#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:42:19 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178439 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/60/4026007.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4026007
loop_
_publ_author_name
'Alessandro Sacchetti'
'Alessandra Silvani'
'Giordano Lesma'
'Tullio Pilati'
_publ_section_title
;
 Phe-Ala-Based Diazaspirocyclic Lactam as Nucleator of Type II' β-Turn
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              833
_journal_page_last               839
_journal_paper_doi               10.1021/jo1019927
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C19 H25 N3 O3'
_chemical_formula_sum            'C19 H25 N3 O3'
_chemical_formula_weight         343.42
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.234(2)
_cell_length_b                   12.588(2)
_cell_length_c                   14.136(3)
_cell_measurement_reflns_used    3838
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      21.24
_cell_measurement_theta_min      2.17
_cell_volume                     1821.1(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565)
Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., 
Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). 
J. Appl. Cryst. 39, 453-457
;
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement
'SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)'
_computing_structure_solution
;
SIR2002 (Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., 
Giacovazzo, C., Polidori, G. & Spagna, R. (2003). 
J. Appl. Cryst. 36, 1103.)
;
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_sigmaI/netI    0.0374
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14683
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.17
_diffrn_standards_decay_%        0.00
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.028
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.934
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         2119
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.934
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0331
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0434P)² where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0707
_refine_ls_wR_factor_ref         0.0774
_reflns_number_gt                1511
_reflns_number_total             2119
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo1019927_si_002.cif
_cod_data_source_block           le07
_cod_database_code               4026007
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.8817(2) 0.68821(18) 0.74033(16) 0.0440(6) Uani 1 1 d .
H1A H 0.9064 0.7605 0.7560 0.053 Uiso 1 1 calc R
H1B H 0.9011 0.6435 0.7945 0.053 Uiso 1 1 calc R
N1 N 0.95827(16) 0.65189(13) 0.65819(12) 0.0366(4) Uani 1 1 d .
C2 C 0.90968(19) 0.56178(15) 0.60119(15) 0.0354(5) Uani 1 1 d .
C3 C 0.79405(18) 0.51020(17) 0.65504(17) 0.0426(6) Uani 1 1 d .
H3A H 0.7557 0.4547 0.6164 0.051 Uiso 1 1 calc R
H3B H 0.8258 0.4780 0.7130 0.051 Uiso 1 1 calc R
C4 C 0.6922(2) 0.59132(18) 0.67828(15) 0.0426(6) Uani 1 1 d .
C5 C 0.5604(2) 0.5814(2) 0.65738(18) 0.0567(7) Uani 1 1 d .
H5 H 0.5291 0.5198 0.6290 0.068 Uiso 1 1 calc R
C6 C 0.4762(2) 0.6631(3) 0.6788(2) 0.0675(8) Uani 1 1 d .
H6 H 0.3874 0.6558 0.6662 0.081 Uiso 1 1 calc R
C7 C 0.5220(3) 0.7553(2) 0.7186(2) 0.0651(8) Uani 1 1 d .
H7 H 0.4644 0.8106 0.7316 0.078 Uiso 1 1 calc R
C8 C 0.6527(2) 0.7663(2) 0.73940(16) 0.0519(6) Uani 1 1 d .
H8 H 0.6833 0.8288 0.7665 0.062 Uiso 1 1 calc R
C9 C 0.7387(2) 0.68402(17) 0.71986(15) 0.0415(6) Uani 1 1 d .
C10 C 1.0183(2) 0.47642(15) 0.59846(16) 0.0364(5) Uani 1 1 d .
O1 O 1.07015(14) 0.45027(11) 0.67288(10) 0.0471(4) Uani 1 1 d .
N2 N 1.04672(17) 0.42904(14) 0.51528(12) 0.0425(5) Uani 1 1 d .
C11 C 0.9928(2) 0.4611(2) 0.42358(16) 0.0561(7) Uani 1 1 d .
H11A H 0.9866 0.3993 0.3828 0.067 Uiso 1 1 calc R
H11B H 1.0515 0.5115 0.3939 0.067 Uiso 1 1 calc R
C12 C 0.8598(2) 0.51069(18) 0.43360(16) 0.0514(6) Uani 1 1 d .
H12A H 0.7977 0.4580 0.4557 0.062 Uiso 1 1 calc R
H12B H 0.8302 0.5368 0.3727 0.062 Uiso 1 1 calc R
C13 C 0.8673(2) 0.60143(16) 0.50345(14) 0.0418(5) Uani 1 1 d .
H13A H 0.7824 0.6353 0.5083 0.050 Uiso 1 1 calc R
H13B H 0.9293 0.6539 0.4809 0.050 Uiso 1 1 calc R
C14 C 1.1554(2) 0.35295(18) 0.51250(17) 0.0557(7) Uani 1 1 d .
H14 H 1.1852 0.3439 0.5779 0.067 Uiso 1 1 calc R
C15 C 1.1127(3) 0.2442(2) 0.4781(2) 0.0851(10) Uani 1 1 d .
H15A H 1.0388 0.2207 0.5143 0.128 Uiso 1 1 calc R
H15B H 1.1832 0.1946 0.4857 0.128 Uiso 1 1 calc R
H15C H 1.0890 0.2483 0.4125 0.128 Uiso 1 1 calc R
C16 C 1.2704(3) 0.3971(2) 0.45729(18) 0.0625(7) Uani 1 1 d .
O2 O 1.3363(2) 0.34000(19) 0.40540(16) 0.1038(8) Uani 1 1 d .
N3 N 1.2987(2) 0.4986(2) 0.47062(16) 0.0706(7) Uani 1 1 d .
H3 H 1.2539 0.5341 0.5112 0.085 Uiso 1 1 calc R
C17 C 1.4022(3) 0.5521(3) 0.4194(2) 0.0896(10) Uani 1 1 d .
H17A H 1.4854 0.5297 0.4437 0.134 Uiso 1 1 calc R
H17B H 1.3934 0.6275 0.4272 0.134 Uiso 1 1 calc R
H17C H 1.3965 0.5346 0.3535 0.134 Uiso 1 1 calc R
C18 C 1.0786(2) 0.69066(17) 0.63777(17) 0.0407(5) Uani 1 1 d .
C19 C 1.1330(2) 0.77711(17) 0.69850(18) 0.0507(6) Uani 1 1 d .
H19A H 1.2154 0.8001 0.6732 0.076 Uiso 1 1 calc R
H19B H 1.1454 0.7509 0.7616 0.076 Uiso 1 1 calc R
H19C H 1.0732 0.8359 0.6996 0.076 Uiso 1 1 calc R
O3 O 1.14217(16) 0.65555(12) 0.57077(11) 0.0532(4) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N1 C1 C9 110.94(18)
N1 C1 H1A 109.5
C9 C1 H1A 109.5
N1 C1 H1B 109.5
C9 C1 H1B 109.5
H1A C1 H1B 108.0
C18 N1 C1 122.61(17)
C18 N1 C2 117.77(16)
C1 N1 C2 119.29(16)
N1 C2 C13 109.70(16)
N1 C2 C10 107.76(16)
C13 C2 C10 114.05(17)
N1 C2 C3 108.10(17)
C13 C2 C3 111.31(17)
C10 C2 C3 105.67(16)
C4 C3 C2 110.73(17)
C4 C3 H3A 109.5
C2 C3 H3A 109.5
C4 C3 H3B 109.5
C2 C3 H3B 109.5
H3A C3 H3B 108.1
C5 C4 C9 119.9(2)
C5 C4 C3 124.7(2)
C9 C4 C3 115.31(19)
C6 C5 C4 119.7(3)
C6 C5 H5 120.1
C4 C5 H5 120.1
C7 C6 C5 120.6(3)
C7 C6 H6 119.7
C5 C6 H6 119.7
C6 C7 C8 120.3(2)
C6 C7 H7 119.9
C8 C7 H7 119.9
C7 C8 C9 120.0(3)
C7 C8 H8 120.0
C9 C8 H8 120.0
C8 C9 C4 119.6(2)
C8 C9 C1 123.9(2)
C4 C9 C1 116.55(19)
O1 C10 N2 122.44(18)
O1 C10 C2 118.51(18)
N2 C10 C2 118.92(18)
C10 N2 C11 124.57(17)
C10 N2 C14 118.35(18)
C11 N2 C14 116.18(18)
N2 C11 C12 111.83(19)
N2 C11 H11A 109.3
C12 C11 H11A 109.3
N2 C11 H11B 109.3
C12 C11 H11B 109.3
H11A C11 H11B 107.9
C11 C12 C13 109.23(18)
C11 C12 H12A 109.8
C13 C12 H12A 109.8
C11 C12 H12B 109.8
C13 C12 H12B 109.8
H12A C12 H12B 108.3
C12 C13 C2 110.93(17)
C12 C13 H13A 109.5
C2 C13 H13A 109.5
C12 C13 H13B 109.5
C2 C13 H13B 109.5
H13A C13 H13B 108.0
N2 C14 C15 112.3(2)
N2 C14 C16 111.24(19)
C15 C14 C16 112.9(2)
N2 C14 H14 106.6
C15 C14 H14 106.6
C16 C14 H14 106.6
C14 C15 H15A 109.5
C14 C15 H15B 109.5
H15A C15 H15B 109.5
C14 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
O2 C16 N3 122.0(3)
O2 C16 C14 121.2(3)
N3 C16 C14 116.7(2)
C16 N3 C17 122.5(2)
C16 N3 H3 118.7
C17 N3 H3 118.7
N3 C17 H17A 109.5
N3 C17 H17B 109.5
H17A C17 H17B 109.5
N3 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
O3 C18 N1 120.97(19)
O3 C18 C19 120.4(2)
N1 C18 C19 118.6(2)
C18 C19 H19A 109.5
C18 C19 H19B 109.5
H19A C19 H19B 109.5
C18 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.473(3)
C1 C9 1.493(3)
C1 H1A 0.9700
C1 H1B 0.9700
N1 C18 1.356(3)
N1 C2 1.478(3)
C2 C13 1.532(3)
C2 C10 1.546(3)
C2 C3 1.550(3)
C3 C4 1.495(3)
C3 H3A 0.9700
C3 H3B 0.9700
C4 C5 1.386(3)
C4 C9 1.390(3)
C5 C6 1.376(4)
C5 H5 0.9300
C6 C7 1.372(4)
C6 H6 0.9300
C7 C8 1.377(4)
C7 H7 0.9300
C8 C9 1.387(3)
C8 H8 0.9300
C10 O1 1.223(2)
C10 N2 1.350(3)
N2 C11 1.466(3)
N2 C14 1.468(3)
C11 C12 1.504(3)
C11 H11A 0.9700
C11 H11B 0.9700
C12 C13 1.512(3)
C12 H12A 0.9700
C12 H12B 0.9700
C13 H13A 0.9700
C13 H13B 0.9700
C14 C15 1.518(4)
C14 C16 1.518(4)
C14 H14 0.9800
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
C16 O2 1.229(3)
C16 N3 1.323(4)
N3 C17 1.450(4)
N3 H3 0.8600
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
C18 O3 1.231(3)
C18 C19 1.494(3)
C19 H19A 0.9600
C19 H19B 0.9600
C19 H19C 0.9600
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C9 C1 N1 C18 148.29(19)
C9 C1 N1 C2 -38.5(3)
C18 N1 C2 C13 -75.5(2)
C1 N1 C2 C13 111.0(2)
C18 N1 C2 C10 49.2(2)
C1 N1 C2 C10 -124.30(19)
C18 N1 C2 C3 163.01(17)
C1 N1 C2 C3 -10.5(2)
N1 C2 C3 C4 54.2(2)
C13 C2 C3 C4 -66.3(2)
C10 C2 C3 C4 169.40(17)
C2 C3 C4 C5 128.1(2)
C2 C3 C4 C9 -48.8(3)
C9 C4 C5 C6 -0.6(4)
C3 C4 C5 C6 -177.4(2)
C4 C5 C6 C7 1.5(4)
C5 C6 C7 C8 -1.3(4)
C6 C7 C8 C9 0.2(4)
C7 C8 C9 C4 0.7(3)
C7 C8 C9 C1 -179.6(2)
C5 C4 C9 C8 -0.5(3)
C3 C4 C9 C8 176.6(2)
C5 C4 C9 C1 179.8(2)
C3 C4 C9 C1 -3.1(3)
N1 C1 C9 C8 -132.8(2)
N1 C1 C9 C4 46.8(3)
N1 C2 C10 O1 48.5(2)
C13 C2 C10 O1 170.58(19)
C3 C2 C10 O1 -66.8(2)
N1 C2 C10 N2 -135.44(18)
C13 C2 C10 N2 -13.4(3)
C3 C2 C10 N2 109.2(2)
O1 C10 N2 C11 -176.6(2)
C2 C10 N2 C11 7.6(3)
O1 C10 N2 C14 -7.8(3)
C2 C10 N2 C14 176.30(18)
C10 N2 C11 C12 -28.5(3)
C14 N2 C11 C12 162.5(2)
N2 C11 C12 C13 54.3(3)
C11 C12 C13 C2 -61.2(2)
N1 C2 C13 C12 161.29(17)
C10 C2 C13 C12 40.3(2)
C3 C2 C13 C12 -79.1(2)
C10 N2 C14 C15 122.3(2)
C11 N2 C14 C15 -68.0(3)
C10 N2 C14 C16 -110.0(2)
C11 N2 C14 C16 59.6(3)
N2 C14 C16 O2 -141.7(2)
C15 C14 C16 O2 -14.4(4)
N2 C14 C16 N3 40.7(3)
C15 C14 C16 N3 168.0(2)
O2 C16 N3 C17 5.2(4)
C14 C16 N3 C17 -177.2(2)
C1 N1 C18 O3 177.1(2)
C2 N1 C18 O3 3.7(3)
C1 N1 C18 C19 -2.8(3)
C2 N1 C18 C19 -176.15(19)
