3,7,7-Tri­methyl-1-phenyl-1,6,7,8-tetrahydro-5H-pyrazolo­[3,4-b]­quinolin-5-one

Low, J.N.; Mera, J.; Quiroga, J.; Cobo, J.

doi:10.1107/S1600536803023675

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3,7,7-Trimethyl-1-phenyl-1,6,7,8-tetrahydro-5H-pyrazolo[3,4-b]quinolin-5-one

J. N. Low, J. Mera, J. Quiroga and J. Cobo

The title compound, C₁₉H₁₉N₃O, crystallizes in the space group P $\overline 1$ , with Z′ = 2. Weak C—H

N, C—H

O and C—H

π interactions link the molecules into ribbons.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803023675/om6187sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803023675/om6187Isup2.hkl Contains datablock I

CCDC reference: 227017

checkCIF report

Key indicators

Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.003 Å
R factor = 0.059
wR factor = 0.138
Data-to-parameter ratio = 16.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 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
   0 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and PLATON (Spek, 2002); software used to prepare material for publication: SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).

3,7,7-trimethyl-1-phenyl-1,6,7,8-tetrahydro-5H-pyrazolo[3,4-b]quinolin-5-one top

Crystal data top

C₁₉H₁₉N₃O	Z = 4
M_r = 305.37	F(000) = 648
Triclinic, P1	D_x = 1.312 Mg m⁻³
a = 10.6825 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.9254 (4) Å	Cell parameters from 7071 reflections
c = 13.1219 (6) Å	θ = 3.2–27.6°
α = 111.2105 (17)°	µ = 0.08 mm⁻¹
β = 90.5164 (18)°	T = 120 K
γ = 96.533 (2)°	Plate, colourless
V = 1546.00 (11) Å³	0.25 × 0.24 × 0.03 mm

Data collection top

Nonius KappaCCD diffractometer	7071 independent reflections
Radiation source: fine-focus sealed X-ray tube	4952 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.080
φ scans and ω scans with κ offsets	θ_max = 27.6°, θ_min = 3.2°
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)	h = −13→13
T_min = 0.980, T_max = 0.998	k = −15→15
32382 measured reflections	l = −16→16

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.138	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.054P)² + 0.5429P] where P = (F_o² + 2F_c²)/3
7071 reflections	(Δ/σ)_max < 0.001
421 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Special details top

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm (Fox & Holmes, 1966) which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N11	0.04422 (15)	1.23023 (14)	0.68166 (13)	0.0211 (4)
C111	−0.08463 (18)	1.24039 (17)	0.70472 (15)	0.0210 (4)
C112	−0.17424 (18)	1.13777 (18)	0.67162 (15)	0.0223 (4)
C113	−0.29929 (18)	1.14911 (18)	0.69513 (16)	0.0242 (4)
C114	−0.33616 (19)	1.26252 (19)	0.75133 (16)	0.0264 (5)
C115	−0.2472 (2)	1.36445 (19)	0.78312 (16)	0.0295 (5)
C116	−0.12125 (19)	1.35480 (18)	0.76066 (16)	0.0270 (5)
N12	0.12629 (15)	1.33529 (14)	0.69604 (13)	0.0239 (4)
C13	0.23988 (18)	1.30240 (17)	0.67598 (15)	0.0219 (4)
C131	0.35280 (19)	1.39413 (18)	0.68840 (18)	0.0276 (5)
C13A	0.23664 (18)	1.17396 (17)	0.64728 (15)	0.0203 (4)
C14	0.32292 (18)	1.09047 (17)	0.61920 (15)	0.0208 (4)
C14A	0.27678 (17)	0.97016 (17)	0.60043 (14)	0.0192 (4)
C15	0.36397 (18)	0.87603 (17)	0.56841 (15)	0.0207 (4)
O15	0.47707 (12)	0.90225 (12)	0.56495 (11)	0.0273 (3)
C16	0.30627 (18)	0.74580 (17)	0.53944 (15)	0.0219 (4)
C17	0.19556 (17)	0.73318 (16)	0.60989 (15)	0.0206 (4)
C171	0.24168 (19)	0.77714 (18)	0.73099 (16)	0.0253 (4)
C172	0.13696 (19)	0.60103 (18)	0.57259 (17)	0.0278 (5)
C18	0.09597 (17)	0.80925 (17)	0.59408 (16)	0.0212 (4)
C18A	0.14686 (17)	0.93831 (16)	0.61199 (14)	0.0188 (4)
N19	0.06208 (14)	1.01717 (14)	0.63733 (12)	0.0204 (3)
C19A	0.10960 (17)	1.13188 (17)	0.65298 (14)	0.0190 (4)
N21	0.44874 (14)	−0.21473 (14)	0.02714 (12)	0.0202 (3)
C211	0.57747 (18)	−0.22687 (17)	0.04346 (15)	0.0209 (4)
C212	0.66926 (18)	−0.12564 (17)	0.07617 (15)	0.0207 (4)
C213	0.79406 (19)	−0.13974 (18)	0.09245 (15)	0.0242 (4)
C214	0.82878 (19)	−0.25360 (18)	0.07592 (15)	0.0260 (5)
C215	0.7368 (2)	−0.35376 (19)	0.04288 (17)	0.0283 (5)
C216	0.61208 (19)	−0.34172 (18)	0.02638 (16)	0.0254 (4)
N22	0.36512 (15)	−0.31713 (14)	−0.03114 (13)	0.0230 (4)
C23	0.25180 (18)	−0.28202 (17)	−0.02669 (15)	0.0214 (4)
C231	0.13683 (18)	−0.36945 (18)	−0.07860 (17)	0.0261 (5)
C23A	0.25735 (17)	−0.15501 (17)	0.03499 (15)	0.0197 (4)
C24	0.17335 (18)	−0.06948 (17)	0.06649 (14)	0.0203 (4)
C24A	0.22161 (17)	0.04887 (17)	0.13057 (14)	0.0185 (4)
C25	0.13772 (17)	0.14541 (17)	0.16137 (15)	0.0206 (4)
O25	0.02425 (12)	0.12182 (12)	0.13713 (11)	0.0266 (3)
C26	0.19797 (18)	0.27398 (17)	0.22043 (16)	0.0228 (4)
C272	0.37090 (19)	0.41465 (18)	0.34851 (18)	0.0291 (5)
C27	0.30996 (18)	0.28323 (17)	0.29859 (15)	0.0211 (4)
C271	0.26486 (19)	0.23943 (19)	0.39044 (16)	0.0260 (4)
C28	0.40655 (17)	0.20504 (16)	0.23195 (15)	0.0202 (4)
C28A	0.35219 (17)	0.07781 (17)	0.16242 (14)	0.0190 (4)
N29	0.43580 (14)	−0.00255 (14)	0.13216 (12)	0.0194 (3)
C29A	0.38532 (17)	−0.11538 (17)	0.06889 (15)	0.0192 (4)
H112	−0.1495	1.0601	0.6330	0.027*
H113	−0.3602	1.0791	0.6728	0.029*
H114	−0.4219	1.2700	0.7678	0.032*
H115	−0.2727	1.4420	0.8208	0.035*
H116	−0.0607	1.4251	0.7830	0.032*
H13A	0.3256	1.4675	0.6828	0.041*
H13B	0.4103	1.3605	0.6305	0.041*
H13C	0.3963	1.4143	0.7600	0.041*
H14	0.4096	1.1143	0.6130	0.025*
H16A	0.3719	0.6977	0.5491	0.026*
H16B	0.2763	0.7121	0.4614	0.026*
H17A	0.1691	0.7779	0.7762	0.038*
H17B	0.2870	0.8592	0.7531	0.038*
H17C	0.2984	0.7223	0.7408	0.038*
H17D	0.1059	0.5733	0.4959	0.042*
H17E	0.0666	0.5938	0.6181	0.042*
H17F	0.2007	0.5510	0.5798	0.042*
H18A	0.0572	0.7701	0.5188	0.025*
H18B	0.0286	0.8096	0.6455	0.025*
H212	0.6463	−0.0476	0.0872	0.025*
H213	0.8565	−0.0709	0.1151	0.029*
H214	0.9144	−0.2628	0.0871	0.031*
H215	0.7602	−0.4318	0.0315	0.034*
H216	0.5501	−0.4110	0.0036	0.030*
H23A	0.1614	−0.4397	−0.1381	0.039*
H23B	0.0785	−0.3296	−0.1081	0.039*
H23C	0.0953	−0.3963	−0.0236	0.039*
H24	0.0861	−0.0910	0.0450	0.024*
H26A	0.1337	0.3226	0.2627	0.027*
H26B	0.2275	0.3091	0.1658	0.027*
H27D	0.4428	0.4204	0.3979	0.044*
H27E	0.3089	0.4656	0.3897	0.044*
H27F	0.4002	0.4424	0.2900	0.044*
H27A	0.3379	0.2390	0.4360	0.039*
H27B	0.2198	0.1572	0.3582	0.039*
H27C	0.2082	0.2941	0.4356	0.039*
H28A	0.4465	0.2448	0.1839	0.024*
H28B	0.4735	0.2014	0.2829	0.024*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N11	0.0192 (8)	0.0197 (8)	0.0242 (9)	0.0013 (7)	−0.0009 (7)	0.0083 (7)
C111	0.0204 (10)	0.0273 (11)	0.0168 (9)	0.0052 (8)	−0.0008 (7)	0.0092 (8)
C112	0.0227 (10)	0.0246 (10)	0.0216 (10)	0.0038 (8)	−0.0009 (8)	0.0105 (8)
C113	0.0224 (10)	0.0295 (11)	0.0248 (10)	0.0030 (9)	0.0002 (8)	0.0150 (9)
C114	0.0237 (10)	0.0374 (12)	0.0219 (10)	0.0092 (9)	0.0018 (8)	0.0139 (9)
C115	0.0319 (12)	0.0312 (12)	0.0236 (11)	0.0129 (10)	0.0008 (9)	0.0052 (9)
C116	0.0260 (11)	0.0267 (11)	0.0246 (11)	0.0043 (9)	−0.0023 (8)	0.0049 (9)
N12	0.0225 (9)	0.0235 (9)	0.0255 (9)	−0.0008 (7)	−0.0028 (7)	0.0102 (7)
C13	0.0243 (10)	0.0238 (10)	0.0189 (10)	0.0028 (8)	−0.0011 (8)	0.0094 (8)
C131	0.0242 (11)	0.0259 (11)	0.0327 (12)	−0.0024 (9)	−0.0011 (9)	0.0123 (9)
C13A	0.0222 (10)	0.0225 (10)	0.0160 (9)	0.0002 (8)	−0.0009 (7)	0.0078 (8)
C14	0.0180 (9)	0.0255 (10)	0.0193 (10)	−0.0001 (8)	0.0012 (8)	0.0096 (8)
C14A	0.0160 (9)	0.0256 (10)	0.0163 (9)	0.0029 (8)	0.0020 (7)	0.0080 (8)
C15	0.0190 (10)	0.0266 (11)	0.0181 (9)	0.0009 (8)	0.0001 (8)	0.0106 (8)
O15	0.0181 (7)	0.0315 (8)	0.0349 (8)	0.0031 (6)	0.0033 (6)	0.0149 (7)
C16	0.0205 (10)	0.0239 (10)	0.0199 (10)	0.0039 (8)	0.0010 (8)	0.0060 (8)
C17	0.0188 (10)	0.0190 (10)	0.0216 (10)	0.0009 (8)	0.0008 (8)	0.0051 (8)
C171	0.0243 (10)	0.0292 (11)	0.0234 (10)	0.0037 (9)	0.0003 (8)	0.0106 (9)
C172	0.0243 (11)	0.0246 (11)	0.0327 (12)	0.0007 (9)	0.0012 (9)	0.0090 (9)
C18	0.0175 (9)	0.0249 (10)	0.0210 (10)	0.0011 (8)	−0.0018 (8)	0.0084 (8)
C18A	0.0194 (10)	0.0220 (10)	0.0145 (9)	0.0029 (8)	−0.0009 (7)	0.0061 (8)
N19	0.0197 (8)	0.0237 (9)	0.0185 (8)	0.0025 (7)	−0.0010 (6)	0.0087 (7)
C19A	0.0207 (10)	0.0218 (10)	0.0150 (9)	0.0023 (8)	−0.0017 (7)	0.0073 (8)
N21	0.0176 (8)	0.0187 (8)	0.0217 (8)	0.0011 (7)	0.0003 (6)	0.0046 (7)
C211	0.0221 (10)	0.0258 (10)	0.0167 (9)	0.0058 (8)	0.0022 (8)	0.0092 (8)
C212	0.0213 (10)	0.0223 (10)	0.0175 (9)	0.0031 (8)	0.0013 (8)	0.0058 (8)
C213	0.0235 (10)	0.0298 (11)	0.0183 (10)	0.0038 (9)	0.0014 (8)	0.0076 (8)
C214	0.0243 (11)	0.0357 (12)	0.0199 (10)	0.0103 (9)	0.0007 (8)	0.0106 (9)
C215	0.0343 (12)	0.0272 (11)	0.0276 (11)	0.0118 (9)	0.0030 (9)	0.0125 (9)
C216	0.0268 (11)	0.0232 (11)	0.0272 (11)	0.0028 (9)	0.0014 (9)	0.0106 (9)
N22	0.0226 (9)	0.0225 (9)	0.0214 (8)	−0.0020 (7)	−0.0017 (7)	0.0066 (7)
C23	0.0250 (10)	0.0220 (10)	0.0174 (9)	0.0005 (8)	−0.0016 (8)	0.0082 (8)
C231	0.0248 (11)	0.0232 (11)	0.0268 (11)	0.0006 (8)	−0.0025 (8)	0.0059 (9)
C23A	0.0192 (9)	0.0231 (10)	0.0161 (9)	0.0003 (8)	−0.0024 (7)	0.0072 (8)
C24	0.0184 (9)	0.0273 (10)	0.0162 (9)	0.0016 (8)	−0.0013 (7)	0.0098 (8)
C24A	0.0179 (9)	0.0213 (10)	0.0166 (9)	0.0023 (8)	−0.0002 (7)	0.0073 (8)
C25	0.0203 (10)	0.0278 (11)	0.0152 (9)	0.0033 (8)	−0.0009 (8)	0.0097 (8)
O25	0.0199 (7)	0.0312 (8)	0.0256 (7)	0.0051 (6)	−0.0032 (6)	0.0062 (6)
C26	0.0230 (10)	0.0224 (10)	0.0222 (10)	0.0049 (8)	−0.0015 (8)	0.0065 (8)
C272	0.0242 (11)	0.0250 (11)	0.0333 (12)	0.0026 (9)	−0.0018 (9)	0.0051 (9)
C27	0.0199 (10)	0.0204 (10)	0.0212 (10)	0.0023 (8)	0.0002 (8)	0.0056 (8)
C271	0.0234 (10)	0.0318 (11)	0.0202 (10)	0.0034 (9)	0.0003 (8)	0.0067 (9)
C28	0.0180 (9)	0.0215 (10)	0.0198 (10)	0.0012 (8)	−0.0016 (7)	0.0063 (8)
C28A	0.0211 (10)	0.0215 (10)	0.0155 (9)	0.0026 (8)	0.0009 (7)	0.0082 (8)
N29	0.0190 (8)	0.0198 (8)	0.0186 (8)	0.0023 (7)	−0.0003 (6)	0.0061 (7)
C29A	0.0195 (9)	0.0205 (10)	0.0185 (9)	0.0027 (8)	0.0006 (7)	0.0080 (8)

Geometric parameters (Å, º) top

N11—C19A	1.370 (2)	N21—C29A	1.372 (2)
N11—N12	1.396 (2)	N21—N22	1.392 (2)
N11—C111	1.421 (2)	N21—C211	1.421 (2)
C111—C112	1.394 (3)	C211—C212	1.397 (3)
C111—C116	1.398 (3)	C211—C216	1.399 (3)
C112—C113	1.384 (3)	C212—C213	1.387 (3)
C112—H112	0.95	C212—H212	0.95
C113—C114	1.390 (3)	C213—C214	1.390 (3)
C113—H113	0.95	C213—H213	0.95
C114—C115	1.385 (3)	C214—C215	1.389 (3)
C114—H114	0.95	C214—H214	0.95
C115—C116	1.389 (3)	C215—C216	1.380 (3)
C115—H115	0.95	C215—H215	0.95
C116—H116	0.95	C216—H216	0.95
N12—C13	1.317 (2)	N22—C23	1.320 (2)
C13—C13A	1.435 (3)	C23—C23A	1.430 (3)
C13—C131	1.498 (3)	C23—C231	1.496 (3)
C131—H13A	0.98	C231—H23A	0.98
C131—H13B	0.98	C231—H23B	0.98
C131—H13C	0.98	C231—H23C	0.98
C13A—C14	1.388 (3)	C23A—C24	1.388 (3)
C13A—C19A	1.405 (3)	C23A—C29A	1.407 (3)
C14—C14A	1.394 (3)	C24—C24A	1.390 (3)
C14—H14	0.95	C24—H24	0.95
C14A—C18A	1.421 (3)	C24A—C28A	1.420 (3)
C14A—C15	1.486 (3)	C24A—C25	1.482 (3)
C15—O15	1.219 (2)	C25—O25	1.225 (2)
C15—C16	1.512 (3)	C25—C26	1.507 (3)
C16—C17	1.535 (3)	C26—C27	1.537 (3)
C16—H16A	0.99	C26—H26A	0.99
C16—H16B	0.99	C26—H26B	0.99
C17—C172	1.525 (3)	C272—C27	1.525 (3)
C17—C18	1.533 (3)	C272—H27D	0.98
C17—C171	1.538 (3)	C272—H27E	0.98
C171—H17A	0.98	C272—H27F	0.98
C171—H17B	0.98	C27—C28	1.531 (3)
C171—H17C	0.98	C27—C271	1.538 (3)
C172—H17D	0.98	C271—H27A	0.98
C172—H17E	0.98	C271—H27B	0.98
C172—H17F	0.98	C271—H27C	0.98
C18—C18A	1.505 (3)	C28—C28A	1.503 (3)
C18—H18A	0.99	C28—H28A	0.99
C18—H18B	0.99	C28—H28B	0.99
C18A—N19	1.337 (2)	C28A—N29	1.341 (2)
N19—C19A	1.345 (2)	N29—C29A	1.345 (2)

C19A—N11—N12	110.13 (15)	C29A—N21—N22	110.37 (15)
C19A—N11—C111	130.80 (16)	C29A—N21—C211	129.90 (16)
N12—N11—C111	118.91 (15)	N22—N21—C211	119.46 (15)
C112—C111—C116	120.04 (18)	C212—C211—C216	119.89 (18)
C112—C111—N11	120.64 (17)	C212—C211—N21	120.73 (17)
C116—C111—N11	119.33 (17)	C216—C211—N21	119.38 (17)
C113—C112—C111	119.94 (18)	C213—C212—C211	119.62 (18)
C113—C112—H112	120.0	C213—C212—H212	120.2
C111—C112—H112	120.0	C211—C212—H212	120.2
C112—C113—C114	120.30 (19)	C212—C213—C214	120.67 (19)
C112—C113—H113	119.8	C212—C213—H213	119.7
C114—C113—H113	119.8	C214—C213—H213	119.7
C115—C114—C113	119.64 (19)	C215—C214—C213	119.23 (19)
C115—C114—H114	120.2	C215—C214—H214	120.4
C113—C114—H114	120.2	C213—C214—H214	120.4
C114—C115—C116	120.86 (19)	C216—C215—C214	121.03 (19)
C114—C115—H115	119.6	C216—C215—H215	119.5
C116—C115—H115	119.6	C214—C215—H215	119.5
C115—C116—C111	119.21 (19)	C215—C216—C211	119.55 (19)
C115—C116—H116	120.4	C215—C216—H216	120.2
C111—C116—H116	120.4	C211—C216—H216	120.2
C13—N12—N11	106.91 (15)	C23—N22—N21	106.87 (15)
N12—C13—C13A	110.85 (17)	N22—C23—C23A	110.78 (16)
N12—C13—C131	121.21 (17)	N22—C23—C231	121.90 (17)
C13A—C13—C131	127.89 (17)	C23A—C23—C231	127.31 (18)
C13—C131—H13A	109.5	C23—C231—H23A	109.5
C13—C131—H13B	109.5	C23—C231—H23B	109.5
H13A—C131—H13B	109.5	H23A—C231—H23B	109.5
C13—C131—H13C	109.5	C23—C231—H23C	109.5
H13A—C131—H13C	109.5	H23A—C231—H23C	109.5
H13B—C131—H13C	109.5	H23B—C231—H23C	109.5
C14—C13A—C19A	118.32 (17)	C24—C23A—C29A	117.69 (17)
C14—C13A—C13	136.80 (18)	C24—C23A—C23	137.16 (18)
C19A—C13A—C13	104.87 (16)	C29A—C23A—C23	105.14 (16)
C13A—C14—C14A	117.06 (17)	C23A—C24—C24A	117.54 (17)
C13A—C14—H14	121.5	C23A—C24—H24	121.2
C14A—C14—H14	121.5	C24A—C24—H24	121.2
C14—C14A—C18A	119.87 (17)	C24—C24A—C28A	119.86 (17)
C14—C14A—C15	119.70 (17)	C24—C24A—C25	119.91 (16)
C18A—C14A—C15	120.44 (16)	C28A—C24A—C25	120.18 (16)
O15—C15—C14A	121.59 (17)	O25—C25—C24A	121.16 (17)
O15—C15—C16	121.26 (17)	O25—C25—C26	121.34 (17)
C14A—C15—C16	117.14 (16)	C24A—C25—C26	117.47 (16)
C15—C16—C17	112.59 (15)	C25—C26—C27	112.94 (15)
C15—C16—H16A	109.1	C25—C26—H26A	109.0
C17—C16—H16A	109.1	C27—C26—H26A	109.0
C15—C16—H16B	109.1	C25—C26—H26B	109.0
C17—C16—H16B	109.1	C27—C26—H26B	109.0
H16A—C16—H16B	107.8	H26A—C26—H26B	107.8
C172—C17—C18	108.76 (15)	C27—C272—H27D	109.5
C172—C17—C16	110.05 (15)	C27—C272—H27E	109.5
C18—C17—C16	107.96 (15)	H27D—C272—H27E	109.5
C172—C17—C171	109.33 (16)	C27—C272—H27F	109.5
C18—C17—C171	110.65 (15)	H27D—C272—H27F	109.5
C16—C17—C171	110.07 (15)	H27E—C272—H27F	109.5
C17—C171—H17A	109.5	C272—C27—C28	109.03 (15)
C17—C171—H17B	109.5	C272—C27—C26	109.47 (16)
H17A—C171—H17B	109.5	C28—C27—C26	108.06 (15)
C17—C171—H17C	109.5	C272—C27—C271	109.47 (16)
H17A—C171—H17C	109.5	C28—C27—C271	110.57 (15)
H17B—C171—H17C	109.5	C26—C27—C271	110.21 (16)
C17—C172—H17D	109.5	C27—C271—H27A	109.5
C17—C172—H17E	109.5	C27—C271—H27B	109.5
H17D—C172—H17E	109.5	H27A—C271—H27B	109.5
C17—C172—H17F	109.5	C27—C271—H27C	109.5
H17D—C172—H17F	109.5	H27A—C271—H27C	109.5
H17E—C172—H17F	109.5	H27B—C271—H27C	109.5
C18A—C18—C17	114.07 (15)	C28A—C28—C27	114.27 (15)
C18A—C18—H18A	108.7	C28A—C28—H28A	108.7
C17—C18—H18A	108.7	C27—C28—H28A	108.7
C18A—C18—H18B	108.7	C28A—C28—H28B	108.7
C17—C18—H18B	108.7	C27—C28—H28B	108.7
H18A—C18—H18B	107.6	H28A—C28—H28B	107.6
N19—C18A—C14A	123.87 (17)	N29—C28A—C24A	123.90 (17)
N19—C18A—C18	115.58 (16)	N29—C28A—C28	115.23 (16)
C14A—C18A—C18	120.55 (16)	C24A—C28A—C28	120.85 (16)
C18A—N19—C19A	114.57 (16)	C28A—N29—C29A	114.18 (16)
N19—C19A—N11	126.45 (17)	N29—C29A—N21	126.38 (17)
N19—C19A—C13A	126.27 (17)	N29—C29A—C23A	126.78 (17)
N11—C19A—C13A	107.23 (16)	N21—C29A—C23A	106.83 (16)

C19A—N11—C111—C112	−17.8 (3)	C29A—N21—C211—C212	−22.8 (3)
N12—N11—C111—C112	167.34 (16)	N22—N21—C211—C212	163.71 (16)
C19A—N11—C111—C116	162.52 (18)	C29A—N21—C211—C216	157.20 (18)
N12—N11—C111—C116	−12.3 (2)	N22—N21—C211—C216	−16.2 (2)
C116—C111—C112—C113	−0.6 (3)	C216—C211—C212—C213	−0.6 (3)
N11—C111—C112—C113	179.71 (17)	N21—C211—C212—C213	179.45 (16)
C111—C112—C113—C114	0.2 (3)	C211—C212—C213—C214	0.4 (3)
C112—C113—C114—C115	0.4 (3)	C212—C213—C214—C215	−0.1 (3)
C113—C114—C115—C116	−0.7 (3)	C213—C214—C215—C216	0.0 (3)
C114—C115—C116—C111	0.3 (3)	C214—C215—C216—C211	−0.2 (3)
C112—C111—C116—C115	0.4 (3)	C212—C211—C216—C215	0.5 (3)
N11—C111—C116—C115	−179.98 (17)	N21—C211—C216—C215	−179.55 (17)
C19A—N11—N12—C13	0.4 (2)	C29A—N21—N22—C23	0.6 (2)
C111—N11—N12—C13	176.21 (16)	C211—N21—N22—C23	175.22 (15)
N11—N12—C13—C13A	0.2 (2)	N21—N22—C23—C23A	−0.1 (2)
N11—N12—C13—C131	−177.43 (16)	N21—N22—C23—C231	−178.49 (17)
N12—C13—C13A—C14	−179.7 (2)	N22—C23—C23A—C24	179.7 (2)
C131—C13—C13A—C14	−2.3 (4)	C231—C23—C23A—C24	−2.0 (4)
N12—C13—C13A—C19A	−0.6 (2)	N22—C23—C23A—C29A	−0.4 (2)
C131—C13—C13A—C19A	176.77 (18)	C231—C23—C23A—C29A	177.88 (19)
C19A—C13A—C14—C14A	−1.1 (3)	C29A—C23A—C24—C24A	−0.9 (3)
C13—C13A—C14—C14A	177.9 (2)	C23—C23A—C24—C24A	179.0 (2)
C13A—C14—C14A—C18A	−0.9 (3)	C23A—C24—C24A—C28A	−0.8 (3)
C13A—C14—C14A—C15	179.06 (16)	C23A—C24—C24A—C25	176.52 (16)
C14—C14A—C15—O15	4.9 (3)	C24—C24A—C25—O25	4.6 (3)
C18A—C14A—C15—O15	−175.13 (17)	C28A—C24A—C25—O25	−178.08 (17)
C14—C14A—C15—C16	−174.70 (16)	C24—C24A—C25—C26	−173.54 (16)
C18A—C14A—C15—C16	5.3 (2)	C28A—C24A—C25—C26	3.8 (3)
O15—C15—C16—C17	144.38 (18)	O25—C25—C26—C27	146.92 (18)
C14A—C15—C16—C17	−36.0 (2)	C24A—C25—C26—C27	−35.0 (2)
C15—C16—C17—C172	176.87 (16)	C25—C26—C27—C272	176.00 (16)
C15—C16—C17—C18	58.3 (2)	C25—C26—C27—C28	57.4 (2)
C15—C16—C17—C171	−62.6 (2)	C25—C26—C27—C271	−63.5 (2)
C172—C17—C18—C18A	−171.38 (16)	C272—C27—C28—C28A	−169.77 (16)
C16—C17—C18—C18A	−52.0 (2)	C26—C27—C28—C28A	−50.9 (2)
C171—C17—C18—C18A	68.5 (2)	C271—C27—C28—C28A	69.8 (2)
C14—C14A—C18A—N19	2.0 (3)	C24—C24A—C28A—N29	1.7 (3)
C15—C14A—C18A—N19	−177.93 (17)	C25—C24A—C28A—N29	−175.63 (16)
C14—C14A—C18A—C18	−178.86 (17)	C24—C24A—C28A—C28	−179.84 (16)
C15—C14A—C18A—C18	1.2 (3)	C25—C24A—C28A—C28	2.8 (3)
C17—C18—C18A—N19	−157.27 (16)	C27—C28—C28A—N29	−159.20 (16)
C17—C18—C18A—C14A	23.6 (2)	C27—C28—C28A—C24A	22.2 (2)
C14A—C18A—N19—C19A	−0.9 (3)	C24A—C28A—N29—C29A	−0.7 (3)
C18—C18A—N19—C19A	179.99 (15)	C28—C28A—N29—C29A	−179.20 (15)
C18A—N19—C19A—N11	−178.62 (17)	C28A—N29—C29A—N21	−179.60 (17)
C18A—N19—C19A—C13A	−1.4 (3)	C28A—N29—C29A—C23A	−1.3 (3)
N12—N11—C19A—N19	176.90 (17)	N22—N21—C29A—N29	177.76 (17)
C111—N11—C19A—N19	1.7 (3)	C211—N21—C29A—N29	3.8 (3)
N12—N11—C19A—C13A	−0.8 (2)	N22—N21—C29A—C23A	−0.8 (2)
C111—N11—C19A—C13A	−175.94 (18)	C211—N21—C29A—C23A	−174.76 (17)
C14—C13A—C19A—N19	2.4 (3)	C24—C23A—C29A—N29	2.1 (3)
C13—C13A—C19A—N19	−176.86 (17)	C23—C23A—C29A—N29	−177.84 (18)
C14—C13A—C19A—N11	−179.90 (16)	C24—C23A—C29A—N21	−179.33 (16)
C13—C13A—C19A—N11	0.81 (19)	C23—C23A—C29A—N21	0.76 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C112—H112···N19	0.95	2.38	3.004 (3)	123
C212—H212···N29	0.95	2.40	3.000 (3)	121
C14—H14···O15ⁱ	0.95	2.59	3.258 (2)	127
C24—H24···O25ⁱⁱ	0.95	2.54	3.221 (2)	129
C113—H113···O15ⁱⁱⁱ	0.95	2.54	3.461 (3)	164
C16—H16B···Cg1^iv	0.99	2.77	3.656 (2)	150
C26—H26B···Cg2^v	0.99	2.90	3.725 (2)	142

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

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