organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoIUCrDATA
ISSN: 2414-3146

2-(2-Oxo-4-phenyl-2,3-di­hydro-1H-1,5-benzodiazepin-1-yl)acetic acid

CROSSMARK_Color_square_no_text.svg

aLaboratoire de Chimie Organique Hétérocyclique, URAC 21, Pôle de Compétence Pharmacochimie, Av Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V, Rabat, Morocco, and bDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
*Correspondence e-mail: essaghouani.hanine@gmail.com

Edited by R. J. Butcher, Howard University, USA (Received 23 December 2016; accepted 23 January 2017; online 27 January 2017)

The asymmetric unit of the title compound, C17H14N2O3, consists of two independent mol­ecules having distinctly different conformations. The components of the asymmetric unit are connected by an O—H⋯N hydrogen bond, with additional O—H⋯N hydrogen bonds connecting this assemblage into chains running parallel to the b axis. Inter­molecular C—H⋯π(ring) inter­actions are also present.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

As a continuation of our studies on substituted 1,5-benzodiazepin-2-one derivatives (Essaghouani et al., 2016[Essaghouani, A., Bouzian, Y., Essassi, E. M., Saadi, M. & El Ammari, L. (2016). IUCrData, 1, x160661.]; Ballo et al., 2010[Ballo, D., Ahabchane, N. H., Zouihri, H., Essassi, E. M. & Ng, S. W. (2010). Acta Cryst. E66, o2070.]), we report the synthesis of a new 1,5-benzodiazepin-2-one derivative by the hydrolysis reaction with an aqueous solution of potassium hydroxide of ethyl 2-(2-oxo-4-phenyl-2,3-di­hydro-1H-1,5-benzodiazepin-1-yl)acetate in ethanol.

The asymmetric unit (Fig. 1[link]) consists of two independent mol­ecules which differ markedly in their conformations. This can be seen, in part, from the puckering parameters for the seven-membered rings. For the ring N1,C1,C6,N2,C7,C8,C9, Q(2) = 0.881 (1) Å, Q(3) = 0.218 (1) Å, φ(2) = 203.79 (7)° and φ(3) = 307.7 (3)° with a total puckering amplitude of 0.907 (1) Å, while for the ring N3,C18,C23,N4,C24,C25,C26, the corresponding values are 0.904 (1) Å, 0.234 (1) Å, 25.64 (7)° and 125.9 (3)° with a total puckering amplitude of 0.934 (1) Å. Additionally, the dihedral angle between the C1–C6 and C12–C17 rings is 72.18 (4)° while that between the C18–C22 and C29–C34 rings is 80.03 (4)°.

[Figure 1]
Figure 1
The asymmetric unit with the atom-labelling scheme and 50% probability ellipsoids. The O—H⋯N hydrogen bond is shown by the dotted line.

In the crystal, the mol­ecules are linked into chains running parallel to the b axis by O2—H2A⋯N4 and O6—H6⋯N2iii [symmetry code: (iii) x, y + 1, z] hydrogen bonds (Table 1[link] and Fig. 2[link]). Finally there are two sets of C—H⋯π(ring) inter­actions (Fig. 3[link]).

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C18–C22 and C29–C34 rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
O2—H2A⋯N4 0.82 1.90 2.7161 (12) 176
O6—H6⋯N2i 0.82 1.95 2.7585 (13) 171
C4—H4⋯Cg2ii 0.989 (16) 2.97 (2) 3.7650 (16) 139 (1)
C17—H17⋯Cg1iii 1.004 (17) 2.82 (2) 3.6431 (14) 140 (1)
Symmetry codes: (i) x, y+1, z; (ii) [-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].
[Figure 2]
Figure 2
Packing viewed along the c axis, with O—H⋯N hydrogen bonds shown as dotted lines.
[Figure 3]
Figure 3
Detail of the C—H⋯π(ring) inter­actions (dotted lines) [symmetry codes: (i) 2 − x, −[{1\over 2}] + y, [{1\over 2}] − z; (ii) x, [{1\over 2}] − y, [{1\over 2}] + z].

Synthesis and crystallization

A solution of potassium hydroxide (12.0 mmol) in water (5 ml) was added to the solution of ethyl 2-(2-oxo-4-phenyl-2,3-di­hydro-1H-1,5-benzodiazepin-1-yl)acetate (3.0 mmol) in ethanol (10 ml). The resulting reaction mixture was stirred at room temperature for 6 h, after completion of the reaction (monitored by TLC). The reaction mixture was poured into water and acidified with 3M HCl to form the title compound as a yellow solid. The solid product was purified by recrystallization from ethanol solution to afford the title compound as yellow crystals (yield 84%).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula C17H14N2O3
Mr 294.30
Crystal system, space group Monoclinic, P21/c
Temperature (K) 298
a, b, c (Å) 17.9752 (8), 17.4403 (8), 9.2472 (4)
β (°) 102.892 (1)
V3) 2825.9 (2)
Z 8
Radiation type Mo Kα
μ (mm−1) 0.10
Crystal size (mm) 0.32 × 0.29 × 0.28
 
Data collection
Diffractometer Bruker SMART APEX CCD
Absorption correction Multi-scan (SADABS; Bruker, 2016[Bruker (2016). APEX3, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.89, 0.97
No. of measured, independent and observed [I > 2σ(I)] reflections 54166, 7627, 5791
Rint 0.033
(sin θ/λ)max−1) 0.687
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.146, 1.11
No. of reflections 7627
No. of parameters 503
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.36, −0.21
Computer programs: APEX3 and SAINT (Bruker, 2016[Bruker (2016). APEX3, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXT (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2014 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]), DIAMOND (Brandenburg & Putz, 2012[Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.]) and SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Structural data


Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

2-(2-Oxo-4-phenyl-2,3-dihydro-1H-1,5-benzodiazepin-1-yl)acetic acid top
Crystal data top
C17H14N2O3F(000) = 1232
Mr = 294.30Dx = 1.384 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 17.9752 (8) ÅCell parameters from 9857 reflections
b = 17.4403 (8) Åθ = 2.3–28.8°
c = 9.2472 (4) ŵ = 0.10 mm1
β = 102.892 (1)°T = 298 K
V = 2825.9 (2) Å3Block, yellow
Z = 80.32 × 0.29 × 0.28 mm
Data collection top
Bruker SMART APEX CCD
diffractometer
7627 independent reflections
Radiation source: fine-focus sealed tube5791 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
Detector resolution: 8.3333 pixels mm-1θmax = 29.2°, θmin = 1.7°
φ and ω scansh = 2424
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
k = 2323
Tmin = 0.89, Tmax = 0.97l = 1212
54166 measured reflections
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)] = 0.048Hydrogen site location: mixed
wR(F2) = 0.146H atoms treated by a mixture of independent and constrained refinement
S = 1.11 w = 1/[σ2(Fo2) + (0.0941P)2 + 0.0156P]
where P = (Fo2 + 2Fc2)/3
7627 reflections(Δ/σ)max = 0.001
503 parametersΔρmax = 0.36 e Å3
0 restraintsΔρmin = 0.21 e Å3
Special details top

Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5° in ω, collected at φ = 0.00, 90.00 and 180.00° and 2 sets of 800 frames, each of width 0.45° in φ, collected at ω = –30.00 and 210.00°. The scan time was 15 sec/frame.

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.

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 > 2sigma(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. Hydrogens attached to oxygen were placed in calculated positions and included as riding contributions.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.60331 (5)0.13791 (5)0.27570 (13)0.0536 (3)
O20.70218 (5)0.30973 (5)0.14443 (10)0.0448 (2)
H2A0.71940.34830.19070.067*
O30.76238 (7)0.24959 (5)0.34987 (10)0.0523 (3)
N10.71781 (5)0.10783 (5)0.22680 (11)0.0335 (2)
N20.72769 (5)0.06012 (5)0.28503 (11)0.0338 (2)
C10.78810 (6)0.06741 (6)0.26215 (12)0.0325 (2)
C20.85619 (7)0.10630 (7)0.26274 (15)0.0429 (3)
H20.8576 (8)0.1607 (10)0.2436 (17)0.054 (4)*
C30.92572 (8)0.06889 (9)0.29592 (17)0.0498 (3)
H30.9738 (9)0.0964 (10)0.3011 (19)0.061 (4)*
C40.92926 (7)0.00864 (9)0.32758 (16)0.0488 (3)
H40.9792 (9)0.0350 (9)0.3519 (17)0.054 (4)*
C50.86265 (7)0.04874 (8)0.32415 (15)0.0428 (3)
H50.8635 (8)0.1047 (9)0.3472 (16)0.049 (4)*
C60.79178 (6)0.01189 (6)0.29224 (13)0.0337 (2)
C70.67194 (6)0.03881 (6)0.34201 (12)0.0306 (2)
C80.67410 (7)0.03717 (6)0.41964 (13)0.0351 (2)
H8A0.6343 (7)0.0428 (7)0.4751 (15)0.038 (3)*
H8B0.7249 (8)0.0453 (8)0.4914 (15)0.043 (4)*
C90.66091 (6)0.09902 (6)0.30295 (13)0.0349 (2)
C100.70987 (8)0.17555 (6)0.13187 (14)0.0371 (3)
H10A0.7430 (8)0.1719 (8)0.0700 (16)0.042 (4)*
H10B0.6579 (9)0.1776 (9)0.0709 (17)0.053 (4)*
C110.72781 (7)0.24848 (6)0.22292 (13)0.0351 (2)
C120.60495 (6)0.08991 (6)0.33007 (13)0.0336 (2)
C130.58545 (8)0.14086 (8)0.21200 (16)0.0478 (3)
H130.6142 (9)0.1415 (9)0.1355 (18)0.058 (4)*
C140.52507 (9)0.19148 (9)0.2063 (2)0.0638 (4)
H140.5166 (13)0.2278 (14)0.127 (3)0.103 (7)*
C150.48451 (9)0.19212 (9)0.3147 (2)0.0627 (4)
H150.4416 (10)0.2285 (10)0.3082 (19)0.068 (5)*
C160.50222 (8)0.14105 (8)0.43070 (19)0.0527 (4)
H160.4772 (11)0.1397 (11)0.505 (2)0.075 (5)*
C170.56172 (7)0.08953 (7)0.43804 (15)0.0410 (3)
H170.5723 (8)0.0524 (10)0.5231 (18)0.056 (4)*
O40.90968 (5)0.61482 (6)0.27642 (12)0.0522 (3)
O50.81149 (7)0.75579 (5)0.35900 (11)0.0582 (3)
O60.74537 (7)0.80350 (5)0.14535 (11)0.0572 (3)
H60.74380.84220.19480.086*
N30.78152 (5)0.60652 (5)0.25031 (11)0.0330 (2)
N40.76233 (5)0.43981 (5)0.28495 (10)0.0323 (2)
C180.71694 (6)0.57473 (6)0.29305 (12)0.0308 (2)
C190.65708 (7)0.62319 (7)0.30917 (14)0.0408 (3)
H190.6625 (8)0.6793 (9)0.3044 (16)0.050 (4)*
C200.59079 (7)0.59410 (8)0.33805 (16)0.0477 (3)
H200.5497 (10)0.6274 (10)0.3508 (18)0.064 (5)*
C210.58232 (7)0.51563 (9)0.35311 (16)0.0492 (3)
H210.5326 (8)0.4907 (9)0.3709 (16)0.047 (4)*
C220.64072 (7)0.46703 (7)0.33788 (14)0.0417 (3)
H220.6367 (7)0.4087 (8)0.3431 (15)0.044 (4)*
C230.70850 (6)0.49519 (6)0.30834 (12)0.0319 (2)
C240.83437 (6)0.45013 (6)0.33622 (12)0.0320 (2)
C250.86337 (7)0.52106 (6)0.42453 (13)0.0361 (2)
H25A0.9180 (8)0.5147 (8)0.4696 (16)0.044 (4)*
H25B0.8342 (8)0.5321 (8)0.4972 (16)0.043 (4)*
C260.85536 (6)0.58557 (6)0.31257 (14)0.0352 (2)
C270.77099 (8)0.67215 (6)0.15010 (14)0.0374 (3)
H27A0.8080 (8)0.6687 (8)0.0928 (16)0.045 (4)*
H27B0.7230 (8)0.6712 (8)0.0886 (15)0.040 (4)*
C280.77890 (7)0.74808 (6)0.23226 (14)0.0370 (3)
C290.88927 (6)0.39373 (6)0.30039 (13)0.0343 (2)
C300.95522 (7)0.37419 (7)0.40601 (14)0.0399 (3)
H300.9649 (8)0.3990 (9)0.5045 (18)0.053 (4)*
C311.00541 (8)0.32027 (8)0.37314 (17)0.0473 (3)
H311.0518 (9)0.3082 (9)0.4463 (16)0.049 (4)*
C320.99114 (8)0.28555 (8)0.23510 (18)0.0522 (3)
H321.0269 (10)0.2474 (10)0.214 (2)0.070 (5)*
C330.92654 (8)0.30505 (8)0.12984 (17)0.0506 (3)
H330.9169 (9)0.2840 (11)0.035 (2)0.062 (5)*
C340.87589 (7)0.35883 (7)0.16167 (14)0.0422 (3)
H340.8301 (9)0.3742 (9)0.0780 (17)0.058 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0432 (5)0.0407 (5)0.0819 (7)0.0120 (4)0.0244 (5)0.0092 (5)
O20.0514 (5)0.0230 (4)0.0563 (5)0.0006 (3)0.0041 (4)0.0014 (3)
O30.0790 (7)0.0336 (5)0.0432 (5)0.0009 (4)0.0113 (5)0.0035 (4)
N10.0369 (5)0.0214 (4)0.0453 (5)0.0001 (3)0.0157 (4)0.0017 (4)
N20.0356 (5)0.0217 (4)0.0458 (5)0.0001 (3)0.0127 (4)0.0007 (4)
C10.0348 (5)0.0251 (5)0.0405 (6)0.0018 (4)0.0146 (4)0.0031 (4)
C20.0420 (7)0.0348 (6)0.0577 (8)0.0076 (5)0.0239 (6)0.0039 (5)
C30.0373 (7)0.0547 (8)0.0625 (8)0.0112 (6)0.0218 (6)0.0108 (6)
C40.0327 (6)0.0549 (8)0.0603 (8)0.0057 (6)0.0140 (6)0.0049 (6)
C50.0394 (6)0.0369 (6)0.0542 (7)0.0066 (5)0.0150 (5)0.0007 (5)
C60.0340 (5)0.0267 (5)0.0428 (6)0.0004 (4)0.0138 (5)0.0024 (4)
C70.0351 (5)0.0225 (5)0.0346 (5)0.0007 (4)0.0087 (4)0.0028 (4)
C80.0398 (6)0.0282 (5)0.0409 (6)0.0046 (4)0.0167 (5)0.0039 (4)
C90.0344 (6)0.0230 (5)0.0497 (6)0.0012 (4)0.0142 (5)0.0036 (4)
C100.0488 (7)0.0226 (5)0.0414 (6)0.0020 (4)0.0134 (5)0.0008 (4)
C110.0400 (6)0.0243 (5)0.0436 (6)0.0009 (4)0.0147 (5)0.0002 (4)
C120.0325 (5)0.0254 (5)0.0428 (6)0.0014 (4)0.0078 (4)0.0045 (4)
C130.0465 (7)0.0399 (7)0.0572 (8)0.0055 (5)0.0120 (6)0.0107 (6)
C140.0528 (9)0.0442 (8)0.0908 (12)0.0123 (6)0.0087 (8)0.0202 (8)
C150.0391 (7)0.0390 (7)0.1101 (14)0.0085 (6)0.0165 (8)0.0043 (8)
C160.0417 (7)0.0420 (7)0.0798 (10)0.0007 (5)0.0249 (7)0.0154 (7)
C170.0395 (6)0.0357 (6)0.0499 (7)0.0009 (5)0.0141 (5)0.0078 (5)
O40.0384 (5)0.0451 (5)0.0777 (7)0.0076 (4)0.0225 (5)0.0028 (5)
O50.0853 (8)0.0354 (5)0.0489 (5)0.0014 (5)0.0047 (5)0.0069 (4)
O60.0824 (7)0.0286 (4)0.0572 (6)0.0155 (5)0.0082 (5)0.0022 (4)
N30.0339 (5)0.0229 (4)0.0435 (5)0.0003 (3)0.0113 (4)0.0007 (4)
N40.0320 (5)0.0222 (4)0.0422 (5)0.0006 (3)0.0073 (4)0.0005 (3)
C180.0293 (5)0.0269 (5)0.0363 (5)0.0009 (4)0.0076 (4)0.0039 (4)
C190.0375 (6)0.0332 (6)0.0516 (7)0.0044 (5)0.0098 (5)0.0073 (5)
C200.0351 (6)0.0536 (8)0.0558 (8)0.0071 (6)0.0134 (6)0.0111 (6)
C210.0349 (6)0.0585 (8)0.0574 (8)0.0066 (6)0.0175 (6)0.0038 (6)
C220.0367 (6)0.0379 (6)0.0508 (7)0.0081 (5)0.0108 (5)0.0003 (5)
C230.0307 (5)0.0277 (5)0.0368 (5)0.0021 (4)0.0066 (4)0.0029 (4)
C240.0330 (5)0.0247 (5)0.0374 (5)0.0002 (4)0.0060 (4)0.0017 (4)
C250.0333 (6)0.0304 (5)0.0420 (6)0.0012 (4)0.0028 (5)0.0040 (4)
C260.0317 (5)0.0265 (5)0.0486 (6)0.0037 (4)0.0113 (5)0.0060 (4)
C270.0477 (7)0.0244 (5)0.0407 (6)0.0005 (4)0.0115 (5)0.0005 (4)
C280.0442 (6)0.0246 (5)0.0453 (6)0.0000 (4)0.0167 (5)0.0006 (4)
C290.0325 (5)0.0253 (5)0.0455 (6)0.0008 (4)0.0098 (5)0.0031 (4)
C300.0370 (6)0.0347 (6)0.0468 (7)0.0028 (5)0.0067 (5)0.0025 (5)
C310.0379 (7)0.0410 (7)0.0612 (8)0.0079 (5)0.0070 (6)0.0076 (6)
C320.0493 (8)0.0383 (7)0.0730 (9)0.0120 (6)0.0218 (7)0.0007 (6)
C330.0529 (8)0.0469 (8)0.0533 (8)0.0097 (6)0.0148 (6)0.0072 (6)
C340.0410 (7)0.0389 (6)0.0464 (7)0.0058 (5)0.0090 (5)0.0013 (5)
Geometric parameters (Å, º) top
O1—C91.2162 (14)O4—C261.2127 (14)
O2—C111.3157 (14)O5—C281.1952 (16)
O2—H2A0.8200O6—C281.3141 (15)
O3—C111.1996 (15)O6—H60.8200
N1—C91.3737 (14)N3—C261.3732 (14)
N1—C11.4197 (14)N3—C181.4197 (14)
N1—C101.4593 (14)N3—C271.4582 (14)
N2—C71.2868 (14)N4—C241.2885 (14)
N2—C61.4159 (14)N4—C231.4175 (14)
C1—C21.3983 (16)C18—C191.4022 (16)
C1—C61.4094 (15)C18—C231.4060 (15)
C2—C31.382 (2)C19—C201.3750 (19)
C2—H20.967 (17)C19—H190.986 (16)
C3—C41.382 (2)C20—C211.387 (2)
C3—H30.980 (16)C20—H200.967 (17)
C4—C51.3808 (19)C21—C221.3807 (19)
C4—H40.989 (16)C21—H211.039 (15)
C5—C61.3984 (16)C22—C231.3959 (16)
C5—H50.999 (15)C22—H221.021 (15)
C7—C121.4823 (15)C24—C291.4822 (15)
C7—C81.5034 (15)C24—C251.5097 (15)
C8—C91.5066 (16)C25—C261.5139 (17)
C8—H8A0.975 (14)C25—H25A0.983 (14)
C8—H8B1.012 (14)C25—H25B0.959 (15)
C10—C111.5198 (15)C27—C281.5176 (15)
C10—H10A0.916 (14)C27—H27A0.941 (15)
C10—H10B0.978 (15)C27—H27B0.921 (14)
C12—C131.3906 (17)C29—C341.3915 (17)
C12—C171.3952 (17)C29—C301.3995 (16)
C13—C141.391 (2)C30—C311.3832 (18)
C13—H130.964 (16)C30—H300.988 (16)
C14—C151.365 (3)C31—C321.384 (2)
C14—H140.96 (3)C31—H310.972 (15)
C15—C161.376 (2)C32—C331.381 (2)
C15—H150.991 (18)C32—H320.974 (19)
C16—C171.3870 (18)C33—C341.3838 (18)
C16—H160.901 (19)C33—H330.933 (18)
C17—H171.004 (17)C34—H341.031 (16)
C11—O2—H2A109.5C28—O6—H6109.5
C9—N1—C1123.54 (9)C26—N3—C18123.59 (9)
C9—N1—C10114.51 (9)C26—N3—C27116.85 (10)
C1—N1—C10120.19 (9)C18—N3—C27119.02 (9)
C7—N2—C6120.58 (9)C24—N4—C23120.87 (9)
C2—C1—C6118.21 (10)C19—C18—C23118.77 (10)
C2—C1—N1119.56 (10)C19—C18—N3119.26 (10)
C6—C1—N1122.20 (9)C23—C18—N3121.78 (9)
C3—C2—C1121.29 (12)C20—C19—C18121.14 (12)
C3—C2—H2116.4 (9)C20—C19—H19118.2 (9)
C1—C2—H2122.3 (9)C18—C19—H19120.6 (9)
C4—C3—C2120.36 (12)C19—C20—C21120.18 (12)
C4—C3—H3118.0 (10)C19—C20—H20121.4 (10)
C2—C3—H3121.6 (10)C21—C20—H20118.4 (10)
C5—C4—C3119.48 (12)C22—C21—C20119.50 (12)
C5—C4—H4120.6 (9)C22—C21—H21117.3 (8)
C3—C4—H4120.0 (9)C20—C21—H21123.1 (8)
C4—C5—C6121.10 (12)C21—C22—C23121.36 (12)
C4—C5—H5121.2 (8)C21—C22—H22122.9 (8)
C6—C5—H5117.7 (8)C23—C22—H22115.7 (8)
C5—C6—C1119.55 (10)C22—C23—C18119.04 (10)
C5—C6—N2115.48 (10)C22—C23—N4116.45 (10)
C1—C6—N2124.88 (10)C18—C23—N4124.34 (9)
N2—C7—C12119.32 (10)N4—C24—C29119.33 (10)
N2—C7—C8120.71 (10)N4—C24—C25120.72 (10)
C12—C7—C8119.97 (10)C29—C24—C25119.86 (10)
C7—C8—C9107.81 (9)C24—C25—C26105.68 (9)
C7—C8—H8A113.3 (8)C24—C25—H25A109.1 (8)
C9—C8—H8A106.8 (8)C26—C25—H25A107.9 (8)
C7—C8—H8B111.1 (8)C24—C25—H25B111.6 (9)
C9—C8—H8B110.1 (8)C26—C25—H25B110.2 (9)
H8A—C8—H8B107.6 (11)H25A—C25—H25B112.1 (12)
O1—C9—N1121.89 (11)O4—C26—N3122.33 (11)
O1—C9—C8122.57 (11)O4—C26—C25122.79 (11)
N1—C9—C8115.54 (10)N3—C26—C25114.83 (10)
N1—C10—C11111.34 (10)N3—C27—C28112.49 (10)
N1—C10—H10A109.3 (9)N3—C27—H27A107.5 (9)
C11—C10—H10A108.5 (9)C28—C27—H27A109.8 (9)
N1—C10—H10B109.2 (9)N3—C27—H27B110.5 (9)
C11—C10—H10B110.3 (9)C28—C27—H27B107.1 (9)
H10A—C10—H10B108.2 (13)H27A—C27—H27B109.5 (12)
O3—C11—O2124.60 (10)O5—C28—O6125.06 (11)
O3—C11—C10123.72 (10)O5—C28—C27124.04 (11)
O2—C11—C10111.66 (10)O6—C28—C27110.90 (10)
C13—C12—C17118.80 (11)C34—C29—C30118.83 (11)
C13—C12—C7120.07 (11)C34—C29—C24120.63 (10)
C17—C12—C7121.11 (11)C30—C29—C24120.54 (10)
C12—C13—C14119.55 (14)C31—C30—C29120.31 (12)
C12—C13—H13120.0 (10)C31—C30—H30120.7 (9)
C14—C13—H13120.4 (10)C29—C30—H30119.0 (9)
C15—C14—C13121.18 (15)C30—C31—C32120.29 (12)
C15—C14—H14122.6 (14)C30—C31—H31119.6 (9)
C13—C14—H14116.1 (14)C32—C31—H31120.1 (9)
C14—C15—C16119.92 (13)C33—C32—C31119.74 (13)
C14—C15—H15119.8 (10)C33—C32—H32121.2 (11)
C16—C15—H15120.3 (10)C31—C32—H32119.1 (11)
C15—C16—C17119.95 (15)C32—C33—C34120.44 (13)
C15—C16—H16122.8 (12)C32—C33—H33121.2 (10)
C17—C16—H16117.2 (12)C34—C33—H33118.4 (10)
C16—C17—C12120.56 (13)C33—C34—C29120.39 (12)
C16—C17—H17117.7 (9)C33—C34—H34118.0 (9)
C12—C17—H17121.7 (9)C29—C34—H34121.5 (9)
C9—N1—C1—C2137.08 (12)C26—N3—C18—C19137.80 (11)
C10—N1—C1—C226.96 (16)C27—N3—C18—C1933.44 (15)
C9—N1—C1—C645.09 (16)C26—N3—C18—C2347.32 (16)
C10—N1—C1—C6150.87 (11)C27—N3—C18—C23141.44 (11)
C6—C1—C2—C31.79 (18)C23—C18—C19—C200.59 (18)
N1—C1—C2—C3179.70 (12)N3—C18—C19—C20174.44 (11)
C1—C2—C3—C40.9 (2)C18—C19—C20—C210.6 (2)
C2—C3—C4—C50.7 (2)C19—C20—C21—C220.4 (2)
C3—C4—C5—C61.4 (2)C20—C21—C22—C230.3 (2)
C4—C5—C6—C10.39 (19)C21—C22—C23—C180.37 (18)
C4—C5—C6—N2177.02 (12)C21—C22—C23—N4175.85 (12)
C2—C1—C6—C51.16 (17)C19—C18—C23—C220.49 (16)
N1—C1—C6—C5179.02 (11)N3—C18—C23—C22174.42 (10)
C2—C1—C6—N2175.12 (11)C19—C18—C23—N4175.58 (10)
N1—C1—C6—N22.73 (18)N3—C18—C23—N40.67 (17)
C7—N2—C6—C5138.67 (11)C24—N4—C23—C22141.09 (11)
C7—N2—C6—C144.91 (17)C24—N4—C23—C1843.70 (16)
C6—N2—C7—C12178.79 (9)C23—N4—C24—C29175.62 (10)
C6—N2—C7—C80.99 (16)C23—N4—C24—C250.86 (16)
N2—C7—C8—C973.67 (13)N4—C24—C25—C2674.56 (13)
C12—C7—C8—C9106.11 (11)C29—C24—C25—C26101.89 (11)
C1—N1—C9—O1175.41 (11)C18—N3—C26—O4178.32 (11)
C10—N1—C9—O110.55 (16)C27—N3—C26—O46.90 (16)
C1—N1—C9—C85.74 (15)C18—N3—C26—C254.16 (15)
C10—N1—C9—C8170.60 (9)C27—N3—C26—C25175.58 (9)
C7—C8—C9—O1111.79 (13)C24—C25—C26—O4108.08 (13)
C7—C8—C9—N167.04 (12)C24—C25—C26—N369.43 (12)
C9—N1—C10—C1172.77 (13)C26—N3—C27—C2881.33 (13)
C1—N1—C10—C1192.65 (13)C18—N3—C27—C2890.50 (13)
N1—C10—C11—O317.87 (18)N3—C27—C28—O521.02 (18)
N1—C10—C11—O2163.44 (10)N3—C27—C28—O6159.08 (11)
N2—C7—C12—C1327.62 (16)N4—C24—C29—C3436.54 (16)
C8—C7—C12—C13152.16 (11)C25—C24—C29—C34139.96 (12)
N2—C7—C12—C17150.59 (11)N4—C24—C29—C30142.93 (11)
C8—C7—C12—C1729.63 (15)C25—C24—C29—C3040.57 (15)
C17—C12—C13—C141.80 (19)C34—C29—C30—C310.92 (18)
C7—C12—C13—C14176.45 (13)C24—C29—C30—C31178.56 (11)
C12—C13—C14—C150.0 (2)C29—C30—C31—C320.5 (2)
C13—C14—C15—C161.3 (3)C30—C31—C32—C330.1 (2)
C14—C15—C16—C170.6 (2)C31—C32—C33—C340.2 (2)
C15—C16—C17—C121.2 (2)C32—C33—C34—C290.2 (2)
C13—C12—C17—C162.43 (18)C30—C29—C34—C330.81 (19)
C7—C12—C17—C16175.80 (11)C24—C29—C34—C33178.67 (12)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C18–C22 and C29–C34 rings, respectively.
D—H···AD—HH···AD···AD—H···A
O2—H2A···N40.821.902.7161 (12)176
O6—H6···N2i0.821.952.7585 (13)171
C4—H4···Cg2ii0.989 (16)2.97 (2)3.7650 (16)139 (1)
C17—H17···Cg1iii1.004 (17)2.82 (2)3.6431 (14)140 (1)
Symmetry codes: (i) x, y+1, z; (ii) x+2, y1/2, z+1/2; (iii) x, y+1/2, z+1/2.
 

Acknowledgements

JTM thanks Tulane University for support of the Tulane Crystallography Laboratory.

References

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First citationSheldrick, G. M. (2015b). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar

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