	−0.0039 (12)
N1	0.0538 (17)	0.0355 (14)	0.0462 (18)	0.0082 (13)	−0.0025 (13)	0.0006 (13)
N2	0.086 (2)	0.0406 (16)	0.064 (2)	0.0180 (16)	−0.0159 (19)	0.0026 (15)
C1	0.0397 (17)	0.0389 (18)	0.0400 (19)	−0.0035 (14)	0.0070 (14)	−0.0018 (14)
C2	0.0469 (19)	0.0388 (17)	0.047 (2)	−0.0018 (15)	0.0051 (16)	0.0008 (15)
C3	0.048 (2)	0.062 (2)	0.047 (2)	−0.0023 (17)	0.0044 (16)	0.0049 (18)
C4	0.062 (2)	0.064 (3)	0.044 (2)	−0.009 (2)	0.0049 (18)	−0.0081 (18)
C5	0.055 (2)	0.0454 (19)	0.056 (2)	−0.0052 (16)	0.0097 (18)	−0.0118 (17)
C6	0.0419 (18)	0.0365 (17)	0.046 (2)	−0.0062 (14)	0.0111 (15)	−0.0050 (14)
C7	0.0450 (19)	0.0341 (17)	0.057 (2)	0.0036 (14)	0.0101 (16)	−0.0059 (15)
C8	0.0452 (18)	0.0321 (16)	0.049 (2)	0.0027 (14)	0.0081 (16)	0.0002 (14)
C9	0.0409 (18)	0.0338 (16)	0.042 (2)	0.0028 (13)	0.0055 (15)	0.0050 (14)
C10	0.053 (2)	0.0391 (19)	0.056 (2)	0.0064 (16)	0.0005 (18)	0.0059 (16)
C11	0.0471 (18)	0.0357 (17)	0.0380 (19)	0.0056 (14)	−0.0055 (15)	−0.0024 (14)
C12	0.059 (2)	0.046 (2)	0.042 (2)	0.0065 (16)	−0.0003 (17)	−0.0042 (15)
C13	0.060 (2)	0.0401 (19)	0.055 (2)	0.0000 (16)	−0.0054 (18)	0.0046 (16)
C14	0.056 (2)	0.0378 (19)	0.068 (3)	−0.0013 (16)	−0.0126 (19)	−0.0054 (18)
C15	0.050 (2)	0.054 (2)	0.048 (2)	0.0091 (17)	−0.0051 (16)	−0.0164 (17)
C16	0.0428 (18)	0.0461 (18)	0.0383 (19)	0.0024 (15)	−0.0106 (14)	−0.0017 (15)

Geometric parameters (Å, º)

Br1—C16	1.887 (3)	C5—C6	1.392 (5)
O1—C1	1.368 (4)	C5—H5	0.9300
O1—C9	1.381 (4)	C6—C7	1.432 (5)
O2—C10	1.229 (4)	C7—C8	1.328 (5)
N1—C9	1.250 (4)	C7—H7	0.9300
N1—C11	1.414 (4)	C8—C9	1.475 (4)
N2—C10	1.310 (5)	C8—C10	1.518 (5)
N2—H2NA	0.8600	C11—C12	1.385 (5)
N2—H2NB	0.8600	C11—C16	1.387 (4)
C1—C2	1.361 (5)	C12—C13	1.375 (5)
C1—C6	1.401 (4)	C12—H12	0.9300
C2—C3	1.367 (5)	C13—C14	1.369 (5)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.386 (5)	C14—C15	1.374 (5)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.361 (5)	C15—C16	1.378 (4)
C4—H4	0.9300	C15—H15	0.9300
C1—O1—C9	123.8 (2)	C7—C8—C10	118.1 (3)
C9—N1—C11	121.4 (3)	C9—C8—C10	122.2 (3)
C10—N2—H2NA	120.0	N1—C9—O1	119.2 (3)
C10—N2—H2NB	120.0	N1—C9—C8	124.9 (3)
H2NA—N2—H2NB	120.0	O1—C9—C8	116.0 (3)
C2—C1—O1	118.0 (3)	O2—C10—N2	123.4 (3)
C2—C1—C6	121.9 (3)	O2—C10—C8	118.1 (3)
O1—C1—C6	120.1 (3)	N2—C10—C8	118.5 (3)
C1—C2—C3	119.4 (3)	C12—C11—C16	117.5 (3)
C1—C2—H2	120.3	C12—C11—N1	121.4 (3)
C3—C2—H2	120.3	C16—C11—N1	120.8 (3)
C2—C3—C4	120.8 (4)	C13—C12—C11	121.2 (3)
C2—C3—H3	119.6	C13—C12—H12	119.4
C4—C3—H3	119.6	C11—C12—H12	119.4
C5—C4—C3	119.0 (4)	C14—C13—C12	120.3 (3)
C5—C4—H4	120.5	C14—C13—H13	119.9
C3—C4—H4	120.5	C12—C13—H13	119.9
C4—C5—C6	122.1 (3)	C13—C14—C15	119.9 (3)
C4—C5—H5	119.0	C13—C14—H14	120.1
C6—C5—H5	119.0	C15—C14—H14	120.1
C5—C6—C1	116.8 (3)	C14—C15—C16	119.7 (3)
C5—C6—C7	126.2 (3)	C14—C15—H15	120.2
C1—C6—C7	117.1 (3)	C16—C15—H15	120.2
C8—C7—C6	123.1 (3)	C15—C16—C11	121.4 (3)
C8—C7—H7	118.5	C15—C16—Br1	118.9 (3)
C6—C7—H7	118.5	C11—C16—Br1	119.7 (2)
C7—C8—C9	119.7 (3)
C9—O1—C1—C2	−177.3 (3)	C7—C8—C9—N1	−175.9 (3)
C9—O1—C1—C6	2.4 (4)	C10—C8—C9—N1	3.0 (5)
O1—C1—C2—C3	179.5 (3)	C7—C8—C9—O1	4.5 (4)
C6—C1—C2—C3	−0.2 (5)	C10—C8—C9—O1	−176.7 (3)
C1—C2—C3—C4	−1.8 (5)	C7—C8—C10—O2	0.7 (5)
C2—C3—C4—C5	2.1 (5)	C9—C8—C10—O2	−178.2 (3)
C3—C4—C5—C6	−0.5 (5)	C7—C8—C10—N2	−179.0 (3)
C4—C5—C6—C1	−1.4 (5)	C9—C8—C10—N2	2.2 (5)
C4—C5—C6—C7	178.4 (3)	C9—N1—C11—C12	−66.3 (4)
C2—C1—C6—C5	1.8 (4)	C9—N1—C11—C16	119.5 (4)
O1—C1—C6—C5	−177.9 (3)	C16—C11—C12—C13	−1.6 (5)
C2—C1—C6—C7	−178.1 (3)	N1—C11—C12—C13	−176.1 (3)
O1—C1—C6—C7	2.2 (4)	C11—C12—C13—C14	−0.4 (6)
C5—C6—C7—C8	176.9 (3)	C12—C13—C14—C15	0.9 (6)
C1—C6—C7—C8	−3.3 (5)	C13—C14—C15—C16	0.6 (6)
C6—C7—C8—C9	−0.1 (5)	C14—C15—C16—C11	−2.7 (5)
C6—C7—C8—C10	−179.0 (3)	C14—C15—C16—Br1	178.2 (3)
C11—N1—C9—O1	−4.5 (5)	C12—C11—C16—C15	3.2 (5)
C11—N1—C9—C8	175.9 (3)	N1—C11—C16—C15	177.7 (3)
C1—O1—C9—N1	174.6 (3)	C12—C11—C16—Br1	−177.7 (2)
C1—O1—C9—C8	−5.7 (4)	N1—C11—C16—Br1	−3.3 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2NB···N1	0.86	2.06	2.746 (4)	136
N2—H2NA···O2^i	0.86	2.12	2.980 (4)	176

Symmetry code: (i) −x+2, −y+1, −z+1.

(1br_2)

Crystal data

C16H11BrN2O2	F(000) = 688
Mr = 343.18	Dx = 1.553 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 6.9397 (5) Å	Cell parameters from 1060 reflections
b = 10.2611 (8) Å	θ = 3.4–18.1°
c = 20.7644 (12) Å	µ = 2.81 mm^−1
β = 96.919 (7)°	T = 293 K
V = 1467.84 (18) Å^3	Block, yellow
Z = 4	0.20 × 0.10 × 0.10 mm

Data collection

Xcalibur, Sapphire3 diffractometer	2581 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1405 reflections with I > 2σ(I)
Detector resolution: 16.1827 pixels mm^-1	Rint = 0.091
ω scans	θmax = 25.0°, θmin = 2.8°
Absorption correction: multi-scan CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −8→8
Tmin = 0.217, Tmax = 1.000	k = −11→12
10135 measured reflections	l = −24→24

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)] = 0.100	w = 1/[σ^2(Fo^2) + (0.1875P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.326	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 1.85 e Å^−3
2581 reflections	Δρmin = −0.67 e Å^−3
191 parameters	Extinction correction: SHELXL-2016/6 (Sheldrick 2016), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.003 (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
Br1	0.53320 (18)	0.19475 (12)	0.24992 (4)	0.0946 (7)
O1	0.2288 (10)	0.4993 (8)	0.3982 (3)	0.0862 (19)
O2	0.3654 (14)	0.1212 (9)	0.5310 (4)	0.113 (3)
N1	0.2514 (12)	0.3024 (8)	0.3469 (3)	0.078 (2)
N2	0.3780 (14)	0.0953 (9)	0.4242 (4)	0.093 (3)
H2NA	0.409846	0.014670	0.429603	0.112*
H2NB	0.365605	0.128808	0.385996	0.112*
C1	0.2212 (15)	0.5720 (10)	0.4535 (5)	0.080 (3)
C2	0.1824 (17)	0.7056 (11)	0.4411 (7)	0.098 (4)
H2	0.161561	0.740247	0.399412	0.118*
C3	0.178 (2)	0.7810 (14)	0.4970 (7)	0.107 (4)
H3	0.155375	0.870045	0.492405	0.128*
C4	0.208 (2)	0.7263 (14)	0.5623 (8)	0.111 (4)
H4	0.199617	0.778252	0.598547	0.133*
C5	0.2482 (18)	0.5947 (14)	0.5685 (6)	0.103 (3)
H5	0.273816	0.558102	0.609567	0.123*
C6	0.2511 (14)	0.5162 (11)	0.5137 (4)	0.075 (3)
C7	0.2882 (14)	0.3794 (10)	0.5169 (4)	0.073 (2)
H7	0.309343	0.339582	0.557382	0.088*
C8	0.2936 (15)	0.3075 (9)	0.4647 (4)	0.071 (3)
C9	0.2611 (14)	0.3657 (10)	0.4009 (4)	0.074 (2)
C10	0.3487 (17)	0.1665 (11)	0.4739 (5)	0.082 (3)
C11	0.1979 (15)	0.3616 (10)	0.2868 (4)	0.075 (2)
C12	0.0443 (19)	0.4429 (12)	0.2725 (6)	0.101 (4)
H12	−0.028533	0.465431	0.305597	0.121*
C13	−0.008 (2)	0.4924 (15)	0.2133 (6)	0.116 (4)
H13	−0.111669	0.550204	0.207362	0.140*
C14	0.087 (2)	0.4606 (13)	0.1611 (6)	0.118 (4)
H14	0.047755	0.494036	0.120016	0.141*
C15	0.247 (2)	0.3754 (13)	0.1724 (5)	0.115 (5)
H15	0.317271	0.352276	0.138761	0.138*
C16	0.298 (2)	0.3257 (10)	0.2354 (5)	0.091 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.1046 (10)	0.1085 (11)	0.0746 (9)	0.0390 (6)	0.0266 (6)	−0.0021 (5)
O1	0.102 (5)	0.081 (5)	0.074 (4)	−0.004 (4)	0.007 (4)	0.000 (4)
O2	0.143 (8)	0.115 (7)	0.082 (5)	0.012 (6)	0.020 (5)	0.026 (5)
N1	0.078 (5)	0.096 (6)	0.063 (4)	0.003 (4)	0.016 (4)	0.000 (4)
N2	0.114 (7)	0.094 (6)	0.071 (5)	−0.002 (6)	0.008 (5)	−0.002 (5)
C1	0.079 (6)	0.075 (7)	0.088 (7)	0.002 (5)	0.015 (5)	−0.008 (5)
C2	0.077 (7)	0.093 (8)	0.128 (10)	−0.006 (6)	0.030 (7)	0.005 (7)
C3	0.098 (9)	0.100 (9)	0.125 (11)	0.001 (7)	0.024 (8)	−0.020 (8)
C4	0.101 (9)	0.102 (10)	0.132 (11)	−0.008 (8)	0.019 (8)	−0.009 (8)
C5	0.093 (8)	0.112 (10)	0.102 (8)	−0.007 (7)	0.008 (6)	−0.019 (7)
C6	0.071 (6)	0.099 (7)	0.056 (5)	−0.005 (5)	0.006 (4)	−0.008 (5)
C7	0.073 (6)	0.080 (7)	0.066 (5)	0.000 (5)	0.002 (4)	0.004 (5)
C8	0.068 (6)	0.084 (7)	0.057 (5)	−0.004 (5)	−0.005 (4)	0.006 (5)
C9	0.078 (6)	0.074 (6)	0.072 (6)	0.000 (5)	0.012 (5)	0.000 (5)
C10	0.088 (7)	0.097 (8)	0.062 (5)	−0.003 (6)	0.016 (5)	0.014 (5)
C11	0.076 (6)	0.079 (6)	0.068 (5)	−0.008 (5)	0.002 (5)	0.002 (5)
C12	0.106 (9)	0.124 (11)	0.072 (6)	0.008 (8)	0.005 (6)	0.021 (6)
C13	0.136 (11)	0.135 (11)	0.073 (7)	0.019 (10)	−0.006 (7)	−0.009 (8)
C14	0.159 (13)	0.092 (9)	0.095 (9)	0.006 (8)	−0.013 (8)	0.001 (7)
C15	0.198 (16)	0.087 (9)	0.063 (6)	−0.030 (10)	0.026 (8)	0.002 (6)
C16	0.122 (9)	0.084 (7)	0.067 (5)	0.001 (6)	0.007 (6)	0.013 (5)

Geometric parameters (Å, º)

Br1—C16	2.109 (13)	C5—C6	1.395 (15)
O1—C1	1.377 (11)	C5—H5	0.9300
O1—C9	1.389 (13)	C6—C7	1.428 (15)
O2—C10	1.265 (11)	C7—C8	1.315 (12)
N1—C9	1.290 (11)	C7—H7	0.9300
N1—C11	1.396 (11)	C8—C9	1.447 (12)
N2—C10	1.299 (13)	C8—C10	1.503 (14)
N2—H2NA	0.8600	C11—C12	1.358 (15)
N2—H2NB	0.8600	C11—C16	1.390 (14)
C1—C6	1.368 (13)	C12—C13	1.338 (18)
C1—C2	1.415 (15)	C12—H12	0.9300
C2—C3	1.399 (16)	C13—C14	1.375 (19)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.458 (17)	C14—C15	1.41 (2)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.382 (18)	C15—C16	1.410 (13)
C4—H4	0.9300	C15—H15	0.9300
C1—O1—C9	121.6 (7)	C7—C8—C10	117.9 (8)
C9—N1—C11	122.5 (9)	C9—C8—C10	121.5 (8)
C10—N2—H2NA	120.0	N1—C9—O1	118.1 (8)
C10—N2—H2NB	120.0	N1—C9—C8	125.1 (10)
H2NA—N2—H2NB	120.0	O1—C9—C8	116.8 (8)
C6—C1—O1	121.2 (9)	O2—C10—N2	122.1 (11)
C6—C1—C2	125.2 (11)	O2—C10—C8	117.7 (10)
O1—C1—C2	113.5 (10)	N2—C10—C8	120.1 (9)
C3—C2—C1	114.0 (12)	C12—C11—C16	116.4 (10)
C3—C2—H2	123.0	C12—C11—N1	125.5 (10)
C1—C2—H2	123.0	C16—C11—N1	117.8 (10)
C2—C3—C4	123.0 (13)	C13—C12—C11	123.5 (14)
C2—C3—H3	118.5	C13—C12—H12	118.2
C4—C3—H3	118.5	C11—C12—H12	118.2
C5—C4—C3	117.8 (13)	C12—C13—C14	122.1 (15)
C5—C4—H4	121.1	C12—C13—H13	118.9
C3—C4—H4	121.1	C14—C13—H13	118.9
C4—C5—C6	120.7 (13)	C13—C14—C15	117.3 (12)
C4—C5—H5	119.6	C13—C14—H14	121.3
C6—C5—H5	119.6	C15—C14—H14	121.3
C1—C6—C5	119.2 (11)	C16—C15—C14	118.9 (13)
C1—C6—C7	117.4 (9)	C16—C15—H15	120.6
C5—C6—C7	123.4 (10)	C14—C15—H15	120.6
C8—C7—C6	122.4 (9)	C11—C16—C15	121.6 (12)
C8—C7—H7	118.8	C11—C16—Br1	120.6 (7)
C6—C7—H7	118.8	C15—C16—Br1	117.8 (10)
C7—C8—C9	120.5 (9)
C9—O1—C1—C6	2.0 (15)	C7—C8—C9—N1	−175.5 (10)
C9—O1—C1—C2	−178.5 (9)	C10—C8—C9—N1	9.1 (15)
C6—C1—C2—C3	0.6 (18)	C7—C8—C9—O1	1.3 (14)
O1—C1—C2—C3	−178.8 (10)	C10—C8—C9—O1	−174.1 (9)
C1—C2—C3—C4	−1 (2)	C7—C8—C10—O2	7.8 (15)
C2—C3—C4—C5	2 (2)	C9—C8—C10—O2	−176.6 (10)
C3—C4—C5—C6	−3.0 (19)	C7—C8—C10—N2	−172.0 (10)
O1—C1—C6—C5	177.9 (10)	C9—C8—C10—N2	3.5 (16)
C2—C1—C6—C5	−1.4 (17)	C9—N1—C11—C12	−46.4 (15)
O1—C1—C6—C7	−0.7 (15)	C9—N1—C11—C16	139.9 (11)
C2—C1—C6—C7	179.9 (10)	C16—C11—C12—C13	−2.7 (18)
C4—C5—C6—C1	2.7 (17)	N1—C11—C12—C13	−176.5 (12)
C4—C5—C6—C7	−178.7 (11)	C11—C12—C13—C14	2 (2)
C1—C6—C7—C8	−0.2 (15)	C12—C13—C14—C15	−2 (2)
C5—C6—C7—C8	−178.8 (10)	C13—C14—C15—C16	1 (2)
C6—C7—C8—C9	−0.1 (15)	C12—C11—C16—C15	2.4 (17)
C6—C7—C8—C10	175.5 (9)	N1—C11—C16—C15	176.7 (10)
C11—N1—C9—O1	−4.3 (14)	C12—C11—C16—Br1	−177.9 (8)
C11—N1—C9—C8	172.5 (9)	N1—C11—C16—Br1	−3.6 (13)
C1—O1—C9—N1	174.7 (9)	C14—C15—C16—C11	−1.7 (19)
C1—O1—C9—C8	−2.3 (13)	C14—C15—C16—Br1	178.5 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2NB···N1	0.86	2.08	2.744 (12)	134
N2—H2NA···O2^i	0.86	2.18	2.928 (13)	146

Symmetry code: (i) −x+1, −y, −z+1.

(1i)

Crystal data

C16H11IN2O2	F(000) = 760
Mr = 390.17	Dx = 1.766 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 6.9395 (2) Å	Cell parameters from 3483 reflections
b = 10.2583 (4) Å	θ = 3.4–22.3°
c = 20.7605 (6) Å	µ = 2.19 mm^−1
β = 96.931 (3)°	T = 293 K
V = 1467.09 (8) Å^3	Block, yellow
Z = 4	0.20 × 0.15 × 0.10 mm

Data collection

Xcalibur, Sapphire3 diffractometer	2578 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1998 reflections with I > 2σ(I)
Detector resolution: 16.1827 pixels mm^-1	Rint = 0.058
ω scans	θmax = 25.0°, θmin = 3.0°
Absorption correction: multi-scan CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −8→8
Tmin = 0.811, Tmax = 1.000	k = −12→12
20021 measured reflections	l = −24→24

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.122	w = 1/[σ^2(Fo^2) + (0.055P)^2 + 0.1508P] where P = (Fo^2 + 2Fc^2)/3
S = 1.19	(Δ/σ)max < 0.001
2578 reflections	Δρmax = 0.47 e Å^−3
190 parameters	Δρmin = −0.77 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
I1	0.53215 (6)	0.19461 (4)	0.24992 (2)	0.0955 (2)
O1	0.2277 (4)	0.4979 (2)	0.39859 (11)	0.0507 (6)
O2	0.3687 (5)	0.1222 (3)	0.53063 (14)	0.0690 (8)
N1	0.2499 (5)	0.3029 (3)	0.34764 (14)	0.0451 (7)
N2	0.3766 (5)	0.0933 (3)	0.42434 (16)	0.0573 (9)
H2NA	0.410008	0.012852	0.429488	0.069*
H2NB	0.361364	0.126831	0.386106	0.069*
C1	0.2204 (5)	0.5731 (3)	0.45323 (18)	0.0459 (9)
C2	0.1834 (7)	0.7032 (4)	0.4445 (2)	0.0575 (11)
H2	0.164366	0.739333	0.403109	0.069*
C3	0.1753 (7)	0.7792 (4)	0.4990 (3)	0.0682 (13)
H3	0.147835	0.867605	0.494106	0.082*
C4	0.2071 (7)	0.7268 (5)	0.5607 (2)	0.0656 (12)
H4	0.203303	0.779968	0.596793	0.079*
C5	0.2439 (6)	0.5970 (4)	0.5683 (2)	0.0570 (10)
H5	0.264612	0.561656	0.609820	0.068*
C6	0.2508 (5)	0.5162 (4)	0.51419 (18)	0.0468 (9)
C7	0.2911 (5)	0.3801 (4)	0.51734 (17)	0.0476 (9)
H7	0.314543	0.340988	0.557943	0.057*
C8	0.2968 (6)	0.3059 (3)	0.46468 (18)	0.0441 (9)
C9	0.2555 (5)	0.3661 (4)	0.40056 (17)	0.0438 (8)
C10	0.3489 (6)	0.1651 (4)	0.47509 (19)	0.0480 (9)
C11	0.1997 (6)	0.3606 (4)	0.28605 (17)	0.0455 (9)
C12	0.0442 (7)	0.4443 (4)	0.2730 (2)	0.0685 (13)
H12	−0.026290	0.469134	0.306311	0.082*
C13	−0.0087 (8)	0.4920 (5)	0.2108 (2)	0.0783 (14)
H13	−0.114010	0.548176	0.202581	0.094*
C14	0.0948 (9)	0.4559 (4)	0.1614 (2)	0.0764 (15)
H14	0.060455	0.488271	0.119768	0.092*
C15	0.2473 (8)	0.3731 (4)	0.17339 (19)	0.0677 (13)
H15	0.317320	0.348853	0.139823	0.081*
C16	0.2993 (7)	0.3245 (4)	0.23512 (19)	0.0547 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.1111 (4)	0.1061 (4)	0.0736 (3)	0.0400 (2)	0.0292 (2)	−0.00234 (18)
O1	0.0649 (17)	0.0482 (15)	0.0383 (15)	−0.0016 (12)	0.0038 (11)	0.0053 (11)
O2	0.104 (2)	0.0662 (19)	0.0393 (16)	0.0161 (17)	0.0203 (15)	0.0160 (14)
N1	0.0532 (19)	0.0513 (18)	0.0314 (17)	0.0032 (14)	0.0073 (13)	0.0048 (13)
N2	0.083 (3)	0.0482 (18)	0.0400 (19)	0.0032 (17)	0.0044 (16)	0.0067 (15)
C1	0.042 (2)	0.051 (2)	0.044 (2)	−0.0042 (16)	0.0043 (15)	−0.0008 (17)
C2	0.060 (3)	0.055 (3)	0.057 (3)	−0.0016 (19)	0.004 (2)	0.004 (2)
C3	0.065 (3)	0.052 (3)	0.088 (4)	−0.002 (2)	0.012 (2)	−0.007 (2)
C4	0.056 (3)	0.072 (3)	0.069 (3)	−0.004 (2)	0.011 (2)	−0.020 (2)
C5	0.055 (2)	0.069 (3)	0.048 (2)	−0.008 (2)	0.0096 (18)	−0.006 (2)
C6	0.041 (2)	0.057 (2)	0.043 (2)	−0.0052 (17)	0.0086 (15)	−0.0011 (17)
C7	0.048 (2)	0.059 (2)	0.037 (2)	−0.0017 (18)	0.0076 (15)	0.0074 (17)
C8	0.044 (2)	0.052 (2)	0.037 (2)	−0.0031 (16)	0.0065 (15)	0.0051 (16)
C9	0.043 (2)	0.046 (2)	0.044 (2)	−0.0023 (15)	0.0073 (15)	0.0079 (16)
C10	0.052 (2)	0.053 (2)	0.040 (2)	−0.0001 (17)	0.0071 (16)	0.0070 (18)
C11	0.058 (2)	0.044 (2)	0.034 (2)	−0.0032 (17)	0.0025 (16)	0.0022 (15)
C12	0.072 (3)	0.087 (4)	0.044 (2)	0.015 (2)	−0.001 (2)	0.006 (2)
C13	0.097 (4)	0.078 (3)	0.054 (3)	0.018 (3)	−0.012 (2)	0.009 (3)
C14	0.126 (4)	0.056 (3)	0.042 (3)	−0.015 (3)	−0.011 (3)	0.012 (2)
C15	0.112 (4)	0.057 (3)	0.036 (2)	−0.014 (3)	0.018 (2)	−0.0020 (19)
C16	0.075 (3)	0.051 (2)	0.037 (2)	−0.0050 (19)	0.0057 (19)	−0.0022 (17)

Geometric parameters (Å, º)

I1—C16	2.088 (4)	C5—C6	1.402 (5)
O1—C9	1.366 (4)	C5—H5	0.9300
O1—C1	1.378 (4)	C6—C7	1.424 (6)
O2—C10	1.227 (4)	C7—C8	1.336 (5)
N1—C9	1.272 (4)	C7—H7	0.9300
N1—C11	1.414 (4)	C8—C9	1.464 (5)
N2—C10	1.319 (5)	C8—C10	1.498 (5)
N2—H2NA	0.8600	C11—C12	1.380 (6)
N2—H2NB	0.8600	C11—C16	1.382 (6)
C1—C2	1.366 (5)	C12—C13	1.388 (7)
C1—C6	1.386 (5)	C12—H12	0.9300
C2—C3	1.382 (6)	C13—C14	1.371 (8)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.381 (7)	C14—C15	1.357 (7)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.361 (6)	C15—C16	1.382 (5)
C4—H4	0.9300	C15—H15	0.9300
C9—O1—C1	123.3 (3)	C7—C8—C10	117.5 (3)
C9—N1—C11	123.1 (3)	C9—C8—C10	123.7 (3)
C10—N2—H2NA	120.0	N1—C9—O1	119.3 (3)
C10—N2—H2NB	120.0	N1—C9—C8	123.5 (3)
H2NA—N2—H2NB	120.0	O1—C9—C8	117.1 (3)
C2—C1—O1	117.5 (3)	O2—C10—N2	122.7 (4)
C2—C1—C6	122.5 (4)	O2—C10—C8	118.7 (4)
O1—C1—C6	119.9 (3)	N2—C10—C8	118.7 (3)
C1—C2—C3	117.9 (4)	C12—C11—C16	117.9 (4)
C1—C2—H2	121.1	C12—C11—N1	122.7 (4)
C3—C2—H2	121.1	C16—C11—N1	119.2 (3)
C2—C3—C4	121.5 (4)	C11—C12—C13	121.0 (5)
C2—C3—H3	119.3	C11—C12—H12	119.5
C4—C3—H3	119.3	C13—C12—H12	119.5
C5—C4—C3	119.7 (4)	C14—C13—C12	119.8 (5)
C5—C4—H4	120.2	C14—C13—H13	120.1
C3—C4—H4	120.2	C12—C13—H13	120.1
C4—C5—C6	120.6 (4)	C15—C14—C13	120.0 (4)
C4—C5—H5	119.7	C15—C14—H14	120.0
C6—C5—H5	119.7	C13—C14—H14	120.0
C1—C6—C5	117.8 (4)	C14—C15—C16	120.4 (5)
C1—C6—C7	117.5 (3)	C14—C15—H15	119.8
C5—C6—C7	124.6 (4)	C16—C15—H15	119.8
C8—C7—C6	123.1 (3)	C15—C16—C11	120.9 (4)
C8—C7—H7	118.5	C15—C16—I1	118.5 (3)
C6—C7—H7	118.5	C11—C16—I1	120.6 (3)
C7—C8—C9	118.8 (3)
C9—O1—C1—C2	−177.3 (3)	C7—C8—C9—N1	−177.2 (4)
C9—O1—C1—C6	3.0 (5)	C10—C8—C9—N1	3.9 (6)
O1—C1—C2—C3	179.8 (4)	C7—C8—C9—O1	4.8 (5)
C6—C1—C2—C3	−0.4 (6)	C10—C8—C9—O1	−174.1 (3)
C1—C2—C3—C4	1.2 (7)	C7—C8—C10—O2	5.7 (6)
C2—C3—C4—C5	−1.2 (7)	C9—C8—C10—O2	−175.4 (4)
C3—C4—C5—C6	0.3 (7)	C7—C8—C10—N2	−172.6 (4)
C2—C1—C6—C5	−0.4 (6)	C9—C8—C10—N2	6.3 (6)
O1—C1—C6—C5	179.3 (3)	C9—N1—C11—C12	−44.8 (6)
C2—C1—C6—C7	−179.0 (4)	C9—N1—C11—C16	140.6 (4)
O1—C1—C6—C7	0.7 (5)	C16—C11—C12—C13	−0.9 (7)
C4—C5—C6—C1	0.5 (6)	N1—C11—C12—C13	−175.5 (4)
C4—C5—C6—C7	179.0 (4)	C11—C12—C13—C14	−0.1 (8)
C1—C6—C7—C8	−1.4 (5)	C12—C13—C14—C15	0.5 (8)
C5—C6—C7—C8	−179.9 (4)	C13—C14—C15—C16	0.0 (7)
C6—C7—C8—C9	−1.4 (6)	C14—C15—C16—C11	−1.1 (7)
C6—C7—C8—C10	177.6 (3)	C14—C15—C16—I1	178.9 (3)
C11—N1—C9—O1	−5.6 (5)	C12—C11—C16—C15	1.5 (6)
C11—N1—C9—C8	176.5 (3)	N1—C11—C16—C15	176.3 (4)
C1—O1—C9—N1	176.2 (3)	C12—C11—C16—I1	−178.5 (3)
C1—O1—C9—C8	−5.7 (5)	N1—C11—C16—I1	−3.7 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2NA···O2^i	0.86	2.16	2.912 (5)	146
N2—H2NB···N1	0.86	2.08	2.756 (4)	134

Symmetry code: (i) −x+1, −y, −z+1.

(1ome)

Crystal data

C17H14N2O3	F(000) = 616
Mr = 294.30	Dx = 1.340 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 6.9921 (13) Å	Cell parameters from 715 reflections
b = 10.1424 (15) Å	θ = 3.6–20.0°
c = 20.862 (3) Å	µ = 0.09 mm^−1
β = 99.570 (16)°	T = 293 K
V = 1458.9 (4) Å^3	Block, yellow
Z = 4	0.35 × 0.30 × 0.14 mm

Data collection

Xcalibur, Sapphire3 diffractometer	2570 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1318 reflections with I > 2σ(I)
Detector resolution: 16.1827 pixels mm^-1	Rint = 0.092
ω scans	θmax = 25.0°, θmin = 3.0°
Absorption correction: multi-scan CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −8→8
Tmin = 0.209, Tmax = 1.000	k = −11→12
10371 measured reflections	l = −24→24

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)] = 0.067	w = 1/[σ^2(Fo^2) + (0.086P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.206	(Δ/σ)max = 0.001
S = 1.00	Δρmax = 0.20 e Å^−3
2570 reflections	Δρmin = −0.21 e Å^−3
201 parameters	Extinction correction: SHELXL-2016/6 (Sheldrick 2016), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.007 (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	0.7893 (3)	1.0113 (2)	1.09307 (10)	0.0662 (7)
O2	0.6130 (3)	0.6305 (2)	0.96041 (10)	0.0750 (7)
O3	0.5459 (4)	0.7538 (3)	1.23034 (12)	0.0983 (10)
N1	0.7599 (4)	0.8138 (3)	1.14338 (12)	0.0623 (7)
N2	0.6360 (4)	0.6016 (3)	1.06834 (12)	0.0700 (8)
H2NA	0.601678	0.520268	1.063893	0.084*
H2NB	0.662101	0.635884	1.106502	0.084*
C1	0.7901 (4)	1.0851 (3)	1.03763 (16)	0.0604 (8)
C2	0.8323 (5)	1.2182 (3)	1.04632 (19)	0.0743 (10)
H2	0.861119	1.254351	1.087765	0.089*
C3	0.8305 (5)	1.2950 (4)	0.9919 (2)	0.0842 (12)
H3	0.856948	1.384703	0.996718	0.101*
C4	0.7900 (5)	1.2413 (4)	0.9304 (2)	0.0844 (12)
H4	0.791501	1.294317	0.894070	0.101*
C5	0.7478 (5)	1.1103 (4)	0.92288 (18)	0.0729 (10)
H5	0.717895	1.074815	0.881306	0.088*
C6	0.7488 (4)	1.0289 (3)	0.97687 (15)	0.0573 (8)
C7	0.7056 (4)	0.8912 (3)	0.97332 (15)	0.0597 (8)
H7	0.675968	0.851617	0.932678	0.072*
C8	0.7062 (4)	0.8173 (3)	1.02642 (14)	0.0530 (8)
C9	0.7532 (4)	0.8772 (3)	1.09056 (15)	0.0554 (8)
C10	0.6487 (5)	0.6743 (3)	1.01632 (16)	0.0598 (8)
C11	0.8114 (5)	0.8708 (3)	1.20570 (14)	0.0629 (9)
C12	0.9692 (6)	0.9505 (4)	1.22375 (17)	0.0854 (12)
H12	1.042563	0.976319	1.192607	0.102*
C13	1.0217 (7)	0.9932 (4)	1.2864 (2)	0.0923 (12)
H13	1.129226	1.047433	1.297779	0.111*
C14	0.9131 (7)	0.9547 (4)	1.33244 (19)	0.0934 (14)
H14	0.948704	0.982483	1.375237	0.112*
C15	0.7535 (6)	0.8761 (4)	1.31617 (17)	0.0835 (12)
H15	0.680062	0.851938	1.347591	0.100*
C16	0.7016 (6)	0.8325 (3)	1.25278 (16)	0.0713 (10)
C17	0.4321 (8)	0.7073 (5)	1.2755 (2)	0.1271 (18)
H17A	0.318729	0.664061	1.252688	0.191*
H17B	0.393723	0.780266	1.299772	0.191*
H17C	0.506416	0.646051	1.304649	0.191*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0811 (16)	0.0629 (14)	0.0533 (14)	0.0006 (11)	0.0072 (11)	−0.0095 (10)
O2	0.1000 (19)	0.0788 (16)	0.0489 (14)	−0.0114 (13)	0.0201 (12)	−0.0174 (11)
O3	0.127 (2)	0.109 (2)	0.0611 (17)	−0.0409 (18)	0.0240 (15)	0.0011 (13)
N1	0.0755 (18)	0.0698 (17)	0.0411 (16)	0.0015 (13)	0.0087 (13)	−0.0087 (12)
N2	0.098 (2)	0.0612 (17)	0.0482 (17)	−0.0027 (15)	0.0052 (14)	−0.0038 (12)
C1	0.060 (2)	0.065 (2)	0.059 (2)	0.0104 (15)	0.0155 (15)	0.0023 (16)
C2	0.075 (2)	0.066 (2)	0.082 (3)	0.0063 (18)	0.0134 (19)	−0.0106 (19)
C3	0.077 (3)	0.071 (2)	0.108 (4)	0.0032 (19)	0.026 (2)	0.012 (2)
C4	0.079 (3)	0.091 (3)	0.087 (3)	0.016 (2)	0.026 (2)	0.018 (2)
C5	0.076 (2)	0.077 (2)	0.069 (2)	0.0084 (18)	0.0199 (17)	0.0035 (19)
C6	0.0516 (19)	0.066 (2)	0.056 (2)	0.0098 (15)	0.0144 (15)	0.0011 (16)
C7	0.061 (2)	0.076 (2)	0.0419 (18)	0.0069 (16)	0.0091 (14)	−0.0079 (15)
C8	0.0562 (18)	0.0630 (19)	0.0408 (17)	−0.0002 (14)	0.0111 (13)	−0.0071 (14)
C9	0.0534 (18)	0.064 (2)	0.0497 (19)	0.0041 (15)	0.0112 (14)	−0.0076 (15)
C10	0.065 (2)	0.069 (2)	0.0466 (19)	0.0051 (15)	0.0127 (15)	−0.0049 (16)
C11	0.080 (2)	0.066 (2)	0.0406 (19)	−0.0014 (18)	0.0050 (16)	−0.0102 (15)
C12	0.096 (3)	0.102 (3)	0.054 (2)	−0.016 (2)	0.0009 (19)	−0.019 (2)
C13	0.113 (3)	0.093 (3)	0.063 (3)	−0.015 (2)	−0.006 (2)	−0.016 (2)
C14	0.141 (4)	0.079 (3)	0.050 (2)	0.018 (3)	−0.014 (2)	−0.0155 (19)
C15	0.133 (4)	0.078 (2)	0.043 (2)	0.005 (2)	0.025 (2)	0.0003 (18)
C16	0.102 (3)	0.066 (2)	0.045 (2)	−0.001 (2)	0.0112 (19)	0.0008 (16)
C17	0.152 (5)	0.150 (4)	0.088 (3)	−0.053 (3)	0.046 (3)	0.012 (3)

Geometric parameters (Å, º)

O1—C1	1.379 (4)	C5—H5	0.9300
O1—C9	1.383 (4)	C6—C7	1.428 (4)
O2—C10	1.234 (3)	C7—C8	1.337 (4)
O3—C16	1.368 (4)	C7—H7	0.9300
O3—C17	1.411 (4)	C8—C9	1.456 (4)
N1—C9	1.270 (4)	C8—C10	1.511 (4)
N1—C11	1.414 (4)	C11—C12	1.369 (5)
N2—C10	1.327 (4)	C11—C16	1.398 (4)
N2—H2NA	0.8600	C12—C13	1.368 (5)
N2—H2NB	0.8600	C12—H12	0.9300
C1—C6	1.376 (4)	C13—C14	1.376 (5)
C1—C2	1.387 (4)	C13—H13	0.9300
C2—C3	1.375 (5)	C14—C15	1.367 (5)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.381 (5)	C15—C16	1.384 (5)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.365 (5)	C17—H17A	0.9600
C4—H4	0.9300	C17—H17B	0.9600
C5—C6	1.395 (4)	C17—H17C	0.9600
C1—O1—C9	121.9 (2)	N1—C9—O1	119.0 (3)
C16—O3—C17	118.1 (3)	N1—C9—C8	123.8 (3)
C9—N1—C11	123.9 (3)	O1—C9—C8	117.2 (3)
C10—N2—H2NA	120.0	O2—C10—N2	122.9 (3)
C10—N2—H2NB	120.0	O2—C10—C8	119.0 (3)
H2NA—N2—H2NB	120.0	N2—C10—C8	118.1 (3)
C6—C1—O1	121.2 (3)	C12—C11—C16	118.8 (3)
C6—C1—C2	122.1 (3)	C12—C11—N1	124.4 (3)
O1—C1—C2	116.7 (3)	C16—C11—N1	116.5 (3)
C3—C2—C1	118.1 (4)	C13—C12—C11	121.7 (4)
C3—C2—H2	120.9	C13—C12—H12	119.1
C1—C2—H2	120.9	C11—C12—H12	119.1
C2—C3—C4	121.1 (4)	C12—C13—C14	119.0 (4)
C2—C3—H3	119.5	C12—C13—H13	120.5
C4—C3—H3	119.5	C14—C13—H13	120.5
C5—C4—C3	119.9 (4)	C15—C14—C13	121.0 (4)
C5—C4—H4	120.1	C15—C14—H14	119.5
C3—C4—H4	120.1	C13—C14—H14	119.5
C4—C5—C6	120.8 (4)	C14—C15—C16	119.8 (4)
C4—C5—H5	119.6	C14—C15—H15	120.1
C6—C5—H5	119.6	C16—C15—H15	120.1
C1—C6—C5	118.1 (3)	O3—C16—C15	125.5 (4)
C1—C6—C7	117.6 (3)	O3—C16—C11	114.8 (3)
C5—C6—C7	124.3 (3)	C15—C16—C11	119.7 (4)
C8—C7—C6	122.3 (3)	O3—C17—H17A	109.5
C8—C7—H7	118.9	O3—C17—H17B	109.5
C6—C7—H7	118.9	H17A—C17—H17B	109.5
C7—C8—C9	119.8 (3)	O3—C17—H17C	109.5
C7—C8—C10	117.3 (3)	H17A—C17—H17C	109.5
C9—C8—C10	122.9 (3)	H17B—C17—H17C	109.5
C9—O1—C1—C6	2.0 (4)	C10—C8—C9—N1	3.7 (4)
C9—O1—C1—C2	−178.6 (3)	C7—C8—C9—O1	2.1 (4)
C6—C1—C2—C3	0.6 (5)	C10—C8—C9—O1	−175.2 (3)
O1—C1—C2—C3	−178.7 (3)	C7—C8—C10—O2	3.4 (4)
C1—C2—C3—C4	−0.7 (5)	C9—C8—C10—O2	−179.2 (3)
C2—C3—C4—C5	1.1 (6)	C7—C8—C10—N2	−175.6 (3)
C3—C4—C5—C6	−1.3 (5)	C9—C8—C10—N2	1.8 (4)
O1—C1—C6—C5	178.5 (3)	C9—N1—C11—C12	−47.4 (5)
C2—C1—C6—C5	−0.8 (4)	C9—N1—C11—C16	138.4 (3)
O1—C1—C6—C7	−0.1 (4)	C16—C11—C12—C13	0.1 (6)
C2—C1—C6—C7	−179.5 (3)	N1—C11—C12—C13	−174.0 (3)
C4—C5—C6—C1	1.2 (5)	C11—C12—C13—C14	0.1 (6)
C4—C5—C6—C7	179.7 (3)	C12—C13—C14—C15	−0.7 (6)
C1—C6—C7—C8	−0.7 (4)	C13—C14—C15—C16	1.1 (6)
C5—C6—C7—C8	−179.2 (3)	C17—O3—C16—C15	−3.0 (6)
C6—C7—C8—C9	−0.4 (4)	C17—O3—C16—C11	177.8 (3)
C6—C7—C8—C10	177.1 (3)	C14—C15—C16—O3	180.0 (3)
C11—N1—C9—O1	−3.1 (4)	C14—C15—C16—C11	−0.9 (5)
C11—N1—C9—C8	178.0 (3)	C12—C11—C16—O3	179.5 (3)
C1—O1—C9—N1	178.0 (3)	N1—C11—C16—O3	−6.0 (5)
C1—O1—C9—C8	−3.0 (4)	C12—C11—C16—C15	0.3 (5)
C7—C8—C9—N1	−178.9 (3)	N1—C11—C16—C15	174.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2NB···N1	0.86	2.03	2.717 (4)	136
N2—H2NA···O2^i	0.86	2.14	2.931 (4)	152

Symmetry code: (i) −x+1, −y+1, −z+2.