Concomitant polymorphs of 1,3-bis­(3-fluoro­phenyl)urea

Hydrogen bonding between urea functionalities is a common structural motif employed in crystal-engineering studies. Crystallization of 1,3-bis(3-fluoro­phenyl)urea, C₁₃H₁₀F₂N₂O, from many solvents yielded concomitant mixtures of at least two polymorphs. In the monoclinic form, one-dimensional chains of hydrogen-bonded urea molecules align in an antiparallel orientation, as is typical of many di­phenyl­ureas. In the ortho­rhom­bic form, one-dimensional chains of hydrogen-bonded urea molecules have a parallel orientation rarely observed in symmetrically substituted di­phenyl­ureas.

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2005) for (I); APEX2 (Bruker, 2014) for (II). Cell refinement: CrysAlis RED (Oxford Diffraction, 2005) for (I); APEX2 (Bruker, 2014) for (II). Data reduction: CrysAlis RED (Oxford Diffraction, 2005) for (I); SAINT (Bruker, 2014) for (II). Program(s) used to solve structure: SHELXTL (Sheldrick, 2008) for (I); SHELXT (Sheldrick, 2015a) for (II). For both compounds, program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: SHELXTL (Bruker, 2014); software used to prepare material for publication: XCIF (Bruker, 2014) and publCIF (Westrip, 2010).

(I) 1,3-Bis(3-fluorophenyl)urea

Crystal data

C13H10F2N2O	F(000) = 1024
Mr = 248.23	Dx = 1.463 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 20.6614 (19) Å	Cell parameters from 2884 reflections
b = 12.6052 (11) Å	θ = 1.9–28.6°
c = 9.1691 (9) Å	µ = 0.12 mm^−1
β = 109.284 (9)°	T = 110 K
V = 2254.0 (4) Å^3	Prism, colorless
Z = 8	0.23 × 0.09 × 0.03 mm

Data collection

Multiwire proportional diffractometer	2858 independent reflections
Radiation source: sealed tube	2048 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
phi and ω scans	θmax = 28.6°, θmin = 3.9°
Absorption correction: numerical (CrysAlis RED; Oxford Diffraction, 2005)	h = −27→27
Tmin = 0.957, Tmax = 0.993	k = −16→16
12889 measured reflections	l = −12→12

Refinement

Refinement on F^2	2 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.145	w = 1/[σ^2(Fo^2) + (0.0722P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.13	(Δ/σ)max < 0.001
2858 reflections	Δρmax = 0.28 e Å^−3
179 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.

Refinement. Structure was phased by direct methods (Sheldrick, 2015). Systematic conditions suggested the unambiguous space group. The space group choice was confirmed by successful convergence of the full-matrix least-squares refinement on F². The final map had no significant features. A final analysis of variance between observed and calculated structure factors showed some dependence on amplitude and little dependence on resolution.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.12765 (6)	0.02147 (9)	0.59284 (12)	0.0251 (3)
N1	0.10058 (7)	−0.07341 (11)	0.77665 (17)	0.0246 (4)
H1	0.1032 (10)	−0.0784 (16)	0.8748 (18)	0.037*
N2	0.14840 (7)	0.09098 (11)	0.83494 (16)	0.0240 (3)
H2	0.1430 (10)	0.0760 (16)	0.9273 (19)	0.036*
F1	0.07380 (7)	−0.44765 (9)	0.73146 (14)	0.0499 (4)
F2	0.24104 (8)	0.35311 (11)	0.57553 (16)	0.0404 (5)	0.806 (4)
F2'	0.1802 (3)	0.4426 (5)	0.9954 (7)	0.045 (2)	0.194 (4)
C1	0.12571 (8)	0.01375 (13)	0.72571 (18)	0.0206 (4)
C2	0.07261 (9)	−0.16392 (13)	0.6848 (2)	0.0235 (4)
C3	0.08879 (9)	−0.26293 (14)	0.7515 (2)	0.0279 (4)
H3	0.1196	−0.2706	0.8540	0.033*
C4	0.05883 (10)	−0.35044 (14)	0.6648 (2)	0.0317 (4)
C5	0.01393 (10)	−0.34403 (15)	0.5156 (2)	0.0335 (5)
H5	−0.0058	−0.4059	0.4591	0.040*
C6	−0.00125 (9)	−0.24426 (14)	0.4516 (2)	0.0294 (4)
H6	−0.0318	−0.2372	0.3488	0.035*
C7	0.02722 (9)	−0.15437 (14)	0.5345 (2)	0.0264 (4)
H7	0.0158	−0.0862	0.4890	0.032*
C8	0.17014 (8)	0.19427 (13)	0.81364 (18)	0.0223 (4)
C9	0.19741 (9)	0.22055 (15)	0.6986 (2)	0.0269 (4)
H9	0.2027	0.1686	0.6283	0.032*
C10	0.21657 (9)	0.32459 (16)	0.6900 (2)	0.0308 (4)
H10	0.2352	0.3428	0.6115	0.037*	0.194 (4)
C11	0.21032 (9)	0.40341 (15)	0.7879 (2)	0.0311 (4)
H11	0.2235	0.4744	0.7773	0.037*
C12	0.18407 (9)	0.37474 (15)	0.9026 (2)	0.0289 (4)
H12	0.1795	0.4270	0.9732	0.035*	0.806 (4)
C13	0.16428 (8)	0.27157 (14)	0.91671 (19)	0.0239 (4)
H13A	0.1466	0.2535	0.9969	0.029*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0324 (7)	0.0267 (7)	0.0168 (6)	0.0021 (5)	0.0089 (5)	−0.0002 (5)
N1	0.0333 (8)	0.0238 (8)	0.0177 (7)	−0.0039 (6)	0.0097 (6)	−0.0033 (6)
N2	0.0315 (8)	0.0248 (8)	0.0157 (7)	−0.0046 (6)	0.0077 (6)	−0.0015 (6)
F1	0.0621 (9)	0.0234 (6)	0.0516 (8)	0.0004 (6)	0.0017 (6)	0.0049 (5)
F2	0.0503 (9)	0.0424 (9)	0.0381 (9)	−0.0132 (7)	0.0274 (7)	0.0032 (6)
F2'	0.051 (4)	0.037 (4)	0.047 (4)	−0.004 (3)	0.015 (3)	−0.014 (3)
C1	0.0207 (8)	0.0242 (9)	0.0160 (8)	0.0032 (7)	0.0046 (6)	0.0000 (6)
C2	0.0245 (9)	0.0243 (9)	0.0229 (9)	0.0001 (7)	0.0096 (7)	−0.0030 (7)
C3	0.0284 (9)	0.0283 (10)	0.0251 (9)	−0.0017 (8)	0.0065 (7)	−0.0007 (7)
C4	0.0361 (11)	0.0211 (9)	0.0364 (11)	0.0015 (8)	0.0100 (8)	0.0022 (8)
C5	0.0361 (11)	0.0259 (10)	0.0348 (11)	−0.0035 (8)	0.0067 (9)	−0.0086 (8)
C6	0.0269 (9)	0.0320 (10)	0.0261 (9)	0.0012 (8)	0.0043 (7)	−0.0034 (8)
C7	0.0273 (9)	0.0263 (9)	0.0245 (9)	0.0036 (7)	0.0072 (7)	−0.0014 (7)
C8	0.0200 (8)	0.0230 (9)	0.0204 (8)	−0.0022 (7)	0.0020 (7)	0.0013 (7)
C9	0.0267 (9)	0.0321 (10)	0.0220 (9)	−0.0023 (8)	0.0083 (7)	−0.0011 (7)
C10	0.0281 (10)	0.0387 (11)	0.0263 (9)	−0.0073 (8)	0.0099 (7)	0.0056 (8)
C11	0.0295 (10)	0.0269 (10)	0.0334 (10)	−0.0048 (8)	0.0054 (8)	0.0042 (8)
C12	0.0284 (10)	0.0271 (9)	0.0272 (10)	−0.0009 (8)	0.0035 (8)	−0.0021 (8)
C13	0.0227 (8)	0.0288 (9)	0.0191 (8)	−0.0017 (7)	0.0055 (7)	0.0004 (7)

Geometric parameters (Å, º)

O1—C1	1.2360 (18)	C5—H5	0.9500
N1—C1	1.362 (2)	C6—C7	1.383 (2)
N1—C2	1.423 (2)	C6—H6	0.9500
N1—H1	0.886 (15)	C7—H7	0.9500
N2—C1	1.364 (2)	C8—C9	1.390 (2)
N2—C8	1.412 (2)	C8—C13	1.390 (2)
N2—H2	0.909 (15)	C9—C10	1.380 (3)
F1—C4	1.359 (2)	C9—H9	0.9500
F2—C10	1.355 (2)	C10—C11	1.374 (3)
F2'—C12	1.227 (6)	C10—H10	0.9500
C2—C3	1.382 (2)	C11—C12	1.381 (3)
C2—C7	1.392 (2)	C11—H11	0.9500
C3—C4	1.381 (3)	C12—C13	1.382 (2)
C3—H3	0.9500	C12—H12	0.9500
C4—C5	1.379 (3)	C13—H13A	0.9500
C5—C6	1.379 (3)
C1—N1—C2	124.76 (14)	C6—C7—H7	120.1
C1—N1—H1	120.2 (13)	C2—C7—H7	120.1
C2—N1—H1	114.9 (13)	C9—C8—C13	119.79 (16)
C1—N2—C8	127.19 (14)	C9—C8—N2	123.51 (16)
C1—N2—H2	114.7 (13)	C13—C8—N2	116.69 (15)
C8—N2—H2	117.6 (13)	C10—C9—C8	117.79 (17)
O1—C1—N1	122.80 (15)	C10—C9—H9	121.1
O1—C1—N2	123.54 (15)	C8—C9—H9	121.1
N1—C1—N2	113.66 (14)	F2—C10—C11	117.00 (17)
C3—C2—C7	120.11 (16)	F2—C10—C9	118.97 (18)
C3—C2—N1	118.08 (16)	C11—C10—C9	123.99 (17)
C7—C2—N1	121.72 (16)	C11—C10—H10	118.0
C4—C3—C2	118.01 (17)	C9—C10—H10	118.0
C4—C3—H3	121.0	C10—C11—C12	117.00 (17)
C2—C3—H3	121.0	C10—C11—H11	121.5
F1—C4—C5	118.55 (16)	C12—C11—H11	121.5
F1—C4—C3	117.99 (17)	F2'—C12—C11	118.5 (3)
C5—C4—C3	123.46 (17)	F2'—C12—C13	120.1 (3)
C4—C5—C6	117.35 (17)	C11—C12—C13	121.35 (17)
C4—C5—H5	121.3	C11—C12—H12	119.3
C6—C5—H5	121.3	C13—C12—H12	119.3
C5—C6—C7	121.17 (17)	C12—C13—C8	120.07 (16)
C5—C6—H6	119.4	C12—C13—H13A	120.0
C7—C6—H6	119.4	C8—C13—H13A	120.0
C6—C7—C2	119.89 (17)
C2—N1—C1—O1	−1.3 (3)	N1—C2—C7—C6	−177.02 (16)
C2—N1—C1—N2	178.71 (15)	C1—N2—C8—C9	−26.6 (3)
C8—N2—C1—O1	7.5 (3)	C1—N2—C8—C13	154.41 (16)
C8—N2—C1—N1	−172.58 (16)	C13—C8—C9—C10	−1.2 (2)
C1—N1—C2—C3	139.16 (17)	N2—C8—C9—C10	179.85 (16)
C1—N1—C2—C7	−44.3 (2)	C8—C9—C10—F2	−177.69 (15)
C7—C2—C3—C4	0.1 (3)	C8—C9—C10—C11	0.0 (3)
N1—C2—C3—C4	176.76 (16)	F2—C10—C11—C12	178.72 (16)
C2—C3—C4—F1	−178.85 (16)	C9—C10—C11—C12	1.0 (3)
C2—C3—C4—C5	0.1 (3)	C10—C11—C12—F2'	177.4 (4)
F1—C4—C5—C6	178.96 (17)	C10—C11—C12—C13	−0.7 (3)
C3—C4—C5—C6	0.0 (3)	F2'—C12—C13—C8	−178.5 (4)
C4—C5—C6—C7	−0.4 (3)	C11—C12—C13—C8	−0.4 (3)
C5—C6—C7—C2	0.7 (3)	C9—C8—C13—C12	1.5 (2)
C3—C2—C7—C6	−0.5 (3)	N2—C8—C13—C12	−179.55 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1^i	0.91 (2)	2.06 (2)	2.9076 (18)	155 (2)
N1—H1···O1^i	0.89 (2)	2.02 (2)	2.8417 (18)	153 (2)

Symmetry code: (i) x, −y, z+1/2.

(II) 1,3-Bis(3-fluorophenyl)urea

Crystal data

C13H10F2N2O	Dx = 1.492 Mg m^−3
Mr = 248.23	Melting point = 143.8–147.6 K
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
a = 23.5797 (19) Å	Cell parameters from 4113 reflections
b = 10.1792 (8) Å	θ = 2.6–27.4°
c = 4.6031 (4) Å	µ = 0.12 mm^−1
V = 1104.85 (16) Å^3	T = 100 K
Z = 4	Needle, colorless
F(000) = 512	0.60 × 0.10 × 0.06 mm

Data collection

Bruker APEXII SMART platform CCD diffractometer	2624 independent reflections
Radiation source: fine-focus sealed tube	2443 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
ω scans	θmax = 28.2°, θmin = 1.7°
Absorption correction: multi-scan SADABS V2014/4 (Bruker, 2014)	h = −31→31
Tmin = 0.932, Tmax = 0.993	k = −12→13
9603 measured reflections	l = −6→6

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.030	w = 1/[σ^2(Fo^2) + (0.034P)^2 + 0.2739P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.072	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.22 e Å^−3
2624 reflections	Δρmin = −0.17 e Å^−3
179 parameters	Absolute structure: Flack x determined using 989 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
3 restraints	Absolute structure parameter: −0.4 (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. Structure was phased by direct methods (Sheldrick, 2015). Systematic conditions suggested the unambiguous space group. The space group choice was confirmed by successful convergence of the full-matrix least-squares refinement on F². The final map had no significant features. A final analysis of variance between observed and calculated structure factors showed little dependence on amplitude and resolution.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.37757 (6)	1.07011 (12)	0.6264 (3)	0.0167 (3)
N1	0.35674 (7)	1.17231 (15)	1.0544 (4)	0.0155 (3)
H1	0.3632 (10)	1.168 (2)	1.239 (5)	0.023*
N2	0.40708 (7)	0.98087 (15)	1.0560 (4)	0.0151 (3)
H2	0.4080 (10)	0.995 (2)	1.238 (5)	0.023*
F1	0.22284 (5)	1.37274 (13)	0.4117 (3)	0.0311 (3)
F2	0.41590 (5)	0.60920 (12)	0.4201 (3)	0.0238 (4)	0.932 (4)
F2'	0.5579 (8)	0.6757 (17)	1.074 (5)	0.033 (6)	0.068 (4)
C1	0.37987 (7)	1.07346 (17)	0.8938 (4)	0.0133 (3)
C2	0.33047 (7)	1.28461 (17)	0.9336 (4)	0.0143 (3)
C3	0.28907 (8)	1.27192 (19)	0.7186 (4)	0.0173 (4)
H3	0.2790	1.1883	0.6430	0.021*
C4	0.26326 (8)	1.38512 (19)	0.6199 (4)	0.0200 (4)
C5	0.27633 (9)	1.5085 (2)	0.7213 (5)	0.0223 (4)
H5	0.2578	1.5842	0.6469	0.027*
C6	0.31752 (8)	1.51897 (18)	0.9358 (5)	0.0206 (4)
H6	0.3271	1.6029	1.0113	0.025*
C7	0.34474 (8)	1.40791 (18)	1.0408 (5)	0.0175 (4)
H7	0.3731	1.4161	1.1861	0.021*
C8	0.43509 (7)	0.86969 (17)	0.9403 (4)	0.0143 (4)
C9	0.41038 (8)	0.79368 (17)	0.7222 (4)	0.0159 (4)
H9	0.3748	0.8166	0.6399	0.019*
C10	0.43970 (8)	0.68379 (18)	0.6308 (4)	0.0182 (4)
H10A	0.4233	0.6316	0.4817	0.022*	0.068 (4)
C11	0.49123 (8)	0.64515 (18)	0.7422 (5)	0.0190 (4)
H11	0.5099	0.5687	0.6729	0.023*
C12	0.51479 (8)	0.72211 (18)	0.9597 (4)	0.0194 (4)
H12	0.5501	0.6976	1.0426	0.023*	0.932 (4)
C13	0.48738 (8)	0.83459 (18)	1.0582 (4)	0.0164 (4)
H13	0.5042	0.8873	1.2051	0.020*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0219 (7)	0.0183 (6)	0.0099 (7)	0.0035 (5)	0.0000 (5)	−0.0003 (5)
N1	0.0220 (8)	0.0153 (7)	0.0091 (7)	0.0034 (6)	−0.0019 (6)	0.0004 (6)
N2	0.0215 (8)	0.0149 (7)	0.0090 (7)	0.0035 (6)	−0.0011 (6)	−0.0024 (6)
F1	0.0274 (6)	0.0424 (7)	0.0236 (7)	0.0102 (5)	−0.0115 (6)	−0.0018 (6)
F2	0.0286 (7)	0.0203 (6)	0.0225 (7)	−0.0011 (5)	−0.0044 (6)	−0.0096 (6)
F2'	0.033 (11)	0.024 (10)	0.041 (12)	0.005 (8)	−0.001 (10)	0.001 (9)
C1	0.0131 (8)	0.0145 (8)	0.0125 (9)	−0.0023 (6)	0.0004 (7)	0.0000 (7)
C2	0.0147 (8)	0.0167 (8)	0.0116 (8)	0.0024 (6)	0.0026 (7)	0.0011 (7)
C3	0.0179 (9)	0.0203 (9)	0.0139 (9)	0.0005 (7)	0.0002 (7)	−0.0024 (7)
C4	0.0162 (9)	0.0303 (10)	0.0135 (9)	0.0049 (8)	−0.0018 (7)	0.0005 (8)
C5	0.0253 (10)	0.0225 (10)	0.0190 (10)	0.0104 (8)	0.0030 (8)	0.0053 (8)
C6	0.0245 (9)	0.0153 (8)	0.0220 (10)	0.0012 (7)	0.0039 (8)	−0.0009 (8)
C7	0.0169 (8)	0.0198 (9)	0.0158 (9)	0.0014 (7)	−0.0006 (8)	−0.0014 (7)
C8	0.0177 (8)	0.0133 (8)	0.0119 (8)	0.0001 (6)	0.0032 (7)	0.0019 (7)
C9	0.0174 (8)	0.0168 (8)	0.0133 (9)	−0.0007 (7)	−0.0010 (7)	0.0007 (7)
C10	0.0252 (10)	0.0151 (8)	0.0143 (9)	−0.0041 (7)	0.0013 (8)	−0.0025 (7)
C11	0.0240 (9)	0.0145 (8)	0.0185 (9)	0.0033 (7)	0.0045 (8)	−0.0006 (7)
C12	0.0186 (9)	0.0200 (9)	0.0197 (10)	0.0032 (7)	0.0011 (8)	0.0016 (8)
C13	0.0186 (9)	0.0169 (9)	0.0136 (9)	−0.0010 (7)	−0.0014 (7)	−0.0006 (7)

Geometric parameters (Å, º)

O1—C1	1.232 (2)	C5—H5	0.9500
N1—C1	1.362 (2)	C6—C7	1.387 (3)
N1—C2	1.414 (2)	C6—H6	0.9500
N1—H1	0.86 (2)	C7—H7	0.9500
N2—C1	1.363 (2)	C8—C13	1.394 (3)
N2—C8	1.415 (2)	C8—C9	1.395 (3)
N2—H2	0.85 (2)	C9—C10	1.381 (3)
F1—C4	1.358 (2)	C9—H9	0.9500
F2—C10	1.354 (2)	C10—C11	1.376 (3)
F2'—C12	1.238 (19)	C10—H10A	0.9500
C2—C7	1.390 (3)	C11—C12	1.387 (3)
C2—C3	1.396 (3)	C11—H11	0.9500
C3—C4	1.380 (3)	C12—C13	1.391 (3)
C3—H3	0.9500	C12—H12	0.9500
C4—C5	1.375 (3)	C13—H13	0.9500
C5—C6	1.389 (3)
C1—N1—C2	123.99 (16)	C6—C7—H7	120.0
C1—N1—H1	115.4 (16)	C2—C7—H7	120.0
C2—N1—H1	120.1 (16)	C13—C8—C9	120.50 (16)
C1—N2—C8	124.53 (16)	C13—C8—N2	118.14 (17)
C1—N2—H2	115.5 (16)	C9—C8—N2	121.31 (16)
C8—N2—H2	119.9 (16)	C10—C9—C8	117.35 (17)
O1—C1—N1	122.99 (17)	C10—C9—H9	121.3
O1—C1—N2	123.28 (16)	C8—C9—H9	121.3
N1—C1—N2	113.70 (16)	F2—C10—C11	118.22 (17)
C7—C2—C3	120.31 (18)	F2—C10—C9	117.73 (17)
C7—C2—N1	118.95 (17)	C11—C10—C9	124.05 (18)
C3—C2—N1	120.69 (17)	C11—C10—H10A	118.0
C4—C3—C2	117.68 (18)	C9—C10—H10A	118.0
C4—C3—H3	121.2	C10—C11—C12	117.47 (17)
C2—C3—H3	121.2	C10—C11—H11	121.3
F1—C4—C5	118.79 (17)	C12—C11—H11	121.3
F1—C4—C3	117.68 (17)	F2'—C12—C11	114.9 (9)
C5—C4—C3	123.53 (18)	F2'—C12—C13	123.8 (10)
C4—C5—C6	117.89 (17)	C11—C12—C13	120.92 (17)
C4—C5—H5	121.1	C11—C12—H12	119.5
C6—C5—H5	121.1	C13—C12—H12	119.5
C7—C6—C5	120.59 (18)	C12—C13—C8	119.70 (18)
C7—C6—H6	119.7	C12—C13—H13	120.2
C5—C6—H6	119.7	C8—C13—H13	120.2
C6—C7—C2	120.01 (19)
C2—N1—C1—O1	−3.6 (3)	N1—C2—C7—C6	−176.84 (18)
C2—N1—C1—N2	174.72 (16)	C1—N2—C8—C13	137.98 (19)
C8—N2—C1—O1	−0.9 (3)	C1—N2—C8—C9	−44.5 (3)
C8—N2—C1—N1	−179.16 (17)	C13—C8—C9—C10	0.1 (3)
C1—N1—C2—C7	−132.70 (19)	N2—C8—C9—C10	−177.35 (17)
C1—N1—C2—C3	50.0 (3)	C8—C9—C10—F2	179.73 (17)
C7—C2—C3—C4	−0.2 (3)	C8—C9—C10—C11	0.3 (3)
N1—C2—C3—C4	177.02 (17)	F2—C10—C11—C12	−179.47 (17)
C2—C3—C4—F1	−179.75 (17)	C9—C10—C11—C12	0.0 (3)
C2—C3—C4—C5	0.2 (3)	C10—C11—C12—F2'	172.5 (11)
F1—C4—C5—C6	179.54 (18)	C10—C11—C12—C13	−0.6 (3)
C3—C4—C5—C6	−0.4 (3)	F2'—C12—C13—C8	−171.5 (12)
C4—C5—C6—C7	0.6 (3)	C11—C12—C13—C8	1.0 (3)
C5—C6—C7—C2	−0.7 (3)	C9—C8—C13—C12	−0.7 (3)
C3—C2—C7—C6	0.5 (3)	N2—C8—C13—C12	176.81 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.86 (2)	2.07 (2)	2.874 (2)	154 (2)
N2—H2···O1^i	0.85 (2)	2.07 (2)	2.864 (2)	155 (2)

Symmetry code: (i) x, y, z+1.