Crystal structures of two new isocoumarin derivatives: 8-amino-6-methyl-3,4-diphenyl-1H-isochromen-1-one and 8-amino-3,4-diethyl-6-methyl-1H-isochromen-1-one

The crystal structures of two new isocoumarin derivatives, 8-amino-6-methyl-3,4-diphenyl-1H-isochromen-1-one and 8-amino-3,4-diethyl-6-methyl-1H-isochromen-1-one, are described. The inter­molecular contacts in the crystals were analysed using Hirshfeld surface analysis and two-dimensional fingerprint plots.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.002 Å
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.040
• wR factor = 0.118
• Data-to-parameter ratio = 15.9

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT420_ALERT_2_C D-H Without Acceptor       N1       --H1N      .     Please Check
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -0.113 Report

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          7 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         15 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
   4 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
   2 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: II


Alert level B
THETM01_ALERT_3_B  The value of sine(theta_max)/wavelength is less than 0.575
            Calculated sin(theta_max)/wavelength =    0.5669
PLAT023_ALERT_3_B Resolution (too) Low [sin(theta)/Lambda < 0.6]..      23.76 Degree

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full value Low .      0.978 Why?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O1A      --C3A      .        6.0 s.u.
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00414 Ang.
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.567         79 Report

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          4 Report
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          4 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   2 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 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
   6 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 structures, data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS2018 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 2012), publCIF (Westrip, 2010) and PLATON (Spek, 2009).

8-Amino-6-methyl-3,4-diphenyl-1H-isochromen-1-one (I)

Crystal data

C22H17NO2	F(000) = 688
Mr = 327.36	Dx = 1.274 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.1652 (3) Å	Cell parameters from 3001 reflections
b = 16.9764 (6) Å	θ = 1.8–26.9°
c = 10.9687 (4) Å	µ = 0.08 mm^−1
β = 91.156 (1)°	T = 296 K
V = 1706.30 (10) Å^3	Block, colourless
Z = 4	0.32 × 0.18 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer	2719 reflections with I > 2σ(I)
ω and φ scans	Rint = 0.025
Absorption correction: multi-scan (SADABS; Bruker, 2008)	θmax = 26.8°, θmin = 2.2°
Tmin = 0.756, Tmax = 0.824	h = −7→11
14904 measured reflections	k = −16→21
3628 independent reflections	l = −13→13

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)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.118	w = 1/[σ^2(Fo^2) + (0.0561P)^2 + 0.3498P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
3628 reflections	Δρmax = 0.22 e Å^−3
228 parameters	Δρmin = −0.15 e Å^−3
0 restraints	Extinction correction: (SHELXL-2018/3; Sheldrick 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.027 (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	0.30517 (11)	0.50819 (6)	−0.13908 (8)	0.0428 (3)
O2	0.34168 (15)	0.45740 (7)	−0.31876 (9)	0.0642 (4)
N1	0.29626 (19)	0.30274 (9)	−0.35783 (12)	0.0693 (5)
H1N	0.296082	0.260175	−0.400359	0.083*
H2N	0.321068	0.346662	−0.390514	0.083*
C1	0.25918 (14)	0.36948 (8)	−0.16525 (11)	0.0369 (3)
C2	0.30400 (16)	0.44376 (9)	−0.21526 (12)	0.0423 (3)
C3	0.26388 (14)	0.50381 (8)	−0.01861 (11)	0.0343 (3)
C4	0.22498 (14)	0.43536 (8)	0.03282 (11)	0.0328 (3)
C5	0.18557 (15)	0.29115 (8)	0.00781 (13)	0.0404 (3)
H5	0.162684	0.287498	0.089835	0.048*
C6	0.18321 (16)	0.22339 (9)	−0.06446 (14)	0.0444 (4)
C7	0.21712 (16)	0.22931 (9)	−0.18611 (14)	0.0466 (4)
H7	0.213012	0.184295	−0.234375	0.056*
C8	0.25737 (16)	0.30058 (9)	−0.23912 (12)	0.0437 (4)
C9	0.22152 (14)	0.36370 (8)	−0.04094 (11)	0.0338 (3)
C10	0.1460 (2)	0.14520 (10)	−0.00914 (18)	0.0717 (6)
H10A	0.063444	0.151158	0.042499	0.108*
H10B	0.227983	0.126275	0.038250	0.108*
H10C	0.122961	0.108174	−0.072811	0.108*
C11	0.19198 (14)	0.43298 (7)	0.16566 (11)	0.0341 (3)
C12	0.05157 (16)	0.41920 (9)	0.20535 (13)	0.0427 (3)
H12	−0.022264	0.406927	0.149128	0.051*
C13	0.02070 (18)	0.42361 (10)	0.32806 (14)	0.0523 (4)
H13	−0.074106	0.415271	0.353831	0.063*
C14	0.1301 (2)	0.44033 (10)	0.41240 (13)	0.0530 (4)
H14	0.108969	0.443448	0.494830	0.064*
C15	0.27035 (18)	0.45239 (9)	0.37447 (13)	0.0471 (4)
H15	0.344296	0.463112	0.431370	0.057*
C16	0.30160 (16)	0.44859 (8)	0.25200 (12)	0.0395 (3)
H16	0.396814	0.456537	0.226936	0.047*
C17	0.27264 (14)	0.58255 (8)	0.03882 (12)	0.0359 (3)
C18	0.16250 (17)	0.60991 (9)	0.11333 (14)	0.0465 (4)
H18	0.081520	0.578437	0.127440	0.056*
C19	0.1727 (2)	0.68360 (9)	0.16655 (15)	0.0556 (4)
H19	0.098591	0.701582	0.216101	0.067*
C20	0.2924 (2)	0.73034 (9)	0.14627 (14)	0.0547 (4)
H20	0.299569	0.779622	0.182915	0.066*
C21	0.40126 (18)	0.70442 (9)	0.07209 (15)	0.0527 (4)
H21	0.482036	0.736185	0.058695	0.063*
C22	0.39120 (16)	0.63116 (9)	0.01716 (14)	0.0447 (4)
H22	0.464196	0.614417	−0.034512	0.054*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0583 (6)	0.0377 (6)	0.0324 (5)	−0.0033 (5)	0.0039 (4)	0.0015 (4)
O2	0.1014 (10)	0.0597 (8)	0.0317 (6)	−0.0104 (7)	0.0110 (6)	0.0030 (5)
N1	0.1126 (13)	0.0608 (9)	0.0347 (7)	−0.0103 (9)	0.0097 (7)	−0.0132 (6)
C1	0.0402 (7)	0.0394 (8)	0.0310 (6)	0.0003 (6)	−0.0027 (5)	−0.0023 (5)
C2	0.0523 (8)	0.0445 (8)	0.0301 (7)	0.0001 (7)	−0.0013 (6)	−0.0002 (6)
C3	0.0358 (7)	0.0364 (7)	0.0307 (6)	0.0014 (6)	−0.0008 (5)	−0.0007 (5)
C4	0.0340 (6)	0.0339 (7)	0.0305 (6)	0.0023 (5)	−0.0008 (5)	−0.0023 (5)
C5	0.0477 (8)	0.0367 (8)	0.0370 (7)	−0.0016 (6)	0.0064 (6)	−0.0021 (6)
C6	0.0440 (8)	0.0362 (8)	0.0531 (8)	−0.0033 (6)	0.0050 (6)	−0.0064 (6)
C7	0.0508 (8)	0.0414 (9)	0.0474 (8)	−0.0016 (7)	−0.0002 (7)	−0.0158 (7)
C8	0.0486 (8)	0.0495 (9)	0.0329 (7)	−0.0003 (7)	−0.0020 (6)	−0.0088 (6)
C9	0.0347 (7)	0.0351 (7)	0.0316 (6)	0.0009 (6)	−0.0017 (5)	−0.0019 (5)
C10	0.0957 (14)	0.0402 (10)	0.0803 (13)	−0.0122 (9)	0.0301 (11)	−0.0094 (9)
C11	0.0424 (7)	0.0271 (7)	0.0328 (7)	0.0027 (6)	0.0010 (5)	−0.0023 (5)
C12	0.0422 (7)	0.0455 (9)	0.0404 (8)	0.0012 (6)	0.0027 (6)	−0.0027 (6)
C13	0.0547 (9)	0.0536 (10)	0.0493 (9)	0.0054 (8)	0.0173 (7)	0.0003 (7)
C14	0.0782 (11)	0.0486 (9)	0.0327 (7)	0.0133 (8)	0.0101 (7)	−0.0031 (6)
C15	0.0650 (10)	0.0406 (8)	0.0354 (7)	0.0070 (7)	−0.0083 (7)	−0.0049 (6)
C16	0.0444 (7)	0.0373 (8)	0.0367 (7)	0.0019 (6)	−0.0020 (6)	−0.0015 (6)
C17	0.0401 (7)	0.0320 (7)	0.0355 (7)	0.0032 (6)	−0.0066 (6)	0.0020 (5)
C18	0.0486 (8)	0.0389 (8)	0.0520 (9)	0.0026 (7)	0.0036 (7)	−0.0011 (7)
C19	0.0721 (11)	0.0435 (9)	0.0513 (9)	0.0128 (9)	0.0072 (8)	−0.0047 (7)
C20	0.0816 (12)	0.0332 (8)	0.0488 (9)	0.0013 (8)	−0.0110 (8)	−0.0042 (7)
C21	0.0570 (9)	0.0399 (9)	0.0609 (10)	−0.0069 (7)	−0.0110 (8)	0.0020 (7)
C22	0.0440 (8)	0.0394 (8)	0.0505 (8)	0.0015 (7)	−0.0020 (6)	0.0003 (6)

Geometric parameters (Å, º)

O1—C2	1.3763 (17)	C11—C12	1.3867 (19)
O1—C3	1.3838 (15)	C11—C16	1.3922 (19)
O2—C2	1.2155 (16)	C12—C13	1.383 (2)
N1—C8	1.3574 (19)	C12—H12	0.9300
N1—H1N	0.8600	C13—C14	1.380 (2)
N1—H2N	0.8600	C13—H13	0.9300
C1—C9	1.4167 (18)	C14—C15	1.374 (2)
C1—C8	1.4227 (19)	C14—H14	0.9300
C1—C2	1.438 (2)	C15—C16	1.3807 (19)
C3—C4	1.3430 (18)	C15—H15	0.9300
C3—C17	1.4792 (18)	C16—H16	0.9300
C4—C9	1.4611 (18)	C17—C22	1.389 (2)
C4—C11	1.4947 (17)	C17—C18	1.391 (2)
C5—C9	1.3851 (19)	C18—C19	1.383 (2)
C5—C6	1.397 (2)	C18—H18	0.9300
C5—H5	0.9300	C19—C20	1.375 (2)
C6—C7	1.380 (2)	C19—H19	0.9300
C6—C10	1.501 (2)	C20—C21	1.373 (2)
C7—C8	1.395 (2)	C20—H20	0.9300
C7—H7	0.9300	C21—C22	1.384 (2)
C10—H10A	0.9600	C21—H21	0.9300
C10—H10B	0.9600	C22—H22	0.9300
C10—H10C	0.9600
C2—O1—C3	122.56 (11)	C12—C11—C16	118.69 (12)
C8—N1—H1N	120.0	C12—C11—C4	121.20 (12)
C8—N1—H2N	120.0	C16—C11—C4	120.04 (12)
H1N—N1—H2N	120.0	C13—C12—C11	120.39 (14)
C9—C1—C8	119.40 (13)	C13—C12—H12	119.8
C9—C1—C2	120.31 (12)	C11—C12—H12	119.8
C8—C1—C2	120.25 (12)	C14—C13—C12	120.22 (15)
O2—C2—O1	114.63 (13)	C14—C13—H13	119.9
O2—C2—C1	127.72 (13)	C12—C13—H13	119.9
O1—C2—C1	117.64 (11)	C15—C14—C13	119.94 (14)
C4—C3—O1	121.84 (12)	C15—C14—H14	120.0
C4—C3—C17	128.00 (12)	C13—C14—H14	120.0
O1—C3—C17	110.16 (11)	C14—C15—C16	120.08 (14)
C3—C4—C9	119.40 (11)	C14—C15—H15	120.0
C3—C4—C11	119.57 (11)	C16—C15—H15	120.0
C9—C4—C11	120.98 (11)	C15—C16—C11	120.64 (14)
C9—C5—C6	120.94 (13)	C15—C16—H16	119.7
C9—C5—H5	119.5	C11—C16—H16	119.7
C6—C5—H5	119.5	C22—C17—C18	118.79 (13)
C7—C6—C5	119.18 (14)	C22—C17—C3	120.00 (12)
C7—C6—C10	120.84 (14)	C18—C17—C3	121.20 (13)
C5—C6—C10	119.98 (14)	C19—C18—C17	120.41 (15)
C6—C7—C8	122.20 (13)	C19—C18—H18	119.8
C6—C7—H7	118.9	C17—C18—H18	119.8
C8—C7—H7	118.9	C20—C19—C18	120.06 (15)
N1—C8—C7	119.99 (14)	C20—C19—H19	120.0
N1—C8—C1	121.59 (14)	C18—C19—H19	120.0
C7—C8—C1	118.41 (13)	C21—C20—C19	120.17 (15)
C5—C9—C1	119.84 (12)	C21—C20—H20	119.9
C5—C9—C4	121.96 (12)	C19—C20—H20	119.9
C1—C9—C4	118.19 (12)	C20—C21—C22	120.21 (15)
C6—C10—H10A	109.5	C20—C21—H21	119.9
C6—C10—H10B	109.5	C22—C21—H21	119.9
H10A—C10—H10B	109.5	C21—C22—C17	120.32 (14)
C6—C10—H10C	109.5	C21—C22—H22	119.8
H10A—C10—H10C	109.5	C17—C22—H22	119.8
H10B—C10—H10C	109.5
C3—O1—C2—O2	179.19 (13)	C3—C4—C9—C5	178.47 (13)
C3—O1—C2—C1	−0.67 (19)	C11—C4—C9—C5	1.05 (19)
C9—C1—C2—O2	178.61 (15)	C3—C4—C9—C1	−0.26 (18)
C8—C1—C2—O2	0.9 (2)	C11—C4—C9—C1	−177.68 (12)
C9—C1—C2—O1	−1.5 (2)	C3—C4—C11—C12	111.95 (15)
C8—C1—C2—O1	−179.26 (12)	C9—C4—C11—C12	−70.64 (17)
C2—O1—C3—C4	2.49 (19)	C3—C4—C11—C16	−64.84 (17)
C2—O1—C3—C17	−178.45 (12)	C9—C4—C11—C16	112.57 (14)
O1—C3—C4—C9	−1.94 (19)	C16—C11—C12—C13	2.2 (2)
C17—C3—C4—C9	179.17 (12)	C4—C11—C12—C13	−174.66 (13)
O1—C3—C4—C11	175.51 (11)	C11—C12—C13—C14	−1.2 (2)
C17—C3—C4—C11	−3.4 (2)	C12—C13—C14—C15	−0.2 (2)
C9—C5—C6—C7	−0.1 (2)	C13—C14—C15—C16	0.7 (2)
C9—C5—C6—C10	179.11 (15)	C14—C15—C16—C11	0.3 (2)
C5—C6—C7—C8	1.6 (2)	C12—C11—C16—C15	−1.7 (2)
C10—C6—C7—C8	−177.57 (16)	C4—C11—C16—C15	175.14 (13)
C6—C7—C8—N1	176.95 (15)	C4—C3—C17—C22	136.31 (15)
C6—C7—C8—C1	−1.8 (2)	O1—C3—C17—C22	−42.68 (16)
C9—C1—C8—N1	−178.25 (14)	C4—C3—C17—C18	−44.8 (2)
C2—C1—C8—N1	−0.5 (2)	O1—C3—C17—C18	136.26 (13)
C9—C1—C8—C7	0.5 (2)	C22—C17—C18—C19	−1.2 (2)
C2—C1—C8—C7	178.22 (13)	C3—C17—C18—C19	179.82 (13)
C6—C5—C9—C1	−1.2 (2)	C17—C18—C19—C20	−0.2 (2)
C6—C5—C9—C4	−179.90 (13)	C18—C19—C20—C21	0.7 (2)
C8—C1—C9—C5	0.97 (19)	C19—C20—C21—C22	0.1 (2)
C2—C1—C9—C5	−176.77 (12)	C20—C21—C22—C17	−1.5 (2)
C8—C1—C9—C4	179.73 (12)	C18—C17—C22—C21	2.0 (2)
C2—C1—C9—C4	1.99 (19)	C3—C17—C22—C21	−178.99 (13)

Hydrogen-bond geometry (Å, º)

Cg1, Cg2 and Cg3 are the centroids of the C17–C22, C11–C16 and C1/C5–C9 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H2N···O2	0.86	2.05	2.6915 (19)	131
N1—H1N···Cg1^i	0.86	2.81	3.631 (2)	157
C20—H20···Cg2^ii	0.93	2.70	3.588 (2)	160
C21—H21···Cg3^iii	0.93	2.84	3.488 (2)	128

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

8-Amino-3,4-diethyl-6-methyl-1H-isochromen-1-one (II)

Crystal data

C14H17NO2	F(000) = 992
Mr = 231.28	Dx = 1.222 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.4844 (8) Å	Cell parameters from 3755 reflections
b = 26.562 (2) Å	θ = 1.8–26.9°
c = 9.3651 (6) Å	µ = 0.08 mm^−1
β = 105.367 (3)°	T = 296 K
V = 2514.8 (3) Å^3	Block, colourless
Z = 8	0.25 × 0.22 × 0.13 mm

Data collection

Bruker Kappa APEXII CCD diffractometer	2132 reflections with I > 2σ(I)
ω and φ scans	Rint = 0.048
Absorption correction: multi-scan (SADABS; Bruker, 2008)	θmax = 23.8°, θmin = 2.2°
Tmin = 0.756, Tmax = 0.824	h = −11→11
13067 measured reflections	k = −29→23
3755 independent reflections	l = −10→7

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.168	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0872P)^2] where P = (Fo^2 + 2Fc^2)/3
3755 reflections	(Δ/σ)max < 0.001
313 parameters	Δρmax = 0.14 e Å^−3
0 restraints	Δρmin = −0.25 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
O1A	0.19526 (18)	−0.03883 (8)	0.3169 (2)	0.0621 (6)
O2A	0.1114 (2)	−0.10719 (9)	0.2007 (2)	0.0765 (7)
N1A	−0.1310 (2)	−0.10445 (9)	0.0078 (2)	0.0688 (7)
H1A1	−0.198031	−0.117045	−0.055946	0.083*
H1A2	−0.062249	−0.122669	0.044001	0.083*
C1A	−0.0241 (2)	−0.03391 (10)	0.1564 (2)	0.0420 (7)
C2A	0.0926 (3)	−0.06286 (12)	0.2204 (3)	0.0529 (8)
C3A	0.1906 (3)	0.01162 (12)	0.3555 (3)	0.0532 (8)
C4A	0.0834 (2)	0.03978 (10)	0.3010 (3)	0.0458 (7)
C5A	−0.1438 (3)	0.04469 (10)	0.1329 (3)	0.0493 (7)
H5A	−0.147825	0.078312	0.159015	0.059*
C6A	−0.2512 (3)	0.02321 (12)	0.0321 (3)	0.0538 (8)
C7A	−0.2452 (3)	−0.02619 (13)	−0.0072 (3)	0.0556 (8)
H7A	−0.317482	−0.040423	−0.074901	0.067*
C8A	−0.1338 (3)	−0.05578 (11)	0.0513 (3)	0.0492 (7)
C9A	−0.0303 (2)	0.01716 (10)	0.1956 (2)	0.0417 (7)
C10A	−0.3711 (3)	0.05465 (13)	−0.0348 (3)	0.0806 (10)
H10A	−0.349955	0.079114	−0.100375	0.121*
H10B	−0.398847	0.071563	0.042527	0.121*
H10C	−0.441292	0.033370	−0.089177	0.121*
C11A	0.3183 (3)	0.02507 (13)	0.4640 (3)	0.0761 (10)
H11A	0.326355	0.061432	0.470382	0.091*
H11B	0.391030	0.012236	0.428775	0.091*
C12A	0.3281 (3)	0.00403 (13)	0.6162 (3)	0.0828 (11)
H12A	0.262132	0.019401	0.656040	0.124*
H12B	0.414351	0.010997	0.679928	0.124*
H12C	0.314202	−0.031714	0.609490	0.124*
C13A	0.0781 (3)	0.09389 (11)	0.3488 (3)	0.0597 (8)
H13A	0.033743	0.113977	0.263609	0.072*
H13B	0.167579	0.106592	0.385238	0.072*
C14A	0.0062 (3)	0.09996 (13)	0.4687 (3)	0.0818 (10)
H14A	−0.082689	0.087702	0.433030	0.123*
H14B	0.004438	0.134906	0.494236	0.123*
H14C	0.051468	0.081108	0.554672	0.123*
O1B	0.34202 (18)	0.19483 (8)	0.14816 (19)	0.0623 (6)
O2B	0.4302 (2)	0.12582 (9)	0.2580 (2)	0.0859 (7)
N1B	0.6446 (2)	0.13134 (10)	0.4921 (3)	0.0786 (8)
H1B1	0.705569	0.119291	0.564264	0.094*
H1B2	0.591805	0.111350	0.431977	0.094*
C1B	0.5316 (2)	0.20312 (11)	0.3560 (3)	0.0442 (7)
C2B	0.4371 (3)	0.17168 (12)	0.2564 (3)	0.0562 (8)
C3B	0.3370 (3)	0.24666 (12)	0.1273 (3)	0.0532 (8)
C4B	0.4230 (3)	0.27743 (10)	0.2151 (3)	0.0479 (7)
C5B	0.6132 (3)	0.28607 (11)	0.4388 (3)	0.0564 (8)
H5B	0.608867	0.320854	0.427094	0.068*
C6B	0.7082 (3)	0.26519 (14)	0.5561 (3)	0.0614 (8)
C7B	0.7174 (3)	0.21419 (14)	0.5708 (3)	0.0628 (9)
H7B	0.782810	0.200493	0.648214	0.075*
C8B	0.6315 (3)	0.18187 (11)	0.4730 (3)	0.0531 (8)
C9B	0.5246 (2)	0.25581 (11)	0.3387 (3)	0.0447 (7)
C10B	0.8005 (3)	0.29914 (14)	0.6652 (4)	0.0914 (12)
H10D	0.861250	0.279047	0.737701	0.137*
H10E	0.750228	0.320132	0.713663	0.137*
H10F	0.848950	0.319861	0.613864	0.137*
C11B	0.2212 (3)	0.25846 (13)	0.0000 (3)	0.0767 (10)
H11C	0.226498	0.238303	−0.084589	0.092*
H11D	0.225174	0.293610	−0.026570	0.092*
C12B	0.0907 (3)	0.24846 (15)	0.0340 (4)	0.1083 (14)
H12D	0.090713	0.214998	0.072749	0.162*
H12E	0.020240	0.251665	−0.055014	0.162*
H12F	0.078047	0.272358	0.105949	0.162*
C13B	0.4150 (3)	0.33380 (11)	0.1925 (3)	0.0604 (8)
H13C	0.374007	0.340940	0.088909	0.073*
H13D	0.503755	0.347615	0.217150	0.073*
C14B	0.3362 (3)	0.35947 (11)	0.2865 (3)	0.0731 (9)
H14D	0.247412	0.346648	0.260456	0.110*
H14E	0.334475	0.395109	0.269095	0.110*
H14F	0.376919	0.352867	0.389239	0.110*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0559 (13)	0.0674 (16)	0.0564 (12)	0.0158 (11)	0.0035 (10)	0.0115 (11)
O2A	0.1035 (18)	0.0453 (15)	0.0803 (14)	0.0221 (13)	0.0241 (12)	0.0094 (12)
N1A	0.0866 (19)	0.0476 (18)	0.0742 (17)	−0.0169 (14)	0.0249 (14)	−0.0101 (13)
C1A	0.0511 (17)	0.0357 (18)	0.0386 (13)	−0.0001 (13)	0.0105 (12)	0.0057 (12)
C2A	0.064 (2)	0.049 (2)	0.0463 (16)	0.0100 (17)	0.0163 (15)	0.0123 (15)
C3A	0.0533 (19)	0.056 (2)	0.0485 (16)	−0.0012 (16)	0.0103 (14)	0.0049 (14)
C4A	0.0430 (16)	0.049 (2)	0.0427 (14)	−0.0015 (14)	0.0061 (13)	0.0024 (13)
C5A	0.0508 (17)	0.0438 (19)	0.0486 (15)	0.0030 (14)	0.0049 (14)	0.0003 (13)
C6A	0.0471 (18)	0.059 (2)	0.0502 (16)	0.0017 (16)	0.0046 (14)	0.0033 (15)
C7A	0.0494 (18)	0.067 (2)	0.0456 (16)	−0.0171 (17)	0.0040 (13)	−0.0008 (15)
C8A	0.067 (2)	0.0393 (19)	0.0470 (15)	−0.0117 (16)	0.0243 (15)	−0.0002 (14)
C9A	0.0415 (16)	0.0449 (19)	0.0371 (13)	−0.0023 (13)	0.0078 (12)	0.0049 (12)
C10A	0.055 (2)	0.092 (3)	0.081 (2)	0.0079 (19)	−0.0065 (16)	0.0077 (19)
C11A	0.0516 (19)	0.096 (3)	0.070 (2)	−0.0024 (18)	−0.0020 (16)	0.0106 (19)
C12A	0.087 (2)	0.090 (3)	0.0563 (19)	0.007 (2)	−0.0078 (17)	−0.0083 (18)
C13A	0.0571 (18)	0.059 (2)	0.0587 (17)	−0.0130 (15)	0.0078 (14)	−0.0117 (15)
C14A	0.093 (2)	0.083 (3)	0.073 (2)	−0.002 (2)	0.0271 (18)	−0.0218 (18)
O1B	0.0632 (13)	0.0536 (15)	0.0614 (12)	−0.0025 (11)	0.0012 (10)	−0.0087 (11)
O2B	0.1026 (18)	0.0414 (16)	0.1027 (17)	−0.0062 (13)	0.0079 (14)	−0.0060 (13)
N1B	0.0833 (19)	0.056 (2)	0.093 (2)	0.0262 (15)	0.0168 (15)	0.0176 (15)
C1B	0.0418 (16)	0.044 (2)	0.0457 (14)	0.0047 (14)	0.0097 (13)	0.0033 (13)
C2B	0.0595 (19)	0.046 (2)	0.0612 (18)	−0.0001 (17)	0.0132 (16)	−0.0027 (16)
C3B	0.0580 (19)	0.050 (2)	0.0506 (16)	0.0081 (16)	0.0120 (14)	0.0028 (15)
C4B	0.0540 (17)	0.0415 (19)	0.0477 (15)	0.0049 (14)	0.0125 (14)	0.0031 (14)
C5B	0.0607 (19)	0.043 (2)	0.0632 (17)	−0.0024 (15)	0.0131 (16)	−0.0019 (15)
C6B	0.0448 (18)	0.074 (3)	0.0608 (18)	−0.0025 (17)	0.0062 (15)	−0.0052 (18)
C7B	0.0483 (18)	0.081 (3)	0.0538 (17)	0.0108 (18)	0.0049 (14)	0.0059 (18)
C8B	0.0516 (18)	0.048 (2)	0.0620 (18)	0.0109 (15)	0.0197 (15)	0.0048 (15)
C9B	0.0437 (16)	0.043 (2)	0.0479 (15)	0.0016 (13)	0.0124 (13)	0.0002 (13)
C10B	0.066 (2)	0.109 (3)	0.087 (2)	−0.010 (2)	−0.0018 (19)	−0.024 (2)
C11B	0.075 (2)	0.086 (3)	0.0574 (18)	0.0129 (19)	−0.0039 (17)	−0.0030 (17)
C12B	0.063 (2)	0.118 (4)	0.125 (3)	0.013 (2)	−0.009 (2)	0.008 (3)
C13B	0.073 (2)	0.052 (2)	0.0570 (16)	0.0107 (16)	0.0178 (15)	0.0086 (15)
C14B	0.092 (2)	0.050 (2)	0.083 (2)	0.0184 (18)	0.0329 (19)	0.0023 (17)

Geometric parameters (Å, º)

O1A—C2A	1.366 (3)	O1B—C2B	1.365 (3)
O1A—C3A	1.392 (3)	O1B—C3B	1.389 (3)
O2A—C2A	1.216 (3)	O2B—C2B	1.221 (3)
N1A—C8A	1.358 (3)	N1B—C8B	1.356 (3)
N1A—H1A1	0.8600	N1B—H1B1	0.8600
N1A—H1A2	0.8600	N1B—H1B2	0.8600
C1A—C9A	1.411 (3)	C1B—C9B	1.409 (3)
C1A—C8A	1.425 (3)	C1B—C8B	1.417 (3)
C1A—C2A	1.435 (4)	C1B—C2B	1.435 (4)
C3A—C4A	1.334 (3)	C3B—C4B	1.328 (4)
C3A—C11A	1.494 (4)	C3B—C11B	1.492 (4)
C4A—C9A	1.461 (3)	C4B—C9B	1.467 (3)
C4A—C13A	1.511 (4)	C4B—C13B	1.511 (4)
C5A—C6A	1.386 (3)	C5B—C6B	1.388 (4)
C5A—C9A	1.387 (3)	C5B—C9B	1.388 (3)
C5A—H5A	0.9300	C5B—H5B	0.9300
C6A—C7A	1.369 (4)	C6B—C7B	1.363 (4)
C6A—C10A	1.501 (4)	C6B—C10B	1.507 (4)
C7A—C8A	1.393 (4)	C7B—C8B	1.396 (4)
C7A—H7A	0.9300	C7B—H7B	0.9300
C10A—H10A	0.9600	C10B—H10D	0.9600
C10A—H10B	0.9600	C10B—H10E	0.9600
C10A—H10C	0.9600	C10B—H10F	0.9600
C11A—C12A	1.509 (4)	C11B—C12B	1.509 (4)
C11A—H11A	0.9700	C11B—H11C	0.9700
C11A—H11B	0.9700	C11B—H11D	0.9700
C12A—H12A	0.9600	C12B—H12D	0.9600
C12A—H12B	0.9600	C12B—H12E	0.9600
C12A—H12C	0.9600	C12B—H12F	0.9600
C13A—C14A	1.517 (4)	C13B—C14B	1.519 (4)
C13A—H13A	0.9700	C13B—H13C	0.9700
C13A—H13B	0.9700	C13B—H13D	0.9700
C14A—H14A	0.9600	C14B—H14D	0.9600
C14A—H14B	0.9600	C14B—H14E	0.9600
C14A—H14C	0.9600	C14B—H14F	0.9600
C2A—O1A—C3A	123.1 (2)	C2B—O1B—C3B	122.9 (2)
C8A—N1A—H1A1	120.0	C8B—N1B—H1B1	120.0
C8A—N1A—H1A2	120.0	C8B—N1B—H1B2	120.0
H1A1—N1A—H1A2	120.0	H1B1—N1B—H1B2	120.0
C9A—C1A—C8A	119.1 (2)	C9B—C1B—C8B	119.3 (2)
C9A—C1A—C2A	120.0 (2)	C9B—C1B—C2B	119.8 (2)
C8A—C1A—C2A	120.9 (3)	C8B—C1B—C2B	120.8 (3)
O2A—C2A—O1A	115.0 (3)	O2B—C2B—O1B	115.1 (3)
O2A—C2A—C1A	127.6 (3)	O2B—C2B—C1B	127.3 (3)
O1A—C2A—C1A	117.5 (3)	O1B—C2B—C1B	117.6 (3)
C4A—C3A—O1A	121.6 (2)	C4B—C3B—O1B	121.9 (2)
C4A—C3A—C11A	129.7 (3)	C4B—C3B—C11B	129.8 (3)
O1A—C3A—C11A	108.7 (3)	O1B—C3B—C11B	108.3 (3)
C3A—C4A—C9A	118.8 (3)	C3B—C4B—C9B	118.6 (3)
C3A—C4A—C13A	120.9 (2)	C3B—C4B—C13B	121.3 (2)
C9A—C4A—C13A	120.3 (2)	C9B—C4B—C13B	120.0 (2)
C6A—C5A—C9A	121.5 (3)	C6B—C5B—C9B	121.0 (3)
C6A—C5A—H5A	119.3	C6B—C5B—H5B	119.5
C9A—C5A—H5A	119.3	C9B—C5B—H5B	119.5
C7A—C6A—C5A	119.4 (3)	C7B—C6B—C5B	119.6 (3)
C7A—C6A—C10A	121.0 (3)	C7B—C6B—C10B	120.7 (3)
C5A—C6A—C10A	119.7 (3)	C5B—C6B—C10B	119.7 (3)
C6A—C7A—C8A	121.9 (3)	C6B—C7B—C8B	121.9 (3)
C6A—C7A—H7A	119.0	C6B—C7B—H7B	119.0
C8A—C7A—H7A	119.0	C8B—C7B—H7B	119.0
N1A—C8A—C7A	120.1 (3)	N1B—C8B—C7B	119.8 (3)
N1A—C8A—C1A	121.2 (3)	N1B—C8B—C1B	121.6 (3)
C7A—C8A—C1A	118.7 (3)	C7B—C8B—C1B	118.6 (3)
C5A—C9A—C1A	119.3 (2)	C5B—C9B—C1B	119.5 (2)
C5A—C9A—C4A	121.6 (3)	C5B—C9B—C4B	121.5 (3)
C1A—C9A—C4A	119.1 (2)	C1B—C9B—C4B	119.0 (2)
C6A—C10A—H10A	109.5	C6B—C10B—H10D	109.5
C6A—C10A—H10B	109.5	C6B—C10B—H10E	109.5
H10A—C10A—H10B	109.5	H10D—C10B—H10E	109.5
C6A—C10A—H10C	109.5	C6B—C10B—H10F	109.5
H10A—C10A—H10C	109.5	H10D—C10B—H10F	109.5
H10B—C10A—H10C	109.5	H10E—C10B—H10F	109.5
C3A—C11A—C12A	112.3 (3)	C3B—C11B—C12B	112.7 (3)
C3A—C11A—H11A	109.1	C3B—C11B—H11C	109.1
C12A—C11A—H11A	109.1	C12B—C11B—H11C	109.1
C3A—C11A—H11B	109.1	C3B—C11B—H11D	109.1
C12A—C11A—H11B	109.1	C12B—C11B—H11D	109.1
H11A—C11A—H11B	107.9	H11C—C11B—H11D	107.8
C11A—C12A—H12A	109.5	C11B—C12B—H12D	109.5
C11A—C12A—H12B	109.5	C11B—C12B—H12E	109.5
H12A—C12A—H12B	109.5	H12D—C12B—H12E	109.5
C11A—C12A—H12C	109.5	C11B—C12B—H12F	109.5
H12A—C12A—H12C	109.5	H12D—C12B—H12F	109.5
H12B—C12A—H12C	109.5	H12E—C12B—H12F	109.5
C4A—C13A—C14A	112.6 (2)	C4B—C13B—C14B	112.5 (2)
C4A—C13A—H13A	109.1	C4B—C13B—H13C	109.1
C14A—C13A—H13A	109.1	C14B—C13B—H13C	109.1
C4A—C13A—H13B	109.1	C4B—C13B—H13D	109.1
C14A—C13A—H13B	109.1	C14B—C13B—H13D	109.1
H13A—C13A—H13B	107.8	H13C—C13B—H13D	107.8
C13A—C14A—H14A	109.5	C13B—C14B—H14D	109.5
C13A—C14A—H14B	109.5	C13B—C14B—H14E	109.5
H14A—C14A—H14B	109.5	H14D—C14B—H14E	109.5
C13A—C14A—H14C	109.5	C13B—C14B—H14F	109.5
H14A—C14A—H14C	109.5	H14D—C14B—H14F	109.5
H14B—C14A—H14C	109.5	H14E—C14B—H14F	109.5
C3A—O1A—C2A—O2A	−178.6 (2)	C3B—O1B—C2B—O2B	−178.2 (2)
C3A—O1A—C2A—C1A	0.4 (3)	C3B—O1B—C2B—C1B	2.8 (4)
C9A—C1A—C2A—O2A	177.9 (3)	C9B—C1B—C2B—O2B	−179.6 (3)
C8A—C1A—C2A—O2A	−3.1 (4)	C8B—C1B—C2B—O2B	−0.2 (4)
C9A—C1A—C2A—O1A	−0.9 (3)	C9B—C1B—C2B—O1B	−0.7 (4)
C8A—C1A—C2A—O1A	178.1 (2)	C8B—C1B—C2B—O1B	178.7 (2)
C2A—O1A—C3A—C4A	0.8 (4)	C2B—O1B—C3B—C4B	−2.0 (4)
C2A—O1A—C3A—C11A	179.3 (2)	C2B—O1B—C3B—C11B	179.9 (2)
O1A—C3A—C4A—C9A	−1.5 (4)	O1B—C3B—C4B—C9B	−1.0 (4)
C11A—C3A—C4A—C9A	−179.6 (2)	C11B—C3B—C4B—C9B	176.7 (3)
O1A—C3A—C4A—C13A	177.5 (2)	O1B—C3B—C4B—C13B	−179.1 (2)
C11A—C3A—C4A—C13A	−0.6 (4)	C11B—C3B—C4B—C13B	−1.4 (4)
C9A—C5A—C6A—C7A	−0.4 (4)	C9B—C5B—C6B—C7B	2.1 (4)
C9A—C5A—C6A—C10A	−179.1 (2)	C9B—C5B—C6B—C10B	−178.3 (3)
C5A—C6A—C7A—C8A	0.1 (4)	C5B—C6B—C7B—C8B	−1.7 (4)
C10A—C6A—C7A—C8A	178.7 (3)	C10B—C6B—C7B—C8B	178.8 (3)
C6A—C7A—C8A—N1A	−179.0 (2)	C6B—C7B—C8B—N1B	−180.0 (3)
C6A—C7A—C8A—C1A	0.8 (4)	C6B—C7B—C8B—C1B	−0.5 (4)
C9A—C1A—C8A—N1A	178.5 (2)	C9B—C1B—C8B—N1B	−178.3 (2)
C2A—C1A—C8A—N1A	−0.5 (4)	C2B—C1B—C8B—N1B	2.3 (4)
C9A—C1A—C8A—C7A	−1.3 (3)	C9B—C1B—C8B—C7B	2.2 (4)
C2A—C1A—C8A—C7A	179.7 (2)	C2B—C1B—C8B—C7B	−177.2 (2)
C6A—C5A—C9A—C1A	−0.2 (4)	C6B—C5B—C9B—C1B	−0.3 (4)
C6A—C5A—C9A—C4A	179.6 (2)	C6B—C5B—C9B—C4B	179.4 (2)
C8A—C1A—C9A—C5A	1.0 (3)	C8B—C1B—C9B—C5B	−1.8 (3)
C2A—C1A—C9A—C5A	−180.0 (2)	C2B—C1B—C9B—C5B	177.6 (2)
C8A—C1A—C9A—C4A	−178.7 (2)	C8B—C1B—C9B—C4B	178.5 (2)
C2A—C1A—C9A—C4A	0.2 (3)	C2B—C1B—C9B—C4B	−2.2 (3)
C3A—C4A—C9A—C5A	−178.8 (2)	C3B—C4B—C9B—C5B	−176.7 (2)
C13A—C4A—C9A—C5A	2.2 (4)	C13B—C4B—C9B—C5B	1.4 (4)
C3A—C4A—C9A—C1A	1.0 (3)	C3B—C4B—C9B—C1B	3.0 (3)
C13A—C4A—C9A—C1A	−178.1 (2)	C13B—C4B—C9B—C1B	−178.9 (2)
C4A—C3A—C11A—C12A	103.6 (4)	C4B—C3B—C11B—C12B	−109.5 (4)
O1A—C3A—C11A—C12A	−74.7 (3)	O1B—C3B—C11B—C12B	68.5 (3)
C3A—C4A—C13A—C14A	−98.1 (3)	C3B—C4B—C13B—C14B	93.8 (3)
C9A—C4A—C13A—C14A	80.9 (3)	C9B—C4B—C13B—C14B	−84.3 (3)

Hydrogen-bond geometry (Å, º)

Cg1 is the centroid of the C1A/C5A–C9A ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A2···O2A	0.86	2.05	2.701 (3)	131
N1B—H1B2···O2B	0.86	2.05	2.696 (3)	131
N1A—H1A1···O1B^i	0.86	2.57	3.328 (3)	148
N1B—H1B1···O1A^ii	0.86	2.50	3.235 (3)	143
N1B—H1B1···O2A^ii	0.86	2.53	3.367 (3)	165
C12A—H12A···Cg1^iii	0.96	2.99	3.773 (2)	140

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