1,1′-Ureylenedi-7,7-dimethyl­bicyclo­[2.2.1]heptan-2-one

Gao, Y.-X.; Liu, P.; Fang, Y.-X.; Tang, G.; Zhao, Y.-F.

doi:10.1107/S1600536807042754

1,1′-Ureylenedi-7,7-dimethylbicyclo[2.2.1]heptan-2-one

Y.-X. Gao, P. Liu, Y.-X. Fang, G. Tang and Y.-F. Zhao

The title compound, C₁₉H₂₈N₂O₃, was obtained by the acidic hydrolysis of (1S,4R)-1-isocyanato-7,7-dimethylbicyclo[2.2.1]heptan-2-one followed by addition of aqueous sodium hydroxide. N—H

O hydrogen bonds link the molecules into chains running along the a axis.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807042754/ci2449sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807042754/ci2449Isup2.hkl Contains datablock I

CCDC reference: 663718

checkCIF report

Key indicators

Single-crystal X-ray study
T = 223 K
Mean (C-C) = 0.003 Å
R factor = 0.045
wR factor = 0.115
Data-to-parameter ratio = 10.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.30 Ratio

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           28.51
           From the CIF: _reflns_number_total               2418
           Count of symmetry unique reflns         2538
           Completeness (_total/calc)             95.27%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13    = .          R

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

   5 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
   1 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

The title compound, (I), is a byproduct in the synthesis of (1S,4R)-1-amino-7,7-dimethylbicyclo[2.2.1]heptan-2-one, which is used in the synthesis of several optically active nitroxyl radicals as a key synthetic intermediate (Braslau et al., 1996). The molecular structure of (I) is shown in Fig. 1. Bond lengths and angles in the camphor moiety are in agreement with the values reported for a related compound (Gao et al., 2006). Both N—H groups are involved in hydrogen-bonding interactions with the carbonyl O atom of a neighboring molecule (Table 1). Molecules are linked into chains, running along the a axis, by N—H···O intermolecular hydrogen bonds.

Related literature top

For related literature, see: Braslau et al. (1996); Gao et al. (2006).

Experimental top

To a solution of (1S,4R)-1-isocyanato-7,7-dimethylbicyclo[2.2.1]heptan-2-one (0.9 g, 5 mmol) in tetrahydrofuran (10 ml) was added a 1 N aqueous HCl solution (15 ml), and the mixture was stirred at reflux for 1 h. 2 N aqueous sodium hydroxide (10 ml) was then added at room temperature and stirred for 30 min. Then the solution was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous MgSO₄, concentrated under vacuum and the crude product was purified by column chromatography (petroleum ether-ethyl acetate, 6:1) to give the title compound as a white solid (0.06 g). Single crystals of (I) were obtained by slow evaporation of a petroleum ether-ethyl acetate solution (6:1 v/v).

Structure description top

For related literature, see: Braslau et al. (1996); Gao et al. (2006).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

Fig. 1. The molecular structure of (I), shown with 50% probability displacement ellipsoids (arbitrary spheres for H atoms).

1,1'-Ureylenedi-7,7-dimethylbicyclo[2.2.1]heptan-2-one top

Crystal data top

C₁₉H₂₈N₂O₃	F(000) = 720
M_r = 332.43	D_x = 1.269 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5524 reflections
a = 6.7578 (16) Å	θ = 2.6–28.3°
b = 12.107 (3) Å	µ = 0.09 mm⁻¹
c = 21.269 (5) Å	T = 223 K
V = 1740.2 (7) Å³	Needle, colourless
Z = 4	0.50 × 0.16 × 0.12 mm

Data collection top

Bruker APEX area-detector diffractometer	2418 independent reflections
Radiation source: fine-focus sealed tube	2280 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
φ and ω scan	θ_max = 28.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −8→9
T_min = 0.958, T_max = 0.990	k = −16→13
10699 measured reflections	l = −27→27

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ²(F_o²) + (0.0653P)² + 0.3373P] where P = (F_o² + 2F_c²)/3
2418 reflections	(Δ/σ)_max = 0.001
225 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₉H₂₈N₂O₃	V = 1740.2 (7) Å³
M_r = 332.43	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.7578 (16) Å	µ = 0.09 mm⁻¹
b = 12.107 (3) Å	T = 223 K
c = 21.269 (5) Å	0.50 × 0.16 × 0.12 mm

Data collection top

Bruker APEX area-detector diffractometer	2418 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2280 reflections with I > 2σ(I)
T_min = 0.958, T_max = 0.990	R_int = 0.022
10699 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	Δρ_max = 0.25 e Å⁻³
2418 reflections	Δρ_min = −0.30 e Å⁻³
225 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > 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

	x	y	z	U_iso*/U_eq
O1	0.0794 (2)	−0.00170 (12)	0.15120 (6)	0.0362 (4)
O2	−0.3852 (3)	0.30420 (16)	0.17297 (8)	0.0575 (6)
O3	0.2716 (3)	0.22757 (12)	−0.02375 (7)	0.0389 (4)
N1	−0.1005 (3)	0.15462 (15)	0.14606 (7)	0.0303 (4)
N2	0.0777 (3)	0.09851 (14)	0.06177 (7)	0.0265 (3)
C1	−0.1793 (3)	0.15398 (16)	0.20795 (8)	0.0259 (4)
C2	−0.3036 (3)	0.05390 (18)	0.22789 (9)	0.0326 (4)
H2A	−0.4341	0.0552	0.2078	0.039*
H2B	−0.2369	−0.0154	0.2171	0.039*
C3	−0.3212 (4)	0.0676 (2)	0.29920 (9)	0.0411 (5)
H3A	−0.4602	0.0699	0.3124	0.049*
H3B	−0.2542	0.0073	0.3214	0.049*
C4	−0.2196 (4)	0.1770 (2)	0.31125 (9)	0.0379 (5)
H4A	−0.1817	0.1891	0.3557	0.045*
C5	−0.3502 (4)	0.2668 (2)	0.28422 (11)	0.0490 (7)
H5A	−0.4892	0.2558	0.2958	0.059*
H5B	−0.3074	0.3402	0.2979	0.059*
C6	−0.3187 (4)	0.25094 (19)	0.21497 (10)	0.0380 (5)
C7	−0.0432 (3)	0.17393 (16)	0.26539 (9)	0.0296 (4)
C8	0.1014 (3)	0.08364 (18)	0.28097 (10)	0.0349 (5)
H8A	0.1785	0.1049	0.3175	0.052*
H8B	0.1891	0.0718	0.2455	0.052*
H8C	0.0298	0.0160	0.2900	0.052*
C9	0.0710 (4)	0.2801 (2)	0.26036 (14)	0.0504 (6)
H9A	0.1540	0.2889	0.2972	0.076*
H9B	−0.0206	0.3416	0.2576	0.076*
H9C	0.1532	0.2784	0.2230	0.076*
C10	0.2530 (3)	0.05642 (15)	0.03347 (7)	0.0227 (4)
C11	0.3229 (3)	0.13360 (16)	−0.01740 (9)	0.0292 (4)
C12	0.4655 (4)	0.07015 (19)	−0.05723 (10)	0.0390 (5)
H12A	0.5976	0.1036	−0.0565	0.047*
H12B	0.4197	0.0649	−0.1008	0.047*
C13	0.4647 (3)	−0.04173 (19)	−0.02532 (10)	0.0351 (5)
H13A	0.5125	−0.1033	−0.0519	0.042*
C14	0.5779 (4)	−0.0266 (2)	0.03588 (11)	0.0457 (6)
H14A	0.7046	0.0107	0.0287	0.055*
H14B	0.6024	−0.0978	0.0564	0.055*
C15	0.4387 (3)	0.0450 (2)	0.07487 (9)	0.0341 (5)
H15A	0.4978	0.1174	0.0834	0.041*
H15B	0.4067	0.0092	0.1149	0.041*
C16	0.2486 (3)	−0.05347 (16)	−0.00295 (8)	0.0279 (4)
C17	0.0970 (4)	−0.0538 (2)	−0.05517 (10)	0.0407 (5)
H17A	−0.0344	−0.0616	−0.0373	0.061*
H17B	0.1231	−0.1150	−0.0834	0.061*
H17C	0.1049	0.0151	−0.0783	0.061*
C18	0.2141 (4)	−0.15394 (18)	0.03774 (11)	0.0422 (5)
H18A	0.0760	−0.1569	0.0501	0.063*
H18B	0.2966	−0.1494	0.0750	0.063*
H18C	0.2474	−0.2200	0.0142	0.063*
C19	0.0236 (3)	0.07774 (15)	0.12232 (8)	0.0252 (4)
H1	−0.146 (4)	0.202 (2)	0.1226 (11)	0.027 (6)*
H2	0.038 (3)	0.1590 (19)	0.0484 (10)	0.023 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0492 (9)	0.0318 (7)	0.0276 (6)	0.0136 (7)	0.0129 (7)	0.0098 (6)
O2	0.0700 (13)	0.0620 (11)	0.0403 (8)	0.0400 (10)	−0.0001 (9)	0.0061 (8)
O3	0.0514 (10)	0.0307 (7)	0.0345 (7)	−0.0025 (7)	0.0111 (7)	0.0075 (6)
N1	0.0371 (9)	0.0327 (8)	0.0211 (7)	0.0111 (8)	0.0058 (7)	0.0083 (6)
N2	0.0298 (8)	0.0286 (8)	0.0210 (7)	0.0054 (7)	0.0048 (6)	0.0060 (6)
C1	0.0281 (9)	0.0299 (9)	0.0198 (8)	0.0049 (8)	0.0015 (7)	0.0000 (7)
C2	0.0309 (10)	0.0426 (11)	0.0244 (8)	−0.0071 (9)	0.0005 (8)	0.0015 (8)
C3	0.0352 (11)	0.0636 (15)	0.0244 (9)	−0.0032 (11)	0.0058 (8)	0.0047 (10)
C4	0.0386 (12)	0.0514 (13)	0.0236 (9)	0.0113 (11)	0.0003 (8)	−0.0084 (8)
C5	0.0487 (14)	0.0646 (16)	0.0338 (11)	0.0264 (13)	0.0004 (10)	−0.0122 (11)
C6	0.0371 (11)	0.0437 (12)	0.0331 (10)	0.0151 (10)	0.0017 (9)	−0.0020 (9)
C7	0.0290 (9)	0.0309 (9)	0.0289 (8)	0.0028 (8)	−0.0023 (8)	−0.0048 (7)
C8	0.0326 (10)	0.0398 (11)	0.0323 (10)	0.0059 (9)	−0.0071 (8)	−0.0014 (8)
C9	0.0512 (15)	0.0341 (11)	0.0660 (15)	−0.0066 (11)	−0.0081 (14)	−0.0043 (11)
C10	0.0251 (9)	0.0254 (8)	0.0176 (7)	−0.0009 (7)	0.0022 (6)	0.0000 (7)
C11	0.0315 (10)	0.0334 (10)	0.0225 (8)	−0.0056 (8)	0.0039 (8)	0.0006 (7)
C12	0.0418 (12)	0.0433 (12)	0.0319 (10)	−0.0048 (10)	0.0153 (9)	−0.0026 (9)
C13	0.0353 (11)	0.0379 (11)	0.0320 (9)	0.0035 (9)	0.0088 (9)	−0.0055 (9)
C14	0.0308 (12)	0.0624 (15)	0.0440 (12)	0.0094 (11)	−0.0011 (10)	−0.0046 (11)
C15	0.0281 (10)	0.0473 (12)	0.0268 (9)	−0.0006 (9)	−0.0044 (8)	−0.0037 (9)
C16	0.0332 (10)	0.0279 (9)	0.0226 (8)	−0.0012 (8)	0.0052 (8)	−0.0039 (7)
C17	0.0430 (12)	0.0502 (13)	0.0288 (10)	−0.0092 (11)	−0.0021 (9)	−0.0085 (9)
C18	0.0580 (15)	0.0269 (10)	0.0417 (11)	0.0003 (10)	0.0093 (11)	−0.0006 (9)
C19	0.0289 (9)	0.0272 (9)	0.0196 (7)	−0.0001 (8)	0.0036 (7)	0.0006 (6)

Geometric parameters (Å, º) top

O1—C19	1.202 (2)	C8—H8C	0.97
O2—C6	1.190 (3)	C9—H9A	0.97
O3—C11	1.197 (3)	C9—H9B	0.97
N1—C19	1.351 (2)	C9—H9C	0.97
N1—C1	1.420 (2)	C10—C11	1.506 (3)
N1—H1	0.82 (3)	C10—C15	1.539 (3)
N2—C19	1.362 (2)	C10—C16	1.540 (2)
N2—C10	1.423 (2)	C11—C12	1.495 (3)
N2—H2	0.83 (2)	C12—C13	1.515 (3)
C1—C6	1.513 (3)	C12—H12A	0.98
C1—C2	1.534 (3)	C12—H12B	0.98
C1—C7	1.548 (3)	C13—C14	1.521 (3)
C2—C3	1.530 (3)	C13—C16	1.543 (3)
C2—H2A	0.98	C13—H13A	0.99
C2—H2B	0.98	C14—C15	1.525 (3)
C3—C4	1.514 (3)	C14—H14A	0.98
C3—H3A	0.98	C14—H14B	0.98
C3—H3B	0.98	C15—H15A	0.98
C4—C5	1.513 (3)	C15—H15B	0.98
C4—C7	1.541 (3)	C16—C17	1.511 (3)
C4—H4A	0.99	C16—C18	1.511 (3)
C5—C6	1.500 (3)	C17—H17A	0.97
C5—H5A	0.98	C17—H17B	0.97
C5—H5B	0.98	C17—H17C	0.97
C7—C8	1.503 (3)	C18—H18A	0.97
C7—C9	1.504 (3)	C18—H18B	0.97
C8—H8A	0.97	C18—H18C	0.97
C8—H8B	0.97

C19—N1—C1	125.14 (16)	H9B—C9—H9C	109.5
C19—N1—H1	119.3 (16)	N2—C10—C11	110.05 (16)
C1—N1—H1	115.1 (16)	N2—C10—C15	117.95 (14)
C19—N2—C10	123.87 (16)	C11—C10—C15	102.19 (16)
C19—N2—H2	113.6 (15)	N2—C10—C16	120.39 (16)
C10—N2—H2	116.0 (16)	C11—C10—C16	100.42 (14)
N1—C1—C6	108.71 (16)	C15—C10—C16	103.08 (15)
N1—C1—C2	117.77 (16)	O3—C11—C12	127.66 (19)
C6—C1—C2	104.15 (17)	O3—C11—C10	125.45 (19)
N1—C1—C7	120.53 (18)	C12—C11—C10	106.89 (17)
C6—C1—C7	99.85 (15)	C11—C12—C13	101.71 (16)
C2—C1—C7	103.32 (15)	C11—C12—H12A	111.4
C3—C2—C1	103.36 (17)	C13—C12—H12A	111.4
C3—C2—H2A	111.1	C11—C12—H12B	111.4
C1—C2—H2A	111.1	C13—C12—H12B	111.4
C3—C2—H2B	111.1	H12A—C12—H12B	109.3
C1—C2—H2B	111.1	C12—C13—C14	105.91 (19)
H2A—C2—H2B	109.1	C12—C13—C16	102.95 (18)
C4—C3—C2	103.12 (18)	C14—C13—C16	102.90 (17)
C4—C3—H3A	111.1	C12—C13—H13A	114.6
C2—C3—H3A	111.1	C14—C13—H13A	114.6
C4—C3—H3B	111.1	C16—C13—H13A	114.6
C2—C3—H3B	111.1	C13—C14—C15	102.93 (18)
H3A—C3—H3B	109.1	C13—C14—H14A	111.2
C5—C4—C3	107.4 (2)	C15—C14—H14A	111.2
C5—C4—C7	103.20 (18)	C13—C14—H14B	111.2
C3—C4—C7	102.86 (16)	C15—C14—H14B	111.2
C5—C4—H4A	114.1	H14A—C14—H14B	109.1
C3—C4—H4A	114.1	C14—C15—C10	104.04 (16)
C7—C4—H4A	114.1	C14—C15—H15A	110.9
C6—C5—C4	101.45 (18)	C10—C15—H15A	110.9
C6—C5—H5A	111.5	C14—C15—H15B	110.9
C4—C5—H5A	111.5	C10—C15—H15B	110.9
C6—C5—H5B	111.5	H15A—C15—H15B	109.0
C4—C5—H5B	111.5	C17—C16—C18	108.32 (18)
H5A—C5—H5B	109.3	C17—C16—C10	112.65 (17)
O2—C6—C5	127.9 (2)	C18—C16—C10	114.24 (15)
O2—C6—C1	125.57 (19)	C17—C16—C13	114.54 (16)
C5—C6—C1	106.52 (18)	C18—C16—C13	113.39 (19)
C8—C7—C9	107.70 (19)	C10—C16—C13	93.27 (15)
C8—C7—C4	112.41 (17)	C16—C17—H17A	109.5
C9—C7—C4	114.92 (19)	C16—C17—H17B	109.5
C8—C7—C1	116.53 (16)	H17A—C17—H17B	109.5
C9—C7—C1	112.47 (18)	C16—C17—H17C	109.5
C4—C7—C1	92.50 (16)	H17A—C17—H17C	109.5
C7—C8—H8A	109.5	H17B—C17—H17C	109.5
C7—C8—H8B	109.5	C16—C18—H18A	109.5
H8A—C8—H8B	109.5	C16—C18—H18B	109.5
C7—C8—H8C	109.5	H18A—C18—H18B	109.5
H8A—C8—H8C	109.5	C16—C18—H18C	109.5
H8B—C8—H8C	109.5	H18A—C18—H18C	109.5
C7—C9—H9A	109.5	H18B—C18—H18C	109.5
C7—C9—H9B	109.5	O1—C19—N1	123.73 (17)
H9A—C9—H9B	109.5	O1—C19—N2	123.13 (18)
C7—C9—H9C	109.5	N1—C19—N2	113.13 (17)
H9A—C9—H9C	109.5

C19—N1—C1—C6	−177.4 (2)	C19—N2—C10—C16	92.3 (2)
C19—N1—C1—C2	−59.3 (3)	N2—C10—C11—O3	16.8 (3)
C19—N1—C1—C7	68.4 (3)	C15—C10—C11—O3	−109.3 (2)
N1—C1—C2—C3	167.25 (19)	C16—C10—C11—O3	144.7 (2)
C6—C1—C2—C3	−72.3 (2)	N2—C10—C11—C12	−163.16 (16)
C7—C1—C2—C3	31.6 (2)	C15—C10—C11—C12	70.73 (19)
C1—C2—C3—C4	4.1 (2)	C16—C10—C11—C12	−35.2 (2)
C2—C3—C4—C5	69.8 (2)	O3—C11—C12—C13	−179.5 (2)
C2—C3—C4—C7	−38.7 (2)	C10—C11—C12—C13	0.4 (2)
C3—C4—C5—C6	−73.0 (2)	C11—C12—C13—C14	−72.8 (2)
C7—C4—C5—C6	35.2 (3)	C11—C12—C13—C16	34.9 (2)
C4—C5—C6—O2	−177.4 (3)	C12—C13—C14—C15	69.8 (2)
C4—C5—C6—C1	1.2 (3)	C16—C13—C14—C15	−37.9 (2)
N1—C1—C6—O2	15.0 (3)	C13—C14—C15—C10	4.0 (2)
C2—C1—C6—O2	−111.3 (3)	N2—C10—C15—C14	166.56 (18)
C7—C1—C6—O2	142.1 (3)	C11—C10—C15—C14	−72.7 (2)
N1—C1—C6—C5	−163.6 (2)	C16—C10—C15—C14	31.2 (2)
C2—C1—C6—C5	70.0 (2)	N2—C10—C16—C17	55.8 (2)
C7—C1—C6—C5	−36.5 (2)	C11—C10—C16—C17	−65.0 (2)
C5—C4—C7—C8	−176.07 (19)	C15—C10—C16—C17	−170.25 (17)
C3—C4—C7—C8	−64.4 (2)	N2—C10—C16—C18	−68.4 (2)
C5—C4—C7—C9	60.3 (2)	C11—C10—C16—C18	170.8 (2)
C3—C4—C7—C9	171.92 (19)	C15—C10—C16—C18	65.6 (2)
C5—C4—C7—C1	−55.97 (19)	N2—C10—C16—C13	174.14 (16)
C3—C4—C7—C1	55.68 (18)	C11—C10—C16—C13	53.35 (16)
N1—C1—C7—C8	−70.1 (2)	C15—C10—C16—C13	−51.91 (16)
C6—C1—C7—C8	171.19 (18)	C12—C13—C16—C17	61.9 (2)
C2—C1—C7—C8	64.0 (2)	C14—C13—C16—C17	171.84 (18)
N1—C1—C7—C9	54.9 (3)	C12—C13—C16—C18	−173.08 (17)
C6—C1—C7—C9	−63.8 (2)	C14—C13—C16—C18	−63.1 (2)
C2—C1—C7—C9	−171.00 (18)	C12—C13—C16—C10	−54.87 (17)
N1—C1—C7—C4	173.26 (19)	C14—C13—C16—C10	55.09 (18)
C6—C1—C7—C4	54.55 (17)	C1—N1—C19—O1	1.2 (3)
C2—C1—C7—C4	−52.67 (17)	C1—N1—C19—N2	−179.62 (19)
C19—N2—C10—C11	−151.76 (18)	C10—N2—C19—O1	−23.8 (3)
C19—N2—C10—C15	−35.1 (3)	C10—N2—C19—N1	156.98 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3ⁱ	0.82 (3)	2.34 (2)	3.090 (2)	153 (2)
N2—H2···O3ⁱ	0.83 (2)	2.32 (2)	3.061 (2)	148 (2)

Symmetry code: (i) x−1/2, −y+1/2, −z.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₈N₂O₃
M_r	332.43
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	223
a, b, c (Å)	6.7578 (16), 12.107 (3), 21.269 (5)
V (Å³)	1740.2 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.50 × 0.16 × 0.12

Data collection
Diffractometer	Bruker APEX area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.958, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	10699, 2418, 2280
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.672

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.115, 1.11
No. of reflections	2418
No. of parameters	225
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.30

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997).