Crystal structure of (E)-9-({[4-(di­ethyl­amino)­phen­yl]imino}­meth­yl)-2,3,6,7-tetra­hydro-1H,5H-pyrido[3,2,1-ij]quinolin-8-ol

In the title compound, the hy­droxy group forms a intra­molecular hydrogen bond to the imine N atom and generates an S(6) ring motif. The conformation about the C=N bond is E, and the aromatic ring of the julolidine moiety is inclined to the benzene ring by 3.74 (14)°.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.064
• wR factor = 0.150
• Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Non-Solvent Resd 1   C   Ueq(max)/Ueq(min) Range        7.7 Ratio

Alert level C
PLAT220_ALERT_2_C Non-Solvent Resd 1   N   Ueq(max)/Ueq(min) Range        3.2 Ratio
PLAT222_ALERT_3_C Non-Solvent Resd 1   H Uiso(max)/Uiso(min) Range        6.3 Ratio

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          3 Note
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT012_ALERT_1_G N.O.K. _shelx_res_checksum found in CIF ........     Please Check
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          1 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1)..         59 % Note
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          1 Note
PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms ....          ! Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          2 Note

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

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

---

Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).

(E)-9-({[4-(Diethylamino)phenyl]imino}methyl)-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-8-ol

Crystal data

C23H29N3O	F(000) = 784
Mr = 363.49	Dx = 1.266 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.565 (2) Å	Cell parameters from 1274 reflections
b = 8.0504 (16) Å	θ = 2.8–25.3°
c = 20.665 (4) Å	µ = 0.08 mm^−1
β = 97.68 (3)°	T = 293 K
V = 1906.7 (7) Å^3	Block, colourless
Z = 4	0.18 × 0.14 × 0.11 mm

Data collection

Bruker APEXII CCD diffractometer	3900 independent reflections
Radiation source: fine-focus sealed tube	2582 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromator	Rint = 0.077
Detector resolution: 9 pixels mm^-1	θmax = 26.4°, θmin = 2.7°
φ scans and ω scans with κ offset	h = −12→14
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −10→10
Tmin = 0.894, Tmax = 0.943	l = −25→25
15990 measured 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)] = 0.064	H-atom parameters constrained
wR(F^2) = 0.150	w = 1/[σ^2(Fo^2) + (0.0313P)^2 + 1.5846P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
3900 reflections	Δρmax = 0.33 e Å^−3
286 parameters	Δρmin = −0.25 e Å^−3
2 restraints	Extinction correction: SHELXL2014 (Sheldrick 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0087 (10)

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)
N3	0.95181 (17)	0.9756 (2)	0.12926 (9)	0.0289 (5)
C1	0.8227 (2)	0.9508 (3)	0.31028 (11)	0.0267 (6)
C2	0.9203 (2)	1.0455 (3)	0.30272 (11)	0.0267 (6)
H2A	0.9582	1.1033	0.3384	0.032*
C3	0.9622 (2)	1.0554 (3)	0.24346 (11)	0.0250 (5)
H3A	1.0274	1.1207	0.2399	0.030*
C4	0.9085 (2)	0.9688 (3)	0.18799 (11)	0.0242 (5)
C5	0.8084 (2)	0.8765 (3)	0.19602 (12)	0.0287 (6)
H5A	0.7691	0.8196	0.1606	0.034*
C6	0.7677 (2)	0.8689 (3)	0.25534 (12)	0.0299 (6)
H6A	0.7010	0.8069	0.2589	0.036*
C7	0.8953 (2)	0.8891 (3)	0.07152 (11)	0.0301 (6)
H7A	0.8613	0.7867	0.0849	0.036*
H7B	0.9537	0.8603	0.0438	0.036*
C8	0.8010 (2)	0.9924 (3)	0.03270 (11)	0.0334 (6)
H8A	0.7665	0.9305	−0.0047	0.050*
H8B	0.7422	1.0193	0.0596	0.050*
H8C	0.8345	1.0929	0.0185	0.050*
C9	1.0547 (2)	1.0715 (3)	0.12163 (11)	0.0289 (6)
H9A	1.0537	1.1734	0.1466	0.035*
H9B	1.0526	1.1015	0.0760	0.035*
C10	1.1672 (2)	0.9792 (3)	0.14382 (12)	0.0342 (6)
H10A	1.2325	1.0485	0.1377	0.051*
H10B	1.1708	0.9513	0.1892	0.051*
H10C	1.1697	0.8794	0.1186	0.051*
O1	0.61126 (18)	0.7817 (3)	0.42135 (9)	0.0284 (6)	0.773 (3)
H1	0.6486	0.8056	0.3916	0.034*	0.773 (3)
N1	0.5791 (6)	0.9127 (8)	0.6414 (3)	0.0271 (15)	0.773 (3)
N2	0.7705 (3)	0.9226 (4)	0.36617 (15)	0.0236 (8)	0.773 (3)
C11	0.8123 (3)	0.9873 (3)	0.42118 (16)	0.0208 (7)	0.773 (3)
H11	0.8803	1.0502	0.4242	0.025*	0.773 (3)
C12	0.75428 (19)	0.9631 (3)	0.47925 (8)	0.0209 (7)	0.773 (3)
C13	0.65542 (19)	0.8636 (2)	0.47575 (8)	0.0190 (8)	0.773 (3)
C14	0.59674 (17)	0.8471 (3)	0.52987 (10)	0.0229 (7)	0.773 (3)
C15	0.6369 (2)	0.9301 (3)	0.58749 (8)	0.0236 (10)	0.773 (3)
C16	0.7358 (2)	1.0296 (3)	0.59099 (7)	0.0225 (7)	0.773 (3)
C17	0.79445 (17)	1.0461 (2)	0.53687 (9)	0.0245 (7)	0.773 (3)
H17A	0.8606	1.1127	0.5392	0.029*	0.773 (3)
C18	0.4822 (3)	0.8028 (4)	0.64386 (18)	0.0275 (8)	0.773 (3)
H18A	0.4100	0.8642	0.6333	0.033*	0.773 (3)
H18B	0.4845	0.7595	0.6878	0.033*	0.773 (3)
C19	0.4846 (3)	0.6604 (4)	0.59677 (19)	0.0279 (8)	0.773 (3)
H19A	0.4141	0.5946	0.5958	0.033*	0.773 (3)
H19B	0.5511	0.5894	0.6106	0.033*	0.773 (3)
C20	0.4932 (3)	0.7308 (4)	0.52849 (15)	0.0260 (7)	0.773 (3)
H20A	0.5014	0.6401	0.4985	0.031*	0.773 (3)
H20B	0.4221	0.7904	0.5128	0.031*	0.773 (3)
C21	0.5959 (5)	1.0430 (7)	0.6951 (2)	0.0239 (11)	0.773 (3)
H21A	0.5196	1.0810	0.7034	0.029*	0.773 (3)
H21B	0.6333	0.9908	0.7348	0.029*	0.773 (3)
C22	0.6643 (5)	1.1862 (8)	0.6814 (3)	0.0324 (13)	0.773 (3)
H22A	0.6863	1.2493	0.7212	0.039*	0.773 (3)
H22B	0.6186	1.2577	0.6500	0.039*	0.773 (3)
C23	0.7737 (3)	1.1264 (5)	0.65402 (19)	0.0279 (9)	0.773 (3)
H23A	0.8212	1.2208	0.6451	0.034*	0.773 (3)
H23B	0.8197	1.0556	0.6856	0.034*	0.773 (3)
O1A	0.8436 (7)	1.0727 (9)	0.5042 (4)	0.034 (2)*	0.227 (3)
H1AA	0.8521	1.0552	0.4660	0.051*	0.227 (3)
N1A	0.5787 (18)	0.935 (3)	0.6525 (10)	0.009 (4)*	0.227 (3)
N2A	0.8007 (11)	0.9666 (15)	0.3807 (6)	0.023 (3)*	0.227 (3)
C11A	0.7106 (9)	0.8852 (13)	0.4005 (5)	0.025 (2)*	0.227 (3)
H11A	0.6618	0.8214	0.3709	0.030*	0.227 (3)
C12A	0.6880 (9)	0.8961 (12)	0.4695 (3)	0.028 (4)*	0.227 (3)
C13A	0.7477 (7)	0.9960 (11)	0.5177 (5)	0.025 (3)*	0.227 (3)
C14A	0.7114 (9)	1.0041 (14)	0.5791 (4)	0.046 (5)*	0.227 (3)
C15A	0.6155 (9)	0.9122 (15)	0.5923 (3)	0.022 (3)*	0.227 (3)
C16A	0.5559 (7)	0.8122 (11)	0.5440 (4)	0.017 (3)*	0.227 (3)
C17A	0.5922 (8)	0.8041 (10)	0.4826 (3)	0.031 (3)*	0.227 (3)
H17B	0.5523	0.7372	0.4504	0.038*	0.227 (3)
C18A	0.4874 (14)	0.8190 (19)	0.6734 (7)	0.038 (4)*	0.227 (3)
H18C	0.5076	0.7940	0.7195	0.046*	0.227 (3)
H18D	0.4126	0.8753	0.6680	0.046*	0.227 (3)
C19A	0.4757 (11)	0.6612 (15)	0.6364 (6)	0.031 (3)*	0.227 (3)
H19C	0.4114	0.5969	0.6490	0.038*	0.227 (3)
H19D	0.5465	0.5963	0.6460	0.038*	0.227 (3)
C20A	0.4527 (11)	0.7013 (15)	0.5615 (7)	0.027 (3)*	0.227 (3)
H20C	0.3793	0.7599	0.5513	0.033*	0.227 (3)
H20D	0.4486	0.5992	0.5364	0.033*	0.227 (3)
C21A	0.607 (4)	1.042 (6)	0.694 (2)	0.131 (15)*	0.227 (3)
H21C	0.6512	0.9897	0.7323	0.157*	0.227 (3)
H21D	0.5369	1.0892	0.7081	0.157*	0.227 (3)
C22A	0.6852 (19)	1.190 (3)	0.6675 (9)	0.024 (5)*	0.227 (3)
H22C	0.6362	1.2647	0.6388	0.028*	0.227 (3)
H22D	0.7251	1.2540	0.7036	0.028*	0.227 (3)
C23A	0.7747 (14)	1.100 (2)	0.6295 (7)	0.029 (4)*	0.227 (3)
H23C	0.8229	1.1815	0.6109	0.035*	0.227 (3)
H23D	0.8251	1.0293	0.6588	0.035*	0.227 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N3	0.0334 (12)	0.0315 (11)	0.0207 (10)	−0.0089 (10)	0.0000 (9)	−0.0024 (9)
C1	0.0270 (13)	0.0232 (12)	0.0307 (13)	0.0075 (11)	0.0067 (11)	0.0096 (11)
C2	0.0303 (13)	0.0252 (12)	0.0235 (12)	0.0024 (11)	0.0000 (10)	−0.0006 (10)
C3	0.0260 (13)	0.0222 (12)	0.0262 (12)	−0.0031 (10)	0.0006 (10)	0.0023 (10)
C4	0.0264 (13)	0.0191 (11)	0.0253 (12)	0.0018 (10)	−0.0027 (10)	0.0034 (10)
C5	0.0286 (13)	0.0250 (13)	0.0306 (13)	−0.0022 (11)	−0.0031 (11)	0.0027 (11)
C6	0.0250 (13)	0.0229 (12)	0.0412 (15)	−0.0017 (11)	0.0018 (11)	0.0097 (11)
C7	0.0414 (15)	0.0241 (12)	0.0241 (12)	−0.0074 (11)	0.0023 (11)	−0.0038 (11)
C8	0.0442 (16)	0.0270 (13)	0.0267 (13)	−0.0092 (12)	−0.0038 (11)	0.0001 (11)
C9	0.0368 (14)	0.0293 (13)	0.0207 (12)	−0.0080 (11)	0.0039 (10)	−0.0007 (10)
C10	0.0367 (15)	0.0369 (15)	0.0291 (13)	−0.0058 (12)	0.0041 (11)	−0.0023 (12)
O1	0.0353 (13)	0.0284 (12)	0.0212 (11)	−0.0021 (10)	0.0027 (9)	−0.0041 (9)
N1	0.038 (2)	0.021 (3)	0.021 (3)	0.0025 (16)	0.0033 (19)	−0.0086 (18)
N2	0.0244 (17)	0.0194 (16)	0.0268 (17)	0.0040 (14)	0.0029 (14)	0.0021 (13)
C11	0.0210 (15)	0.0143 (14)	0.0269 (18)	0.0029 (12)	0.0022 (13)	0.0026 (13)
C12	0.0241 (17)	0.0124 (14)	0.0252 (17)	0.0024 (13)	−0.0008 (13)	0.0028 (13)
C13	0.0208 (19)	0.0129 (15)	0.0221 (16)	0.0025 (16)	−0.0012 (13)	−0.0030 (12)
C14	0.0276 (18)	0.0196 (16)	0.0222 (17)	0.0055 (14)	0.0054 (14)	0.0048 (13)
C15	0.033 (2)	0.0161 (17)	0.0201 (17)	0.0108 (16)	−0.0008 (14)	0.0040 (13)
C16	0.0298 (18)	0.0170 (16)	0.0192 (16)	0.0081 (15)	−0.0022 (15)	0.0061 (14)
C17	0.0245 (17)	0.0188 (15)	0.0278 (17)	−0.0010 (14)	−0.0060 (15)	0.0006 (14)
C18	0.0267 (18)	0.034 (2)	0.0224 (19)	0.0030 (15)	0.0054 (15)	0.0011 (17)
C19	0.0286 (18)	0.0233 (17)	0.032 (2)	0.0009 (14)	0.0030 (16)	0.0018 (16)
C20	0.0325 (18)	0.0235 (16)	0.0219 (16)	0.0062 (15)	0.0036 (14)	0.0007 (14)
C21	0.035 (2)	0.0291 (19)	0.0078 (14)	0.0111 (15)	0.0027 (12)	−0.0008 (13)
C22	0.047 (3)	0.031 (2)	0.018 (2)	0.003 (2)	0.000 (2)	−0.005 (2)
C23	0.035 (2)	0.0259 (19)	0.021 (2)	−0.0021 (15)	−0.0018 (17)	−0.0045 (17)

Geometric parameters (Å, º)

N3—C4	1.375 (3)	C19—C20	1.536 (4)
N3—C9	1.445 (3)	C19—H19A	0.9700
N3—C7	1.458 (3)	C19—H19B	0.9700
C1—C2	1.388 (3)	C20—H20A	0.9700
C1—C6	1.391 (3)	C20—H20B	0.9700
C1—N2	1.392 (4)	C21—C22	1.447 (9)
C1—N2A	1.516 (12)	C21—H21A	0.9700
C2—C3	1.378 (3)	C21—H21B	0.9700
C2—H2A	0.9300	C22—C23	1.532 (7)
C3—C4	1.412 (3)	C22—H22A	0.9700
C3—H3A	0.9300	C22—H22B	0.9700
C4—C5	1.404 (3)	C23—H23A	0.9700
C5—C6	1.372 (3)	C23—H23B	0.9700
C5—H5A	0.9300	O1A—C13A	1.331 (11)
C6—H6A	0.9300	O1A—H1AA	0.8200
C7—C8	1.514 (3)	N1A—C21A	1.23 (4)
C7—H7A	0.9700	N1A—C15A	1.38 (2)
C7—H7B	0.9700	N1A—C18A	1.51 (3)
C8—H8A	0.9600	N2A—C11A	1.341 (16)
C8—H8B	0.9600	C11A—C12A	1.485 (12)
C8—H8C	0.9600	C11A—H11A	0.9300
C9—C10	1.515 (3)	C12A—C13A	1.3900
C9—H9A	0.9700	C12A—C17A	1.3900
C9—H9B	0.9700	C13A—C14A	1.3900
C10—H10A	0.9600	C14A—C15A	1.3900
C10—H10B	0.9600	C14A—C23A	1.421 (16)
C10—H10C	0.9600	C15A—C16A	1.3900
O1—C13	1.344 (2)	C16A—C17A	1.3900
O1—H1	0.8200	C16A—C20A	1.571 (14)
N1—C15	1.381 (6)	C17A—H17B	0.9300
N1—C18	1.434 (8)	C18A—C19A	1.479 (18)
N1—C21	1.521 (7)	C18A—H18C	0.9700
N2—C11	1.285 (5)	C18A—H18D	0.9700
C11—C12	1.464 (3)	C19A—C20A	1.568 (17)
C11—H11	0.9300	C19A—H19C	0.9700
C12—C13	1.3900	C19A—H19D	0.9700
C12—C17	1.3900	C20A—H20C	0.9700
C13—C14	1.3900	C20A—H20D	0.9700
C14—C15	1.3900	C21A—C22A	1.64 (5)
C14—C20	1.517 (4)	C21A—H21C	0.9700
C15—C16	1.3900	C21A—H21D	0.9700
C16—C17	1.3900	C22A—C23A	1.56 (2)
C16—C23	1.531 (4)	C22A—H22C	0.9700
C17—H17A	0.9300	C22A—H22D	0.9700
C18—C19	1.506 (5)	C23A—H23C	0.9700
C18—H18A	0.9700	C23A—H23D	0.9700
C18—H18B	0.9700
C4—N3—C9	121.33 (19)	C14—C20—H20A	109.4
C4—N3—C7	121.8 (2)	C19—C20—H20A	109.4
C9—N3—C7	116.83 (19)	C14—C20—H20B	109.4
C2—C1—C6	117.3 (2)	C19—C20—H20B	109.4
C2—C1—N2	129.3 (3)	H20A—C20—H20B	108.0
C6—C1—N2	113.4 (2)	C22—C21—N1	115.2 (5)
C2—C1—N2A	107.8 (5)	C22—C21—H21A	108.5
C6—C1—N2A	134.9 (5)	N1—C21—H21A	108.5
C3—C2—C1	121.3 (2)	C22—C21—H21B	108.5
C3—C2—H2A	119.3	N1—C21—H21B	108.5
C1—C2—H2A	119.3	H21A—C21—H21B	107.5
C2—C3—C4	121.6 (2)	C21—C22—C23	108.8 (5)
C2—C3—H3A	119.2	C21—C22—H22A	109.9
C4—C3—H3A	119.2	C23—C22—H22A	109.9
N3—C4—C5	121.9 (2)	C21—C22—H22B	109.9
N3—C4—C3	121.6 (2)	C23—C22—H22B	109.9
C5—C4—C3	116.5 (2)	H22A—C22—H22B	108.3
C6—C5—C4	121.1 (2)	C16—C23—C22	108.5 (3)
C6—C5—H5A	119.5	C16—C23—H23A	110.0
C4—C5—H5A	119.5	C22—C23—H23A	110.0
C5—C6—C1	122.2 (2)	C16—C23—H23B	110.0
C5—C6—H6A	118.9	C22—C23—H23B	110.0
C1—C6—H6A	118.9	H23A—C23—H23B	108.4
N3—C7—C8	112.5 (2)	C13A—O1A—H1AA	109.5
N3—C7—H7A	109.1	C21A—N1A—C15A	130 (3)
C8—C7—H7A	109.1	C21A—N1A—C18A	111 (3)
N3—C7—H7B	109.1	C15A—N1A—C18A	119.1 (16)
C8—C7—H7B	109.1	C11A—N2A—C1	119.3 (10)
H7A—C7—H7B	107.8	N2A—C11A—C12A	120.5 (10)
C7—C8—H8A	109.5	N2A—C11A—H11A	119.7
C7—C8—H8B	109.5	C12A—C11A—H11A	119.7
H8A—C8—H8B	109.5	C13A—C12A—C17A	120.0
C7—C8—H8C	109.5	C13A—C12A—C11A	126.0 (8)
H8A—C8—H8C	109.5	C17A—C12A—C11A	113.8 (8)
H8B—C8—H8C	109.5	O1A—C13A—C12A	117.8 (8)
N3—C9—C10	113.1 (2)	O1A—C13A—C14A	122.1 (8)
N3—C9—H9A	109.0	C12A—C13A—C14A	120.0
C10—C9—H9A	109.0	C15A—C14A—C13A	120.0
N3—C9—H9B	109.0	C15A—C14A—C23A	119.5 (9)
C10—C9—H9B	109.0	C13A—C14A—C23A	120.4 (9)
H9A—C9—H9B	107.8	N1A—C15A—C14A	117.2 (11)
C9—C10—H10A	109.5	N1A—C15A—C16A	122.6 (11)
C9—C10—H10B	109.5	C14A—C15A—C16A	120.0
H10A—C10—H10B	109.5	C17A—C16A—C15A	120.0
C9—C10—H10C	109.5	C17A—C16A—C20A	121.0 (7)
H10A—C10—H10C	109.5	C15A—C16A—C20A	118.9 (7)
H10B—C10—H10C	109.5	C16A—C17A—C12A	120.0
C13—O1—H1	109.5	C16A—C17A—H17B	120.0
C15—N1—C18	123.8 (4)	C12A—C17A—H17B	120.0
C15—N1—C21	119.4 (5)	C19A—C18A—N1A	113.6 (13)
C18—N1—C21	115.1 (5)	C19A—C18A—H18C	108.8
C11—N2—C1	120.9 (3)	N1A—C18A—H18C	108.8
N2—C11—C12	120.8 (3)	C19A—C18A—H18D	108.8
N2—C11—H11	119.6	N1A—C18A—H18D	108.8
C12—C11—H11	119.6	H18C—C18A—H18D	107.7
C13—C12—C17	120.0	C18A—C19A—C20A	109.0 (11)
C13—C12—C11	119.86 (18)	C18A—C19A—H19C	109.9
C17—C12—C11	120.06 (18)	C20A—C19A—H19C	109.9
O1—C13—C14	117.02 (18)	C18A—C19A—H19D	109.9
O1—C13—C12	122.97 (18)	C20A—C19A—H19D	109.9
C14—C13—C12	120.0	H19C—C19A—H19D	108.3
C13—C14—C15	120.0	C19A—C20A—C16A	108.1 (9)
C13—C14—C20	120.86 (18)	C19A—C20A—H20C	110.1
C15—C14—C20	119.03 (18)	C16A—C20A—H20C	110.1
N1—C15—C14	120.0 (3)	C19A—C20A—H20D	110.1
N1—C15—C16	120.0 (3)	C16A—C20A—H20D	110.1
C14—C15—C16	120.0	H20C—C20A—H20D	108.4
C17—C16—C15	120.0	N1A—C21A—C22A	112 (3)
C17—C16—C23	121.4 (2)	N1A—C21A—H21C	109.2
C15—C16—C23	118.6 (2)	C22A—C21A—H21C	109.2
C16—C17—C12	120.0	N1A—C21A—H21D	109.2
C16—C17—H17A	120.0	C22A—C21A—H21D	109.2
C12—C17—H17A	120.0	H21C—C21A—H21D	107.9
N1—C18—C19	111.4 (3)	C23A—C22A—C21A	105 (2)
N1—C18—H18A	109.3	C23A—C22A—H22C	110.6
C19—C18—H18A	109.3	C21A—C22A—H22C	110.6
N1—C18—H18B	109.3	C23A—C22A—H22D	110.6
C19—C18—H18B	109.3	C21A—C22A—H22D	110.6
H18A—C18—H18B	108.0	H22C—C22A—H22D	108.8
C18—C19—C20	108.8 (3)	C14A—C23A—C22A	108.1 (14)
C18—C19—H19A	109.9	C14A—C23A—H23C	110.1
C20—C19—H19A	109.9	C22A—C23A—H23C	110.1
C18—C19—H19B	109.9	C14A—C23A—H23D	110.1
C20—C19—H19B	109.9	C22A—C23A—H23D	110.1
H19A—C19—H19B	108.3	H23C—C23A—H23D	108.4
C14—C20—C19	111.0 (2)
C6—C1—C2—C3	−1.2 (3)	N1—C18—C19—C20	−53.5 (4)
N2—C1—C2—C3	178.0 (3)	C13—C14—C20—C19	149.3 (2)
N2A—C1—C2—C3	179.9 (5)	C15—C14—C20—C19	−26.9 (3)
C1—C2—C3—C4	−0.6 (4)	C18—C19—C20—C14	54.4 (3)
C9—N3—C4—C5	179.8 (2)	C15—N1—C21—C22	5.9 (8)
C7—N3—C4—C5	0.9 (3)	C18—N1—C21—C22	−159.6 (5)
C9—N3—C4—C3	0.2 (3)	N1—C21—C22—C23	−46.1 (6)
C7—N3—C4—C3	−178.7 (2)	C17—C16—C23—C22	139.8 (3)
C2—C3—C4—N3	−178.5 (2)	C15—C16—C23—C22	−36.9 (4)
C2—C3—C4—C5	1.9 (3)	C21—C22—C23—C16	60.4 (5)
N3—C4—C5—C6	178.9 (2)	C2—C1—N2A—C11A	−179.7 (9)
C3—C4—C5—C6	−1.5 (3)	C6—C1—N2A—C11A	1.6 (15)
C4—C5—C6—C1	−0.2 (4)	C1—N2A—C11A—C12A	179.0 (8)
C2—C1—C6—C5	1.5 (3)	N2A—C11A—C12A—C13A	5.3 (14)
N2—C1—C6—C5	−177.8 (2)	N2A—C11A—C12A—C17A	−179.6 (9)
N2A—C1—C6—C5	−179.9 (7)	C17A—C12A—C13A—O1A	175.5 (8)
C4—N3—C7—C8	87.5 (3)	C11A—C12A—C13A—O1A	−9.7 (10)
C9—N3—C7—C8	−91.5 (3)	C17A—C12A—C13A—C14A	0.0
C4—N3—C9—C10	83.4 (3)	C11A—C12A—C13A—C14A	174.9 (10)
C7—N3—C9—C10	−97.6 (2)	O1A—C13A—C14A—C15A	−175.3 (9)
C2—C1—N2—C11	−0.4 (4)	C12A—C13A—C14A—C15A	0.0
C6—C1—N2—C11	178.8 (2)	O1A—C13A—C14A—C23A	2.1 (12)
C1—N2—C11—C12	177.4 (2)	C12A—C13A—C14A—C23A	177.3 (12)
N2—C11—C12—C13	2.7 (3)	C21A—N1A—C15A—C14A	11 (4)
N2—C11—C12—C17	−174.1 (2)	C18A—N1A—C15A—C14A	−170.4 (12)
C17—C12—C13—O1	179.2 (2)	C21A—N1A—C15A—C16A	−164 (3)
C11—C12—C13—O1	2.4 (2)	C18A—N1A—C15A—C16A	14 (2)
C17—C12—C13—C14	0.0	C13A—C14A—C15A—N1A	−175.3 (14)
C11—C12—C13—C14	−176.8 (2)	C23A—C14A—C15A—N1A	7.3 (13)
O1—C13—C14—C15	−179.2 (2)	C13A—C14A—C15A—C16A	0.0
C12—C13—C14—C15	0.0	C23A—C14A—C15A—C16A	−177.4 (12)
O1—C13—C14—C20	4.6 (2)	N1A—C15A—C16A—C17A	175.1 (15)
C12—C13—C14—C20	−176.1 (2)	C14A—C15A—C16A—C17A	0.0
C18—N1—C15—C14	4.7 (7)	N1A—C15A—C16A—C20A	−8.7 (15)
C21—N1—C15—C14	−159.5 (4)	C14A—C15A—C16A—C20A	176.3 (9)
C18—N1—C15—C16	−174.9 (4)	C15A—C16A—C17A—C12A	0.0
C21—N1—C15—C16	20.9 (7)	C20A—C16A—C17A—C12A	−176.2 (9)
C13—C14—C15—N1	−179.6 (4)	C13A—C12A—C17A—C16A	0.0
C20—C14—C15—N1	−3.3 (4)	C11A—C12A—C17A—C16A	−175.4 (9)
C13—C14—C15—C16	0.0	C21A—N1A—C18A—C19A	−162 (3)
C20—C14—C15—C16	176.2 (2)	C15A—N1A—C18A—C19A	19 (2)
N1—C15—C16—C17	179.6 (4)	N1A—C18A—C19A—C20A	−54.2 (16)
C14—C15—C16—C17	0.0	C18A—C19A—C20A—C16A	57.0 (13)
N1—C15—C16—C23	−3.7 (4)	C17A—C16A—C20A—C19A	149.1 (8)
C14—C15—C16—C23	176.8 (3)	C15A—C16A—C20A—C19A	−27.1 (11)
C15—C16—C17—C12	0.0	C15A—N1A—C21A—C22A	10 (5)
C23—C16—C17—C12	−176.7 (3)	C18A—N1A—C21A—C22A	−169 (2)
C13—C12—C17—C16	0.0	N1A—C21A—C22A—C23A	−44 (4)
C11—C12—C17—C16	176.8 (2)	C15A—C14A—C23A—C22A	−42.8 (15)
C15—N1—C18—C19	25.3 (7)	C13A—C14A—C23A—C22A	139.8 (12)
C21—N1—C18—C19	−169.9 (4)	C21A—C22A—C23A—C14A	58 (2)

Hydrogen-bond geometry (Å, º)

Cg1 is the centroid of the C12–C17 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2	0.82	1.83	2.557 (4)	147
C7—H7A···Cg1^i	0.97	2.79	3.574 (3)	138
C20—H20B···Cg1^ii	0.97	2.62	3.521 (3)	154

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