Packing polymorphism in the crystal structure of 4,5-dimeth­oxy-2-nitro­benzyl acetate

The title compound shows two packing polymorphs, in which the mol­ecular structures are planar and essentially similar. One crystal shows inter­molecular C—H...O and π–π inter­actions, while the other crystal exhibits several modes of inter­molecular C—H...O inter­actions.

Key indicators

Structure: orange

• Single-crystal X-ray study
• T = 93 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.051
• wR factor = 0.132
• Data-to-parameter ratio = 15.7

Structure: yellow

• Single-crystal X-ray study
• T = 93 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.049
• wR factor = 0.130
• Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found



Datablock: orange



Alert level C
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      7.401 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          3 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          2 Note
PLAT934_ALERT_3_C Number of (Iobs-Icalc)/SigmaW > 10 Outliers ....          1 Check

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ...          3 Report
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          9 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 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
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check




Datablock: yellow



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N1     --  C2      ..        6.3 su
PLAT411_ALERT_2_C Short Inter H...H Contact  H7A    ..  H7A     ..       2.05 Ang.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.898 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          5 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          2 Note

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2014 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ...          3 Report

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   5 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
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

Computing details

For both compounds, data collection: CrystalClear-SM Expert (Rigaku, 2011). Cell refinement: CrystalClear-SM Expert (Rigaku, 2011) for orange; CrystalClear-SM Expert for yellow. Data reduction: CrystalClear-SM Expert (Rigaku, 2011) for orange; CrystalClear-SM Expert for yellow. For both compounds, program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: Yadokari-XG (Wakita, 2001).

(orange) 4,5-Dimethoxy-2-nitrobenzyl acetate

Crystal data

C11H13NO6	F(000) = 536
Mr = 255.22	Dx = 1.48 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 2655 reflections
a = 8.8751 (13) Å	θ = 3.1–27.5°
b = 19.555 (2) Å	µ = 0.12 mm^−1
c = 6.8688 (9) Å	T = 93 K
β = 106.298 (6)°	Platelet, orange
V = 1144.2 (3) Å^3	0.45 × 0.42 × 0.39 mm
Z = 4

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	2612 independent reflections
Radiation source: fine-focus sealed tube	2098 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
Detector resolution: 13.6612 pixels mm^-1	θmax = 27.5°, θmin = 3.2°
profile data from ω–scans	h = −11→11
Absorption correction: multi-scan (REQAB; Rigaku, 1998)	k = −25→25
Tmin = 0.960, Tmax = 0.970	l = −8→8
11495 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.132	H-atom parameters not refined
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0597P)^2 + 0.5862P] where P = (Fo^2 + 2Fc^2)/3
2612 reflections	(Δ/σ)max < 0.001
166 parameters	Δρmax = 0.39 e Å^−3
0 restraints	Δρmin = −0.30 e Å^−3

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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
C1	0.19328 (19)	0.29434 (8)	0.7664 (2)	0.0124 (3)
C2	0.04911 (19)	0.26435 (9)	0.7614 (3)	0.0139 (3)
C3	0.02606 (19)	0.19342 (8)	0.7577 (3)	0.0140 (3)
H3	−0.0739	0.1752	0.7541	0.017*
C4	0.1487 (2)	0.15013 (8)	0.7593 (3)	0.0139 (3)
C5	0.29755 (19)	0.17865 (8)	0.7678 (2)	0.0125 (3)
C6	0.31701 (19)	0.24911 (8)	0.7700 (2)	0.0128 (3)
H6	0.4171	0.2673	0.7740	0.015*
C7	0.22141 (19)	0.37064 (8)	0.7674 (3)	0.0138 (3)
H7A	0.1502	0.3919	0.6450	0.017*
H7B	0.2010	0.3916	0.8887	0.017*
C8	0.4225 (2)	0.44786 (9)	0.7575 (3)	0.0155 (4)
C9	0.5882 (2)	0.45412 (9)	0.7490 (3)	0.0218 (4)
H9A	0.5938	0.4425	0.6124	0.033*
H9B	0.6550	0.4227	0.8475	0.033*
H9C	0.6247	0.5012	0.7816	0.033*
C10	−0.0084 (2)	0.05009 (9)	0.7387 (3)	0.0200 (4)
H10A	−0.0436	0.0632	0.8565	0.030*
H10B	0.0007	0.0002	0.7344	0.030*
H10C	−0.0848	0.0660	0.6144	0.030*
C11	0.5657 (2)	0.15867 (9)	0.7809 (3)	0.0187 (4)
H11A	0.5598	0.1883	0.6639	0.028*
H11B	0.6370	0.1205	0.7803	0.028*
H11C	0.6051	0.1850	0.9063	0.028*
N1	−0.08677 (17)	0.30611 (7)	0.7608 (2)	0.0154 (3)
O1	−0.08009 (15)	0.36827 (7)	0.7379 (2)	0.0252 (3)
O2	−0.20491 (15)	0.27751 (7)	0.7846 (2)	0.0236 (3)
O3	0.38271 (14)	0.38139 (6)	0.7701 (2)	0.0154 (3)
O4	0.33181 (16)	0.49408 (7)	0.7520 (2)	0.0257 (3)
O5	0.14161 (14)	0.08062 (6)	0.7543 (2)	0.0176 (3)
O6	0.41110 (14)	0.13243 (6)	0.7695 (2)	0.0164 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0128 (8)	0.0155 (8)	0.0088 (8)	0.0001 (6)	0.0027 (6)	0.0011 (6)
C2	0.0112 (8)	0.0174 (8)	0.0137 (8)	0.0022 (6)	0.0046 (6)	0.0009 (6)
C3	0.0121 (8)	0.0174 (8)	0.0127 (8)	−0.0021 (6)	0.0037 (6)	0.0004 (6)
C4	0.0147 (8)	0.0137 (8)	0.0133 (8)	−0.0031 (6)	0.0040 (6)	0.0003 (6)
C5	0.0134 (8)	0.0152 (8)	0.0095 (8)	0.0014 (6)	0.0041 (6)	−0.0001 (6)
C6	0.0113 (8)	0.0160 (8)	0.0117 (8)	−0.0008 (6)	0.0043 (6)	−0.0002 (6)
C7	0.0105 (8)	0.0147 (8)	0.0177 (9)	−0.0003 (6)	0.0065 (6)	0.0002 (6)
C8	0.0161 (8)	0.0149 (8)	0.0164 (9)	−0.0025 (6)	0.0063 (7)	−0.0006 (6)
C9	0.0140 (8)	0.0182 (9)	0.0347 (11)	−0.0021 (7)	0.0094 (8)	−0.0009 (8)
C10	0.0173 (9)	0.0163 (8)	0.0271 (10)	−0.0074 (7)	0.0075 (7)	−0.0016 (7)
C11	0.0120 (8)	0.0170 (8)	0.0277 (10)	−0.0006 (6)	0.0065 (7)	−0.0011 (7)
N1	0.0113 (7)	0.0171 (7)	0.0177 (8)	−0.0005 (5)	0.0041 (6)	−0.0007 (5)
O1	0.0179 (7)	0.0159 (6)	0.0437 (9)	0.0031 (5)	0.0119 (6)	0.0037 (6)
O2	0.0133 (6)	0.0236 (7)	0.0364 (8)	−0.0016 (5)	0.0111 (6)	0.0010 (6)
O3	0.0114 (6)	0.0131 (6)	0.0227 (7)	−0.0011 (4)	0.0063 (5)	0.0000 (5)
O4	0.0203 (7)	0.0141 (6)	0.0461 (9)	0.0008 (5)	0.0147 (6)	0.0018 (6)
O5	0.0160 (6)	0.0120 (6)	0.0264 (7)	−0.0022 (5)	0.0085 (5)	−0.0001 (5)
O6	0.0124 (6)	0.0137 (6)	0.0244 (7)	0.0013 (5)	0.0071 (5)	0.0005 (5)

Geometric parameters (Å, º)

C1—C2	1.399 (2)	C8—O3	1.356 (2)
C1—C6	1.405 (2)	C8—C9	1.494 (2)
C1—C7	1.512 (2)	C9—H9A	0.9800
C2—C3	1.401 (2)	C9—H9B	0.9800
C2—N1	1.456 (2)	C9—H9C	0.9800
C3—C4	1.377 (2)	C10—O5	1.436 (2)
C3—H3	0.9500	C10—H10A	0.9800
C4—O5	1.361 (2)	C10—H10B	0.9800
C4—C5	1.420 (2)	C10—H10C	0.9800
C5—O6	1.351 (2)	C11—O6	1.446 (2)
C5—C6	1.388 (2)	C11—H11A	0.9800
C6—H6	0.9500	C11—H11B	0.9800
C7—O3	1.4419 (19)	C11—H11C	0.9800
C7—H7A	0.9900	N1—O1	1.229 (2)
C7—H7B	0.9900	N1—O2	1.2390 (19)
C8—O4	1.204 (2)
C2—C1—C6	116.20 (15)	O3—C8—C9	110.96 (15)
C2—C1—C7	124.21 (15)	C8—C9—H9A	109.5
C6—C1—C7	119.59 (15)	C8—C9—H9B	109.5
C1—C2—C3	122.90 (15)	H9A—C9—H9B	109.5
C1—C2—N1	121.08 (15)	C8—C9—H9C	109.5
C3—C2—N1	116.02 (15)	H9A—C9—H9C	109.5
C4—C3—C2	119.83 (15)	H9B—C9—H9C	109.5
C4—C3—H3	120.1	O5—C10—H10A	109.5
C2—C3—H3	120.1	O5—C10—H10B	109.5
O5—C4—C3	125.67 (15)	H10A—C10—H10B	109.5
O5—C4—C5	115.43 (15)	O5—C10—H10C	109.5
C3—C4—C5	118.90 (15)	H10A—C10—H10C	109.5
O6—C5—C6	125.00 (15)	H10B—C10—H10C	109.5
O6—C5—C4	114.87 (15)	O6—C11—H11A	109.5
C6—C5—C4	120.12 (15)	O6—C11—H11B	109.5
C5—C6—C1	122.03 (15)	H11A—C11—H11B	109.5
C5—C6—H6	119.0	O6—C11—H11C	109.5
C1—C6—H6	119.0	H11A—C11—H11C	109.5
O3—C7—C1	107.82 (13)	H11B—C11—H11C	109.5
O3—C7—H7A	110.1	O1—N1—O2	122.43 (15)
C1—C7—H7A	110.1	O1—N1—C2	119.04 (14)
O3—C7—H7B	110.1	O2—N1—C2	118.53 (14)
C1—C7—H7B	110.1	C8—O3—C7	114.47 (13)
H7A—C7—H7B	108.5	C4—O5—C10	116.93 (13)
O4—C8—O3	122.58 (16)	C5—O6—C11	117.20 (13)
O4—C8—C9	126.45 (16)
C6—C1—C2—C3	−0.7 (2)	C7—C1—C6—C5	−179.55 (15)
C7—C1—C2—C3	179.08 (16)	C2—C1—C7—O3	−179.18 (15)
C6—C1—C2—N1	178.95 (15)	C6—C1—C7—O3	0.6 (2)
C7—C1—C2—N1	−1.2 (3)	C1—C2—N1—O1	9.5 (2)
C1—C2—C3—C4	0.1 (3)	C3—C2—N1—O1	−170.83 (16)
N1—C2—C3—C4	−179.59 (15)	C1—C2—N1—O2	−170.13 (16)
C2—C3—C4—O5	−179.39 (16)	C3—C2—N1—O2	9.6 (2)
C2—C3—C4—C5	1.0 (2)	O4—C8—O3—C7	2.5 (2)
O5—C4—C5—O6	0.1 (2)	C9—C8—O3—C7	−176.69 (15)
C3—C4—C5—O6	179.78 (15)	C1—C7—O3—C8	175.79 (14)
O5—C4—C5—C6	178.91 (14)	C3—C4—O5—C10	2.4 (3)
C3—C4—C5—C6	−1.4 (2)	C5—C4—O5—C10	−177.96 (15)
O6—C5—C6—C1	179.47 (15)	C6—C5—O6—C11	2.1 (2)
C4—C5—C6—C1	0.8 (2)	C4—C5—O6—C11	−179.17 (15)
C2—C1—C6—C5	0.3 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···O4^i	0.98	2.50	3.369 (2)	147

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

(yellow) 4,5-Dimethoxy-2-nitrobenzyl Acetate

Crystal data

C11H13NO6	F(000) = 536
Mr = 255.22	Dx = 1.52 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 2424 reflections
a = 10.476 (3) Å	θ = 3.1–27.5°
b = 10.714 (3) Å	µ = 0.13 mm^−1
c = 10.266 (3) Å	T = 93 K
β = 105.077 (10)°	Neecle, yellow
V = 1112.6 (6) Å^3	0.56 × 0.54 × 0.25 mm
Z = 4

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	2058 independent reflections
Radiation source: fine-focus sealed tube	1769 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
Detector resolution: 13.6612 pixels mm^-1	θmax = 25.5°, θmin = 3.1°
profile data from ω–scan	h = −12→12
Absorption correction: multi-scan (REQAB; Rigaku, 1998)	k = −12→12
Tmin = 0.797, Tmax = 0.970	l = −12→12
9498 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.130	H-atom parameters not refined
S = 1.13	w = 1/[σ^2(Fo^2) + (0.0689P)^2 + 0.4454P] where P = (Fo^2 + 2Fc^2)/3
2058 reflections	(Δ/σ)max < 0.001
166 parameters	Δρmax = 0.38 e Å^−3
0 restraints	Δρmin = −0.35 e Å^−3

Special details

Experimental. Rigaku (1998). REQAB. Rigaku Corporation, Tokyo, Japan.

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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
C1	0.22297 (15)	0.82305 (16)	0.58154 (16)	0.0158 (4)
C2	0.29963 (16)	0.88543 (15)	0.69423 (17)	0.0154 (4)
C3	0.37895 (16)	0.82230 (16)	0.80564 (16)	0.0168 (4)
H3	0.4307	0.8681	0.8801	0.020*
C4	0.38181 (16)	0.69396 (16)	0.80717 (16)	0.0167 (4)
C5	0.30317 (15)	0.62775 (16)	0.69555 (17)	0.0154 (4)
C6	0.22676 (16)	0.69258 (16)	0.58567 (16)	0.0158 (4)
H6	0.1754	0.6469	0.5109	0.019*
C7	0.13844 (16)	0.88840 (15)	0.45857 (17)	0.0166 (4)
H7A	0.0754	0.9456	0.4852	0.020*
H7B	0.1948	0.9379	0.4140	0.020*
C8	−0.01205 (16)	0.83679 (16)	0.25084 (16)	0.0175 (4)
C9	−0.08377 (18)	0.73342 (16)	0.16403 (18)	0.0216 (4)
H9A	−0.1781	0.7378	0.1603	0.032*
H9B	−0.0481	0.6529	0.2022	0.032*
H9C	−0.0721	0.7418	0.0728	0.032*
C10	0.53711 (16)	0.68572 (16)	1.02246 (16)	0.0186 (4)
H10A	0.6026	0.7354	0.9923	0.028*
H10B	0.5826	0.6245	1.0895	0.028*
H10C	0.4834	0.7409	1.0630	0.028*
C11	0.22990 (18)	0.43083 (16)	0.59702 (17)	0.0211 (4)
H11A	0.1368	0.4538	0.5832	0.032*
H11B	0.2410	0.3417	0.6185	0.032*
H11C	0.2574	0.4480	0.5146	0.032*
O1	0.23683 (12)	1.08224 (11)	0.60592 (12)	0.0219 (3)
O2	0.36433 (12)	1.07109 (11)	0.80903 (12)	0.0228 (3)
O3	0.06713 (11)	0.79354 (11)	0.36698 (12)	0.0186 (3)
O4	−0.02320 (12)	0.94638 (11)	0.22241 (12)	0.0229 (3)
O5	0.45330 (11)	0.62196 (11)	0.90924 (12)	0.0183 (3)
O6	0.30975 (12)	0.50251 (11)	0.70663 (12)	0.0187 (3)
N1	0.30069 (14)	1.02142 (14)	0.70366 (14)	0.0175 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0163 (8)	0.0161 (8)	0.0155 (8)	0.0025 (6)	0.0052 (7)	0.0004 (6)
C2	0.0196 (8)	0.0084 (8)	0.0189 (9)	0.0000 (6)	0.0064 (7)	−0.0011 (6)
C3	0.0179 (8)	0.0159 (8)	0.0154 (8)	−0.0026 (7)	0.0023 (7)	−0.0015 (6)
C4	0.0189 (8)	0.0155 (9)	0.0149 (8)	0.0008 (7)	0.0031 (7)	0.0008 (6)
C5	0.0163 (8)	0.0136 (9)	0.0158 (8)	−0.0006 (6)	0.0033 (7)	−0.0002 (6)
C6	0.0177 (8)	0.0137 (9)	0.0153 (8)	−0.0009 (6)	0.0033 (7)	−0.0023 (6)
C7	0.0193 (8)	0.0115 (8)	0.0163 (8)	−0.0006 (6)	0.0000 (7)	−0.0022 (6)
C8	0.0169 (8)	0.0188 (9)	0.0148 (8)	0.0001 (7)	0.0006 (7)	0.0014 (7)
C9	0.0233 (9)	0.0158 (9)	0.0212 (9)	0.0007 (7)	−0.0025 (7)	0.0003 (7)
C10	0.0199 (8)	0.0181 (9)	0.0144 (8)	−0.0017 (7)	−0.0018 (7)	−0.0009 (7)
C11	0.0278 (9)	0.0134 (9)	0.0188 (9)	−0.0016 (7)	0.0000 (7)	−0.0029 (6)
O1	0.0277 (7)	0.0145 (6)	0.0204 (7)	0.0032 (5)	0.0009 (5)	0.0035 (5)
O2	0.0307 (7)	0.0153 (7)	0.0189 (7)	−0.0016 (5)	−0.0001 (5)	−0.0052 (5)
O3	0.0215 (6)	0.0127 (6)	0.0173 (6)	0.0004 (5)	−0.0027 (5)	−0.0002 (5)
O4	0.0277 (7)	0.0140 (6)	0.0229 (7)	0.0001 (5)	−0.0008 (5)	0.0031 (5)
O5	0.0222 (6)	0.0131 (6)	0.0146 (6)	−0.0007 (5)	−0.0040 (5)	0.0008 (5)
O6	0.0245 (6)	0.0095 (6)	0.0183 (6)	−0.0001 (5)	−0.0013 (5)	−0.0001 (4)
N1	0.0195 (7)	0.0153 (8)	0.0168 (7)	−0.0007 (6)	0.0029 (6)	−0.0007 (6)

Geometric parameters (Å, º)

C1—C2	1.395 (2)	C8—O3	1.345 (2)
C1—C6	1.399 (2)	C8—C9	1.496 (2)
C1—C7	1.512 (2)	C9—H9A	0.9800
C2—C3	1.401 (2)	C9—H9B	0.9800
C2—N1	1.460 (2)	C9—H9C	0.9800
C3—C4	1.375 (3)	C10—O5	1.4344 (19)
C3—H3	0.9500	C10—H10A	0.9800
C4—O5	1.359 (2)	C10—H10B	0.9800
C4—C5	1.416 (2)	C10—H10C	0.9800
C5—O6	1.347 (2)	C11—O6	1.437 (2)
C5—C6	1.388 (2)	C11—H11A	0.9800
C6—H6	0.9500	C11—H11B	0.9800
C7—O3	1.4524 (19)	C11—H11C	0.9800
C7—H7A	0.9900	O1—N1	1.2368 (19)
C7—H7B	0.9900	O2—N1	1.2339 (19)
C8—O4	1.208 (2)
C2—C1—C6	116.61 (15)	O3—C8—C9	111.81 (14)
C2—C1—C7	123.79 (16)	C8—C9—H9A	109.5
C6—C1—C7	119.60 (14)	C8—C9—H9B	109.5
C1—C2—C3	122.48 (16)	H9A—C9—H9B	109.5
C1—C2—N1	121.72 (15)	C8—C9—H9C	109.5
C3—C2—N1	115.79 (15)	H9A—C9—H9C	109.5
C4—C3—C2	119.91 (15)	H9B—C9—H9C	109.5
C4—C3—H3	120.0	O5—C10—H10A	109.5
C2—C3—H3	120.0	O5—C10—H10B	109.5
O5—C4—C3	125.62 (15)	H10A—C10—H10B	109.5
O5—C4—C5	115.33 (15)	O5—C10—H10C	109.5
C3—C4—C5	119.04 (15)	H10A—C10—H10C	109.5
O6—C5—C6	124.98 (15)	H10B—C10—H10C	109.5
O6—C5—C4	115.13 (14)	O6—C11—H11A	109.5
C6—C5—C4	119.89 (16)	O6—C11—H11B	109.5
C5—C6—C1	122.05 (15)	H11A—C11—H11B	109.5
C5—C6—H6	119.0	O6—C11—H11C	109.5
C1—C6—H6	119.0	H11A—C11—H11C	109.5
O3—C7—C1	107.90 (13)	H11B—C11—H11C	109.5
O3—C7—H7A	110.1	C8—O3—C7	115.31 (13)
C1—C7—H7A	110.1	C4—O5—C10	116.94 (13)
O3—C7—H7B	110.1	C5—O6—C11	117.37 (13)
C1—C7—H7B	110.1	O2—N1—O1	122.61 (15)
H7A—C7—H7B	108.4	O2—N1—C2	118.78 (14)
O4—C8—O3	123.19 (15)	O1—N1—C2	118.60 (13)
O4—C8—C9	125.01 (15)
C6—C1—C2—C3	1.2 (2)	C7—C1—C6—C5	179.61 (14)
C7—C1—C2—C3	−178.75 (15)	C2—C1—C7—O3	−176.32 (14)
C6—C1—C2—N1	−178.07 (14)	C6—C1—C7—O3	3.7 (2)
C7—C1—C2—N1	2.0 (2)	O4—C8—O3—C7	0.8 (2)
C1—C2—C3—C4	−0.8 (2)	C9—C8—O3—C7	−178.75 (13)
N1—C2—C3—C4	178.48 (15)	C1—C7—O3—C8	−179.24 (13)
C2—C3—C4—O5	−179.33 (14)	C3—C4—O5—C10	−2.8 (2)
C2—C3—C4—C5	−0.4 (2)	C5—C4—O5—C10	178.28 (13)
O5—C4—C5—O6	0.4 (2)	C6—C5—O6—C11	−1.0 (2)
C3—C4—C5—O6	−178.65 (15)	C4—C5—O6—C11	178.91 (13)
O5—C4—C5—C6	−179.73 (14)	C1—C2—N1—O2	175.79 (14)
C3—C4—C5—C6	1.3 (2)	C3—C2—N1—O2	−3.5 (2)
O6—C5—C6—C1	179.03 (15)	C1—C2—N1—O1	−3.7 (2)
C4—C5—C6—C1	−0.9 (2)	C3—C2—N1—O1	177.02 (14)
C2—C1—C6—C5	−0.3 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···O4^i	0.98	2.40	3.375 (2)	174
C10—H10B···O6^ii	0.98	2.51	3.472 (2)	169

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