(E)-1-Ethoxy­carbonyl-2-[(2-hydroxy-1-naphthyl)(phenyl)methyliminio]propan-1-ide

In the title compound, C₂₃H₂₃NO₃, the amino, hydr­oxy and carbonyl groups are involved in hydrogen bonding, forming a dimer. The crystal packing is further stabilized by inter­molecular π–π stacking.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.049
• wR factor = 0.166
• Data-to-parameter ratio = 17.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.62 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C2     -   C11     ..       5.78 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C15    -   C16     ..       6.26 su
PLAT410_ALERT_2_C Short Intra H...H Contact  H1     ..  H4      ..       1.95 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

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

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Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

(E)-1-Ethoxycarbonyl-3-[(2-hydroxynaphthalen-1-ylmethyl)phenyliminio]butan-2-ide

Crystal data

C23H23NO3	Z = 2
Mr = 361.44	F(000) = 384.00
Triclinic, P1	Dx = 1.257 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71075 Å
a = 9.602 (4) Å	Cell parameters from 7862 reflections
b = 9.962 (5) Å	θ = 3.1–27.6°
c = 10.899 (5) Å	µ = 0.08 mm^−1
α = 100.775 (19)°	T = 298 K
β = 109.714 (14)°	Chunk, colorless
γ = 93.722 (18)°	0.30 × 0.24 × 0.18 mm
V = 954.9 (7) Å^3

Data collection

Rigaku R-AXIS RAPID diffractometer	Rint = 0.023
Detector resolution: 10.00 pixels mm^-1	θmax = 27.5°
ω scans	h = −12→11
9527 measured reflections	k = −12→12
4346 independent reflections	l = −14→14
3124 reflections with F^2 > 2σ(F^2)

Refinement

Refinement on F^2	w = 1/[0.0031Fo^2 + σ(Fo^2)]/(4Fo^2)
R[F^2 > 2σ(F^2)] = 0.050	(Δ/σ)max < 0.001
wR(F^2) = 0.166	Δρmax = 0.29 e Å^−3
S = 1.00	Δρmin = −0.23 e Å^−3
4346 reflections	Extinction correction: Larson (1970)
245 parameters	Extinction coefficient: 119 (38)
H-atom parameters constrained

Special details

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
O31	0.18246 (10)	0.53722 (11)	0.64227 (12)	0.0453 (2)
O32	−0.01737 (11)	0.71146 (12)	0.40394 (12)	0.0517 (3)
O33	−0.06574 (13)	0.83611 (13)	0.24492 (12)	0.0661 (3)
N2	0.24609 (12)	0.80909 (12)	0.61792 (12)	0.0398 (3)
C1	0.36652 (12)	0.78535 (13)	0.73398 (13)	0.0355 (3)
C2	0.42380 (13)	0.65073 (13)	0.69751 (12)	0.0341 (3)
C3	0.57588 (13)	0.64680 (14)	0.70721 (13)	0.0376 (3)
C4	0.68307 (16)	0.76502 (18)	0.74675 (17)	0.0483 (4)
C5	0.82626 (18)	0.7566 (2)	0.7505 (2)	0.0618 (5)
C6	0.87158 (18)	0.6273 (2)	0.7193 (2)	0.0624 (5)
C7	0.77362 (18)	0.5128 (2)	0.68143 (17)	0.0540 (4)
C8	0.62282 (16)	0.51591 (17)	0.67392 (13)	0.0415 (3)
C9	0.51910 (17)	0.39689 (16)	0.62937 (14)	0.0445 (4)
C10	0.37352 (17)	0.40114 (14)	0.61832 (14)	0.0419 (3)
C11	0.32730 (13)	0.53007 (14)	0.65342 (13)	0.0371 (3)
C12	0.32249 (14)	0.79830 (14)	0.85641 (13)	0.0394 (3)
C13	0.3810 (2)	0.7225 (2)	0.95251 (18)	0.0617 (5)
C14	0.3486 (3)	0.7423 (2)	1.0670 (2)	0.0842 (7)
C15	0.2541 (2)	0.8339 (3)	1.0872 (2)	0.0891 (7)
C16	0.1941 (2)	0.9058 (2)	0.9946 (2)	0.0810 (7)
C17	0.22885 (18)	0.8924 (2)	0.87835 (19)	0.0576 (4)
C18	0.25072 (14)	0.90910 (13)	0.55280 (14)	0.0398 (3)
C19	0.14278 (17)	0.91370 (16)	0.43419 (17)	0.0483 (4)
C20	0.01721 (16)	0.81249 (16)	0.36429 (16)	0.0448 (4)
C21	−0.1872 (2)	0.7349 (2)	0.1551 (2)	0.0710 (5)
C22	−0.1341 (3)	0.6298 (3)	0.0722 (2)	0.0862 (9)
C23	0.3816 (2)	1.02309 (18)	0.6117 (2)	0.0619 (5)
H1	0.4492	0.8594	0.7561	0.040*
H4	0.6557	0.8513	0.7700	0.057*
H5	0.8939	0.8367	0.7754	0.071*
H6	0.9695	0.6222	0.7238	0.077*
H7	0.8046	0.4277	0.6605	0.068*
H9	0.5495	0.3118	0.6072	0.056*
H10	0.3060	0.3204	0.5881	0.050*
H13	0.4456	0.6602	0.9398	0.074*
H14	0.3889	0.6909	1.1303	0.100*
H15	0.2305	0.8456	1.1642	0.102*
H16	0.1308	0.9690	1.0086	0.091*
H17	0.1877	0.9439	0.8154	0.065*
H19	0.1530	0.9886	0.3967	0.057*
H201	0.1686	0.7417	0.5831	0.045*
H211	−0.2611	0.7793	0.0972	0.077*
H212	−0.2322	0.6899	0.2069	0.078*
H221	−0.2171	0.5780	−0.0032	0.103*
H222	−0.0842	0.5683	0.1252	0.103*
H223	−0.0657	0.6755	0.0413	0.103*
H231	0.3672	1.0912	0.5584	0.069*
H232	0.4716	0.9850	0.6140	0.069*
H233	0.3896	1.0653	0.7009	0.070*
H301	0.1286	0.4495	0.6175	0.055*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O31	0.0361 (5)	0.0358 (5)	0.0649 (7)	−0.0002 (4)	0.0212 (4)	0.0090 (5)
O32	0.0430 (5)	0.0488 (6)	0.0568 (6)	−0.0030 (4)	0.0077 (4)	0.0186 (5)
O33	0.0670 (7)	0.0640 (8)	0.0522 (7)	0.0004 (6)	−0.0021 (5)	0.0239 (6)
N2	0.0342 (5)	0.0343 (6)	0.0449 (6)	0.0019 (4)	0.0062 (4)	0.0103 (5)
C1	0.0292 (5)	0.0329 (7)	0.0406 (7)	0.0035 (4)	0.0087 (5)	0.0060 (5)
C2	0.0333 (6)	0.0351 (7)	0.0345 (6)	0.0054 (5)	0.0124 (5)	0.0088 (5)
C3	0.0337 (6)	0.0448 (8)	0.0344 (6)	0.0100 (5)	0.0109 (5)	0.0100 (5)
C4	0.0344 (7)	0.0505 (9)	0.0574 (9)	0.0036 (6)	0.0140 (6)	0.0107 (7)
C5	0.0341 (7)	0.0743 (12)	0.0709 (11)	0.0044 (7)	0.0141 (7)	0.0112 (10)
C6	0.0355 (7)	0.0910 (14)	0.0653 (11)	0.0192 (8)	0.0199 (7)	0.0212 (10)
C7	0.0456 (8)	0.0725 (11)	0.0502 (9)	0.0282 (8)	0.0202 (7)	0.0159 (8)
C8	0.0417 (7)	0.0529 (9)	0.0352 (7)	0.0173 (6)	0.0158 (5)	0.0149 (6)
C9	0.0556 (8)	0.0406 (8)	0.0419 (7)	0.0207 (6)	0.0193 (6)	0.0118 (6)
C10	0.0506 (7)	0.0341 (7)	0.0422 (7)	0.0069 (5)	0.0170 (6)	0.0100 (6)
C11	0.0361 (6)	0.0385 (7)	0.0374 (7)	0.0081 (5)	0.0134 (5)	0.0085 (5)
C12	0.0335 (6)	0.0385 (7)	0.0385 (7)	0.0003 (5)	0.0087 (5)	−0.0002 (5)
C13	0.0819 (12)	0.0619 (11)	0.0416 (8)	0.0179 (9)	0.0213 (8)	0.0112 (8)
C14	0.1155 (18)	0.0905 (17)	0.0439 (10)	0.0058 (14)	0.0280 (11)	0.0119 (10)
C15	0.0825 (14)	0.121 (2)	0.0510 (11)	−0.0230 (14)	0.0360 (10)	−0.0218 (13)
C16	0.0513 (10)	0.1112 (18)	0.0654 (13)	0.0098 (10)	0.0239 (9)	−0.0223 (12)
C17	0.0433 (7)	0.0670 (11)	0.0545 (9)	0.0133 (7)	0.0151 (7)	−0.0030 (8)
C18	0.0429 (7)	0.0290 (6)	0.0470 (7)	0.0042 (5)	0.0158 (6)	0.0085 (5)
C19	0.0537 (8)	0.0370 (8)	0.0521 (9)	0.0037 (6)	0.0132 (7)	0.0166 (6)
C20	0.0456 (7)	0.0431 (8)	0.0464 (8)	0.0114 (6)	0.0135 (6)	0.0154 (6)
C21	0.0590 (10)	0.0826 (14)	0.0533 (10)	−0.0027 (9)	−0.0020 (8)	0.0176 (10)
C22	0.073 (2)	0.097 (2)	0.0683 (15)	−0.0077 (16)	0.0071 (14)	0.0108 (14)
C23	0.0607 (10)	0.0432 (9)	0.0690 (11)	−0.0107 (7)	0.0073 (8)	0.0177 (8)

Geometric parameters (Å, º)

O31—C11	1.3624 (17)	C18—C23	1.510 (2)
O32—C20	1.235 (2)	C19—C20	1.4092 (19)
O33—C20	1.350 (2)	C21—C22	1.483 (4)
O33—C21	1.429 (2)	O31—H301	0.929
N2—C1	1.4675 (16)	N2—H201	0.893
N2—C18	1.333 (2)	C1—H1	0.980
C1—C2	1.5175 (19)	C4—H4	0.930
C1—C12	1.516 (2)	C5—H5	0.930
C2—C3	1.4318 (19)	C6—H6	0.930
C2—C11	1.3687 (18)	C7—H7	0.930
C3—C4	1.409 (2)	C9—H9	0.930
C3—C8	1.430 (2)	C10—H10	0.930
C4—C5	1.370 (2)	C13—H13	0.930
C5—C6	1.405 (3)	C14—H14	0.930
C6—C7	1.334 (2)	C15—H15	0.930
C7—C8	1.425 (2)	C16—H16	0.930
C8—C9	1.392 (2)	C17—H17	0.930
C9—C10	1.366 (2)	C19—H19	0.930
C10—C11	1.413 (2)	C21—H211	0.970
C12—C13	1.392 (2)	C21—H212	0.970
C12—C17	1.384 (2)	C22—H221	0.960
C13—C14	1.368 (3)	C22—H222	0.960
C14—C15	1.368 (4)	C22—H223	0.960
C15—C16	1.340 (3)	C23—H231	0.960
C16—C17	1.400 (3)	C23—H232	0.960
C18—C19	1.368 (2)	C23—H233	0.960
O31···O32^i	2.7182 (15)	H10···C20^i	3.531
O31···C6^ii	3.490 (2)	H10···C21^i	3.477
O32···O31^i	2.7182 (15)	H10···C23^xi	3.131
O32···C7^iii	3.564 (2)	H10···H14^x	3.482
O32···C10^i	3.443 (2)	H10···H19^xi	3.487
O32···C11^i	3.5056 (17)	H10···H212^i	2.579
O33···C17^iv	3.473 (2)	H10···H231^xi	2.385
C3···C9^iii	3.402 (2)	H10···H233^xi	3.063
C6···O31^v	3.490 (2)	H13···C21^vii	3.452
C6···C10^iii	3.584 (2)	H13···H211^vii	2.798
C7···O32^iii	3.564 (2)	H13···H212^vii	3.409
C7···C10^iii	3.390 (2)	H13···H221^vii	3.275
C7···C11^iii	3.379 (2)	H13···H221^i	3.448
C8···C9^iii	3.424 (2)	H14···C8^x	3.254
C8···C10^iii	3.447 (2)	H14···C9^x	2.793
C9···C3^iii	3.402 (2)	H14···C10^x	3.247
C9···C8^iii	3.424 (2)	H14···C23^viii	3.590
C10···O32^i	3.443 (2)	H14···H9^x	2.726
C10···C6^iii	3.584 (2)	H14···H10^x	3.482
C10···C7^iii	3.390 (2)	H14···H211^vii	3.571
C10···C8^iii	3.447 (2)	H14···H212^vii	3.448
C11···O32^i	3.5056 (17)	H14···H221^i	2.884
C11···C7^iii	3.379 (2)	H14···H231^viii	3.596
C17···O33^iv	3.473 (2)	H14···H233^viii	2.970
O31···H6^ii	2.619	H15···O33^xii	3.249
O31···H7^iii	3.425	H15···C19^xii	3.291
O31···H201	2.247	H15···C20^xii	3.500
O31···H212^i	3.008	H15···H4^viii	3.010
O31···H222^i	3.302	H15···H5^viii	3.481
O31···H301^i	3.383	H15···H9^x	3.387
O32···H6^iii	3.479	H15···H19^xii	3.011
O32···H7^iii	2.750	H15···H223^xii	2.951
O32···H10^i	2.802	H15···H232^viii	3.172
O32···H201	2.110	H15···H233^viii	3.425
O32···H301^i	1.799	H16···O33^iv	3.576
O33···H15^vi	3.249	H16···C4^viii	3.295
O33···H16^iv	3.576	H16···C5^ii	3.515
O33···H17^iv	2.638	H16···C5^viii	3.313
O33···H233^iv	3.522	H16···C16^xiii	3.426
O33···H301^i	3.562	H16···H4^viii	2.794
N2···H7^iii	3.345	H16···H5^ii	2.798
N2···H201	0.893	H16···H5^viii	2.842
C1···H201	2.005	H16···H16^xiii	2.580
C2···H9^iii	3.501	H16···H211^iv	3.290
C2···H201	2.651	H16···H223^xii	3.516
C3···H9^iii	3.342	H17···O33^iv	2.638
C3···H221^vii	3.337	H17···C21^iv	3.155
C4···H16^viii	3.295	H17···H5^ii	2.810
C4···H221^vii	3.491	H17···H6^ii	3.490
C5···H10^iii	3.387	H17···H19^iv	3.502
C5···H16^v	3.515	H17···H201	2.870
C5···H16^viii	3.313	H17···H211^iv	2.705
C5···H19^ix	3.275	H19···C5^ix	3.275
C5···H223^vii	3.259	H19···H4^ix	3.489
C6···H10^iii	3.364	H19···H5^ix	2.738
C6···H221^vii	3.514	H19···H10^xv	3.487
C6···H222^iii	3.202	H19···H15^vi	3.011
C6···H223^vii	3.288	H19···H17^iv	3.502
C6···H301^v	3.484	H19···H201	3.452
C7···H10^iii	3.528	H201···O31	2.247
C7···H221^vii	3.346	H201···O32	2.110
C7···H222^iii	3.271	H201···N2	0.893
C8···H14^x	3.254	H201···C1	2.005
C8···H221^vii	3.247	H201···C2	2.651
C9···H14^x	2.793	H201···C11	2.754
C9···H231^xi	3.128	H201···C12	2.769
C10···H14^x	3.247	H201···C17	3.125
C10···H212^i	2.919	H201···C18	1.930
C10···H231^xi	3.026	H201···C19	2.541
C11···H7^iii	3.343	H201···C20	2.593
C11···H201	2.754	H201···C23	3.262
C11···H212^i	3.143	H201···H1	2.743
C12···H6^ii	3.410	H201···H6^ii	3.128
C12···H201	2.769	H201···H7^iii	2.968
C13···H211^vii	3.221	H201···H17	2.870
C13···H221^i	3.513	H201···H19	3.452
C14···H9^x	3.507	H201···H232	3.546
C14···H221^i	3.212	H201···H233	3.503
C14···H233^viii	3.108	H201···H301	3.020
C15···H4^viii	3.150	H201···H301^i	3.175
C15···H223^xii	3.194	H211···C13^xiv	3.221
C15···H232^viii	3.493	H211···C16^iv	3.549
C15···H233^viii	3.377	H211···C17^iv	3.217
C16···H4^viii	3.041	H211···H13^xiv	2.798
C16···H5^ii	2.995	H211···H14^xiv	3.571
C16···H5^viii	3.589	H211···H16^iv	3.290
C16···H16^xiii	3.426	H211···H17^iv	2.705
C16···H211^iv	3.549	H211···H233^iv	3.093
C16···H223^xii	3.507	H212···O31^i	3.008
C17···H5^ii	3.002	H212···C10^i	2.919
C17···H6^ii	3.300	H212···C11^i	3.143
C17···H201	3.125	H212···H10^i	2.579
C17···H211^iv	3.217	H212···H13^xiv	3.409
C18···H9^iii	3.596	H212···H14^xiv	3.448
C18···H201	1.930	H212···H233^iv	3.135
C19···H7^iii	3.486	H212···H301^i	2.543
C19···H15^vi	3.291	H221···C3^xiv	3.337
C19···H201	2.541	H221···C4^xiv	3.491
C20···H7^iii	3.054	H221···C6^xiv	3.514
C20···H10^i	3.531	H221···C7^xiv	3.346
C20···H15^vi	3.500	H221···C8^xiv	3.247
C20···H201	2.593	H221···C13^i	3.513
C20···H301^i	2.953	H221···C14^i	3.212
C21···H13^xiv	3.452	H221···H13^xiv	3.275
C21···H17^iv	3.155	H221···H13^i	3.448
C21···H233^iv	3.405	H221···H14^i	2.884
C21···H301^i	3.275	H222···O31^i	3.302
C22···H301^i	3.598	H222···C6^iii	3.202
C23···H9^xv	3.221	H222···C7^iii	3.271
C23···H10^xv	3.131	H222···H6^iii	2.782
C23···H14^viii	3.590	H222···H7^iii	2.896
C23···H201	3.262	H222···H223^xvi	3.439
C23···H232^ix	3.213	H222···H301^i	3.010
H1···H201	2.743	H223···C5^xiv	3.259
H4···C15^viii	3.150	H223···C6^xiv	3.288
H4···C16^viii	3.041	H223···C15^vi	3.194
H4···H15^viii	3.010	H223···C16^vi	3.507
H4···H16^viii	2.794	H223···H5^xiv	3.492
H4···H19^ix	3.489	H223···H6^xiv	3.534
H5···C16^v	2.995	H223···H15^vi	2.951
H5···C16^viii	3.589	H223···H16^vi	3.516
H5···C17^v	3.002	H223···H222^xvi	3.439
H5···H15^viii	3.481	H231···C9^xv	3.128
H5···H16^v	2.798	H231···C10^xv	3.026
H5···H16^viii	2.842	H231···H9^xv	2.572
H5···H17^v	2.810	H231···H10^xv	2.385
H5···H19^ix	2.738	H231···H14^viii	3.596
H5···H223^vii	3.492	H231···H232^ix	2.844
H6···O31^v	2.619	H232···C15^viii	3.493
H6···O32^iii	3.479	H232···C23^ix	3.213
H6···C12^v	3.410	H232···H9^xv	3.313
H6···C17^v	3.300	H232···H9^iii	3.395
H6···H17^v	3.490	H232···H15^viii	3.172
H6···H201^v	3.128	H232···H201	3.546
H6···H222^iii	2.782	H232···H231^ix	2.844
H6···H223^vii	3.534	H232···H232^ix	2.781
H6···H301^v	2.726	H233···O33^iv	3.522
H6···H301^iii	3.434	H233···C14^viii	3.108
H7···O31^iii	3.425	H233···C15^viii	3.377
H7···O32^iii	2.750	H233···C21^iv	3.405
H7···N2^iii	3.345	H233···H9^xv	3.307
H7···C11^iii	3.343	H233···H10^xv	3.063
H7···C19^iii	3.486	H233···H14^viii	2.970
H7···C20^iii	3.054	H233···H15^viii	3.425
H7···H201^iii	2.968	H233···H201	3.503
H7···H222^iii	2.896	H233···H211^iv	3.093
H7···H301^v	3.299	H233···H212^iv	3.135
H9···C2^iii	3.501	H301···O31^i	3.383
H9···C3^iii	3.342	H301···O32^i	1.799
H9···C14^x	3.507	H301···O33^i	3.562
H9···C18^iii	3.596	H301···C6^ii	3.484
H9···C23^xi	3.221	H301···C20^i	2.953
H9···H14^x	2.726	H301···C21^i	3.275
H9···H15^x	3.387	H301···C22^i	3.598
H9···H231^xi	2.572	H301···H6^ii	2.726
H9···H232^xi	3.313	H301···H6^iii	3.434
H9···H232^iii	3.395	H301···H7^ii	3.299
H9···H233^xi	3.307	H301···H201	3.020
H10···O32^i	2.802	H301···H201^i	3.175
H10···C5^iii	3.387	H301···H212^i	2.543
H10···C6^iii	3.364	H301···H222^i	3.010
H10···C7^iii	3.528	H301···H301^i	3.270
C20—O33—C21	119.63 (15)	C2—C1—H1	106.7
C1—N2—C18	126.54 (10)	C12—C1—H1	106.3
N2—C1—C2	110.49 (10)	C3—C4—H4	119.2
N2—C1—C12	112.19 (11)	C5—C4—H4	119.0
C2—C1—C12	114.04 (12)	C4—C5—H5	119.8
C1—C2—C3	121.71 (11)	C6—C5—H5	120.1
C1—C2—C11	119.12 (12)	C5—C6—H6	119.7
C3—C2—C11	119.17 (13)	C7—C6—H6	120.4
C2—C3—C4	123.87 (13)	C6—C7—H7	119.3
C2—C3—C8	118.64 (12)	C8—C7—H7	118.5
C4—C3—C8	117.49 (13)	C8—C9—H9	119.4
C3—C4—C5	121.84 (16)	C10—C9—H9	118.8
C4—C5—C6	120.10 (17)	C9—C10—H10	120.4
C5—C6—C7	119.93 (17)	C11—C10—H10	120.6
C6—C7—C8	122.18 (18)	C12—C13—H13	119.3
C3—C8—C7	118.41 (14)	C14—C13—H13	120.0
C3—C8—C9	119.38 (14)	C13—C14—H14	119.6
C7—C8—C9	122.14 (15)	C15—C14—H14	119.9
C8—C9—C10	121.84 (14)	C14—C15—H15	120.3
C9—C10—C11	118.95 (13)	C16—C15—H15	120.0
O31—C11—C2	117.91 (13)	C15—C16—H16	119.8
O31—C11—C10	120.10 (12)	C17—C16—H16	118.6
C2—C11—C10	121.99 (13)	C12—C17—H17	120.2
C1—C12—C13	121.32 (15)	C16—C17—H17	120.8
C1—C12—C17	120.11 (15)	C18—C19—H19	117.8
C13—C12—C17	118.48 (17)	C20—C19—H19	117.6
C12—C13—C14	120.7 (2)	O33—C21—H211	109.6
C13—C14—C15	120.5 (2)	O33—C21—H212	108.7
C14—C15—C16	119.7 (2)	C22—C21—H211	109.2
C15—C16—C17	121.6 (2)	C22—C21—H212	109.0
C12—C17—C16	119.00 (19)	H211—C21—H212	109.5
N2—C18—C19	123.32 (12)	C21—C22—H221	110.1
N2—C18—C23	118.79 (12)	C21—C22—H222	109.4
C19—C18—C23	117.89 (15)	C21—C22—H223	108.9
C18—C19—C20	124.60 (16)	H221—C22—H222	109.4
O32—C20—O33	121.65 (12)	H221—C22—H223	109.5
O32—C20—C19	125.62 (14)	H222—C22—H223	109.5
O33—C20—C19	112.73 (15)	C18—C23—H231	110.0
O33—C21—C22	110.74 (18)	C18—C23—H232	109.4
C11—O31—H301	110.8	C18—C23—H233	109.0
C1—N2—H201	114.1	H231—C23—H232	109.5
C18—N2—H201	118.8	H231—C23—H233	109.5
N2—C1—H1	106.5	H232—C23—H233	109.5
C20—O33—C21—C22	−85.7 (2)	C4—C3—C8—C7	−0.6 (2)
C21—O33—C20—O32	−7.0 (2)	C4—C3—C8—C9	−177.53 (15)
C21—O33—C20—C19	172.89 (16)	C8—C3—C4—C5	1.5 (2)
C1—N2—C18—C19	170.30 (15)	C3—C4—C5—C6	−2.4 (3)
C1—N2—C18—C23	−9.3 (2)	C4—C5—C6—C7	2.4 (3)
C18—N2—C1—C2	−113.44 (16)	C5—C6—C7—C8	−1.5 (3)
C18—N2—C1—C12	118.09 (16)	C6—C7—C8—C3	0.6 (2)
N2—C1—C2—C3	119.32 (14)	C6—C7—C8—C9	177.45 (18)
N2—C1—C2—C11	−60.26 (18)	C3—C8—C9—C10	−1.0 (2)
N2—C1—C12—C13	149.65 (13)	C7—C8—C9—C10	−177.85 (16)
N2—C1—C12—C17	−33.99 (16)	C8—C9—C10—C11	−0.1 (2)
C2—C1—C12—C13	23.07 (16)	C9—C10—C11—O31	179.47 (14)
C2—C1—C12—C17	−160.57 (11)	C9—C10—C11—C2	0.3 (2)
C12—C1—C2—C3	−113.21 (14)	C1—C12—C13—C14	175.34 (16)
C12—C1—C2—C11	67.20 (15)	C1—C12—C17—C16	−177.75 (14)
C1—C2—C3—C4	−1.9 (2)	C13—C12—C17—C16	−1.3 (2)
C1—C2—C3—C8	178.66 (13)	C17—C12—C13—C14	−1.1 (2)
C1—C2—C11—O31	1.1 (2)	C12—C13—C14—C15	2.2 (3)
C1—C2—C11—C10	−179.75 (14)	C13—C14—C15—C16	−0.8 (3)
C3—C2—C11—O31	−178.53 (13)	C14—C15—C16—C17	−1.7 (3)
C3—C2—C11—C10	0.6 (2)	C15—C16—C17—C12	2.7 (2)
C11—C2—C3—C4	177.66 (15)	N2—C18—C19—C20	−2.2 (2)
C11—C2—C3—C8	−1.7 (2)	C23—C18—C19—C20	177.45 (17)
C2—C3—C4—C5	−177.89 (17)	C18—C19—C20—O32	4.8 (3)
C2—C3—C8—C7	178.89 (14)	C18—C19—C20—O33	−175.09 (16)
C2—C3—C8—C9	1.9 (2)

Symmetry codes: (i) −x, −y+1, −z+1; (ii) x−1, y, z; (iii) −x+1, −y+1, −z+1; (iv) −x, −y+2, −z+1; (v) x+1, y, z; (vi) x, y, z−1; (vii) x+1, y, z+1; (viii) −x+1, −y+2, −z+2; (ix) −x+1, −y+2, −z+1; (x) −x+1, −y+1, −z+2; (xi) x, y−1, z; (xii) x, y, z+1; (xiii) −x, −y+2, −z+2; (xiv) x−1, y, z−1; (xv) x, y+1, z; (xvi) −x, −y+1, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O31—H301···O32^i	0.93	1.80	2.7182 (15)	170
N2—H201···O31	0.89	2.25	2.8182 (17)	122
N2—H201···O32	0.89	2.11	2.7634 (13)	129

Symmetry code: (i) −x, −y+1, −z+1.