#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/36/4023672.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_4023672
loop_
_publ_author_name
'Dusan Hesek'
'Mijoon Lee'
'Takao Yamaguchi'
'Bruce C. Noll'
'Shahriar Mobashery'
_publ_contact_author_address
;University of Notre Dame
Department of Chemistry and Biochemistry
251 Nieuwland Science Hall
Notre Dame, IN 46556-5670
USA
;
_publ_contact_author_email       mobashery@nd.edu
_publ_contact_author_fax         1(574)6316652
_publ_contact_author_name        'Professor Shahriar Mobashery'
_publ_contact_author_phone       1(574)6312933
_publ_section_title
;
 Facile Preparation of a Highly Functionalized Tetrahydropyran
 by Catalytic Hydrogenation of an Oxazoline
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7349
_journal_page_last               7352
_journal_paper_doi               10.1021/jo801037z
_journal_volume                  73
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_compound_source        synthesized
_chemical_formula_moiety         'C17 H21 N O6'
_chemical_formula_sum            'C17 H21 N O6'
_chemical_formula_weight         335.35
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 92.166(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.7630(4)
_cell_length_b                   4.9097(2)
_cell_length_c                   16.0598(7)
_cell_measurement_reflns_used    3619
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.0596
_cell_measurement_theta_min      4.1104
_cell_volume                     848.04(6)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2007; Sheldrick, 2008)'
_computing_molecular_graphics    'XP (Sheldrick, 2008)'
_computing_publication_material  'XCIF (Sheldrick, 2008)/enCIFer (CCDC, 2005)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker SMART Apex CCD diffractometer'
_diffrn_measurement_method       'φ and ω scns'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0364
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9644
_diffrn_reflns_theta_full        69.49
_diffrn_reflns_theta_max         69.49
_diffrn_reflns_theta_min         4.11
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Siemens KFFCU2K-90'
_exptl_absorpt_coefficient_mu    0.835
_exptl_absorpt_correction_T_max  0.9340
_exptl_absorpt_correction_T_min  0.7207
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Sheldrick, G. M. (2007). SADABS. University of Göttingen, Germany.'
_exptl_crystal_colour            'clear colorless'
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         2587
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0380
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0601P)²+0.1229P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1021
_reflns_number_gt                2378
_reflns_number_total             2587
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo801037z_si_001.cif
_cod_data_source_block           compound_8f
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4023672
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.49636(15) 0.8563(4) 0.84923(12) 0.0283(4) Uani 1 1 d . . .
H1 H 0.474(2) 0.685(7) 0.8457(15) 0.033(7) Uiso 1 1 d . . .
O1 O 0.81196(11) 0.7838(4) 0.94741(8) 0.0301(4) Uani 1 1 d . . .
O2 O 0.45064(14) 1.2989(4) 0.86742(11) 0.0394(4) Uani 1 1 d . . .
O3 O 0.66944(12) 0.9032(3) 0.70824(8) 0.0297(4) Uani 1 1 d . . .
O4 O 0.53306(18) 0.5980(5) 0.65372(11) 0.0506(5) Uani 1 1 d . . .
O5 O 0.88348(12) 0.5624(3) 0.73764(8) 0.0263(3) Uani 1 1 d . . .
O6 O 1.04716(12) 0.4370(4) 0.82996(8) 0.0322(4) Uani 1 1 d . . .
C1 C 0.67885(17) 0.7808(5) 0.94011(12) 0.0307(5) Uani 1 1 d . . .
H1A H 0.6450 0.8939 0.9850 0.037 Uiso 1 1 calc R . .
H1B H 0.6489 0.5920 0.9475 0.037 Uiso 1 1 calc R . .
C2 C 0.63057(16) 0.8891(5) 0.85536(12) 0.0272(5) Uani 1 1 d . . .
H2 H 0.6504 1.0877 0.8521 0.033 Uiso 1 1 calc R . .
C3 C 0.69110(17) 0.7434(4) 0.78320(12) 0.0250(4) Uani 1 1 d . . .
H3 H 0.6559 0.5561 0.7758 0.030 Uiso 1 1 calc R . .
C4 C 0.83014(17) 0.7304(5) 0.79941(11) 0.0244(4) Uani 1 1 d . . .
H4 H 0.8656 0.9181 0.7959 0.029 Uiso 1 1 calc R . .
C5 C 0.86111(17) 0.6126(5) 0.88543(12) 0.0270(5) Uani 1 1 d . . .
H5 H 0.8250 0.4257 0.8897 0.032 Uiso 1 1 calc R . .
C6 C 1.00198(18) 0.5984(5) 0.89647(12) 0.0308(5) Uani 1 1 d . . .
H6A H 1.0380 0.7838 0.8948 0.037 Uiso 1 1 calc R . .
H6B H 1.0257 0.5147 0.9508 0.037 Uiso 1 1 calc R . .
C7 C 1.01429(18) 0.5518(5) 0.75051(12) 0.0284(5) Uani 1 1 d . . .
H7 H 1.0500 0.7392 0.7465 0.034 Uiso 1 1 calc R . .
C8 C 1.06800(19) 0.3710(5) 0.68518(12) 0.0319(5) Uani 1 1 d . . .
C9 C 0.9953(2) 0.1884(5) 0.63949(13) 0.0383(6) Uani 1 1 d . . .
H9 H 0.9085 0.1782 0.6477 0.046 Uiso 1 1 calc R . .
C10 C 1.0492(3) 0.0201(6) 0.58163(16) 0.0515(7) Uani 1 1 d . . .
H10 H 0.9995 -0.1048 0.5498 0.062 Uiso 1 1 calc R . .
C11 C 1.1764(3) 0.0352(7) 0.57057(17) 0.0586(9) Uani 1 1 d . . .
H11 H 1.2133 -0.0806 0.5311 0.070 Uiso 1 1 calc R . .
C12 C 1.2492(3) 0.2142(7) 0.61567(16) 0.0548(8) Uani 1 1 d . . .
H12 H 1.3362 0.2214 0.6078 0.066 Uiso 1 1 calc R . .
C13 C 1.1957(2) 0.3854(6) 0.67301(15) 0.0434(6) Uani 1 1 d . . .
H13 H 1.2457 0.5120 0.7039 0.052 Uiso 1 1 calc R . .
C14 C 0.41663(18) 1.0618(5) 0.85789(12) 0.0270(4) Uani 1 1 d . . .
C15 C 0.28124(18) 0.9811(5) 0.85528(14) 0.0340(5) Uani 1 1 d . . .
H15A H 0.2433 1.0274 0.8007 0.051 Uiso 1 1 calc R . .
H15B H 0.2382 1.0789 0.8989 0.051 Uiso 1 1 calc R . .
H15C H 0.2743 0.7845 0.8646 0.051 Uiso 1 1 calc R . .
C16 C 0.59306(19) 0.8042(5) 0.64763(13) 0.0336(5) Uani 1 1 d . . .
C17 C 0.5942(2) 0.9848(6) 0.57302(14) 0.0445(6) Uani 1 1 d . . .
H17A H 0.5278 0.9297 0.5331 0.067 Uiso 1 1 calc R . .
H17B H 0.6747 0.9694 0.5469 0.067 Uiso 1 1 calc R . .
H17C H 0.5810 1.1739 0.5900 0.067 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 N1 C2 123.38(19) . . ?
C14 N1 H1 123.5(17) . . ?
C2 N1 H1 112.7(17) . . ?
C5 O1 C1 109.52(15) . . ?
C16 O3 C3 118.80(18) . . ?
C7 O5 C4 110.10(14) . . ?
C7 O6 C6 111.66(17) . . ?
O1 C1 C2 111.91(15) . . ?
O1 C1 H1A 109.2 . . ?
C2 C1 H1A 109.2 . . ?
O1 C1 H1B 109.2 . . ?
C2 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
N1 C2 C3 110.35(16) . . ?
N1 C2 C1 108.92(16) . . ?
C3 C2 C1 111.76(17) . . ?
N1 C2 H2 108.6 . . ?
C3 C2 H2 108.6 . . ?
C1 C2 H2 108.6 . . ?
O3 C3 C4 107.06(15) . . ?
O3 C3 C2 108.46(17) . . ?
C4 C3 C2 109.69(15) . . ?
O3 C3 H3 110.5 . . ?
C4 C3 H3 110.5 . . ?
C2 C3 H3 110.5 . . ?
O5 C4 C3 109.06(15) . . ?
O5 C4 C5 109.34(17) . . ?
C3 C4 C5 110.72(15) . . ?
O5 C4 H4 109.2 . . ?
C3 C4 H4 109.2 . . ?
C5 C4 H4 109.2 . . ?
O1 C5 C6 109.96(16) . . ?
O1 C5 C4 109.67(18) . . ?
C6 C5 C4 107.82(15) . . ?
O1 C5 H5 109.8 . . ?
C6 C5 H5 109.8 . . ?
C4 C5 H5 109.8 . . ?
O6 C6 C5 107.69(16) . . ?
O6 C6 H6A 110.2 . . ?
C5 C6 H6A 110.2 . . ?
O6 C6 H6B 110.2 . . ?
C5 C6 H6B 110.2 . . ?
H6A C6 H6B 108.5 . . ?
O5 C7 O6 110.88(15) . . ?
O5 C7 C8 109.00(17) . . ?
O6 C7 C8 107.54(17) . . ?
O5 C7 H7 109.8 . . ?
O6 C7 H7 109.8 . . ?
C8 C7 H7 109.8 . . ?
C9 C8 C13 119.9(2) . . ?
C9 C8 C7 121.84(19) . . ?
C13 C8 C7 118.2(2) . . ?
C8 C9 C10 119.9(2) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C9 C10 C11 119.6(3) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C12 C11 C10 121.0(2) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 119.8(3) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C12 C13 C8 119.8(3) . . ?
C12 C13 H13 120.1 . . ?
C8 C13 H13 120.1 . . ?
O2 C14 N1 122.66(19) . . ?
O2 C14 C15 122.4(2) . . ?
N1 C14 C15 115.0(2) . . ?
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 . . ?
O4 C16 O3 124.1(2) . . ?
O4 C16 C17 125.8(2) . . ?
O3 C16 C17 110.1(2) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C14 1.335(3) . ?
N1 C2 1.453(2) . ?
N1 H1 0.88(3) . ?
O1 C5 1.420(3) . ?
O1 C1 1.433(2) . ?
O2 C14 1.228(3) . ?
O3 C16 1.341(3) . ?
O3 C3 1.448(2) . ?
O4 C16 1.207(3) . ?
O5 C7 1.416(2) . ?
O5 C4 1.427(2) . ?
O6 C7 1.427(2) . ?
O6 C6 1.430(3) . ?
C1 C2 1.534(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.528(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.511(2) . ?
C3 H3 1.0000 . ?
C4 C5 1.523(3) . ?
C4 H4 1.0000 . ?
C5 C6 1.521(2) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.506(3) . ?
C7 H7 1.0000 . ?
C8 C9 1.382(4) . ?
C8 C13 1.397(3) . ?
C9 C10 1.387(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.388(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.367(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.388(4) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.509(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.491(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_distance_DA
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 0.88(3) 1.95(3) 164 2.798(3) O2 1_545 y
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
_geom_torsion_publ_flag
C5 O1 C1 C2 -61.4(2) . . . . ?
C14 N1 C2 C3 -133.1(2) . . . . ?
C14 N1 C2 C1 103.8(2) . . . . ?
O1 C1 C2 N1 174.66(18) . . . . ?
O1 C1 C2 C3 52.5(3) . . . . ?
C16 O3 C3 C4 130.53(18) . . . . ?
C16 O3 C3 C2 -111.18(19) . . . . ?
N1 C2 C3 O3 74.7(2) . . . . ?
C1 C2 C3 O3 -163.94(16) . . . . ?
N1 C2 C3 C4 -168.68(17) . . . . ?
C1 C2 C3 C4 -47.3(2) . . . . ?
C7 O5 C4 C3 178.76(17) . . . . ?
C7 O5 C4 C5 -60.1(2) . . . . ?
O3 C3 C4 O5 -70.3(2) . . . . ?
C2 C3 C4 O5 172.17(16) . . . . ?
O3 C3 C4 C5 169.31(17) . . . . ?
C2 C3 C4 C5 51.8(2) . . . . ?
C1 O1 C5 C6 -176.00(18) . . . . ?
C1 O1 C5 C4 65.6(2) . . . . ?
O5 C4 C5 O1 178.01(15) . . . . ?
C3 C4 C5 O1 -61.8(2) . . . . ?
O5 C4 C5 C6 58.3(2) . . . . ?
C3 C4 C5 C6 178.47(19) . . . . ?
C7 O6 C6 C5 59.7(2) . . . . ?
O1 C5 C6 O6 -176.73(18) . . . . ?
C4 C5 C6 O6 -57.2(2) . . . . ?
C4 O5 C7 O6 61.2(2) . . . . ?
C4 O5 C7 C8 179.37(17) . . . . ?
C6 O6 C7 O5 -62.0(2) . . . . ?
C6 O6 C7 C8 178.89(17) . . . . ?
O5 C7 C8 C9 -17.7(3) . . . . ?
O6 C7 C8 C9 102.5(2) . . . . ?
O5 C7 C8 C13 164.16(19) . . . . ?
O6 C7 C8 C13 -75.6(2) . . . . ?
C13 C8 C9 C10 0.0(3) . . . . ?
C7 C8 C9 C10 -178.1(2) . . . . ?
C8 C9 C10 C11 0.5(4) . . . . ?
C9 C10 C11 C12 -0.2(4) . . . . ?
C10 C11 C12 C13 -0.5(5) . . . . ?
C11 C12 C13 C8 0.9(4) . . . . ?
C9 C8 C13 C12 -0.7(4) . . . . ?
C7 C8 C13 C12 177.5(2) . . . . ?
C2 N1 C14 O2 4.0(3) . . . . ?
C2 N1 C14 C15 -175.92(18) . . . . ?
C3 O3 C16 O4 5.8(3) . . . . ?
C3 O3 C16 C17 -173.98(17) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658742
