#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:50:43 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178408 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/29/4022945.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_4022945
loop_
_publ_author_name
'Mercedes Amat'
'Oscar Lozano'
'Carmen Escolano'
'Elies Molins'
'Joan Bosch'
_publ_section_title
;
 Enantioselective Synthesis of 3,3-Disubstituted Piperidine
 Derivatives by Enolate Dialkylation of Phenylglycinol-Derived
 Oxazolopiperidone Lactams
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4431
_journal_page_last               4439
_journal_paper_doi               10.1021/jo070397q
_journal_volume                  72
_journal_year                    2007
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C18 H23 N1 O2'
_chemical_formula_structural     'C18 H23 N O2'
_chemical_formula_sum            'C18 H23 N O2'
_chemical_formula_weight         285.37
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.2
_audit_creation_date             2003-01-29T09:40:08-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7028(13)
_cell_length_b                   11.6954(10)
_cell_length_c                   13.7099(14)
_cell_measurement_reflns_used    15
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.53
_cell_measurement_theta_min      11.84
_cell_measurement_wavelength     0.71073
_cell_volume                     1555.8(3)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled omega/2theta scans'
_diffrn_orient_matrix_type
;
  x-axis points to radiation source
  the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_UB_11      -0.83699E-1
_diffrn_orient_matrix_UB_12      0.01905
_diffrn_orient_matrix_UB_13      -0.03942
_diffrn_orient_matrix_UB_21      0.38718E-1
_diffrn_orient_matrix_UB_22      0.07761
_diffrn_orient_matrix_UB_23      -0.13816E-1
_diffrn_orient_matrix_UB_31      0.04617
_diffrn_orient_matrix_UB_32      -0.30429E-1
_diffrn_orient_matrix_UB_33      -0.59787E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.024
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            2666
_diffrn_reflns_theta_full        30.4
_diffrn_reflns_theta_max         30.4
_diffrn_reflns_theta_min         2.29
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.04
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.4(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2665
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0426
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0823P)²+0.1430P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1181
_refine_ls_wR_factor_ref         0.1318
_reflns_number_gt                2072
_reflns_number_total             2665
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070397qsi20070302_094450.cif
_cod_data_source_block           jb32
_cod_database_code               4022945
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.56151(18) 0.32468(14) 0.05173(11) 0.0511(4) Uani 1 1 d . . .
O5 O 0.29040(17) 0.51300(16) 0.25782(9) 0.0558(4) Uani 1 1 d . . .
N4 N 0.39802(17) 0.40180(14) 0.14830(10) 0.0378(3) Uani 1 1 d . . .
C2 C 0.5851(3) 0.28082(18) 0.14816(17) 0.0519(5) Uani 1 1 d . . .
H2A H 0.6826 0.2819 0.1638 0.062 Uiso 1 1 calc R . .
H2B H 0.5514 0.203 0.1538 0.062 Uiso 1 1 calc R . .
C3 C 0.5042(2) 0.36158(16) 0.21606(13) 0.0386(4) Uani 1 1 d . . .
H3 H 0.4618 0.3179 0.2692 0.046 Uiso 1 1 calc R . .
C5 C 0.30088(19) 0.47852(17) 0.17343(11) 0.0391(4) Uani 1 1 d . . .
C6 C 0.2085(2) 0.52734(17) 0.09246(12) 0.0409(4) Uani 1 1 d . . .
C7 C 0.2262(2) 0.4647(2) -0.00556(13) 0.0529(5) Uani 1 1 d . . .
H7A H 0.1713 0.3954 -0.0048 0.063 Uiso 1 1 calc R . .
H7B H 0.1917 0.513 -0.0576 0.063 Uiso 1 1 calc R . .
C8 C 0.3762(2) 0.4337(2) -0.02680(13) 0.0512(5) Uani 1 1 d . . .
H8A H 0.3842 0.3984 -0.0906 0.061 Uiso 1 1 calc R . .
H8B H 0.4336 0.5016 -0.0255 0.061 Uiso 1 1 calc R . .
C8A C 0.4197(2) 0.35168(17) 0.05132(13) 0.0429(4) Uani 1 1 d . . .
H8A1 H 0.3658 0.2811 0.0456 0.052 Uiso 1 1 calc R . .
C31 C 0.59228(18) 0.45668(14) 0.25716(12) 0.0361(3) Uani 1 1 d . . .
C32 C 0.6293(2) 0.45346(17) 0.35493(14) 0.0439(4) Uani 1 1 d . . .
H32 H 0.594 0.3963 0.3949 0.053 Uiso 1 1 calc R . .
C33 C 0.7184(2) 0.5347(2) 0.39380(16) 0.0535(5) Uani 1 1 d . . .
H33 H 0.742 0.5319 0.4595 0.064 Uiso 1 1 calc R . .
C34 C 0.7718(2) 0.61901(19) 0.33520(18) 0.0529(5) Uani 1 1 d . . .
H34 H 0.8324 0.6728 0.3609 0.063 Uiso 1 1 calc R . .
C35 C 0.7351(2) 0.62358(18) 0.23815(18) 0.0513(5) Uani 1 1 d . . .
H35 H 0.7703 0.6812 0.1986 0.062 Uiso 1 1 calc R . .
C36 C 0.6463(2) 0.54293(18) 0.19906(14) 0.0457(4) Uani 1 1 d . . .
H36 H 0.6227 0.5466 0.1334 0.055 Uiso 1 1 calc R . .
C61 C 0.0578(2) 0.51840(18) 0.12757(16) 0.0481(4) Uani 1 1 d . . .
H61A H 0.0478 0.5634 0.1866 0.058 Uiso 1 1 calc R . .
H61B H -0.0016 0.5519 0.0783 0.058 Uiso 1 1 calc R . .
C62 C 0.0092(3) 0.3992(2) 0.1479(2) 0.0625(6) Uani 1 1 d . . .
H62 H 0.0002 0.3506 0.0946 0.075 Uiso 1 1 calc R . .
C63 C -0.0210(4) 0.3579(3) 0.2315(3) 0.0852(10) Uani 1 1 d . . .
H63A H -0.0135 0.4032 0.287 0.102 Uiso 1 1 calc R . .
H63B H -0.0504 0.2824 0.2369 0.102 Uiso 1 1 calc R . .
C64 C 0.2513(3) 0.65449(19) 0.08375(17) 0.0574(6) Uani 1 1 d . . .
H64A H 0.2471 0.6889 0.1481 0.069 Uiso 1 1 calc R . .
H64B H 0.3464 0.6578 0.0622 0.069 Uiso 1 1 calc R . .
C65 C 0.1641(5) 0.7260(3) 0.0144(3) 0.1084(16) Uani 1 1 d . . .
H65A H 0.1741 0.6973 -0.0508 0.163 Uiso 1 1 calc R . .
H65B H 0.1941 0.8042 0.0168 0.163 Uiso 1 1 calc R . .
H65C H 0.0691 0.7216 0.0336 0.163 Uiso 1 1 calc R . .
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
1 3 -7
5 -2 -3
1 6 4
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C8A O1 C2 103.83(15) . .
C5 N4 C3 122.97(14) . .
C5 N4 C8A 126.75(16) . .
C3 N4 C8A 110.20(15) . .
O1 C2 C3 104.82(16) . .
N4 C3 C31 113.44(15) . .
N4 C3 C2 99.91(15) . .
C31 C3 C2 112.84(17) . .
O5 C5 N4 121.16(17) . .
O5 C5 C6 120.64(18) . .
N4 C5 C6 118.11(14) . .
C5 C6 C7 112.87(16) . .
C5 C6 C61 107.58(15) . .
C7 C6 C61 110.21(16) . .
C5 C6 C64 104.84(16) . .
C7 C6 C64 111.08(18) . .
C61 C6 C64 110.08(19) . .
C8 C7 C6 112.64(16) . .
C8A C8 C7 106.50(18) . .
O1 C8A N4 103.03(15) . .
O1 C8A C8 114.87(16) . .
N4 C8A C8 110.55(16) . .
C36 C31 C32 118.44(17) . .
C36 C31 C3 122.29(16) . .
C32 C31 C3 119.09(16) . .
C31 C32 C33 120.80(19) . .
C34 C33 C32 120.1(2) . .
C33 C34 C35 119.7(2) . .
C34 C35 C36 120.5(2) . .
C35 C36 C31 120.51(19) . .
C62 C61 C6 114.80(19) . .
C63 C62 C61 126.2(3) . .
C65 C64 C6 115.2(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C8A 1.412(3) .
O1 C2 1.436(3) .
O5 C5 1.229(2) .
N4 C5 1.346(3) .
N4 C3 1.465(2) .
N4 C8A 1.468(2) .
C2 C3 1.541(3) .
C3 C31 1.512(2) .
C5 C6 1.537(2) .
C6 C7 1.540(2) .
C6 C61 1.543(3) .
C6 C64 1.549(3) .
C7 C8 1.528(3) .
C8 C8A 1.499(3) .
C31 C36 1.388(3) .
C31 C32 1.388(2) .
C32 C33 1.391(3) .
C33 C34 1.373(4) .
C34 C35 1.378(3) .
C35 C36 1.386(3) .
C61 C62 1.498(3) .
C62 C63 1.278(4) .
C64 C65 1.523(4) .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C8A O1 C2 C3 -42.5(2) . . . .
C5 N4 C3 C31 -58.1(2) . . . .
C8A N4 C3 C31 118.66(16) . . . .
C5 N4 C3 C2 -178.47(18) . . . .
C8A N4 C3 C2 -1.68(19) . . . .
O1 C2 C3 N4 26.19(19) . . . .
O1 C2 C3 C31 -94.6(2) . . . .
C3 N4 C5 O5 -5.3(3) . . . .
C8A N4 C5 O5 178.43(19) . . . .
C3 N4 C5 C6 171.17(16) . . . .
C8A N4 C5 C6 -5.1(3) . . . .
O5 C5 C6 C7 -173.9(2) . . . .
N4 C5 C6 C7 9.6(3) . . . .
O5 C5 C6 C61 -52.1(2) . . . .
N4 C5 C6 C61 131.38(18) . . . .
O5 C5 C6 C64 65.1(2) . . . .
N4 C5 C6 C64 -111.5(2) . . . .
C5 C6 C7 C8 -39.6(3) . . . .
C61 C6 C7 C8 -159.86(19) . . . .
C64 C6 C7 C8 77.9(3) . . . .
C6 C7 C8 C8A 63.3(3) . . . .
C2 O1 C8A N4 40.26(18) . . . .
C2 O1 C8A C8 160.56(16) . . . .
C5 N4 C8A O1 153.01(18) . . . .
C3 N4 C8A O1 -23.63(19) . . . .
C5 N4 C8A C8 29.8(3) . . . .
C3 N4 C8A C8 -146.85(17) . . . .
C7 C8 C8A O1 -171.95(16) . . . .
C7 C8 C8A N4 -55.9(2) . . . .
N4 C3 C31 C36 -45.4(2) . . . .
C2 C3 C31 C36 67.3(2) . . . .
N4 C3 C31 C32 139.48(18) . . . .
C2 C3 C31 C32 -107.81(19) . . . .
C36 C31 C32 C33 0.0(3) . . . .
C3 C31 C32 C33 175.22(19) . . . .
C31 C32 C33 C34 -0.4(3) . . . .
C32 C33 C34 C35 0.9(3) . . . .
C33 C34 C35 C36 -0.8(3) . . . .
C34 C35 C36 C31 0.4(3) . . . .
C32 C31 C36 C35 0.1(3) . . . .
C3 C31 C36 C35 -175.03(19) . . . .
C5 C6 C61 C62 -60.7(2) . . . .
C7 C6 C61 C62 62.7(3) . . . .
C64 C6 C61 C62 -174.4(2) . . . .
C6 C61 C62 C63 112.1(3) . . . .
C5 C6 C64 C65 -174.2(3) . . . .
C7 C6 C64 C65 63.6(3) . . . .
C61 C6 C64 C65 -58.7(3) . . . .
