Crystal structures of 4-(2/3-meth­oxy­phen­oxy)phthalo­nitrile

The syntheses and crystal structures are reported of 4-phen­oxy-substituted phthalo­nitriles with meth­oxy groups in the ortho- and meta-positions of the terminal benzene rings. Short contacts play a more decisive role in the mol­ecular packing compared to van der Waals inter­actions.

Key indicators

Structure: o-C15H10N2O2

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.045
• wR factor = 0.095
• Data-to-parameter ratio = 17.5

Structure: m-C15H10N2O2

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.001 Å
• R factor = 0.039
• wR factor = 0.105
• Data-to-parameter ratio = 19.6

checkCIF/PLATON results

No syntax errors found



Datablock: o-C15H10N2O2



Alert level C
PLAT481_ALERT_4_C Long D...A H-Bond Reported C11      ..O2       .       3.73 Ang.

Alert level G
PLAT480_ALERT_4_G Long H...A H-Bond Reported H3A      ..O2       .       2.95 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H5A      ..N2       .       2.66 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H5A      ..N1       .       2.90 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H5A      ..O1       .       2.96 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H8A      ..N2       .       2.69 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H11A     ..O2       .       2.82 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H11A     ..O1       .       2.75 Ang.
PLAT954_ALERT_1_G Reported (CIF) and Actual (FCF) Kmax Differ by .          1 Units
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          4 Info

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

   1 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
   0 ALERT type 3 Indicator that the structure quality may be low
   8 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: m-C15H10N2O2



Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.043 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report

Alert level G
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.001 Degree
PLAT230_ALERT_2_G Hirshfeld Test Diff for    C9       --C13      .        6.8 s.u.
PLAT230_ALERT_2_G Hirshfeld Test Diff for    C10      --C14      .        7.0 s.u.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H2A      ..N2       .       2.64 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H12A     ..N1       .       2.74 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H12A     ..O2       .       2.67 Ang.
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          3 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          1 Note
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ...........        3.0 Low
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         15 Info
PLAT992_ALERT_5_G Repd & Actual _reflns_number_gt Values Differ by          2 Check

   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
  11 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   4 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

Computing details

For both structures, data collection: APEX3 (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXT2014/5 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: Mercury (Macrae et al., 2020).

4-(2-Methoxyphenoxy)benzene-1,2-dicarbonitrile (o-C15H10N2O2)

Crystal data

C15H10N2O2	Dx = 1.354 Mg m^−3
Mr = 250.25	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 9781 reflections
a = 7.7329 (3) Å	θ = 2.7–30.1°
b = 8.2536 (3) Å	µ = 0.09 mm^−1
c = 19.2301 (7) Å	T = 100 K
V = 1227.35 (8) Å^3	Prism, colorless
Z = 4	0.24 × 0.24 × 0.07 mm
F(000) = 520

Data collection

Bruker D8 Quest (CMOS) diffractometer	2616 reflections with I > 2σ(I)
Radiation source: microfocus tube	Rint = 0.046
ω scans	θmax = 28.3°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −10→10
Tmin = 0.903, Tmax = 0.971	k = −11→11
19395 measured reflections	l = −25→25
3035 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.045	H-atom parameters constrained
wR(F^2) = 0.095	w = 1/[σ^2(Fo^2) + (0.0385P)^2 + 0.3865P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
3035 reflections	Δρmax = 0.21 e Å^−3
173 parameters	Δρmin = −0.32 e Å^−3
0 restraints	Absolute structure: Flack x determined using 931 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013)
Primary atom site location: dual

Special details

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

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

	x	y	z	Uiso*/Ueq
O1	0.6870 (2)	0.31404 (19)	0.64727 (8)	0.0195 (4)
O2	0.9772 (2)	0.4854 (2)	0.66084 (9)	0.0268 (4)
N1	0.4498 (4)	0.9100 (3)	0.50573 (12)	0.0377 (6)
N2	0.3018 (3)	0.6112 (3)	0.36049 (11)	0.0244 (5)
C1	0.7085 (3)	0.4120 (3)	0.70640 (12)	0.0172 (5)
C2	0.8609 (3)	0.5003 (3)	0.71355 (12)	0.0193 (5)
C3	0.8807 (3)	0.5958 (3)	0.77286 (13)	0.0235 (5)
H3A	0.982511	0.658542	0.779084	0.028*
C4	0.7515 (3)	0.5990 (3)	0.82256 (12)	0.0249 (6)
H4A	0.765466	0.665266	0.862552	0.030*
C5	0.6029 (3)	0.5081 (3)	0.81540 (12)	0.0242 (5)
H5A	0.516618	0.509974	0.850546	0.029*
C6	0.5809 (3)	0.4138 (3)	0.75631 (12)	0.0210 (5)
H6A	0.478840	0.351196	0.750360	0.025*
C7	0.6104 (3)	0.3826 (3)	0.59041 (11)	0.0160 (5)
C8	0.5802 (3)	0.5471 (3)	0.58379 (11)	0.0166 (5)
H8A	0.611760	0.619803	0.619924	0.020*
C9	0.5027 (3)	0.6041 (3)	0.52311 (11)	0.0174 (5)
C10	0.4544 (3)	0.4968 (3)	0.46957 (11)	0.0170 (5)
C11	0.4861 (3)	0.3315 (3)	0.47775 (12)	0.0178 (5)
H11A	0.454353	0.257754	0.442035	0.021*
C12	0.5635 (3)	0.2752 (3)	0.53775 (12)	0.0180 (5)
H12A	0.584819	0.162514	0.543185	0.022*
C13	0.4736 (3)	0.7744 (3)	0.51398 (12)	0.0235 (5)
C14	0.3705 (3)	0.5595 (3)	0.40833 (12)	0.0187 (5)
C15	1.1358 (3)	0.5737 (4)	0.66790 (16)	0.0365 (7)
H15A	1.209911	0.552231	0.627585	0.055*
H15B	1.195310	0.539339	0.710413	0.055*
H15C	1.110784	0.689945	0.670515	0.055*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0259 (9)	0.0151 (8)	0.0175 (8)	0.0017 (7)	−0.0029 (7)	−0.0003 (6)
O2	0.0213 (8)	0.0321 (10)	0.0270 (9)	−0.0034 (8)	0.0053 (8)	0.0023 (8)
N1	0.0639 (18)	0.0183 (11)	0.0310 (12)	0.0001 (11)	−0.0236 (13)	−0.0027 (10)
N2	0.0281 (11)	0.0235 (11)	0.0216 (11)	0.0009 (10)	−0.0029 (10)	−0.0021 (9)
C1	0.0213 (11)	0.0130 (10)	0.0172 (11)	0.0032 (10)	−0.0023 (10)	0.0017 (9)
C2	0.0193 (11)	0.0204 (11)	0.0183 (11)	0.0025 (10)	0.0003 (9)	0.0067 (10)
C3	0.0216 (12)	0.0234 (13)	0.0255 (12)	−0.0002 (11)	−0.0092 (11)	0.0033 (10)
C4	0.0317 (14)	0.0266 (13)	0.0165 (12)	0.0070 (12)	−0.0083 (10)	−0.0031 (10)
C5	0.0267 (13)	0.0280 (13)	0.0177 (11)	0.0067 (12)	0.0025 (10)	0.0004 (10)
C6	0.0197 (11)	0.0193 (12)	0.0241 (12)	0.0019 (10)	−0.0016 (10)	0.0053 (10)
C7	0.0137 (10)	0.0174 (11)	0.0168 (10)	−0.0005 (9)	0.0038 (9)	0.0016 (9)
C8	0.0192 (11)	0.0162 (11)	0.0144 (10)	−0.0032 (9)	0.0003 (9)	−0.0029 (9)
C9	0.0183 (11)	0.0150 (11)	0.0187 (11)	−0.0016 (9)	0.0010 (10)	−0.0004 (9)
C10	0.0162 (10)	0.0183 (11)	0.0164 (10)	−0.0011 (10)	0.0009 (9)	−0.0026 (9)
C11	0.0162 (11)	0.0183 (11)	0.0191 (11)	−0.0029 (9)	0.0020 (9)	−0.0042 (9)
C12	0.0175 (11)	0.0123 (11)	0.0243 (12)	0.0000 (9)	0.0028 (10)	−0.0015 (9)
C13	0.0320 (14)	0.0208 (13)	0.0175 (11)	−0.0029 (11)	−0.0098 (11)	−0.0038 (10)
C14	0.0196 (11)	0.0167 (11)	0.0199 (12)	−0.0030 (9)	0.0021 (10)	−0.0054 (9)
C15	0.0195 (12)	0.0447 (17)	0.0451 (17)	−0.0050 (13)	0.0056 (12)	0.0081 (14)

Geometric parameters (Å, º)

O1—C7	1.366 (3)	C6—H6A	0.9500
O1—C1	1.405 (3)	C7—C8	1.384 (3)
O2—C2	1.360 (3)	C7—C12	1.394 (3)
O2—C15	1.434 (3)	C8—C9	1.394 (3)
N1—C13	1.145 (3)	C8—H8A	0.9500
N2—C14	1.145 (3)	C9—C10	1.408 (3)
C1—C6	1.377 (3)	C9—C13	1.434 (3)
C1—C2	1.393 (3)	C10—C11	1.395 (3)
C2—C3	1.395 (3)	C10—C14	1.441 (3)
C3—C4	1.382 (4)	C11—C12	1.381 (3)
C3—H3A	0.9500	C11—H11A	0.9500
C4—C5	1.379 (4)	C12—H12A	0.9500
C4—H4A	0.9500	C15—H15A	0.9800
C5—C6	1.388 (3)	C15—H15B	0.9800
C5—H5A	0.9500	C15—H15C	0.9800
C7—O1—C1	117.45 (17)	C7—C8—C9	118.8 (2)
C2—O2—C15	116.7 (2)	C7—C8—H8A	120.6
C6—C1—C2	122.1 (2)	C9—C8—H8A	120.6
C6—C1—O1	119.1 (2)	C8—C9—C10	120.9 (2)
C2—C1—O1	118.8 (2)	C8—C9—C13	120.1 (2)
O2—C2—C1	116.0 (2)	C10—C9—C13	119.0 (2)
O2—C2—C3	126.0 (2)	C11—C10—C9	119.1 (2)
C1—C2—C3	118.0 (2)	C11—C10—C14	121.5 (2)
C4—C3—C2	119.8 (2)	C9—C10—C14	119.4 (2)
C4—C3—H3A	120.1	C12—C11—C10	120.0 (2)
C2—C3—H3A	120.1	C12—C11—H11A	120.0
C5—C4—C3	121.5 (2)	C10—C11—H11A	120.0
C5—C4—H4A	119.2	C11—C12—C7	120.4 (2)
C3—C4—H4A	119.2	C11—C12—H12A	119.8
C4—C5—C6	119.3 (2)	C7—C12—H12A	119.8
C4—C5—H5A	120.4	N1—C13—C9	179.0 (3)
C6—C5—H5A	120.4	N2—C14—C10	178.6 (2)
C1—C6—C5	119.3 (2)	O2—C15—H15A	109.5
C1—C6—H6A	120.4	O2—C15—H15B	109.5
C5—C6—H6A	120.4	H15A—C15—H15B	109.5
O1—C7—C8	123.6 (2)	O2—C15—H15C	109.5
O1—C7—C12	115.53 (19)	H15A—C15—H15C	109.5
C8—C7—C12	120.9 (2)	H15B—C15—H15C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O2^i	0.95	2.95	3.629 (3)	129
C5—H5A···N2^ii	0.95	2.66	3.394 (3)	134
C5—H5A···N1^iii	0.95	2.90	3.557 (3)	128
C5—H5A···O1^iv	0.95	2.96	3.453 (3)	113
C8—H8A···N2^v	0.95	2.69	3.469 (3)	140
C11—H11A···O2^vi	0.95	2.82	3.735 (3)	161
C11—H11A···O1^vi	0.95	2.75	3.546 (3)	142
C12—H12A···N1^vii	0.95	2.44	3.199 (3)	137

Symmetry codes: (i) −x+2, y+1/2, −z+3/2; (ii) −x+1/2, −y+1, z+1/2; (iii) −x+1, y−1/2, −z+3/2; (iv) −x+1, y+1/2, −z+3/2; (v) x+1/2, −y+3/2, −z+1; (vi) x−1/2, −y+1/2, −z+1; (vii) x, y−1, z.

4-(3-Methoxyphenoxy)benzene-1,2-dicarbonitrile (m-C15H10N2O2)

Crystal data

C15H10N2O2	Z = 2
Mr = 250.25	F(000) = 260
Triclinic, P1	Dx = 1.371 Mg m^−3
a = 8.0609 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.4672 (4) Å	Cell parameters from 9781 reflections
c = 9.9999 (4) Å	θ = 2.7–30.1°
α = 104.638 (1)°	µ = 0.09 mm^−1
β = 95.078 (1)°	T = 100 K
γ = 110.570 (1)°	Prism, colorless
V = 606.31 (4) Å^3	0.45 × 0.30 × 0.27 mm

Data collection

Bruker D8 Quest (CMOS) diffractometer	3040 reflections with I > 2σ(I)
Radiation source: microfocus tube	Rint = 0.017
ω scans	θmax = 29.6°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −11→11
Tmin = 0.903, Tmax = 0.971	k = −11→11
10029 measured reflections	l = −13→13
3395 independent reflections

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.105	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0528P)^2 + 0.2143P] where P = (Fo^2 + 2Fc^2)/3
3395 reflections	(Δ/σ)max < 0.001
173 parameters	Δρmax = 0.37 e Å^−3
0 restraints	Δρmin = −0.27 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
O1	0.56496 (10)	0.59440 (10)	0.80203 (7)	0.01795 (16)
O2	0.87906 (10)	0.47550 (9)	1.17760 (7)	0.01716 (16)
N1	0.95411 (13)	0.23336 (15)	0.44743 (10)	0.0277 (2)
N2	0.46049 (13)	−0.06002 (13)	0.21559 (10)	0.0253 (2)
C1	0.69339 (13)	0.64698 (13)	0.92463 (10)	0.01494 (18)
C2	0.72490 (12)	0.52173 (12)	0.97939 (9)	0.01389 (18)
H2A	0.668855	0.398795	0.929816	0.017*
C3	0.84135 (13)	0.58336 (12)	1.10919 (9)	0.01423 (18)
C4	0.92411 (14)	0.76450 (13)	1.18106 (10)	0.01779 (19)
H4A	1.004512	0.805311	1.269112	0.021*
C5	0.88827 (14)	0.88403 (13)	1.12324 (11)	0.0203 (2)
H5A	0.943632	1.007075	1.172592	0.024*
C6	0.77200 (14)	0.82629 (13)	0.99356 (10)	0.0186 (2)
H6A	0.747571	0.908341	0.953705	0.022*
C7	0.55405 (13)	0.45928 (12)	0.68822 (9)	0.01418 (18)
C8	0.70450 (12)	0.42664 (12)	0.65164 (9)	0.01438 (18)
H8A	0.820847	0.493469	0.709832	0.017*
C9	0.67994 (12)	0.29370 (12)	0.52775 (9)	0.01387 (18)
C10	0.50752 (12)	0.19245 (12)	0.44232 (9)	0.01434 (18)
C11	0.35970 (13)	0.22881 (13)	0.48119 (10)	0.01664 (19)
H11A	0.242865	0.161880	0.423787	0.020*
C12	0.38297 (13)	0.36220 (13)	0.60321 (10)	0.01613 (19)
H12A	0.282369	0.387620	0.629065	0.019*
C13	0.83370 (13)	0.26098 (14)	0.48459 (10)	0.0185 (2)
C14	0.48277 (13)	0.05290 (13)	0.31588 (10)	0.01762 (19)
C15	0.79525 (14)	0.28892 (13)	1.10841 (11)	0.0189 (2)
H15A	0.829282	0.225820	1.168675	0.028*
H15B	0.835383	0.260815	1.018882	0.028*
H15C	0.663676	0.252294	1.090253	0.028*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0233 (4)	0.0224 (4)	0.0123 (3)	0.0155 (3)	0.0020 (3)	0.0032 (3)
O2	0.0211 (3)	0.0165 (3)	0.0143 (3)	0.0086 (3)	0.0001 (3)	0.0046 (3)
N1	0.0205 (4)	0.0418 (6)	0.0197 (4)	0.0167 (4)	0.0019 (3)	0.0014 (4)
N2	0.0272 (5)	0.0235 (5)	0.0203 (4)	0.0083 (4)	0.0016 (4)	0.0019 (3)
C1	0.0167 (4)	0.0193 (4)	0.0115 (4)	0.0094 (3)	0.0045 (3)	0.0051 (3)
C2	0.0156 (4)	0.0145 (4)	0.0126 (4)	0.0073 (3)	0.0041 (3)	0.0034 (3)
C3	0.0163 (4)	0.0164 (4)	0.0124 (4)	0.0081 (3)	0.0049 (3)	0.0052 (3)
C4	0.0195 (4)	0.0176 (5)	0.0135 (4)	0.0060 (4)	0.0021 (3)	0.0022 (3)
C5	0.0246 (5)	0.0141 (4)	0.0198 (5)	0.0064 (4)	0.0047 (4)	0.0027 (4)
C6	0.0240 (5)	0.0170 (4)	0.0184 (4)	0.0105 (4)	0.0063 (4)	0.0068 (4)
C7	0.0187 (4)	0.0165 (4)	0.0110 (4)	0.0097 (3)	0.0042 (3)	0.0059 (3)
C8	0.0139 (4)	0.0178 (4)	0.0123 (4)	0.0070 (3)	0.0019 (3)	0.0050 (3)
C9	0.0136 (4)	0.0179 (4)	0.0122 (4)	0.0078 (3)	0.0025 (3)	0.0056 (3)
C10	0.0148 (4)	0.0164 (4)	0.0126 (4)	0.0063 (3)	0.0022 (3)	0.0055 (3)
C11	0.0126 (4)	0.0212 (5)	0.0167 (4)	0.0060 (3)	0.0022 (3)	0.0076 (4)
C12	0.0150 (4)	0.0222 (5)	0.0160 (4)	0.0100 (4)	0.0055 (3)	0.0090 (3)
C13	0.0170 (4)	0.0247 (5)	0.0127 (4)	0.0096 (4)	0.0003 (3)	0.0026 (3)
C14	0.0159 (4)	0.0196 (5)	0.0166 (4)	0.0060 (3)	0.0012 (3)	0.0062 (4)
C15	0.0244 (5)	0.0160 (4)	0.0181 (4)	0.0099 (4)	0.0029 (4)	0.0058 (3)

Geometric parameters (Å, º)

O1—C7	1.3658 (11)	C6—H6A	0.9500
O1—C1	1.3959 (11)	C7—C12	1.3939 (14)
O2—C3	1.3669 (11)	C7—C8	1.3942 (13)
O2—C15	1.4303 (12)	C8—C9	1.3914 (12)
N1—C13	1.1464 (14)	C8—H8A	0.9500
N2—C14	1.1468 (14)	C9—C10	1.4067 (13)
C1—C6	1.3782 (14)	C9—C13	1.4404 (13)
C1—C2	1.3954 (13)	C10—C11	1.3946 (13)
C2—C3	1.3915 (13)	C10—C14	1.4384 (13)
C2—H2A	0.9500	C11—C12	1.3834 (13)
C3—C4	1.3975 (13)	C11—H11A	0.9500
C4—C5	1.3835 (14)	C12—H12A	0.9500
C4—H4A	0.9500	C15—H15A	0.9800
C5—C6	1.3934 (15)	C15—H15B	0.9800
C5—H5A	0.9500	C15—H15C	0.9800
C7—O1—C1	120.56 (7)	C9—C8—C7	118.33 (8)
C3—O2—C15	117.05 (7)	C9—C8—H8A	120.8
C6—C1—C2	122.83 (9)	C7—C8—H8A	120.8
C6—C1—O1	116.08 (8)	C8—C9—C10	121.08 (8)
C2—C1—O1	120.80 (8)	C8—C9—C13	119.63 (8)
C3—C2—C1	117.62 (8)	C10—C9—C13	119.28 (8)
C3—C2—H2A	121.2	C11—C10—C9	119.29 (8)
C1—C2—H2A	121.2	C11—C10—C14	119.99 (8)
O2—C3—C2	123.86 (8)	C9—C10—C14	120.72 (8)
O2—C3—C4	115.26 (8)	C12—C11—C10	120.09 (9)
C2—C3—C4	120.85 (9)	C12—C11—H11A	120.0
C5—C4—C3	119.61 (9)	C10—C11—H11A	120.0
C5—C4—H4A	120.2	C11—C12—C7	119.99 (9)
C3—C4—H4A	120.2	C11—C12—H12A	120.0
C4—C5—C6	120.85 (9)	C7—C12—H12A	120.0
C4—C5—H5A	119.6	N1—C13—C9	178.59 (10)
C6—C5—H5A	119.6	N2—C14—C10	178.88 (11)
C1—C6—C5	118.24 (9)	O2—C15—H15A	109.5
C1—C6—H6A	120.9	O2—C15—H15B	109.5
C5—C6—H6A	120.9	H15A—C15—H15B	109.5
O1—C7—C12	115.57 (8)	O2—C15—H15C	109.5
O1—C7—C8	123.07 (8)	H15A—C15—H15C	109.5
C12—C7—C8	121.20 (9)	H15B—C15—H15C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···N2^i	0.95	2.64	3.5839 (13)	175
C8—H8A···O2^ii	0.95	2.47	3.3447 (11)	153
C11—H11A···N1^iii	0.95	2.62	3.2718 (13)	126
C12—H12A···N1^iii	0.95	2.74	3.3325 (13)	121
C12—H12A···O2^iv	0.95	2.67	3.5343 (12)	151

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