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Acta Cryst. (2007). E63, o4264
https://doi.org/10.1107/S1600536807048519
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2,4,4-Trimethyl-N-phenyl-2,3,4,5-tetra­hydro-1H-1,5-benzodiazepine-1-carboxamide

A. Thiruvalluvar and S. Ponnuswamy
In the title compound, C19H23N3O, the seven-membered diazepine ring adopts a boat conformation. The phenyl­carbamoyl group is coplanar with the N atom and its two attached C atoms. The methyl group at position 2 has an equatorial orientation. The dihedral angle between the two benzene rings is 81.07 (9)°. The crystal structure is stabilized by intra­molecular C—H...O and inter­molecular N—H...O hydrogen bonds.
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Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807048519/cf2151sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807048519/cf2151Isup2.hkl
Contains datablock I

CCDC reference: 667313

checkCIF report

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.045
  • wR factor = 0.116
  • Data-to-parameter ratio = 17.8

checkCIF/PLATON results

No syntax errors found




Alert level A
DIFF020_ALERT_1_A  _diffrn_standards_interval_count and
            _diffrn_standards_interval_time are missing. Number of measurements
            between standards or time (min) between standards.
Author Response: In the Kappa apex2 CCD diffractometer there is no provision for repeat measurement of standard intensity. Instead, the decay correction is achieved indirectly by noting the intensity of equivalent reflections and time of their measurement during the data collection. 
DIFF022_ALERT_1_A  _diffrn_standards_decay_% is missing
            Percentage decrease in standards intensity.


Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.868     1.000
            Tmin(prime) and Tmax expected:      0.983     0.985
            RR(prime) =      0.870
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.87
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.99
PLAT420_ALERT_2_C D-H Without Acceptor       N11    -   H11    ...          ?


Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.985
            Tmax scaled      0.985 Tmin scaled      0.855
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT793_ALERT_1_G Check the Absolute Configuration of C2     = ...          S


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

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

Benzodiazepines are a class of psychotherapeutic drugs discovered at the end of the 1950 s and now widely used owing to their broad spectrum of biological activities. They are mainly used as tranquillizers but are also of interest for their muscle relaxant, anticonvulsant and sleep-induction effects (Gilli et al., 1978; Gałdecki & Główka, 1980; Chananont et al., 1980). The X-ray structure analysis of the title compound was carried out to determine the crystal structure as well as to study the substituent effects on the geometry and conformation of the diazepine ring.

The conformation of the title molecule was established by NMR spectroscopy and semiempirical MO calculations by Ponnuswamy et al. (2006). The title molecule, C19H23N3O, contains a benzene ring fused to a diazepine ring. The phenylcarbamoyl group is substituted at N1. The methyl groups are substituted at C2 and C4 as expected. The seven-membered diazepine ring has a boat conformation (Fig. 1). The phenylcarbamoyl group is coplanar with the C2—N1—C10 plane of the diazepine ring. The methyl group substituted on the C2 atom is in an equatorial position. The dihedral angle between the two benzene rings is 81.07 (9)°. An N—H···O intermolecular hydrogen bond exists between H5 (on N5 of the diazepine ring) and atom O1i [(i): -x + 1/2, y + 1/2, z] of the phenylcarbamoyl group (Fig. 2), forming an infinite one-dimensional chain, with base vector [010]. C—H···O type intramolecular interactions [C2—H2A···O1 and C116—H116···O1] are also present.

Related literature top

For related literature, see: Chananont et al. (1980); Gałdecki & Główka (1980); Gilli et al. (1978); Ponnuswamy et al. (2006).

Experimental top

The title compound was prepared and characterized using NMR techniques by Ponnuswamy et al., 2006.

Refinement top

Atoms H11 at N11 and H5 at N5 were located in a difference Fourier map and refined isotropically. Remaining H atoms were positioned geometrically and allowed to ride on their parent atoms with C—H = 0.93–0.98 Å and Uiso = 1.2–1.5 Ueq(parent atom).

Structure description top

Benzodiazepines are a class of psychotherapeutic drugs discovered at the end of the 1950 s and now widely used owing to their broad spectrum of biological activities. They are mainly used as tranquillizers but are also of interest for their muscle relaxant, anticonvulsant and sleep-induction effects (Gilli et al., 1978; Gałdecki & Główka, 1980; Chananont et al., 1980). The X-ray structure analysis of the title compound was carried out to determine the crystal structure as well as to study the substituent effects on the geometry and conformation of the diazepine ring.

The conformation of the title molecule was established by NMR spectroscopy and semiempirical MO calculations by Ponnuswamy et al. (2006). The title molecule, C19H23N3O, contains a benzene ring fused to a diazepine ring. The phenylcarbamoyl group is substituted at N1. The methyl groups are substituted at C2 and C4 as expected. The seven-membered diazepine ring has a boat conformation (Fig. 1). The phenylcarbamoyl group is coplanar with the C2—N1—C10 plane of the diazepine ring. The methyl group substituted on the C2 atom is in an equatorial position. The dihedral angle between the two benzene rings is 81.07 (9)°. An N—H···O intermolecular hydrogen bond exists between H5 (on N5 of the diazepine ring) and atom O1i [(i): -x + 1/2, y + 1/2, z] of the phenylcarbamoyl group (Fig. 2), forming an infinite one-dimensional chain, with base vector [010]. C—H···O type intramolecular interactions [C2—H2A···O1 and C116—H116···O1] are also present.

For related literature, see: Chananont et al. (1980); Gałdecki & Główka (1980); Gilli et al. (1978); Ponnuswamy et al. (2006).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: SAINT-NT (Bruker, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The molecular structure with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level. H atoms involved in hydrogen bonds are shown as small spheres of arbitrary radii.
[Figure 2] Fig. 2. The molecular packing, viewed down the a axis. Hydrogen bonds are shown as dashed lines.
2,4,4-Trimethyl-N-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-carboxamide top
Crystal data top
C19H23N3ODx = 1.192 Mg m−3
Mr = 309.40Melting point: 440.5 K
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 5251 reflections
a = 6.6010 (1) Åθ = 2.9–27.2°
b = 13.8353 (2) ŵ = 0.08 mm−1
c = 37.7572 (6) ÅT = 293 K
V = 3448.25 (9) Å3Rectangular block, colourless
Z = 80.22 × 0.20 × 0.20 mm
F(000) = 1328
Data collection top
Bruker APEXII
diffractometer		3834 independent reflections
Radiation source: fine-focus sealed tube2674 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
φ and ω scansθmax = 27.2°, θmin = 2.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2004)		h = −8→8
Tmin = 0.868, Tmax = 1.000k = −17→17
18554 measured reflectionsl = −48→32
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0477P)2 + 0.7067P]
where P = (Fo2 + 2Fc2)/3
3834 reflections(Δ/σ)max < 0.001
216 parametersΔρmax = 0.13 e Å−3
0 restraintsΔρmin = −0.18 e Å−3
Crystal data top
C19H23N3OV = 3448.25 (9) Å3
Mr = 309.40Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 6.6010 (1) ŵ = 0.08 mm−1
b = 13.8353 (2) ÅT = 293 K
c = 37.7572 (6) Å0.22 × 0.20 × 0.20 mm
Data collection top
Bruker APEXII
diffractometer		3834 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2004)		2674 reflections with I > 2σ(I)
Tmin = 0.868, Tmax = 1.000Rint = 0.029
18554 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.116H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.13 e Å−3
3834 reflectionsΔρmin = −0.18 e Å−3
216 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.25792 (18)−0.14773 (7)0.13677 (3)0.0589 (4)
N10.51148 (18)−0.03994 (8)0.14618 (3)0.0425 (4)
N50.4053 (2)0.15447 (10)0.15438 (4)0.0519 (5)
N110.3963 (2)−0.06939 (10)0.08966 (3)0.0505 (4)
C10.3802 (2)−0.08931 (9)0.12488 (4)0.0425 (4)
C20.4970 (3)−0.05268 (10)0.18463 (4)0.0475 (5)
C30.5002 (2)0.04477 (10)0.20331 (4)0.0453 (5)
C40.3515 (2)0.12114 (10)0.19023 (4)0.0440 (5)
C60.7016 (2)0.20114 (10)0.12087 (4)0.0477 (5)
C70.8697 (3)0.17729 (12)0.10145 (4)0.0557 (6)
C80.9295 (3)0.08264 (12)0.09829 (4)0.0552 (5)
C90.8157 (2)0.01174 (11)0.11412 (4)0.0472 (5)
C100.6412 (2)0.03434 (9)0.13268 (4)0.0378 (4)
C110.5825 (2)0.13084 (9)0.13702 (4)0.0371 (4)
C210.6649 (3)−0.11839 (12)0.19792 (5)0.0736 (7)
C410.1354 (3)0.08303 (14)0.18925 (5)0.0658 (6)
C420.3633 (3)0.20749 (12)0.21531 (5)0.0658 (7)
C1110.2814 (2)−0.10638 (11)0.06149 (4)0.0470 (5)
C1120.2901 (3)−0.05737 (14)0.02975 (5)0.0650 (6)
C1130.1836 (3)−0.08972 (18)0.00075 (5)0.0837 (9)
C1140.0668 (3)−0.1704 (2)0.00327 (6)0.0902 (9)
C1150.0577 (3)−0.21940 (17)0.03451 (6)0.0848 (8)
C1160.1655 (3)−0.18920 (13)0.06388 (5)0.0630 (6)
H2A0.36710−0.083850.189840.0569*
H3A0.474180.033810.228270.0544*
H3B0.635910.071080.201340.0544*
H50.365 (3)0.2120 (15)0.1507 (5)0.081 (6)*
H60.666260.265860.123320.0573*
H70.943910.225650.090300.0668*
H81.045580.066780.085600.0662*
H90.85644−0.052420.112340.0567*
H110.481 (3)−0.0247 (12)0.0847 (4)0.061 (5)*
H21A0.65873−0.179090.185650.1104*
H21B0.79383−0.088490.193640.1104*
H21C0.64823−0.129130.222870.1104*
H41A0.046310.132920.180920.0987*
H41B0.128310.028470.173590.0987*
H41C0.095300.063650.212640.0987*
H42A0.499680.231510.215910.0987*
H42B0.274070.257520.207120.0987*
H42C0.323500.187740.238670.0987*
H1120.36869−0.001820.027920.0780*
H1130.19159−0.05639−0.020600.1004*
H114−0.00641−0.19204−0.016230.1080*
H115−0.02290−0.274370.036120.1018*
H1160.16011−0.224100.084910.0755*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0731 (8)0.0487 (6)0.0549 (7)−0.0256 (6)−0.0001 (6)0.0033 (5)
N10.0550 (7)0.0340 (6)0.0385 (7)−0.0098 (5)−0.0033 (6)0.0035 (5)
N50.0586 (9)0.0495 (8)0.0476 (8)0.0184 (7)0.0105 (6)0.0130 (6)
N110.0569 (8)0.0520 (7)0.0425 (8)−0.0177 (7)−0.0036 (6)0.0001 (6)
C10.0514 (9)0.0317 (6)0.0445 (8)−0.0032 (6)−0.0021 (7)−0.0005 (6)
C20.0627 (10)0.0402 (7)0.0395 (8)−0.0070 (7)−0.0047 (8)0.0077 (6)
C30.0557 (9)0.0459 (8)0.0343 (8)−0.0041 (7)−0.0057 (7)0.0038 (6)
C40.0474 (8)0.0490 (8)0.0357 (8)0.0008 (7)0.0006 (7)−0.0004 (6)
C60.0611 (10)0.0353 (7)0.0468 (9)−0.0069 (7)−0.0017 (8)0.0012 (6)
C70.0558 (10)0.0571 (10)0.0542 (10)−0.0199 (8)0.0039 (8)0.0053 (8)
C80.0429 (8)0.0692 (10)0.0534 (10)−0.0027 (8)0.0075 (8)−0.0020 (8)
C90.0500 (9)0.0423 (8)0.0494 (9)0.0061 (7)−0.0009 (7)−0.0048 (7)
C100.0415 (8)0.0345 (6)0.0373 (8)−0.0037 (6)−0.0043 (6)0.0010 (6)
C110.0415 (8)0.0348 (7)0.0350 (7)−0.0005 (6)−0.0029 (6)0.0031 (5)
C210.1081 (16)0.0491 (9)0.0635 (12)0.0131 (10)−0.0160 (11)0.0123 (8)
C410.0509 (10)0.0903 (12)0.0562 (11)−0.0045 (9)0.0035 (9)0.0037 (10)
C420.0811 (13)0.0586 (10)0.0577 (11)0.0095 (9)−0.0019 (10)−0.0114 (8)
C1110.0423 (8)0.0542 (9)0.0446 (9)0.0022 (7)−0.0024 (7)−0.0113 (7)
C1120.0717 (12)0.0752 (11)0.0481 (10)−0.0008 (10)−0.0028 (9)−0.0062 (9)
C1130.0843 (15)0.1195 (18)0.0473 (11)0.0095 (14)−0.0113 (10)−0.0109 (12)
C1140.0669 (13)0.140 (2)0.0637 (14)−0.0025 (14)−0.0154 (11)−0.0363 (14)
C1150.0680 (13)0.1096 (16)0.0768 (15)−0.0270 (12)−0.0058 (11)−0.0325 (13)
C1160.0581 (10)0.0719 (11)0.0589 (11)−0.0140 (9)−0.0041 (9)−0.0146 (9)
Geometric parameters (Å, º) top
O1—C11.2273 (17)C6—H60.930
N1—C11.3654 (18)C7—H70.930
N1—C21.4656 (19)C8—H80.930
N1—C101.4315 (17)C9—H90.930
N5—C41.473 (2)C111—C1161.381 (2)
N5—C111.3801 (19)C111—C1121.378 (2)
N11—C11.3622 (19)C112—C1131.376 (3)
N11—C1111.4030 (19)C113—C1141.360 (3)
N5—H50.85 (2)C114—C1151.362 (3)
N11—H110.854 (18)C115—C1161.382 (3)
C2—C211.519 (3)C21—H21A0.960
C2—C31.522 (2)C21—H21B0.960
C3—C41.5244 (19)C21—H21C0.960
C4—C411.521 (2)C41—H41A0.960
C4—C421.526 (2)C41—H41B0.960
C6—C111.3914 (19)C41—H41C0.960
C6—C71.370 (2)C42—H42A0.960
C7—C81.373 (2)C42—H42B0.960
C8—C91.373 (2)C42—H42C0.960
C9—C101.3841 (19)C112—H1120.930
C10—C111.3998 (18)C113—H1130.930
C2—H2A0.980C114—H1140.930
C3—H3A0.970C115—H1150.930
C3—H3B0.970C116—H1160.930
O1···C1162.877 (2)H3B···C102.640
O1···N5i3.0153 (17)H3B···C112.590
O1···H2A2.310H3B···H21B2.460
O1···H1162.320H3B···H42A2.460
O1···H5i2.17 (2)H5···H62.360
N1···N52.7967 (18)H5···H42B2.300
N1···C413.421 (2)H5···O1ii2.17 (2)
N5···N12.7967 (18)H6···H52.360
N5···O1ii3.0153 (17)H6···H9iv2.550
N11···C93.1269 (19)H7···C1iv3.100
N1···H41B2.890H7···C116iv3.010
C6···C116ii3.578 (2)H8···C111vi3.000
C9···N113.1269 (19)H9···H6iii2.550
C41···N13.421 (2)H11···C92.524 (19)
C1···H41B2.970H11···C102.251 (16)
C1···H1162.800H11···C112.997 (16)
C1···H7iii3.100H11···H1122.290
C2···H41B2.710H21A···C6iii3.090
C6···H21Aiv3.090H21B···C103.030
C6···H116ii2.930H21B···H3B2.460
C8···H113v3.060H21C···H3A2.540
C9···H41Bvi3.060H41A···H42B2.490
C9···H112.524 (19)H41B···N12.890
C10···H3B2.640H41B···C12.970
C10···H112.251 (16)H41B···C22.710
C10···H21B3.030H41B···C9viii3.060
C11···H3B2.590H41B···H2A2.300
C11···H112.997 (16)H41C···H42C2.490
C113···C113vii3.470 (3)H41C···H3Axi2.410
C116···O12.877 (2)H42A···H3B2.460
C116···C6i3.578 (2)H42B···H52.300
C41···H2A2.770H42B···H41A2.490
C111···H8viii3.000H42B···H2Aii2.470
C113···H115ix3.040H42C···H3A2.380
C116···H7iii3.010H42C···H41C2.490
H2A···O12.310H112···H112.290
H2A···C412.770H113···C8v3.060
H2A···H41B2.300H115···C113xii3.040
H2A···H42Bi2.470H116···O12.320
H3A···H21C2.540H116···C12.800
H3A···H42C2.380H116···C6i2.930
H3A···H41Cx2.410
C1—N1—C2118.81 (12)C6—C7—H7120.0
C1—N1—C10121.94 (12)C8—C7—H7120.0
C2—N1—C10118.56 (12)C9—C8—H8120.0
C4—N5—C11124.50 (13)C7—C8—H8120.0
C1—N11—C111128.62 (13)C8—C9—H9120.0
C4—N5—H5111.6 (13)C10—C9—H9120.0
C11—N5—H5114.2 (13)N11—C111—C112117.21 (14)
C1—N11—H11114.3 (10)C112—C111—C116119.23 (15)
C111—N11—H11116.8 (10)N11—C111—C116123.55 (15)
N1—C1—N11115.10 (12)C111—C112—C113120.71 (18)
O1—C1—N1122.10 (14)C112—C113—C114120.06 (19)
O1—C1—N11122.79 (13)C113—C114—C115119.6 (2)
C3—C2—C21111.54 (14)C114—C115—C116121.5 (2)
N1—C2—C21110.59 (14)C111—C116—C115118.93 (17)
N1—C2—C3110.59 (11)C2—C21—H21A109.0
C2—C3—C4117.07 (13)C2—C21—H21B109.0
N5—C4—C3111.06 (12)C2—C21—H21C109.0
N5—C4—C41108.19 (13)H21A—C21—H21B109.0
N5—C4—C42108.22 (12)H21A—C21—H21C109.0
C3—C4—C41111.80 (12)H21B—C21—H21C109.0
C3—C4—C42107.98 (13)C4—C41—H41A109.0
C41—C4—C42109.52 (13)C4—C41—H41B109.0
C7—C6—C11121.58 (13)C4—C41—H41C109.0
C6—C7—C8120.60 (16)H41A—C41—H41B109.0
C7—C8—C9119.11 (16)H41A—C41—H41C109.0
C8—C9—C10120.97 (14)H41B—C41—H41C109.0
C9—C10—C11120.34 (13)C4—C42—H42A109.0
N1—C10—C9121.06 (12)C4—C42—H42B109.0
N1—C10—C11118.52 (12)C4—C42—H42C109.0
N5—C11—C10121.07 (12)H42A—C42—H42B109.0
C6—C11—C10117.32 (13)H42A—C42—H42C109.0
N5—C11—C6121.43 (12)H42B—C42—H42C109.0
C21—C2—H2A108.0C111—C112—H112120.0
N1—C2—H2A108.0C113—C112—H112120.0
C3—C2—H2A108.0C112—C113—H113120.0
C2—C3—H3A108.0C114—C113—H113120.0
C2—C3—H3B108.0C113—C114—H114120.0
C4—C3—H3A108.0C115—C114—H114120.0
C4—C3—H3B108.0C114—C115—H115119.0
H3A—C3—H3B107.0C116—C115—H115119.0
C7—C6—H6119.0C111—C116—H116121.0
C11—C6—H6119.0C115—C116—H116121.0
C2—N1—C1—O1−3.9 (2)C2—C3—C4—C42173.30 (13)
C10—N1—C1—O1−174.28 (12)C2—C3—C4—N5−68.20 (16)
C2—N1—C1—N11176.52 (12)C2—C3—C4—C4152.76 (18)
C10—N1—C1—N116.17 (18)C7—C6—C11—C100.0 (2)
C2—N1—C10—C9112.01 (16)C11—C6—C7—C8−2.1 (2)
C1—N1—C10—C1199.09 (16)C7—C6—C11—N5−175.22 (15)
C1—N1—C2—C3−132.63 (13)C6—C7—C8—C91.6 (2)
C10—N1—C2—C338.05 (19)C7—C8—C9—C100.9 (2)
C1—N1—C2—C21103.31 (16)C8—C9—C10—C11−3.0 (2)
C10—N1—C2—C21−86.01 (15)C8—C9—C10—N1173.69 (14)
C1—N1—C10—C9−77.61 (18)N1—C10—C11—C6−174.28 (13)
C2—N1—C10—C11−71.29 (18)C9—C10—C11—N5177.72 (14)
C4—N5—C11—C1053.8 (2)C9—C10—C11—C62.4 (2)
C11—N5—C4—C3−8.98 (19)N1—C10—C11—N51.0 (2)
C11—N5—C4—C42109.37 (16)N11—C111—C112—C113179.24 (17)
C4—N5—C11—C6−131.10 (16)C116—C111—C112—C1130.5 (3)
C11—N5—C4—C41−132.04 (15)N11—C111—C116—C115179.94 (16)
C1—N11—C111—C116−17.8 (2)C112—C111—C116—C115−1.4 (3)
C111—N11—C1—N1−178.55 (13)C111—C112—C113—C1140.6 (3)
C111—N11—C1—O11.9 (2)C112—C113—C114—C115−0.7 (3)
C1—N11—C111—C112163.52 (16)C113—C114—C115—C116−0.3 (3)
N1—C2—C3—C451.20 (19)C114—C115—C116—C1111.3 (3)
C21—C2—C3—C4174.72 (13)
Symmetry codes: (i) −x+1/2, y−1/2, z; (ii) −x+1/2, y+1/2, z; (iii) −x+3/2, y−1/2, z; (iv) −x+3/2, y+1/2, z; (v) −x+1, −y, −z; (vi) x+1, y, z; (vii) −x, −y, −z; (viii) x−1, y, z; (ix) x+1/2, −y−1/2, −z; (x) x+1/2, y, −z+1/2; (xi) x−1/2, y, −z+1/2; (xii) x−1/2, −y−1/2, −z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5···O1ii0.85 (2)2.17 (2)3.0153 (17)174 (2)
C2—H2A···O10.982.312.736 (2)106
C116—H116···O10.932.322.877 (2)118
Symmetry code: (ii) −x+1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formulaC19H23N3O
Mr309.40
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)293
a, b, c (Å)6.6010 (1), 13.8353 (2), 37.7572 (6)
V (Å3)3448.25 (9)
Z8
Radiation typeMo Kα
µ (mm−1)0.08
Crystal size (mm)0.22 × 0.20 × 0.20
Data collection
DiffractometerBruker APEXII
Absorption correctionMulti-scan
(SADABS; Bruker, 2004)
Tmin, Tmax0.868, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections		18554, 3834, 2674
Rint0.029
(sin θ/λ)max (Å−1)0.644
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.116, 1.03
No. of reflections3834
No. of parameters216
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.13, −0.18

Computer programs: APEX2 (Bruker, 2004), SAINT-NT (Bruker, 2004), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5···O1i0.85 (2)2.17 (2)3.0153 (17)174 (2)
C2—H2A···O10.982.312.736 (2)106
C116—H116···O10.932.322.877 (2)118
Symmetry code: (i) −x+1/2, y+1/2, z.
 

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