Conformations of substituted benzophenones

The inclination of the two aryl rings (ring twists) in a series of benzophenone molecules has been examined. For each structure the dihedral angle (between the planes of the two sets of six aromatic C atoms) relates to both the steric considerations of the single molecule and the packing forces related to the crystal structure. Six new benzophenone structures are incorporated into the study including 2,2'-dihydroxy-4,4'-dimethoxybenzophenone (I), C₁₅H₁₄O₅, that appears to have the smallest reported twist angle, 37.85 (5)°, of any substituted benzophenone reported to date. Three further benzophenones, 4,4'-bis(diethylamino)benzophenone (II), C₂₁H₂₈N₂O, 3,4-dihydroxybenzophenone (III), C₁₃H₁₀O₃, and 3-hydroxybenzophenone (IV), C₁₃H₁₀O₂, have similar ring twists [49.83 (5), 49.84 (5) and 51.61 (5)°, respectively] that are comparable with the value of 54° found for the orthorhombic form of unsubstituted benzophenone. 4-Chloro-4'-hydroxybenzophenone (V), C₁₃H₉ClO₂, has a ring twist of 64.66 (8)° that is close to the value of 65° found in the metastable monoclinic form of unsubstituted benzophenone and 2-amino-2',5-dichlorobenzophenone (VI), C₁₃H₉Cl₂NO₂, has a large ring twist of 83.72 (6)°. Comparisons with a further 98 substituted benzophenone molecules from the Cambridge Structural Database (CSD) have been made.

Computing details

For all compounds, data collection: DENZO (Otwinowski and Minor, 1997), COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SIR97 (Altomare et al.,1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek,2002); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).

Figures

(2d4d)

Crystal data

C15H14O5	F(000) = 576
Mr = 274.26	Dx = 1.452 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 3.8466 (1) Å	Cell parameters from 5660 reflections
b = 25.1521 (12) Å	θ = 2.9–27.5°
c = 12.9802 (6) Å	µ = 0.11 mm^−1
β = 92.545 (3)°	T = 120 K
V = 1254.60 (9) Å^3	Rod, yellow
Z = 4	0.52 × 0.08 × 0.06 mm

Data collection

Bruker-Nonius 95mm CCD camers on κ-goniostat diffractometer	1759 reflections with I > 2σ(I)
ϕ and ω scans to fill Ewald sphere	Rint = 0.083
Absorption correction: multi-scan using multiple and symmetry-related data measurements via the program SORTAV (Blessing, 1995, 1997)	θmax = 27.5°, θmin = 3.1°
Tmin = 0.727, Tmax = 0.994	h = −4→4
13532 measured reflections	k = −32→32
2798 independent reflections	l = −16→16

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.047	w = 1/[σ^2(Fo^2) + (0.0601P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.119	(Δ/σ)max < 0.001
S = 0.99	Δρmax = 0.23 e Å^−3
2798 reflections	Δρmin = −0.30 e Å^−3
189 parameters

Special details

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

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

	x	y	z	Uiso*/Ueq
O1	0.2426 (4)	0.33006 (5)	0.61210 (10)	0.0338 (4)
O2	0.4075 (3)	0.42282 (5)	0.55737 (10)	0.0276 (3)
H2	0.381 (5)	0.3930 (8)	0.5979 (16)	0.036*
O3	−0.0324 (4)	0.24312 (5)	0.67400 (10)	0.0317 (4)
H3	0.070 (6)	0.2763 (9)	0.6786 (17)	0.041*
O4	0.0095 (3)	0.48074 (5)	0.22432 (9)	0.0239 (3)
O5	−0.1132 (3)	0.10187 (4)	0.43090 (10)	0.0260 (3)
C1	0.1229 (5)	0.35934 (7)	0.44219 (14)	0.0196 (4)
C2	0.2486 (5)	0.41104 (7)	0.46524 (14)	0.0214 (4)
C3	0.2200 (4)	0.45220 (7)	0.39415 (14)	0.0213 (4)
H3A	0.3132	0.4863	0.4106	0.026*
C4	0.0548 (4)	0.44305 (7)	0.29931 (14)	0.0195 (4)
C5	−0.0861 (4)	0.39294 (7)	0.27505 (14)	0.0216 (4)
H5	−0.2036	0.3871	0.2101	0.026*
C6	−0.0537 (5)	0.35252 (7)	0.34528 (14)	0.0201 (4)
H6	−0.1527	0.3189	0.3284	0.024*
C7	0.1609 (5)	0.31745 (7)	0.51936 (14)	0.0226 (4)
C8	0.0985 (4)	0.26080 (7)	0.49646 (14)	0.0204 (4)
C9	−0.0052 (5)	0.22660 (7)	0.57542 (13)	0.0214 (4)
C10	−0.0920 (4)	0.17398 (7)	0.55475 (14)	0.0210 (4)
H10	−0.1814	0.1522	0.6072	0.025*
C11	−0.0477 (4)	0.15351 (7)	0.45766 (14)	0.0206 (4)
C12	0.0805 (5)	0.18543 (7)	0.37953 (14)	0.0224 (4)
H12	0.1201	0.1708	0.3136	0.027*
C13	0.1481 (4)	0.23805 (7)	0.39920 (14)	0.0204 (4)
H13	0.2309	0.2598	0.3456	0.024*
C14	0.1601 (5)	0.53209 (7)	0.24568 (15)	0.0268 (5)
H14A	0.4127	0.5285	0.2567	0.032*
H14B	0.0613	0.5469	0.3077	0.032*
H14C	0.1091	0.5559	0.1871	0.032*
C15	−0.2433 (5)	0.06766 (7)	0.50848 (16)	0.0294 (5)
H15A	−0.4637	0.0818	0.5319	0.035*
H15B	−0.0737	0.0657	0.567	0.035*
H15C	−0.2816	0.032	0.4797	0.035*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0563 (10)	0.0266 (7)	0.0184 (7)	−0.0064 (7)	−0.0016 (7)	−0.0016 (6)
O2	0.0406 (8)	0.0223 (7)	0.0194 (7)	−0.0049 (6)	−0.0034 (6)	0.0001 (6)
O3	0.0506 (9)	0.0258 (7)	0.0192 (7)	−0.0043 (7)	0.0088 (7)	0.0000 (6)
O4	0.0298 (7)	0.0190 (6)	0.0227 (7)	−0.0003 (6)	−0.0025 (6)	0.0017 (5)
O5	0.0340 (8)	0.0168 (7)	0.0275 (8)	−0.0036 (5)	0.0026 (6)	0.0012 (5)
C1	0.0198 (9)	0.0188 (9)	0.0207 (10)	0.0000 (7)	0.0055 (8)	−0.0017 (7)
C2	0.0201 (10)	0.0242 (10)	0.0198 (10)	0.0001 (8)	0.0017 (8)	−0.0047 (8)
C3	0.0209 (10)	0.0181 (9)	0.0251 (10)	−0.0012 (8)	0.0033 (8)	−0.0022 (8)
C4	0.0190 (9)	0.0196 (9)	0.0202 (10)	0.0016 (7)	0.0039 (8)	0.0009 (8)
C5	0.0208 (10)	0.0230 (10)	0.0208 (10)	−0.0004 (8)	−0.0004 (8)	−0.0040 (8)
C6	0.0179 (9)	0.0173 (9)	0.0254 (10)	−0.0008 (7)	0.0038 (8)	−0.0031 (8)
C7	0.0243 (10)	0.0219 (9)	0.0219 (10)	−0.0013 (8)	0.0051 (8)	−0.0028 (8)
C8	0.0200 (10)	0.0193 (9)	0.0219 (10)	0.0003 (7)	0.0019 (8)	0.0004 (8)
C9	0.0214 (9)	0.0242 (10)	0.0188 (10)	0.0029 (8)	0.0035 (8)	−0.0006 (8)
C10	0.0207 (10)	0.0212 (9)	0.0214 (10)	0.0011 (7)	0.0026 (8)	0.0050 (8)
C11	0.0181 (9)	0.0166 (9)	0.0269 (10)	0.0003 (7)	−0.0014 (8)	0.0006 (8)
C12	0.0257 (10)	0.0223 (9)	0.0196 (10)	0.0004 (8)	0.0036 (8)	−0.0006 (8)
C13	0.0212 (9)	0.0204 (9)	0.0199 (10)	0.0013 (7)	0.0041 (8)	0.0030 (8)
C14	0.0305 (11)	0.0210 (10)	0.0289 (11)	−0.0042 (8)	−0.0006 (9)	0.0030 (8)
C15	0.0314 (11)	0.0215 (10)	0.0351 (12)	−0.0070 (8)	−0.0001 (10)	0.0051 (9)

Geometric parameters (Å, º)

O1—C7	1.271 (2)	C6—H6	0.95
O2—C2	1.352 (2)	C7—C8	1.473 (2)
O2—H2	0.92 (2)	C8—C13	1.407 (2)
O3—C9	1.354 (2)	C8—C9	1.409 (2)
O3—H3	0.92 (2)	C9—C10	1.388 (2)
O4—C4	1.364 (2)	C10—C11	1.379 (2)
O4—C14	1.438 (2)	C10—H10	0.95
O5—C11	1.365 (2)	C11—C12	1.400 (2)
O5—C15	1.432 (2)	C12—C13	1.370 (2)
C1—C6	1.413 (2)	C12—H12	0.95
C1—C2	1.415 (2)	C13—H13	0.95
C1—C7	1.457 (2)	C14—H14A	0.98
C2—C3	1.388 (2)	C14—H14B	0.98
C3—C4	1.379 (2)	C14—H14C	0.98
C3—H3A	0.95	C15—H15A	0.98
C4—C5	1.402 (2)	C15—H15B	0.98
C5—C6	1.368 (2)	C15—H15C	0.98
C5—H5	0.95
C2—O2—H2	105.6 (13)	O3—C9—C10	116.57 (16)
C9—O3—H3	106.8 (14)	O3—C9—C8	122.43 (16)
C4—O4—C14	116.68 (14)	C10—C9—C8	120.99 (16)
C11—O5—C15	117.33 (14)	C11—C10—C9	119.62 (16)
C6—C1—C2	116.50 (16)	C11—C10—H10	120.2
C6—C1—C7	123.63 (16)	C9—C10—H10	120.2
C2—C1—C7	119.77 (16)	O5—C11—C10	123.98 (16)
O2—C2—C3	116.37 (16)	O5—C11—C12	115.36 (16)
O2—C2—C1	121.71 (17)	C10—C11—C12	120.64 (16)
C3—C2—C1	121.92 (17)	C13—C12—C11	119.26 (17)
C4—C3—C2	119.25 (17)	C13—C12—H12	120.4
C4—C3—H3A	120.4	C11—C12—H12	120.4
C2—C3—H3A	120.4	C12—C13—C8	121.86 (16)
O4—C4—C3	124.06 (15)	C12—C13—H13	119.1
O4—C4—C5	115.37 (16)	C8—C13—H13	119.1
C3—C4—C5	120.57 (16)	O4—C14—H14A	109.5
C6—C5—C4	119.71 (17)	O4—C14—H14B	109.5
C6—C5—H5	120.1	H14A—C14—H14B	109.5
C4—C5—H5	120.1	O4—C14—H14C	109.5
C5—C6—C1	121.94 (16)	H14A—C14—H14C	109.5
C5—C6—H6	119	H14B—C14—H14C	109.5
C1—C6—H6	119	O5—C15—H15A	109.5
O1—C7—C1	118.94 (16)	O5—C15—H15B	109.5
O1—C7—C8	117.64 (16)	H15A—C15—H15B	109.5
C1—C7—C8	123.40 (16)	O5—C15—H15C	109.5
C13—C8—C9	117.28 (16)	H15A—C15—H15C	109.5
C13—C8—C7	123.18 (16)	H15B—C15—H15C	109.5
C9—C8—C7	119.51 (16)
C6—C1—C2—O2	176.98 (15)	O1—C7—C8—C13	−152.89 (17)
C7—C1—C2—O2	0.6 (2)	C1—C7—C8—C13	29.1 (3)
C6—C1—C2—C3	−3.9 (2)	O1—C7—C8—C9	25.0 (3)
C7—C1—C2—C3	179.70 (16)	C1—C7—C8—C9	−153.03 (17)
O2—C2—C3—C4	−178.80 (15)	C13—C8—C9—O3	174.32 (16)
C1—C2—C3—C4	2.0 (3)	C7—C8—C9—O3	−3.7 (3)
C14—O4—C4—C3	3.0 (2)	C13—C8—C9—C10	−7.0 (3)
C14—O4—C4—C5	−178.19 (14)	C7—C8—C9—C10	174.99 (16)
C2—C3—C4—O4	179.36 (16)	O3—C9—C10—C11	−175.60 (16)
C2—C3—C4—C5	0.6 (3)	C8—C9—C10—C11	5.7 (3)
O4—C4—C5—C6	179.93 (15)	C15—O5—C11—C10	1.5 (3)
C3—C4—C5—C6	−1.2 (3)	C15—O5—C11—C12	179.74 (16)
C4—C5—C6—C1	−0.8 (3)	C9—C10—C11—O5	177.49 (16)
C2—C1—C6—C5	3.3 (2)	C9—C10—C11—C12	−0.7 (3)
C7—C1—C6—C5	179.52 (16)	O5—C11—C12—C13	178.96 (16)
C6—C1—C7—O1	−162.36 (17)	C10—C11—C12—C13	−2.7 (3)
C2—C1—C7—O1	13.8 (2)	C11—C12—C13—C8	1.2 (3)
C6—C1—C7—C8	15.6 (3)	C9—C8—C13—C12	3.6 (3)
C2—C1—C7—C8	−168.26 (17)	C7—C8—C13—C12	−178.52 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.92 (2)	1.68 (2)	2.5278 (18)	150.4 (19)
O3—H3···O1	0.92 (2)	1.75 (2)	2.5733 (18)	147 (2)

(orla1)

Crystal data

C21H28N2O	F(000) = 704
Mr = 324.45	Dx = 1.148 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.8519 (6) Å	Cell parameters from 7747 reflections
b = 8.0488 (3) Å	θ = 2.9–27.5°
c = 14.3060 (5) Å	µ = 0.07 mm^−1
β = 104.6390 (18)°	T = 120 K
V = 1877.44 (12) Å^3	Block, yellow
Z = 4	0.4 × 0.35 × 0.3 mm

Data collection

Bruker-Nonius 95mm CCD camers on κ-goniostat diffractometer	2862 reflections with I > 2σ(I)
ϕ and ω scans to fill Ewald sphere	Rint = 0.077
Absorption correction: multi-scan using multiple and symmetry-related data measurements via the program SORTAV (Blessing, 1995, 1997)	θmax = 27.6°, θmin = 2.9°
Tmin = 0.948, Tmax = 0.979	h = −21→20
18012 measured reflections	k = −10→10
4315 independent reflections	l = −18→17

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0604P)^2 + 0.1446P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.047	(Δ/σ)max < 0.001
wR(F^2) = 0.122	Δρmax = 0.21 e Å^−3
S = 1.01	Δρmin = −0.22 e Å^−3
4315 reflections	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
288 parameters	Extinction coefficient: 0.022 (3)
12 restraints

Special details

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

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.21302 (6)	0.37913 (13)	−0.03565 (6)	0.0378 (3)
N1	0.04238 (6)	0.46832 (13)	0.30992 (8)	0.0276 (3)
C1	0.19625 (8)	0.41149 (15)	0.12139 (9)	0.0248 (3)
C2	0.11718 (8)	0.47691 (16)	0.08965 (9)	0.0279 (3)
H2	0.0979	0.5087	0.0238	0.033*
C3	0.06650 (8)	0.49685 (16)	0.15005 (9)	0.0283 (3)
H3	0.0133	0.5424	0.1255	0.034*
C4	0.09226 (7)	0.45064 (15)	0.24850 (9)	0.0239 (3)
C5	0.17115 (7)	0.38146 (15)	0.28030 (9)	0.0250 (3)
H5	0.1903	0.3466	0.3456	0.03*
C6	0.22097 (8)	0.36365 (16)	0.21806 (9)	0.0255 (3)
H6	0.2741	0.3171	0.2418	0.031*
C7	0.24639 (8)	0.38725 (16)	0.05165 (9)	0.0277 (3)
C8	0.33683 (8)	0.37333 (16)	0.08431 (9)	0.0280 (3)
C9	0.37810 (9)	0.2873 (2)	0.02651 (11)	0.0418 (4)
H9	0.3474	0.2209	−0.0249	0.05*
C12	0.46909 (8)	0.45890 (18)	0.18373 (10)	0.0338 (3)
H12	0.5002	0.5094	0.2414	0.041*
C13	0.38483 (8)	0.45762 (16)	0.16373 (9)	0.0280 (3)
H13	0.3586	0.5159	0.2053	0.034*
C14	−0.03863 (8)	0.54452 (16)	0.27895 (11)	0.0320 (3)
H14A	−0.0376	0.6301	0.2296	0.038*
H14B	−0.0514	0.6008	0.3349	0.038*
C15	−0.10576 (8)	0.42046 (18)	0.23747 (12)	0.0398 (4)
H15A	−0.1086	0.3378	0.2868	0.052*
H15B	−0.0937	0.3647	0.1817	0.052*
H15C	−0.1584	0.4785	0.217	0.052*
C16	0.06846 (8)	0.41796 (18)	0.41061 (10)	0.0322 (3)
H16A	0.1012	0.3148	0.4153	0.039*
H16B	0.0194	0.3929	0.4342	0.039*
C17	0.11913 (10)	0.5493 (2)	0.47512 (11)	0.0480 (4)
H17A	0.0866	0.651	0.4722	0.062*
H17B	0.1684	0.5733	0.453	0.062*
H17C	0.1351	0.5086	0.5418	0.062*
N21	0.59266 (12)	0.3978 (3)	0.13297 (18)	0.0346 (5)	0.745 (5)
C101	0.4608 (3)	0.2954 (4)	0.0414 (3)	0.0331 (8)	0.745 (5)
H101	0.4863	0.2388	−0.0016	0.043*	0.745 (5)
C111	0.5095 (2)	0.3858 (4)	0.1191 (3)	0.0286 (8)	0.745 (5)
C181	0.63371 (13)	0.3154 (3)	0.06763 (16)	0.0355 (7)	0.745 (5)
H18A	0.6867	0.3718	0.0716	0.046*	0.745 (5)
H18B	0.5996	0.3278	0.0006	0.046*	0.745 (5)
C191	0.64962 (15)	0.1329 (3)	0.0888 (2)	0.0467 (7)	0.745 (5)
H19A	0.598	0.0772	0.089	0.061*	0.745 (5)
H19B	0.6884	0.1198	0.1521	0.061*	0.745 (5)
H19C	0.6728	0.0834	0.0389	0.061*	0.745 (5)
C201	0.6426 (3)	0.5046 (5)	0.2070 (4)	0.0395 (11)	0.745 (5)
H20A	0.6101	0.604	0.2142	0.051*	0.745 (5)
H20B	0.6907	0.5427	0.1848	0.051*	0.745 (5)
C211	0.6729 (7)	0.4228 (15)	0.3050 (5)	0.0508 (14)	0.745 (5)
H21A	0.7075	0.3272	0.2995	0.066*	0.745 (5)
H21B	0.6259	0.3853	0.3281	0.066*	0.745 (5)
H21C	0.705	0.503	0.3509	0.066*	0.745 (5)
N22	0.5980 (3)	0.3237 (10)	0.1681 (5)	0.0337 (16)	0.255 (5)
C102	0.4655 (8)	0.2415 (13)	0.0661 (8)	0.036 (2)	0.255 (5)
H102	0.4883	0.15	0.04	0.047*	0.255 (5)
C112	0.5143 (6)	0.3344 (12)	0.1424 (7)	0.027 (2)	0.255 (5)
C182	0.6415 (4)	0.1982 (8)	0.1290 (5)	0.0361 (18)	0.255 (5)
H18C	0.6087	0.0947	0.1204	0.047*	0.255 (5)
H18D	0.6939	0.1751	0.177	0.047*	0.255 (5)
C192	0.6599 (5)	0.2417 (10)	0.0337 (5)	0.049 (2)	0.255 (5)
H19D	0.6924	0.3442	0.0411	0.064*	0.255 (5)
H19E	0.6084	0.2581	−0.0156	0.064*	0.255 (5)
H19F	0.691	0.1511	0.0139	0.064*	0.255 (5)
C202	0.6463 (9)	0.4550 (16)	0.2279 (11)	0.044 (4)	0.255 (5)
H20C	0.6128	0.5573	0.222	0.057*	0.255 (5)
H20D	0.695	0.4801	0.2035	0.057*	0.255 (5)
C212	0.674 (2)	0.407 (5)	0.3327 (13)	0.059 (5)	0.255 (5)
H21D	0.7157	0.3191	0.3406	0.076*	0.255 (5)
H21E	0.6271	0.3652	0.3546	0.076*	0.255 (5)
H21F	0.6975	0.5036	0.3713	0.076*	0.255 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0358 (6)	0.0525 (6)	0.0240 (5)	−0.0097 (5)	0.0058 (4)	−0.0074 (5)
N1	0.0218 (6)	0.0312 (6)	0.0303 (6)	0.0034 (4)	0.0077 (5)	0.0001 (5)
C1	0.0237 (7)	0.0243 (6)	0.0255 (7)	−0.0039 (5)	0.0046 (5)	−0.0019 (5)
C2	0.0288 (7)	0.0282 (7)	0.0238 (6)	−0.0016 (5)	0.0014 (5)	0.0024 (6)
C3	0.0225 (7)	0.0274 (6)	0.0320 (7)	0.0023 (5)	0.0017 (6)	0.0008 (6)
C4	0.0221 (7)	0.0207 (6)	0.0285 (7)	−0.0024 (5)	0.0058 (5)	−0.0017 (5)
C5	0.0216 (7)	0.0283 (6)	0.0242 (6)	0.0006 (5)	0.0044 (5)	0.0025 (6)
C6	0.0214 (7)	0.0259 (6)	0.0280 (7)	0.0005 (5)	0.0039 (5)	0.0004 (6)
C7	0.0303 (7)	0.0274 (6)	0.0250 (7)	−0.0075 (5)	0.0066 (6)	−0.0031 (6)
C8	0.0274 (7)	0.0315 (7)	0.0274 (7)	−0.0069 (5)	0.0109 (6)	−0.0047 (6)
C9	0.0338 (9)	0.0522 (9)	0.0421 (8)	−0.0124 (7)	0.0145 (7)	−0.0230 (8)
C12	0.0291 (8)	0.0399 (8)	0.0324 (7)	−0.0070 (6)	0.0076 (6)	−0.0095 (6)
C13	0.0280 (8)	0.0305 (7)	0.0269 (7)	−0.0026 (5)	0.0093 (6)	−0.0033 (6)
C14	0.0257 (7)	0.0288 (7)	0.0430 (8)	0.0069 (5)	0.0117 (6)	0.0025 (6)
C15	0.0245 (8)	0.0379 (8)	0.0545 (10)	0.0048 (6)	0.0054 (7)	0.0056 (7)
C16	0.0262 (7)	0.0411 (8)	0.0319 (7)	0.0011 (6)	0.0121 (6)	0.0015 (6)
C17	0.0391 (9)	0.0709 (11)	0.0366 (8)	−0.0087 (8)	0.0145 (7)	−0.0130 (8)
N21	0.0243 (10)	0.0374 (12)	0.0430 (12)	−0.0042 (8)	0.0101 (9)	−0.0046 (10)
C101	0.0317 (14)	0.0358 (19)	0.0353 (18)	−0.0047 (14)	0.0149 (13)	−0.0091 (14)
C111	0.0248 (13)	0.0262 (17)	0.0357 (19)	−0.0009 (11)	0.0095 (11)	0.0028 (12)
C181	0.0272 (11)	0.0411 (13)	0.0418 (12)	0.0015 (9)	0.0154 (9)	0.0045 (11)
C191	0.0513 (15)	0.0457 (15)	0.0489 (16)	0.0135 (11)	0.0233 (12)	0.0083 (13)
C201	0.0300 (16)	0.040 (2)	0.049 (2)	−0.0108 (15)	0.0091 (15)	−0.0056 (18)
C211	0.046 (2)	0.047 (3)	0.053 (4)	−0.007 (2)	0.001 (3)	−0.004 (3)
N22	0.021 (3)	0.040 (4)	0.042 (4)	0.000 (2)	0.012 (2)	−0.006 (3)
C102	0.036 (4)	0.035 (5)	0.043 (6)	−0.001 (4)	0.021 (4)	−0.004 (4)
C112	0.029 (4)	0.028 (5)	0.026 (5)	0.000 (3)	0.008 (3)	0.006 (3)
C182	0.039 (4)	0.035 (4)	0.036 (4)	0.003 (3)	0.013 (3)	0.004 (3)
C192	0.046 (4)	0.056 (4)	0.049 (4)	0.009 (3)	0.020 (3)	0.017 (4)
C202	0.020 (5)	0.056 (8)	0.061 (9)	−0.017 (6)	0.019 (5)	0.001 (6)
C212	0.061 (7)	0.048 (8)	0.057 (10)	−0.003 (5)	−0.003 (9)	−0.002 (9)

Geometric parameters (Å, º)

O1—C7	1.2350 (15)	C17—H17B	0.98
N1—C4	1.3682 (16)	C17—H17C	0.98
N1—C16	1.4535 (17)	N21—C111	1.368 (4)
N1—C14	1.4596 (16)	N21—C201	1.455 (5)
C1—C6	1.3940 (18)	N21—C181	1.456 (3)
C1—C2	1.3976 (18)	C101—C111	1.407 (4)
C1—C7	1.4742 (17)	C101—H101	0.95
C2—C3	1.3692 (18)	C181—C191	1.510 (3)
C2—H2	0.95	C181—H18A	0.99
C3—C4	1.4148 (18)	C181—H18B	0.99
C3—H3	0.95	C191—H19A	0.98
C4—C5	1.4066 (17)	C191—H19B	0.98
C5—C6	1.3770 (17)	C191—H19C	0.98
C5—H5	0.95	C201—C211	1.517 (6)
C6—H6	0.95	C201—H20A	0.99
C7—C8	1.4811 (18)	C201—H20B	0.99
C8—C9	1.3919 (19)	C211—H21A	0.98
C8—C13	1.3933 (18)	C211—H21B	0.98
C9—C101	1.357 (5)	C211—H21C	0.98
C9—C102	1.485 (13)	N22—C112	1.368 (10)
C9—H9	0.95	N22—C182	1.441 (9)
C12—C13	1.3758 (19)	N22—C202	1.470 (12)
C12—C111	1.408 (4)	C102—C112	1.405 (12)
C12—C112	1.470 (11)	C102—H102	0.95
C12—H12	0.95	C182—C192	1.515 (9)
C13—H13	0.95	C182—H18C	0.99
C14—C15	1.513 (2)	C182—H18D	0.99
C14—H14A	0.99	C192—H19D	0.98
C14—H14B	0.99	C192—H19E	0.98
C15—H15A	0.98	C192—H19F	0.98
C15—H15B	0.98	C202—C212	1.505 (14)
C15—H15C	0.98	C202—H20C	0.99
C16—C17	1.517 (2)	C202—H20D	0.99
C16—H16A	0.99	C212—H21D	0.98
C16—H16B	0.99	C212—H21E	0.98
C17—H17A	0.98	C212—H21F	0.98
C4—N1—C16	121.77 (10)	C16—C17—H17B	109.5
C4—N1—C14	121.88 (11)	H17A—C17—H17B	109.5
C16—N1—C14	116.32 (10)	C16—C17—H17C	109.5
C6—C1—C2	116.59 (11)	H17A—C17—H17C	109.5
C6—C1—C7	123.79 (12)	H17B—C17—H17C	109.5
C2—C1—C7	119.50 (11)	C111—N21—C201	122.0 (3)
C3—C2—C1	122.33 (12)	C111—N21—C181	120.7 (2)
C3—C2—H2	118.8	C201—N21—C181	117.0 (3)
C1—C2—H2	118.8	C9—C101—C111	121.3 (3)
C2—C3—C4	120.93 (12)	C9—C101—H101	119.4
C2—C3—H3	119.5	C111—C101—H101	119.4
C4—C3—H3	119.5	N21—C111—C101	121.5 (3)
N1—C4—C5	121.16 (11)	N21—C111—C12	121.5 (3)
N1—C4—C3	121.88 (11)	C101—C111—C12	116.9 (3)
C5—C4—C3	116.94 (11)	N21—C181—C191	113.8 (2)
C6—C5—C4	120.87 (12)	N21—C181—H18A	108.8
C6—C5—H5	119.6	C191—C181—H18A	108.8
C4—C5—H5	119.6	N21—C181—H18B	108.8
C5—C6—C1	122.32 (12)	C191—C181—H18B	108.8
C5—C6—H6	118.8	H18A—C181—H18B	107.7
C1—C6—H6	118.8	N21—C201—C211	114.5 (5)
O1—C7—C1	119.94 (12)	N21—C201—H20A	108.6
O1—C7—C8	118.96 (11)	C211—C201—H20A	108.6
C1—C7—C8	121.10 (11)	N21—C201—H20B	108.6
C9—C8—C13	116.89 (12)	C211—C201—H20B	108.6
C9—C8—C7	118.62 (12)	H20A—C201—H20B	107.6
C13—C8—C7	124.02 (11)	C112—N22—C182	122.1 (6)
C101—C9—C8	122.1 (2)	C112—N22—C202	119.6 (8)
C8—C9—C102	119.6 (5)	C182—N22—C202	117.9 (8)
C101—C9—H9	119	C112—C102—C9	119.6 (9)
C8—C9—H9	119	C112—C102—H102	120.2
C102—C9—H9	116.7	C9—C102—H102	120.2
C13—C12—C111	120.36 (18)	N22—C112—C102	122.5 (10)
C13—C12—C112	121.6 (4)	N22—C112—C12	122.6 (7)
C13—C12—H12	119.8	C102—C112—C12	114.5 (8)
C111—C12—H12	119.8	N22—C182—C192	115.3 (7)
C112—C12—H12	114.4	N22—C182—H18C	108.5
C12—C13—C8	121.95 (12)	C192—C182—H18C	108.5
C12—C13—H13	119	N22—C182—H18D	108.5
C8—C13—H13	119	C192—C182—H18D	108.5
N1—C14—C15	113.02 (11)	H18C—C182—H18D	107.5
N1—C14—H14A	109	C182—C192—H19D	109.5
C15—C14—H14A	109	C182—C192—H19E	109.5
N1—C14—H14B	109	H19D—C192—H19E	109.5
C15—C14—H14B	109	C182—C192—H19F	109.5
H14A—C14—H14B	107.8	H19D—C192—H19F	109.5
C14—C15—H15A	109.5	H19E—C192—H19F	109.5
C14—C15—H15B	109.5	N22—C202—C212	112.4 (16)
H15A—C15—H15B	109.5	N22—C202—H20C	109.1
C14—C15—H15C	109.5	C212—C202—H20C	109.1
H15A—C15—H15C	109.5	N22—C202—H20D	109.1
H15B—C15—H15C	109.5	C212—C202—H20D	109.1
N1—C16—C17	113.04 (12)	H20C—C202—H20D	107.9
N1—C16—H16A	109	C202—C212—H21D	109.5
C17—C16—H16A	109	C202—C212—H21E	109.5
N1—C16—H16B	109	H21D—C212—H21E	109.5
C17—C16—H16B	109	C202—C212—H21F	109.5
H16A—C16—H16B	107.8	H21D—C212—H21F	109.5
C16—C17—H17A	109.5	H21E—C212—H21F	109.5
C6—C1—C2—C3	1.28 (19)	C14—N1—C16—C17	−94.02 (14)
C7—C1—C2—C3	177.60 (12)	C8—C9—C101—C111	2.9 (4)
C1—C2—C3—C4	−0.3 (2)	C102—C9—C101—C111	−87.2 (16)
C16—N1—C4—C5	0.45 (18)	C201—N21—C111—C101	173.5 (3)
C14—N1—C4—C5	178.07 (11)	C181—N21—C111—C101	−0.6 (4)
C16—N1—C4—C3	178.87 (12)	C201—N21—C111—C12	−8.5 (4)
C14—N1—C4—C3	−3.51 (19)	C181—N21—C111—C12	177.4 (3)
C2—C3—C4—N1	−179.50 (12)	C9—C101—C111—N21	−178.3 (3)
C2—C3—C4—C5	−1.01 (18)	C9—C101—C111—C12	3.6 (4)
N1—C4—C5—C6	179.85 (12)	C13—C12—C111—N21	174.3 (2)
C3—C4—C5—C6	1.36 (18)	C112—C12—C111—N21	−86.1 (13)
C4—C5—C6—C1	−0.39 (19)	C13—C12—C111—C101	−7.7 (3)
C2—C1—C6—C5	−0.93 (18)	C112—C12—C111—C101	91.9 (13)
C7—C1—C6—C5	−177.08 (12)	C111—N21—C181—C191	−81.1 (3)
C6—C1—C7—O1	155.74 (13)	C201—N21—C181—C191	104.5 (3)
C2—C1—C7—O1	−20.30 (18)	C111—N21—C201—C211	88.3 (7)
C6—C1—C7—C8	−24.64 (18)	C181—N21—C201—C211	−97.4 (7)
C2—C1—C7—C8	159.32 (12)	C101—C9—C102—C112	78.4 (15)
O1—C7—C8—C9	−25.90 (19)	C8—C9—C102—C112	−24.6 (10)
C1—C7—C8—C9	154.48 (13)	C182—N22—C112—C102	−10.0 (12)
O1—C7—C8—C13	146.07 (13)	C202—N22—C112—C102	162.5 (9)
C1—C7—C8—C13	−33.55 (19)	C182—N22—C112—C12	178.3 (7)
C13—C8—C9—C101	−5.3 (3)	C202—N22—C112—C12	−9.3 (12)
C7—C8—C9—C101	167.2 (2)	C9—C102—C112—N22	−165.2 (7)
C13—C8—C9—C102	20.0 (5)	C9—C102—C112—C12	7.2 (11)
C7—C8—C9—C102	−167.4 (5)	C13—C12—C112—N22	−173.9 (6)
C111—C12—C13—C8	5.4 (2)	C111—C12—C112—N22	93.1 (15)
C112—C12—C13—C8	−18.9 (5)	C13—C12—C112—C102	13.8 (8)
C9—C8—C13—C12	1.1 (2)	C111—C12—C112—C102	−79.3 (14)
C7—C8—C13—C12	−170.99 (13)	C112—N22—C182—C192	86.2 (9)
C4—N1—C14—C15	89.47 (15)	C202—N22—C182—C192	−86.3 (10)
C16—N1—C14—C15	−92.79 (15)	C112—N22—C202—C212	100 (2)
C4—N1—C16—C17	83.72 (15)	C182—N22—C202—C212	−88 (2)

(orla2)

Crystal data

C13H10O3	F(000) = 896
Mr = 214.21	Dx = 1.404 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 24.4619 (9) Å	Cell parameters from 11394 reflections
b = 7.3737 (2) Å	θ = 2.9–27.5°
c = 12.3961 (4) Å	µ = 0.1 mm^−1
β = 115.019 (2)°	T = 120 K
V = 2026.14 (11) Å^3	Plate, colourless
Z = 8	0.24 × 0.14 × 0.03 mm

Data collection

Bruker-Nonius 95mm CCD camers on κ-goniostat diffractometer	1733 reflections with I > 2σ(I)
ϕ and ω scans to fill Ewald sphere	Rint = 0.074
Absorption correction: multi-scan using multiple and symmetry-related data measurements via the program SORTAV (Blessing, 1995, 1997)	θmax = 27.5°, θmin = 2.9°
Tmin = 0.913, Tmax = 0.997	h = −31→31
16476 measured reflections	k = −9→9
2319 independent reflections	l = −15→16

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.048	w = 1/[σ^2(Fo^2) + (0.0555P)^2 + 1.1706P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.114	(Δ/σ)max = 0.001
S = 1.03	Δρmax = 0.19 e Å^−3
2319 reflections	Δρmin = −0.29 e Å^−3
152 parameters

Special details

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

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

	x	y	z	Uiso*/Ueq
O1	0.66586 (5)	0.08148 (16)	0.40009 (9)	0.0243 (3)
O2	0.56113 (5)	0.05271 (16)	0.75039 (10)	0.0242 (3)
H2	0.5968 (9)	−0.006 (3)	0.8012 (16)	0.029*
O3	0.46801 (5)	0.24018 (16)	0.58310 (10)	0.0270 (3)
H3	0.4682 (8)	0.172 (3)	0.6473 (17)	0.032*
C1	0.62252 (7)	0.1488 (2)	0.53207 (13)	0.0185 (3)
C2	0.61879 (7)	0.0841 (2)	0.63465 (13)	0.0185 (3)
H2A	0.6517	0.0193	0.6925	0.022*
C3	0.56755 (7)	0.1140 (2)	0.65227 (13)	0.0188 (3)
C4	0.51906 (7)	0.2092 (2)	0.56816 (14)	0.0204 (3)
C5	0.52305 (7)	0.2761 (2)	0.46731 (14)	0.0220 (3)
H5	0.4905	0.3437	0.4106	0.026*
C6	0.57402 (7)	0.2450 (2)	0.44867 (13)	0.0217 (4)
H6A	0.5761	0.2895	0.3785	0.026*
C7	0.67428 (7)	0.1048 (2)	0.50480 (13)	0.0193 (3)
C8	0.73631 (7)	0.0819 (2)	0.60007 (13)	0.0194 (3)
C9	0.77717 (7)	−0.0204 (2)	0.57393 (14)	0.0232 (4)
H9	0.7649	−0.072	0.497	0.028*
C10	0.83534 (7)	−0.0471 (2)	0.65921 (15)	0.0268 (4)
H10	0.8629	−0.118	0.6413	0.032*
C11	0.85344 (7)	0.0300 (2)	0.77117 (15)	0.0273 (4)
H11	0.8932	0.0102	0.8302	0.033*
C12	0.81387 (7)	0.1355 (2)	0.79721 (14)	0.0248 (4)
H12	0.8268	0.1901	0.8735	0.03*
C13	0.75534 (7)	0.1618 (2)	0.71223 (13)	0.0210 (3)
H13	0.7282	0.2342	0.7303	0.025*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0232 (6)	0.0325 (6)	0.0190 (6)	−0.0024 (5)	0.0106 (5)	−0.0016 (5)
O2	0.0197 (6)	0.0345 (7)	0.0208 (6)	0.0036 (5)	0.0109 (5)	0.0058 (5)
O3	0.0187 (6)	0.0359 (7)	0.0290 (6)	0.0052 (5)	0.0126 (5)	0.0051 (5)
C1	0.0173 (7)	0.0202 (8)	0.0177 (7)	−0.0019 (6)	0.0071 (6)	−0.0013 (6)
C2	0.0163 (7)	0.0203 (8)	0.0172 (7)	0.0004 (6)	0.0056 (6)	−0.0009 (6)
C3	0.0191 (7)	0.0208 (8)	0.0167 (7)	−0.0023 (6)	0.0080 (6)	−0.0010 (6)
C4	0.0166 (8)	0.0211 (8)	0.0239 (8)	−0.0010 (6)	0.0089 (7)	−0.0023 (6)
C5	0.0184 (8)	0.0236 (8)	0.0202 (8)	0.0032 (6)	0.0046 (6)	0.0018 (6)
C6	0.0242 (8)	0.0236 (8)	0.0172 (7)	−0.0007 (6)	0.0086 (7)	0.0011 (6)
C7	0.0216 (8)	0.0181 (8)	0.0192 (8)	−0.0028 (6)	0.0096 (6)	−0.0004 (6)
C8	0.0189 (8)	0.0195 (8)	0.0214 (8)	−0.0018 (6)	0.0099 (6)	0.0020 (6)
C9	0.0230 (8)	0.0227 (9)	0.0266 (8)	−0.0005 (6)	0.0133 (7)	0.0017 (6)
C10	0.0219 (8)	0.0240 (9)	0.0373 (9)	0.0035 (7)	0.0152 (7)	0.0059 (7)
C11	0.0170 (8)	0.0262 (9)	0.0340 (9)	−0.0022 (7)	0.0063 (7)	0.0091 (7)
C12	0.0238 (8)	0.0251 (8)	0.0223 (8)	−0.0045 (7)	0.0067 (7)	0.0028 (6)
C13	0.0202 (8)	0.0201 (8)	0.0232 (8)	−0.0019 (6)	0.0098 (6)	0.0007 (6)

Geometric parameters (Å, º)

O1—C7	1.2373 (18)	C6—H6A	0.95
O2—C3	1.3675 (18)	C7—C8	1.487 (2)
O2—H2	0.94 (2)	C8—C9	1.395 (2)
O3—C4	1.3571 (18)	C8—C13	1.396 (2)
O3—H3	0.94 (2)	C9—C10	1.382 (2)
C1—C6	1.394 (2)	C9—H9	0.95
C1—C2	1.397 (2)	C10—C11	1.388 (2)
C1—C7	1.478 (2)	C10—H10	0.95
C2—C3	1.378 (2)	C11—C12	1.382 (2)
C2—H2A	0.95	C11—H11	0.95
C3—C4	1.393 (2)	C12—C13	1.386 (2)
C4—C5	1.385 (2)	C12—H12	0.95
C5—C6	1.380 (2)	C13—H13	0.95
C5—H5	0.95
C3—O2—H2	108.9 (11)	O1—C7—C8	118.60 (13)
C4—O3—H3	110.4 (11)	C1—C7—C8	121.91 (12)
C6—C1—C2	119.11 (14)	C9—C8—C13	119.30 (14)
C6—C1—C7	118.99 (13)	C9—C8—C7	117.89 (13)
C2—C1—C7	121.70 (13)	C13—C8—C7	122.79 (14)
C3—C2—C1	120.25 (14)	C10—C9—C8	120.44 (15)
C3—C2—H2A	119.9	C10—C9—H9	119.8
C1—C2—H2A	119.9	C8—C9—H9	119.8
O2—C3—C2	122.86 (14)	C9—C10—C11	119.76 (15)
O2—C3—C4	116.77 (13)	C9—C10—H10	120.1
C2—C3—C4	120.37 (14)	C11—C10—H10	120.1
O3—C4—C5	118.92 (14)	C12—C11—C10	120.36 (15)
O3—C4—C3	121.60 (14)	C12—C11—H11	119.8
C5—C4—C3	119.47 (14)	C10—C11—H11	119.8
C6—C5—C4	120.38 (14)	C11—C12—C13	120.10 (15)
C6—C5—H5	119.8	C11—C12—H12	119.9
C4—C5—H5	119.8	C13—C12—H12	119.9
C5—C6—C1	120.41 (14)	C12—C13—C8	119.99 (15)
C5—C6—H6A	119.8	C12—C13—H13	120
C1—C6—H6A	119.8	C8—C13—H13	120
O1—C7—C1	119.47 (13)
C6—C1—C2—C3	0.6 (2)	C6—C1—C7—C8	151.66 (14)
C7—C1—C2—C3	−174.22 (14)	C2—C1—C7—C8	−33.5 (2)
C1—C2—C3—O2	179.45 (14)	O1—C7—C8—C9	−20.9 (2)
C1—C2—C3—C4	−0.1 (2)	C1—C7—C8—C9	157.17 (14)
O2—C3—C4—O3	0.2 (2)	O1—C7—C8—C13	157.44 (15)
C2—C3—C4—O3	179.83 (14)	C1—C7—C8—C13	−24.5 (2)
O2—C3—C4—C5	179.46 (14)	C13—C8—C9—C10	2.0 (2)
C2—C3—C4—C5	−0.9 (2)	C7—C8—C9—C10	−179.63 (14)
O3—C4—C5—C6	−179.18 (14)	C8—C9—C10—C11	−0.7 (2)
C3—C4—C5—C6	1.6 (2)	C9—C10—C11—C12	−0.9 (2)
C4—C5—C6—C1	−1.1 (2)	C10—C11—C12—C13	1.4 (2)
C2—C1—C6—C5	0.1 (2)	C11—C12—C13—C8	−0.1 (2)
C7—C1—C6—C5	174.99 (14)	C9—C8—C13—C12	−1.5 (2)
C6—C1—C7—O1	−30.3 (2)	C7—C8—C13—C12	−179.88 (14)
C2—C1—C7—O1	144.53 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1^i	0.94 (2)	1.71 (2)	2.6391 (16)	171.7 (18)
O3—H3···O2^ii	0.94 (2)	1.91 (2)	2.8149 (16)	159.6 (16)
C2—H2A···O1^i	0.95	2.56	3.2309 (18)	128

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

(3hbz2)

Crystal data

C13H10O2	F(000) = 416
Mr = 198.21	Dx = 1.363 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 4.0462 (1) Å	Cell parameters from 2247 reflections
b = 20.2165 (6) Å	θ = 2.9–27.5°
c = 11.8058 (3) Å	µ = 0.09 mm^−1
β = 90.929 (2)°	T = 120 K
V = 965.59 (4) Å^3	Lath, colourless
Z = 4	0.16 × 0.1 × 0.04 mm

Data collection

Bruker-Nonius 95mm CCD camers on κ-goniostat diffractometer	1795 reflections with I > 2σ(I)
ϕ and ω scans to fill Ewald sphere	Rint = 0.049
Absorption correction: multi-scan SADABS V2.10 (Sheldrick, G.M., 2003)	θmax = 27.5°, θmin = 3.5°
Tmin = 0.729, Tmax = 0.996	h = −5→5
13634 measured reflections	k = −24→26
2197 independent reflections	l = −15→15

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.074	w = 1/[σ^2(Fo^2) + (0.0718P)^2 + 2.095P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.216	(Δ/σ)max = 0.001
S = 1.17	Δρmax = 0.42 e Å^−3
2197 reflections	Δρmin = −0.30 e Å^−3
140 parameters

Special details

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

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

	x	y	z	Uiso*/Ueq
O1	0.9906 (7)	0.21701 (11)	0.39677 (18)	0.0345 (6)
O2	0.7594 (6)	0.39136 (11)	0.79324 (19)	0.0328 (6)
H2	0.663 (13)	0.347 (3)	0.832 (5)	0.076 (16)*
C1	1.0098 (7)	0.29194 (14)	0.5484 (2)	0.0229 (6)
C2	0.8767 (7)	0.30776 (15)	0.6536 (2)	0.0234 (6)
H21	0.7778	0.2743	0.6983	0.028*
C3	0.8897 (8)	0.37273 (15)	0.6925 (2)	0.0240 (6)
C4	1.0392 (8)	0.42159 (15)	0.6276 (3)	0.0271 (7)
H4	1.0482	0.4659	0.6543	0.032*
C5	1.1750 (8)	0.40546 (15)	0.5239 (3)	0.0290 (7)
H5	1.2795	0.4388	0.4804	0.035*
C6	1.1593 (8)	0.34118 (15)	0.4831 (2)	0.0260 (7)
H6	1.2492	0.3306	0.4115	0.031*
C7	0.9927 (8)	0.22421 (15)	0.5002 (2)	0.0254 (6)
C8	0.9787 (7)	0.16500 (14)	0.5754 (2)	0.0222 (6)
C9	0.8240 (8)	0.10799 (15)	0.5333 (3)	0.0262 (6)
H9	0.7225	0.1082	0.4602	0.031*
C10	0.8197 (8)	0.05098 (15)	0.5991 (3)	0.0278 (7)
H10	0.7105	0.0125	0.5716	0.033*
C11	0.9747 (8)	0.05024 (15)	0.7047 (3)	0.0280 (7)
H11	0.9739	0.011	0.749	0.034*
C12	1.1300 (8)	0.10633 (15)	0.7457 (3)	0.0257 (6)
H12	1.2371	0.1054	0.8178	0.031*
C13	1.1310 (7)	0.16412 (14)	0.6823 (2)	0.0233 (6)
H13	1.2347	0.2028	0.7114	0.028*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0619 (16)	0.0256 (12)	0.0163 (11)	0.0033 (10)	0.0036 (10)	0.0004 (8)
O2	0.0522 (15)	0.0232 (12)	0.0233 (11)	−0.0008 (10)	0.0054 (10)	−0.0032 (9)
C1	0.0289 (15)	0.0208 (14)	0.0189 (13)	0.0022 (11)	−0.0005 (11)	0.0010 (11)
C2	0.0297 (15)	0.0215 (14)	0.0192 (13)	−0.0001 (11)	0.0011 (11)	0.0022 (11)
C3	0.0310 (15)	0.0222 (14)	0.0189 (13)	0.0020 (11)	−0.0004 (11)	−0.0005 (11)
C4	0.0349 (16)	0.0199 (14)	0.0263 (15)	−0.0020 (12)	−0.0037 (12)	0.0011 (11)
C5	0.0339 (16)	0.0247 (15)	0.0284 (16)	−0.0045 (12)	0.0010 (12)	0.0075 (12)
C6	0.0325 (16)	0.0255 (15)	0.0201 (14)	0.0007 (12)	0.0026 (12)	0.0038 (11)
C7	0.0316 (15)	0.0239 (15)	0.0208 (14)	0.0033 (12)	0.0047 (11)	0.0004 (11)
C8	0.0284 (15)	0.0204 (14)	0.0180 (13)	0.0038 (11)	0.0045 (11)	0.0004 (10)
C9	0.0305 (15)	0.0268 (15)	0.0213 (14)	0.0006 (12)	0.0021 (11)	−0.0036 (11)
C10	0.0316 (15)	0.0216 (15)	0.0304 (16)	−0.0005 (12)	0.0060 (12)	−0.0047 (12)
C11	0.0330 (16)	0.0214 (15)	0.0298 (16)	0.0050 (12)	0.0058 (12)	0.0022 (12)
C12	0.0300 (15)	0.0270 (15)	0.0200 (14)	0.0062 (12)	0.0032 (11)	0.0017 (11)
C13	0.0276 (14)	0.0215 (14)	0.0209 (14)	0.0018 (11)	0.0037 (11)	−0.0030 (11)

Geometric parameters (Å, º)

O1—C7	1.230 (4)	C6—H6	0.95
O2—C3	1.362 (4)	C7—C8	1.491 (4)
O2—H2	1.09 (6)	C8—C13	1.395 (4)
C1—C2	1.399 (4)	C8—C9	1.399 (4)
C1—C6	1.402 (4)	C9—C10	1.390 (4)
C1—C7	1.484 (4)	C9—H9	0.95
C2—C3	1.392 (4)	C10—C11	1.387 (5)
C2—H21	0.95	C10—H10	0.95
C3—C4	1.394 (4)	C11—C12	1.380 (4)
C4—C5	1.390 (4)	C11—H11	0.95
C4—H4	0.95	C12—C13	1.388 (4)
C5—C6	1.387 (4)	C12—H12	0.95
C5—H5	0.95	C13—H13	0.95
C3—O2—H2	107 (3)	O1—C7—C8	119.7 (3)
C2—C1—C6	120.1 (3)	C1—C7—C8	121.0 (3)
C2—C1—C7	122.3 (3)	C13—C8—C9	119.9 (3)
C6—C1—C7	117.6 (3)	C13—C8—C7	121.8 (3)
C3—C2—C1	119.7 (3)	C9—C8—C7	118.1 (3)
C3—C2—H21	120.1	C10—C9—C8	119.7 (3)
C1—C2—H21	120.1	C10—C9—H9	120.2
O2—C3—C2	122.4 (3)	C8—C9—H9	120.2
O2—C3—C4	117.5 (3)	C11—C10—C9	120.1 (3)
C2—C3—C4	120.1 (3)	C11—C10—H10	119.9
C5—C4—C3	120.0 (3)	C9—C10—H10	119.9
C5—C4—H4	120	C12—C11—C10	120.2 (3)
C3—C4—H4	120	C12—C11—H11	119.9
C6—C5—C4	120.6 (3)	C10—C11—H11	119.9
C6—C5—H5	119.7	C11—C12—C13	120.6 (3)
C4—C5—H5	119.7	C11—C12—H12	119.7
C5—C6—C1	119.5 (3)	C13—C12—H12	119.7
C5—C6—H6	120.2	C12—C13—C8	119.6 (3)
C1—C6—H6	120.2	C12—C13—H13	120.2
O1—C7—C1	119.3 (3)	C8—C13—H13	120.2
C6—C1—C2—C3	0.8 (4)	C6—C1—C7—C8	153.4 (3)
C7—C1—C2—C3	−177.7 (3)	O1—C7—C8—C13	148.7 (3)
C1—C2—C3—O2	178.8 (3)	C1—C7—C8—C13	−31.1 (4)
C1—C2—C3—C4	−0.9 (4)	O1—C7—C8—C9	−27.5 (4)
O2—C3—C4—C5	−179.7 (3)	C1—C7—C8—C9	152.7 (3)
C2—C3—C4—C5	0.1 (5)	C13—C8—C9—C10	0.8 (4)
C3—C4—C5—C6	0.9 (5)	C7—C8—C9—C10	177.1 (3)
C4—C5—C6—C1	−1.1 (5)	C8—C9—C10—C11	−1.5 (4)
C2—C1—C6—C5	0.2 (4)	C9—C10—C11—C12	0.9 (5)
C7—C1—C6—C5	178.8 (3)	C10—C11—C12—C13	0.5 (5)
C2—C1—C7—O1	152.0 (3)	C11—C12—C13—C8	−1.2 (4)
C6—C1—C7—O1	−26.5 (4)	C9—C8—C13—C12	0.5 (4)
C2—C1—C7—C8	−28.1 (4)	C7—C8—C13—C12	−175.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1^i	1.09 (6)	1.66 (6)	2.742 (3)	175 (5)

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

(dimit1)

Crystal data

C13H9ClO2	Dx = 1.435 Mg m^−3
Mr = 232.65	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21	Cell parameters from 17704 reflections
a = 23.3058 (11) Å	θ = 2.9–27.5°
b = 5.5770 (2) Å	µ = 0.33 mm^−1
c = 8.2847 (4) Å	T = 120 K
V = 1076.82 (8) Å^3	Prism, colourless
Z = 4	0.2 × 0.15 × 0.1 mm
F(000) = 480

Data collection

Bruker-Nonius 95mm CCD camers on κ-goniostat diffractometer	1681 reflections with I > 2σ(I)
ϕ and ω scans to fill Ewald sphere	Rint = 0.064
Absorption correction: multi-scan using multiple and symmetry-related data measurements via the program SORTAV (Blessing, 1995, 1997)	θmax = 27.5°, θmin = 3.0°
Tmin = 0.881, Tmax = 0.967	h = −30→29
9569 measured reflections	k = −6→7
2143 independent reflections	l = −10→8

Refinement

Refinement on F^2	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.043P)^2] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.038	(Δ/σ)max < 0.001
wR(F^2) = 0.085	Δρmax = 0.20 e Å^−3
S = 1.04	Δρmin = −0.26 e Å^−3
2143 reflections	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
149 parameters	Absolute structure parameter: −0.13 (7)
1 restraint

Special details

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

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

	x	y	z	Uiso*/Ueq
Cl1	0.20287 (3)	−0.16954 (11)	0.42794 (10)	0.0447 (2)
O1	0.43169 (7)	0.5397 (3)	0.4458 (2)	0.0374 (4)
O2	0.46228 (8)	0.7846 (3)	1.1812 (2)	0.0362 (5)
H2	0.4502 (13)	0.694 (5)	1.257 (3)	0.043*
C1	0.35389 (10)	0.3051 (4)	0.5321 (3)	0.0281 (5)
C2	0.36014 (10)	0.1095 (4)	0.4304 (3)	0.0316 (5)
H2A	0.3962	0.0782	0.3812	0.038*
C3	0.31403 (11)	−0.0407 (4)	0.4000 (3)	0.0348 (6)
H3	0.3186	−0.1787	0.3341	0.042*
C4	0.26151 (10)	0.0130 (4)	0.4667 (3)	0.0321 (6)
C5	0.25378 (11)	0.2102 (4)	0.5654 (3)	0.0312 (6)
H5	0.217	0.2469	0.6081	0.037*
C6	0.30041 (10)	0.3528 (5)	0.6007 (3)	0.0299 (6)
H6	0.2961	0.4846	0.6723	0.036*
C7	0.40295 (10)	0.4708 (4)	0.5614 (3)	0.0273 (5)
C8	0.41568 (9)	0.5508 (4)	0.7258 (3)	0.0262 (5)
C9	0.44722 (11)	0.7632 (5)	0.7488 (3)	0.0288 (6)
H9	0.4589	0.855	0.658	0.035*
C10	0.46132 (9)	0.8388 (4)	0.9013 (3)	0.0282 (6)
H10	0.4814	0.9854	0.9156	0.034*
C11	0.44630 (10)	0.7019 (4)	1.0350 (3)	0.0276 (5)
C12	0.41600 (10)	0.4884 (4)	1.0139 (3)	0.0284 (6)
H12	0.4061	0.3929	1.1047	0.034*
C13	0.40060 (10)	0.4171 (4)	0.8607 (3)	0.0274 (5)
H13	0.3792	0.2735	0.8471	0.033*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0423 (4)	0.0388 (4)	0.0530 (4)	−0.0074 (3)	−0.0099 (3)	−0.0088 (3)
O1	0.0379 (9)	0.0445 (10)	0.0297 (9)	−0.0006 (7)	0.0069 (9)	0.0014 (9)
O2	0.0442 (11)	0.0350 (11)	0.0294 (11)	−0.0105 (8)	−0.0017 (8)	−0.0013 (8)
C1	0.0311 (13)	0.0276 (12)	0.0255 (12)	0.0024 (10)	−0.0034 (11)	0.0010 (11)
C2	0.0340 (12)	0.0360 (13)	0.0247 (12)	0.0075 (10)	0.0018 (13)	−0.0032 (12)
C3	0.0452 (15)	0.0286 (13)	0.0307 (16)	0.0046 (11)	−0.0054 (12)	−0.0064 (11)
C4	0.0364 (14)	0.0287 (13)	0.0313 (14)	−0.0039 (10)	−0.0086 (12)	−0.0004 (11)
C5	0.0319 (14)	0.0292 (13)	0.0326 (15)	−0.0003 (11)	0.0002 (10)	−0.0021 (11)
C6	0.0313 (14)	0.0322 (14)	0.0263 (13)	0.0005 (11)	−0.0004 (10)	−0.0036 (10)
C7	0.0270 (13)	0.0298 (12)	0.0249 (13)	0.0050 (10)	0.0017 (10)	0.0024 (11)
C8	0.0251 (12)	0.0256 (13)	0.0280 (13)	0.0022 (10)	0.0009 (10)	−0.0019 (11)
C9	0.0282 (13)	0.0301 (13)	0.0280 (14)	0.0015 (10)	−0.0012 (10)	0.0033 (12)
C10	0.0272 (11)	0.0238 (11)	0.0337 (16)	−0.0042 (9)	−0.0006 (11)	0.0029 (11)
C11	0.0248 (12)	0.0315 (13)	0.0265 (13)	0.0015 (10)	−0.0025 (11)	−0.0019 (11)
C12	0.0294 (13)	0.0267 (13)	0.0290 (14)	−0.0014 (10)	0.0052 (10)	0.0038 (11)
C13	0.0267 (12)	0.0243 (12)	0.0312 (13)	−0.0003 (10)	0.0005 (10)	0.0006 (11)

Geometric parameters (Å, º)

Cl1—C4	1.734 (2)	C5—H5	0.95
O1—C7	1.230 (3)	C6—H6	0.95
O2—C11	1.349 (3)	C7—C8	1.463 (3)
O2—H2	0.86 (3)	C8—C13	1.389 (3)
C1—C2	1.386 (3)	C8—C9	1.407 (4)
C1—C6	1.396 (3)	C9—C10	1.372 (3)
C1—C7	1.490 (3)	C9—H9	0.95
C2—C3	1.385 (3)	C10—C11	1.390 (3)
C2—H2A	0.95	C10—H10	0.95
C3—C4	1.376 (3)	C11—C12	1.395 (3)
C3—H3	0.95	C12—C13	1.378 (3)
C4—C5	1.382 (3)	C12—H12	0.95
C5—C6	1.378 (3)	C13—H13	0.95
C11—O2—H2	112 (2)	O1—C7—C1	119.0 (2)
C2—C1—C6	119.4 (2)	C8—C7—C1	119.7 (2)
C2—C1—C7	120.4 (2)	C13—C8—C9	118.3 (2)
C6—C1—C7	120.0 (2)	C13—C8—C7	122.3 (2)
C3—C2—C1	120.3 (2)	C9—C8—C7	119.3 (2)
C3—C2—H2A	119.9	C10—C9—C8	120.6 (2)
C1—C2—H2A	119.9	C10—C9—H9	119.7
C4—C3—C2	119.1 (2)	C8—C9—H9	119.7
C4—C3—H3	120.5	C9—C10—C11	120.3 (2)
C2—C3—H3	120.5	C9—C10—H10	119.9
C3—C4—C5	121.8 (2)	C11—C10—H10	119.9
C3—C4—Cl1	119.94 (19)	O2—C11—C10	117.2 (2)
C5—C4—Cl1	118.30 (19)	O2—C11—C12	122.9 (2)
C6—C5—C4	118.8 (2)	C10—C11—C12	119.8 (2)
C6—C5—H5	120.6	C13—C12—C11	119.6 (2)
C4—C5—H5	120.6	C13—C12—H12	120.2
C5—C6—C1	120.5 (2)	C11—C12—H12	120.2
C5—C6—H6	119.7	C12—C13—C8	121.4 (2)
C1—C6—H6	119.7	C12—C13—H13	119.3
O1—C7—C8	121.3 (2)	C8—C13—H13	119.3
C6—C1—C2—C3	−1.5 (4)	O1—C7—C8—C13	−155.0 (2)
C7—C1—C2—C3	−178.3 (2)	C1—C7—C8—C13	25.8 (3)
C1—C2—C3—C4	2.7 (3)	O1—C7—C8—C9	21.2 (3)
C2—C3—C4—C5	−1.1 (3)	C1—C7—C8—C9	−158.1 (2)
C2—C3—C4—Cl1	178.97 (19)	C13—C8—C9—C10	−1.7 (3)
C3—C4—C5—C6	−1.7 (4)	C7—C8—C9—C10	−178.0 (2)
Cl1—C4—C5—C6	178.2 (2)	C8—C9—C10—C11	2.2 (3)
C4—C5—C6—C1	2.9 (4)	C9—C10—C11—O2	178.9 (2)
C2—C1—C6—C5	−1.4 (4)	C9—C10—C11—C12	−1.0 (3)
C7—C1—C6—C5	175.5 (2)	O2—C11—C12—C13	179.2 (2)
C2—C1—C7—O1	45.3 (3)	C10—C11—C12—C13	−0.9 (3)
C6—C1—C7—O1	−131.4 (3)	C11—C12—C13—C8	1.4 (4)
C2—C1—C7—C8	−135.4 (2)	C9—C8—C13—C12	−0.2 (3)
C6—C1—C7—C8	47.8 (3)	C7—C8—C13—C12	176.0 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1^i	0.86 (3)	1.83 (3)	2.679 (3)	169 (3)

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

(dimit2)

Crystal data

C13H9Cl2NO	F(000) = 544
Mr = 266.11	Dx = 1.464 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.8897 (3) Å	Cell parameters from 8581 reflections
b = 9.5581 (4) Å	θ = 2.9–27.5°
c = 16.1101 (5) Å	µ = 0.52 mm^−1
β = 96.416 (2)°	T = 120 K
V = 1207.26 (8) Å^3	Shard, yellow
Z = 4	0.24 × 0.16 × 0.06 mm

Data collection

Bruker-Nonius 95mm CCD camers on κ-goniostat diffractometer	2133 reflections with I > 2σ(I)
ϕ and ω scans to fill Ewald sphere	Rint = 0.075
Absorption correction: multi-scan using multiple and symmetry-related data measurements via the program SORTAV (Blessing, 1995, 1997)	θmax = 27.5°, θmin = 3.3°
Tmin = 0.849, Tmax = 0.970	h = −10→10
16326 measured reflections	k = −12→12
2765 independent reflections	l = −20→20

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.040	w = 1/[σ^2(Fo^2) + (0.0547P)^2 + 0.2206P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.103	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.38 e Å^−3
2765 reflections	Δρmin = −0.46 e Å^−3
161 parameters

Special details

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

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

	x	y	z	Uiso*/Ueq
Cl1	0.10399 (6)	0.05770 (5)	−0.13621 (3)	0.02752 (15)
Cl2	0.39712 (7)	0.46355 (5)	0.08406 (3)	0.03637 (16)
O1	0.35091 (17)	0.19480 (14)	0.24038 (8)	0.0284 (3)
N1	0.4739 (2)	−0.05029 (19)	0.19551 (11)	0.0295 (4)
H1A	0.534 (3)	−0.125 (3)	0.2006 (14)	0.035*
H1B	0.475 (3)	0.013 (3)	0.2325 (15)	0.035*
C1	0.2857 (2)	0.09936 (18)	0.10484 (11)	0.0203 (4)
C2	0.3840 (2)	−0.02415 (19)	0.12098 (11)	0.0224 (4)
C3	0.3836 (2)	−0.12392 (19)	0.05608 (12)	0.0258 (4)
H3	0.4436	−0.2094	0.0664	0.031*
C4	0.2983 (2)	−0.09969 (19)	−0.02131 (12)	0.0253 (4)
H4	0.3015	−0.1672	−0.0644	0.03*
C5	0.2066 (2)	0.02441 (19)	−0.03684 (11)	0.0234 (4)
C6	0.1991 (2)	0.12077 (18)	0.02498 (11)	0.0207 (4)
H6	0.1341	0.2037	0.0138	0.025*
C7	0.2727 (2)	0.20316 (18)	0.16985 (11)	0.0214 (4)
C8	0.1505 (2)	0.32416 (18)	0.15294 (10)	0.0226 (4)
C9	0.1950 (3)	0.44843 (19)	0.11733 (12)	0.0265 (4)
C10	0.0842 (3)	0.5611 (2)	0.10734 (13)	0.0326 (5)
H10	0.1178	0.6457	0.0828	0.039*
C11	−0.0755 (3)	0.5486 (2)	0.13359 (12)	0.0312 (5)
H11	−0.1524	0.6253	0.1275	0.037*
C12	−0.1244 (3)	0.4251 (2)	0.16884 (13)	0.0302 (4)
H12	−0.2354	0.4171	0.1859	0.036*
C13	−0.0136 (3)	0.3135 (2)	0.17935 (12)	0.0272 (4)
H13	−0.0476	0.2295	0.2043	0.033*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0319 (3)	0.0278 (3)	0.0222 (2)	−0.00214 (18)	0.00011 (19)	−0.00133 (17)
Cl2	0.0316 (3)	0.0343 (3)	0.0449 (3)	−0.0007 (2)	0.0120 (2)	0.0089 (2)
O1	0.0329 (8)	0.0260 (7)	0.0247 (7)	0.0007 (6)	−0.0034 (6)	−0.0010 (5)
N1	0.0311 (10)	0.0287 (9)	0.0276 (9)	0.0097 (7)	−0.0006 (8)	0.0018 (7)
C1	0.0179 (9)	0.0193 (9)	0.0239 (8)	−0.0004 (7)	0.0027 (7)	0.0010 (7)
C2	0.0191 (9)	0.0232 (9)	0.0258 (9)	0.0005 (7)	0.0067 (7)	0.0032 (7)
C3	0.0264 (10)	0.0182 (9)	0.0335 (10)	0.0023 (7)	0.0071 (8)	0.0004 (7)
C4	0.0280 (10)	0.0203 (9)	0.0285 (9)	−0.0013 (8)	0.0070 (8)	−0.0041 (7)
C5	0.0225 (9)	0.0256 (9)	0.0222 (9)	−0.0030 (7)	0.0026 (7)	0.0005 (7)
C6	0.0181 (9)	0.0186 (8)	0.0258 (9)	0.0002 (7)	0.0046 (7)	0.0007 (7)
C7	0.0194 (9)	0.0206 (9)	0.0245 (9)	−0.0021 (7)	0.0031 (7)	0.0007 (7)
C8	0.0253 (10)	0.0218 (9)	0.0199 (8)	0.0009 (7)	−0.0004 (8)	−0.0031 (7)
C9	0.0254 (10)	0.0276 (10)	0.0270 (9)	−0.0009 (8)	0.0046 (8)	−0.0011 (7)
C10	0.0386 (12)	0.0248 (10)	0.0335 (10)	0.0048 (9)	0.0010 (9)	0.0030 (8)
C11	0.0335 (11)	0.0257 (10)	0.0335 (11)	0.0078 (8)	−0.0006 (9)	−0.0050 (8)
C12	0.0256 (10)	0.0328 (11)	0.0326 (10)	0.0021 (8)	0.0052 (9)	−0.0079 (8)
C13	0.0307 (11)	0.0229 (9)	0.0269 (9)	−0.0009 (8)	−0.0016 (8)	−0.0032 (7)

Geometric parameters (Å, º)

Cl1—C5	1.7407 (18)	C5—C6	1.363 (3)
Cl2—C9	1.744 (2)	C6—H6	0.95
O1—C7	1.233 (2)	C7—C8	1.511 (3)
N1—C2	1.348 (2)	C8—C9	1.381 (3)
N1—H1A	0.86 (3)	C8—C13	1.411 (3)
N1—H1B	0.85 (3)	C9—C10	1.385 (3)
C1—C6	1.403 (2)	C10—C11	1.378 (3)
C1—C2	1.420 (3)	C10—H10	0.95
C1—C7	1.455 (2)	C11—C12	1.384 (3)
C2—C3	1.415 (3)	C11—H11	0.95
C3—C4	1.369 (3)	C12—C13	1.377 (3)
C3—H3	0.95	C12—H12	0.95
C4—C5	1.397 (3)	C13—H13	0.95
C4—H4	0.95
C2—N1—H1A	118.1 (16)	O1—C7—C1	123.42 (16)
C2—N1—H1B	117.3 (16)	O1—C7—C8	117.33 (16)
H1A—N1—H1B	124 (2)	C1—C7—C8	119.16 (15)
C6—C1—C2	119.29 (16)	C9—C8—C13	118.13 (17)
C6—C1—C7	119.64 (15)	C9—C8—C7	123.14 (17)
C2—C1—C7	121.07 (16)	C13—C8—C7	118.62 (16)
N1—C2—C3	119.41 (17)	C8—C9—C10	122.04 (19)
N1—C2—C1	122.63 (17)	C8—C9—Cl2	118.84 (15)
C3—C2—C1	117.95 (16)	C10—C9—Cl2	119.12 (15)
C4—C3—C2	121.30 (17)	C11—C10—C9	118.91 (18)
C4—C3—H3	119.3	C11—C10—H10	120.5
C2—C3—H3	119.3	C9—C10—H10	120.5
C3—C4—C5	119.91 (17)	C10—C11—C12	120.43 (18)
C3—C4—H4	120	C10—C11—H11	119.8
C5—C4—H4	120	C12—C11—H11	119.8
C6—C5—C4	120.46 (17)	C13—C12—C11	120.59 (19)
C6—C5—Cl1	119.66 (14)	C13—C12—H12	119.7
C4—C5—Cl1	119.88 (14)	C11—C12—H12	119.7
C5—C6—C1	121.00 (16)	C12—C13—C8	119.88 (18)
C5—C6—H6	119.5	C12—C13—H13	120.1
C1—C6—H6	119.5	C8—C13—H13	120.1
C6—C1—C2—N1	178.38 (17)	C2—C1—C7—C8	−172.82 (16)
C7—C1—C2—N1	−2.0 (3)	O1—C7—C8—C9	94.9 (2)
C6—C1—C2—C3	−2.9 (3)	C1—C7—C8—C9	−88.4 (2)
C7—C1—C2—C3	176.71 (16)	O1—C7—C8—C13	−81.1 (2)
N1—C2—C3—C4	−177.97 (18)	C1—C7—C8—C13	95.7 (2)
C1—C2—C3—C4	3.2 (3)	C13—C8—C9—C10	0.2 (3)
C2—C3—C4—C5	−1.3 (3)	C7—C8—C9—C10	−175.78 (18)
C3—C4—C5—C6	−1.1 (3)	C13—C8—C9—Cl2	−179.84 (14)
C3—C4—C5—Cl1	177.91 (14)	C7—C8—C9—Cl2	4.2 (2)
C4—C5—C6—C1	1.4 (3)	C8—C9—C10—C11	−0.2 (3)
Cl1—C5—C6—C1	−177.58 (13)	Cl2—C9—C10—C11	179.88 (15)
C2—C1—C6—C5	0.6 (3)	C9—C10—C11—C12	−0.4 (3)
C7—C1—C6—C5	−178.96 (17)	C10—C11—C12—C13	0.9 (3)
C6—C1—C7—O1	−176.73 (17)	C11—C12—C13—C8	−0.9 (3)
C2—C1—C7—O1	3.7 (3)	C9—C8—C13—C12	0.3 (3)
C6—C1—C7—C8	6.7 (2)	C7—C8—C13—C12	176.49 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1^i	0.86 (3)	2.12 (3)	2.932 (2)	158 (2)
N1—H1B···O1	0.85 (3)	2.01 (3)	2.666 (2)	134 (2)

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