Mol­ecular and crystal structure, lattice energy and DFT calculations of two 2′-(nitro­benzo­yloxy)aceto­phenone isomers

The two isomers 2′-(4-nitro­benzo­yloxy)aceto­phenone with para and ortho positions of the nitro substituent have been crystallized and studied. It is evident that the variation in the position of the nitro group causes a significant difference in the mol­ecular conformations.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• Disorder in solvent or counterion
• R factor = 0.042
• wR factor = 0.116
• Data-to-parameter ratio = 16.4

Structure: II

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.040
• wR factor = 0.122
• Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H13A     ..O2       .       2.64 Ang.
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          3 Report

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C15 H11.15 N1 O5.07
            Atom count from _chemical_formula_moiety:C15 H11.14 N1 O5.07
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          3 Note
PLAT012_ALERT_1_G N.O.K.   _shelx_res_checksum Found in CIF ......     Please Check
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT128_ALERT_4_G Alternate Setting for Input Space Group     C2/c       I2/a Note
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          3 Report
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  2  )       100% Note
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd  2  )       0.44 Check
PLAT432_ALERT_2_G Short Inter X...Y Contact  O4       ..C15              2.98 Ang.
                                         1/2-x,-1/2+y,1/2-z  =      4_545 Check
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          4 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         46 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         13 Info

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

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




Datablock: II


Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full value Low .      0.956 Why?

Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H11      ..O1       .       2.65 Ang.
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600        103 Report

Alert level G
PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety .....        C13 Check
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        674 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         16 Info

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

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


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

For both structures, data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT2017/1 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2017/1 (Sheldrick, 2015b), OLEX2 (Dolomanov et al., 2009); molecular graphics: Mercury (Macrae et al., 2020); software used to prepare material for publication: Mercury (Macrae et al., 2020).

2-Acetylphenyl 4-nitrobenzoate 0.07-hydrate (I)

Crystal data

C15H11NO5·0.07H2O	F(000) = 1190
Mr = 286.58	Dx = 1.413 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 26.225 (6) Å	Cell parameters from 5275 reflections
b = 7.9955 (17) Å	θ = 2.7–29.6°
c = 13.772 (3) Å	µ = 0.11 mm^−1
β = 111.080 (3)°	T = 150 K
V = 2694.5 (10) Å^3	Block, yellow
Z = 8	0.21 × 0.18 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer	2983 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.056
Absorption correction: multi-scan (SADABS; Bruker, 2016)	θmax = 30.4°, θmin = 2.7°
Tmin = 0.687, Tmax = 0.746	h = −36→37
22632 measured reflections	k = −11→11
4010 independent reflections	l = −19→19

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.116	Only H-atom coordinates refined
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0487P)^2 + 1.2105P] where P = (Fo^2 + 2Fc^2)/3
4010 reflections	(Δ/σ)max < 0.001
244 parameters	Δρmax = 0.28 e Å^−3
4 restraints	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	Occ. (<1)
O1	0.35357 (3)	0.44264 (11)	0.29788 (7)	0.0308 (2)
O2	0.42547 (3)	0.33442 (12)	0.26638 (7)	0.0371 (2)
O5	0.40200 (4)	0.22975 (12)	0.45589 (8)	0.0418 (2)
O3	0.24003 (4)	−0.15624 (13)	−0.10893 (8)	0.0420 (2)
O4	0.17571 (4)	−0.07242 (14)	−0.05770 (8)	0.0455 (3)
N1	0.22348 (4)	−0.07748 (13)	−0.04993 (8)	0.0323 (2)
C6	0.42127 (4)	0.52092 (15)	0.46672 (9)	0.0271 (2)
C7	0.33704 (5)	0.21458 (15)	0.18295 (9)	0.0266 (2)
C1	0.38789 (5)	0.56226 (15)	0.36503 (9)	0.0280 (2)
C14	0.37775 (5)	0.33207 (15)	0.25404 (9)	0.0275 (2)
C10	0.26387 (5)	0.01845 (14)	0.03499 (9)	0.0281 (2)
C12	0.35454 (5)	0.11618 (16)	0.11749 (10)	0.0321 (3)
C15	0.42406 (5)	0.34790 (16)	0.51033 (10)	0.0304 (3)
C9	0.24572 (5)	0.10844 (16)	0.10176 (10)	0.0325 (3)
C5	0.45180 (5)	0.65194 (17)	0.52810 (10)	0.0327 (3)
C11	0.31776 (5)	0.01690 (16)	0.04198 (10)	0.0320 (3)
C8	0.28291 (5)	0.20799 (16)	0.17673 (10)	0.0313 (3)
C4	0.44849 (6)	0.81349 (17)	0.48991 (11)	0.0382 (3)
C2	0.38375 (6)	0.72310 (17)	0.32635 (11)	0.0355 (3)
C3	0.41424 (6)	0.84948 (17)	0.38984 (12)	0.0397 (3)
C13	0.45479 (7)	0.3244 (2)	0.62472 (11)	0.0419 (3)
O6	0.500000	0.0754 (11)	0.250000	0.040 (2)	0.148 (2)
H6	0.474 (2)	0.151 (3)	0.256 (8)	0.048*	0.148 (2)
H5	0.4747 (7)	0.626 (2)	0.5957 (13)	0.040 (4)*
H12	0.3931 (6)	0.1215 (19)	0.1236 (12)	0.038 (4)*
H13A	0.4407 (7)	0.398 (2)	0.6677 (14)	0.054 (5)*
H2	0.3589 (7)	0.745 (2)	0.2553 (14)	0.047 (4)*
H3	0.4122 (7)	0.961 (2)	0.3652 (13)	0.051 (5)*
H11	0.3295 (6)	−0.048 (2)	−0.0046 (12)	0.045 (4)*
H13B	0.4515 (7)	0.208 (2)	0.6428 (14)	0.057 (5)*
H9	0.2081 (7)	0.1025 (19)	0.0956 (12)	0.040 (4)*
H4	0.4692 (7)	0.901 (2)	0.5340 (13)	0.052 (5)*
H8	0.2717 (6)	0.273 (2)	0.2253 (12)	0.041 (4)*
H13C	0.4953 (9)	0.353 (3)	0.6436 (16)	0.074 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0267 (4)	0.0308 (4)	0.0320 (4)	−0.0018 (3)	0.0072 (3)	−0.0082 (4)
O2	0.0277 (4)	0.0466 (6)	0.0372 (5)	−0.0066 (4)	0.0119 (4)	−0.0124 (4)
O5	0.0580 (6)	0.0288 (5)	0.0387 (5)	−0.0050 (4)	0.0177 (5)	−0.0028 (4)
O3	0.0455 (5)	0.0399 (5)	0.0357 (5)	−0.0030 (4)	0.0085 (4)	−0.0104 (4)
O4	0.0296 (5)	0.0521 (6)	0.0491 (6)	−0.0116 (4)	0.0072 (4)	−0.0051 (5)
N1	0.0325 (5)	0.0279 (5)	0.0311 (5)	−0.0047 (4)	0.0050 (4)	0.0009 (4)
C6	0.0260 (5)	0.0281 (6)	0.0286 (6)	−0.0013 (4)	0.0116 (4)	−0.0052 (5)
C7	0.0277 (5)	0.0264 (5)	0.0256 (5)	−0.0025 (4)	0.0096 (4)	−0.0011 (4)
C1	0.0262 (5)	0.0282 (6)	0.0297 (6)	−0.0021 (4)	0.0101 (4)	−0.0067 (5)
C14	0.0285 (5)	0.0289 (6)	0.0243 (5)	−0.0018 (4)	0.0088 (4)	−0.0023 (4)
C10	0.0276 (5)	0.0243 (5)	0.0292 (6)	−0.0046 (4)	0.0064 (4)	−0.0012 (4)
C12	0.0261 (5)	0.0355 (6)	0.0358 (6)	−0.0024 (5)	0.0127 (5)	−0.0067 (5)
C15	0.0327 (6)	0.0312 (6)	0.0304 (6)	0.0023 (5)	0.0152 (5)	−0.0021 (5)
C9	0.0263 (6)	0.0346 (6)	0.0386 (7)	−0.0053 (5)	0.0139 (5)	−0.0032 (5)
C5	0.0312 (6)	0.0370 (7)	0.0309 (6)	−0.0041 (5)	0.0124 (5)	−0.0086 (5)
C11	0.0312 (6)	0.0316 (6)	0.0335 (6)	−0.0012 (5)	0.0120 (5)	−0.0070 (5)
C8	0.0303 (6)	0.0333 (6)	0.0336 (6)	−0.0038 (5)	0.0153 (5)	−0.0063 (5)
C4	0.0428 (7)	0.0335 (7)	0.0429 (8)	−0.0110 (6)	0.0212 (6)	−0.0148 (6)
C2	0.0390 (7)	0.0313 (6)	0.0354 (7)	0.0028 (5)	0.0125 (6)	−0.0002 (5)
C3	0.0508 (8)	0.0262 (6)	0.0471 (8)	−0.0023 (6)	0.0238 (7)	−0.0027 (6)
C13	0.0488 (8)	0.0444 (8)	0.0318 (7)	0.0086 (6)	0.0138 (6)	0.0034 (6)
O6	0.037 (5)	0.033 (5)	0.044 (5)	0.000	0.008 (4)	0.000

Geometric parameters (Å, º)

O1—C1	1.4076 (14)	C15—C13	1.5010 (19)
O1—C14	1.3503 (14)	C9—C8	1.3879 (17)
O2—C14	1.2011 (14)	C9—H9	0.960 (16)
O5—C15	1.2154 (15)	C5—C4	1.386 (2)
O3—N1	1.2242 (15)	C5—H5	0.932 (17)
O4—N1	1.2192 (14)	C11—H11	0.960 (16)
N1—C10	1.4788 (15)	C8—H8	0.971 (16)
C6—C1	1.3981 (17)	C4—C3	1.378 (2)
C6—C15	1.4994 (18)	C4—H4	0.958 (18)
C6—C5	1.4022 (17)	C2—C3	1.3865 (19)
C7—C14	1.4928 (16)	C2—H2	0.976 (17)
C7—C12	1.3928 (17)	C3—H3	0.945 (18)
C7—C8	1.3922 (16)	C13—H13A	0.998 (19)
C1—C2	1.3813 (18)	C13—H13B	0.976 (19)
C10—C9	1.3801 (18)	C13—H13C	1.02 (2)
C10—C11	1.3818 (17)	O6—H6	0.941 (14)
C12—C11	1.3857 (17)	O6—H6^i	0.941 (14)
C12—H12	0.985 (15)
C14—O1—C1	116.52 (9)	C8—C9—H9	121.2 (9)
O3—N1—C10	117.89 (10)	C6—C5—H5	117.4 (10)
O4—N1—O3	123.86 (11)	C4—C5—C6	121.56 (13)
O4—N1—C10	118.25 (11)	C4—C5—H5	121.1 (10)
C1—C6—C15	122.83 (10)	C10—C11—C12	117.74 (11)
C1—C6—C5	116.31 (11)	C10—C11—H11	121.6 (9)
C5—C6—C15	120.85 (11)	C12—C11—H11	120.7 (9)
C12—C7—C14	117.11 (10)	C7—C8—H8	119.4 (9)
C8—C7—C14	122.48 (11)	C9—C8—C7	119.71 (11)
C8—C7—C12	120.32 (11)	C9—C8—H8	120.9 (9)
C6—C1—O1	121.30 (11)	C5—C4—H4	119.9 (10)
C2—C1—O1	115.86 (11)	C3—C4—C5	120.25 (12)
C2—C1—C6	122.72 (11)	C3—C4—H4	119.9 (10)
O1—C14—C7	111.42 (10)	C1—C2—C3	119.19 (13)
O2—C14—O1	124.01 (11)	C1—C2—H2	119.0 (10)
O2—C14—C7	124.44 (11)	C3—C2—H2	121.8 (10)
C9—C10—N1	118.48 (10)	C4—C3—C2	119.95 (13)
C9—C10—C11	123.20 (11)	C4—C3—H3	119.2 (10)
C11—C10—N1	118.30 (11)	C2—C3—H3	120.9 (10)
C7—C12—H12	119.1 (9)	C15—C13—H13A	112.0 (10)
C11—C12—C7	120.47 (11)	C15—C13—H13B	108.9 (11)
C11—C12—H12	120.4 (9)	C15—C13—H13C	110.8 (11)
O5—C15—C6	121.75 (11)	H13A—C13—H13B	109.1 (15)
O5—C15—C13	120.46 (12)	H13A—C13—H13C	106.8 (16)
C6—C15—C13	117.79 (11)	H13B—C13—H13C	109.1 (15)
C10—C9—C8	118.44 (11)	H6—O6—H6^i	99 (3)
C10—C9—H9	120.3 (9)
O1—C1—C2—C3	176.78 (11)	C14—C7—C8—C9	173.48 (12)
O3—N1—C10—C9	179.69 (11)	C10—C9—C8—C7	−0.10 (19)
O3—N1—C10—C11	1.29 (17)	C12—C7—C14—O1	167.74 (11)
O4—N1—C10—C9	0.32 (17)	C12—C7—C14—O2	−8.35 (19)
O4—N1—C10—C11	−178.08 (12)	C12—C7—C8—C9	−2.88 (19)
N1—C10—C9—C8	−175.42 (11)	C15—C6—C1—O1	1.58 (17)
N1—C10—C11—C12	175.74 (11)	C15—C6—C1—C2	177.36 (12)
C6—C1—C2—C3	0.8 (2)	C15—C6—C5—C4	−178.13 (12)
C6—C5—C4—C3	0.7 (2)	C9—C10—C11—C12	−2.58 (19)
C7—C12—C11—C10	−0.5 (2)	C5—C6—C1—O1	−177.11 (10)
C1—O1—C14—O2	−2.64 (17)	C5—C6—C1—C2	−1.33 (18)
C1—O1—C14—C7	−178.76 (10)	C5—C6—C15—O5	−173.02 (12)
C1—C6—C15—O5	8.35 (18)	C5—C6—C15—C13	7.54 (17)
C1—C6—C15—C13	−171.09 (12)	C5—C4—C3—C2	−1.3 (2)
C1—C6—C5—C4	0.58 (18)	C11—C10—C9—C8	2.9 (2)
C1—C2—C3—C4	0.5 (2)	C8—C7—C14—O1	−8.72 (16)
C14—O1—C1—C6	−77.59 (14)	C8—C7—C14—O2	175.18 (12)
C14—O1—C1—C2	106.36 (13)	C8—C7—C12—C11	3.2 (2)
C14—C7—C12—C11	−173.34 (12)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6···O2	0.94 (1)	1.98 (2)	2.912 (6)	173 (2)
C13—H13A···O2^ii	0.998 (19)	2.638 (19)	3.594 (2)	160.6 (14)
C11—H11···O5^iii	0.960 (16)	2.600 (17)	3.4725 (17)	151.3 (12)

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

2-Acetylphenyl 2-nitrobenzoate (II)

Crystal data

C15H11NO5	F(000) = 592
Mr = 285.25	Dx = 1.464 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.209 (5) Å	Cell parameters from 2439 reflections
b = 14.307 (6) Å	θ = 2.2–31.6°
c = 7.418 (3) Å	µ = 0.11 mm^−1
β = 92.815 (7)°	T = 100 K
V = 1294.2 (9) Å^3	Prism, yellow
Z = 4	0.15 × 0.15 × 0.1 mm

Data collection

Bruker APEXII CCD diffractometer	2913 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.016
Absorption correction: multi-scan (SADABS, Bruker, 2016)	θmax = 31.8°, θmin = 1.7°
Tmin = 0.650, Tmax = 0.746	h = −17→16
5087 measured reflections	k = −20→14
3620 independent reflections	l = −3→10

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	Hydrogen site location: difference Fourier map
wR(F^2) = 0.122	All H-atom parameters refined
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0675P)^2 + 0.172P] where P = (Fo^2 + 2Fc^2)/3
3620 reflections	(Δ/σ)max < 0.001
234 parameters	Δρmax = 0.43 e Å^−3
0 restraints	Δρmin = −0.23 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
C6	0.65734 (8)	0.01262 (7)	0.45205 (14)	0.0158 (2)
O1	0.79222 (6)	−0.00491 (5)	0.70582 (10)	0.01756 (18)
O3	0.84475 (8)	−0.14564 (6)	0.97495 (13)	0.0314 (2)
C5	0.60515 (9)	−0.03010 (8)	0.30108 (16)	0.0193 (2)
O5	0.67276 (8)	0.15066 (6)	0.63086 (13)	0.0319 (2)
C12	0.88232 (8)	−0.00579 (7)	1.12279 (15)	0.0166 (2)
N1	0.89918 (7)	−0.10690 (6)	1.09597 (14)	0.0207 (2)
C7	0.80754 (8)	0.04285 (7)	1.00989 (15)	0.0164 (2)
C8	0.79381 (9)	0.13811 (7)	1.04287 (17)	0.0214 (2)
C1	0.73215 (8)	−0.04200 (7)	0.55600 (14)	0.0160 (2)
O2	0.64412 (7)	−0.02330 (6)	0.87287 (12)	0.0282 (2)
C2	0.75414 (9)	−0.13411 (7)	0.51264 (16)	0.0201 (2)
C14	0.73772 (8)	−0.00042 (7)	0.86012 (15)	0.0174 (2)
C11	0.94230 (9)	0.03733 (8)	1.26288 (16)	0.0212 (2)
C3	0.69989 (10)	−0.17469 (8)	0.36297 (17)	0.0237 (2)
O4	0.96613 (8)	−0.14724 (7)	1.19635 (15)	0.0395 (3)
C15	0.63287 (9)	0.11279 (7)	0.49603 (16)	0.0191 (2)
C4	0.62600 (10)	−0.12258 (8)	0.25762 (16)	0.0226 (2)
C13	0.55711 (10)	0.16657 (8)	0.36771 (19)	0.0268 (3)
C10	0.92771 (10)	0.13212 (9)	1.29225 (18)	0.0258 (3)
C9	0.85407 (10)	0.18239 (8)	1.18253 (18)	0.0255 (3)
H2	0.8073 (13)	−0.1705 (11)	0.587 (2)	0.035 (4)*
H8	0.7406 (12)	0.1752 (10)	0.968 (2)	0.028 (4)*
H11	0.9935 (13)	0.0017 (11)	1.333 (2)	0.032 (4)*
H5	0.5541 (13)	0.0044 (10)	0.226 (2)	0.031 (4)*
H13A	0.4825 (13)	0.1366 (11)	0.359 (2)	0.040 (4)*
H10	0.9702 (14)	0.1641 (12)	1.387 (2)	0.043 (5)*
H4	0.5886 (13)	−0.1483 (11)	0.149 (2)	0.039 (4)*
H3	0.7153 (12)	−0.2407 (11)	0.337 (2)	0.033 (4)*
H9	0.8436 (13)	0.2498 (12)	1.199 (2)	0.041 (4)*
H13B	0.5874 (14)	0.1732 (12)	0.248 (2)	0.048 (5)*
H13C	0.5493 (16)	0.2303 (14)	0.415 (3)	0.061 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C6	0.0176 (4)	0.0157 (4)	0.0141 (5)	−0.0014 (3)	−0.0002 (4)	0.0012 (3)
O1	0.0176 (3)	0.0212 (4)	0.0135 (4)	−0.0011 (3)	−0.0029 (3)	−0.0015 (3)
O3	0.0479 (5)	0.0180 (4)	0.0272 (5)	−0.0031 (4)	−0.0111 (4)	−0.0016 (3)
C5	0.0222 (5)	0.0208 (5)	0.0145 (6)	−0.0019 (4)	−0.0033 (4)	0.0015 (4)
O5	0.0454 (5)	0.0182 (4)	0.0307 (6)	0.0037 (4)	−0.0132 (4)	−0.0063 (3)
C12	0.0171 (4)	0.0169 (5)	0.0155 (5)	0.0000 (3)	−0.0006 (4)	0.0006 (4)
N1	0.0220 (4)	0.0186 (4)	0.0213 (5)	0.0013 (3)	−0.0006 (4)	0.0030 (3)
C7	0.0178 (4)	0.0180 (5)	0.0133 (5)	−0.0013 (3)	−0.0016 (4)	0.0003 (3)
C8	0.0252 (5)	0.0185 (5)	0.0201 (6)	0.0016 (4)	−0.0030 (4)	0.0003 (4)
C1	0.0171 (4)	0.0178 (5)	0.0129 (5)	−0.0010 (3)	−0.0003 (4)	−0.0004 (4)
O2	0.0227 (4)	0.0441 (5)	0.0177 (5)	−0.0094 (3)	−0.0019 (3)	−0.0001 (4)
C2	0.0243 (5)	0.0173 (5)	0.0186 (6)	0.0030 (4)	−0.0006 (4)	0.0010 (4)
C14	0.0197 (5)	0.0180 (5)	0.0141 (6)	0.0003 (4)	−0.0040 (4)	0.0016 (4)
C11	0.0195 (5)	0.0262 (5)	0.0174 (6)	0.0004 (4)	−0.0048 (4)	−0.0003 (4)
C3	0.0340 (6)	0.0169 (5)	0.0202 (6)	0.0003 (4)	0.0019 (5)	−0.0032 (4)
O4	0.0411 (5)	0.0269 (5)	0.0484 (7)	0.0120 (4)	−0.0185 (5)	0.0045 (4)
C15	0.0210 (5)	0.0153 (5)	0.0207 (6)	−0.0008 (4)	−0.0006 (4)	0.0024 (4)
C4	0.0311 (5)	0.0211 (5)	0.0152 (6)	−0.0044 (4)	−0.0029 (4)	−0.0029 (4)
C13	0.0288 (6)	0.0190 (5)	0.0319 (7)	0.0034 (4)	−0.0064 (5)	0.0058 (5)
C10	0.0267 (5)	0.0291 (6)	0.0209 (7)	−0.0042 (4)	−0.0052 (5)	−0.0079 (5)
C9	0.0314 (6)	0.0193 (5)	0.0256 (7)	−0.0013 (4)	−0.0004 (5)	−0.0052 (4)

Geometric parameters (Å, º)

C6—C5	1.4014 (16)	C1—C2	1.3860 (15)
C6—C1	1.4036 (15)	O2—C14	1.1969 (14)
C6—C15	1.5031 (15)	C2—C3	1.3914 (17)
O1—C1	1.4053 (13)	C2—H2	0.981 (16)
O1—C14	1.3534 (14)	C11—C10	1.3865 (17)
O3—N1	1.2232 (13)	C11—H11	0.941 (16)
C5—C4	1.3884 (17)	C3—C4	1.3824 (18)
C5—H5	0.954 (15)	C3—H3	0.984 (16)
O5—C15	1.2179 (15)	C15—C13	1.5057 (17)
C12—N1	1.4762 (15)	C4—H4	0.981 (17)
C12—C7	1.3943 (15)	C13—H13A	1.006 (16)
C12—C11	1.3864 (16)	C13—H13B	0.986 (18)
N1—O4	1.2230 (13)	C13—H13C	0.98 (2)
C7—C8	1.3961 (16)	C10—C9	1.3843 (19)
C7—C14	1.5004 (15)	C10—H10	0.969 (17)
C8—C9	1.3932 (17)	C9—H9	0.981 (17)
C8—H8	0.987 (15)
C5—C6—C1	117.02 (9)	O2—C14—O1	124.38 (10)
C5—C6—C15	120.13 (10)	O2—C14—C7	124.35 (10)
C1—C6—C15	122.85 (10)	C12—C11—C10	119.06 (11)
C14—O1—C1	115.32 (8)	C12—C11—H11	118.9 (9)
C6—C5—H5	120.0 (9)	C10—C11—H11	122.0 (9)
C4—C5—C6	121.32 (11)	C2—C3—H3	118.0 (9)
C4—C5—H5	118.7 (9)	C4—C3—C2	119.87 (10)
C7—C12—N1	119.98 (9)	C4—C3—H3	122.2 (9)
C11—C12—N1	117.71 (9)	C6—C15—C13	118.20 (10)
C11—C12—C7	122.30 (10)	O5—C15—C6	121.78 (10)
O3—N1—C12	117.94 (9)	O5—C15—C13	120.02 (10)
O4—N1—O3	123.77 (10)	C5—C4—H4	117.8 (9)
O4—N1—C12	118.29 (10)	C3—C4—C5	120.31 (11)
C12—C7—C8	117.55 (10)	C3—C4—H4	121.9 (9)
C12—C7—C14	124.77 (9)	C15—C13—H13A	110.4 (9)
C8—C7—C14	117.64 (10)	C15—C13—H13B	112.0 (10)
C7—C8—H8	120.5 (8)	C15—C13—H13C	108.5 (11)
C9—C8—C7	120.71 (11)	H13A—C13—H13B	111.2 (14)
C9—C8—H8	118.8 (8)	H13A—C13—H13C	108.4 (15)
C6—C1—O1	121.64 (9)	H13B—C13—H13C	106.1 (15)
C2—C1—C6	122.01 (10)	C11—C10—H10	120.5 (10)
C2—C1—O1	116.30 (9)	C9—C10—C11	120.04 (11)
C1—C2—C3	119.46 (10)	C9—C10—H10	119.5 (10)
C1—C2—H2	120.3 (9)	C8—C9—H9	118.1 (10)
C3—C2—H2	120.3 (9)	C10—C9—C8	120.33 (11)
O1—C14—C7	111.15 (9)	C10—C9—H9	121.5 (10)
C6—C5—C4—C3	−0.37 (17)	C8—C7—C14—O2	−79.61 (14)
C6—C1—C2—C3	−0.77 (16)	C1—C6—C5—C4	0.55 (16)
O1—C1—C2—C3	−178.27 (9)	C1—C6—C15—O5	−3.97 (16)
C5—C6—C1—O1	177.39 (9)	C1—C6—C15—C13	175.80 (10)
C5—C6—C1—C2	0.02 (15)	C1—O1—C14—C7	−178.19 (8)
C5—C6—C15—O5	176.43 (10)	C1—O1—C14—O2	−1.95 (15)
C5—C6—C15—C13	−3.80 (15)	C1—C2—C3—C4	0.95 (17)
C12—C7—C8—C9	0.76 (16)	C2—C3—C4—C5	−0.40 (18)
C12—C7—C14—O1	−85.81 (12)	C14—O1—C1—C6	81.05 (12)
C12—C7—C14—O2	97.95 (14)	C14—O1—C1—C2	−101.44 (11)
C12—C11—C10—C9	0.02 (18)	C14—C7—C8—C9	178.50 (10)
N1—C12—C7—C8	179.17 (9)	C11—C12—N1—O3	178.49 (10)
N1—C12—C7—C14	1.61 (15)	C11—C12—N1—O4	−1.10 (15)
N1—C12—C11—C10	−179.57 (10)	C11—C12—C7—C8	−0.38 (15)
C7—C12—N1—O3	−1.08 (14)	C11—C12—C7—C14	−177.94 (10)
C7—C12—N1—O4	179.33 (10)	C11—C10—C9—C8	0.36 (18)
C7—C12—C11—C10	−0.01 (16)	C15—C6—C5—C4	−179.82 (10)
C7—C8—C9—C10	−0.76 (18)	C15—C6—C1—O1	−2.23 (15)
C8—C7—C14—O1	96.63 (11)	C15—C6—C1—C2	−179.60 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O1^i	0.941 (16)	2.646 (15)	3.2711 (19)	124.4 (12)

Symmetry code: (i) −x+2, −y, −z+2.