#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:54:20 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178449 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/70/4027068.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_4027068
loop_
_publ_author_name
'Hai Xie'
'Ding Yuan'
'Ming-Wu Ding'
_publ_section_title
;
 Unexpected Synthesis of 2,4,5-Trisubstituted Oxazoles via a Tandem
 Aza-Wittig/Michael/Isomerization Reaction of Vinyliminophosphorane
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2954
_journal_page_last               2958
_journal_paper_doi               10.1021/jo202588j
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C17 H15 N O2'
_chemical_formula_sum            'C17 H15 N O2'
_chemical_formula_weight         265.30
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 116.514(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.856(4)
_cell_length_b                   7.3460(13)
_cell_length_c                   20.945(4)
_cell_measurement_reflns_used    6740
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.90
_cell_measurement_theta_min      2.17
_cell_volume                     2733.8(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0216
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            16162
_diffrn_reflns_theta_full        28.35
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.0047(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         3404
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0479
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0841P)²+0.6395P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1358
_refine_ls_wR_factor_ref         0.1429
_reflns_number_gt                2849
_reflns_number_total             3404
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo202588j_si_001.cif
_cod_data_source_block           110426lm
_cod_original_cell_volume        2733.8(8)
_cod_database_code               4027068
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
C1 C 0.14268(6) 0.42497(16) 0.39349(6) 0.0435(3) Uani 1 1 d .
C2 C 0.12321(8) 0.60056(18) 0.36828(8) 0.0564(3) Uani 1 1 d .
H2 H 0.1057 0.6245 0.3199 0.068 Uiso 1 1 calc R
C3 C 0.12962(9) 0.7415(2) 0.41492(10) 0.0688(4) Uani 1 1 d .
H3 H 0.1163 0.8594 0.3978 0.083 Uiso 1 1 calc R
C4 C 0.15571(9) 0.7060(3) 0.48670(10) 0.0726(4) Uani 1 1 d .
H4 H 0.1608 0.8007 0.5180 0.087 Uiso 1 1 calc R
C5 C 0.17407(8) 0.5323(3) 0.51208(8) 0.0677(4) Uani 1 1 d .
H5 H 0.1908 0.5086 0.5604 0.081 Uiso 1 1 calc R
C6 C 0.16776(7) 0.3927(2) 0.46601(7) 0.0548(3) Uani 1 1 d .
H6 H 0.1804 0.2749 0.4836 0.066 Uiso 1 1 calc R
C7 C 0.13647(6) 0.26475(16) 0.34506(6) 0.0446(3) Uani 1 1 d .
H7 H 0.1818 0.1909 0.3704 0.054 Uiso 1 1 calc R
C8 C 0.13533(6) 0.31999(16) 0.27522(6) 0.0435(3) Uani 1 1 d .
C9 C 0.08607(7) 0.37465(17) 0.16343(7) 0.0489(3) Uani 1 1 d .
C10 C 0.19272(7) 0.35719(16) 0.25888(6) 0.0438(3) Uani 1 1 d .
C11 C 0.03645(8) 0.4030(2) 0.08661(7) 0.0641(4) Uani 1 1 d .
H11A H 0.0425 0.3038 0.0598 0.096 Uiso 1 1 calc R
H11B H 0.0497 0.5151 0.0714 0.096 Uiso 1 1 calc R
H11C H -0.0150 0.4087 0.0788 0.096 Uiso 1 1 calc R
C12 C 0.27437(7) 0.36947(15) 0.29760(7) 0.0449(3) Uani 1 1 d .
C13 C 0.31897(8) 0.3650(2) 0.26157(8) 0.0576(3) Uani 1 1 d .
H13 H 0.2964 0.3522 0.2122 0.069 Uiso 1 1 calc R
C14 C 0.39621(8) 0.3795(2) 0.29857(9) 0.0672(4) Uani 1 1 d .
H14 H 0.4253 0.3783 0.2739 0.081 Uiso 1 1 calc R
C15 C 0.43047(8) 0.3956(2) 0.37173(9) 0.0680(4) Uani 1 1 d .
H15 H 0.4826 0.4036 0.3965 0.082 Uiso 1 1 calc R
C16 C 0.38722(8) 0.4000(2) 0.40827(8) 0.0653(4) Uani 1 1 d .
H16 H 0.4104 0.4106 0.4577 0.078 Uiso 1 1 calc R
C17 C 0.30975(7) 0.38850(18) 0.37158(7) 0.0547(3) Uani 1 1 d .
H17 H 0.2810 0.3935 0.3964 0.066 Uiso 1 1 calc R
N1 N 0.06755(5) 0.33330(15) 0.21347(5) 0.0478(3) Uani 1 1 d .
O1 O 0.07439(5) 0.15178(12) 0.33438(5) 0.0542(3) Uani 1 1 d D
H1 H 0.0352(7) 0.216(2) 0.3166(9) 0.073(5) Uiso 1 1 d D
O2 O 0.16102(5) 0.39148(12) 0.18613(4) 0.0497(2) 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
C2 C1 C6 118.61(12)
C2 C1 C7 122.78(11)
C6 C1 C7 118.59(11)
C1 C2 C3 120.30(13)
C1 C2 H2 119.8
C3 C2 H2 119.8
C4 C3 C2 119.85(14)
C4 C3 H3 120.1
C2 C3 H3 120.1
C5 C4 C3 120.34(14)
C5 C4 H4 119.8
C3 C4 H4 119.8
C4 C5 C6 119.88(14)
C4 C5 H5 120.1
C6 C5 H5 120.1
C5 C6 C1 121.00(13)
C5 C6 H6 119.5
C1 C6 H6 119.5
O1 C7 C8 111.63(10)
O1 C7 C1 111.32(9)
C8 C7 C1 113.56(9)
O1 C7 H7 106.6
C8 C7 H7 106.6
C1 C7 H7 106.6
C10 C8 N1 108.91(10)
C10 C8 C7 130.43(11)
N1 C8 C7 120.62(10)
N1 C9 O2 113.82(11)
N1 C9 C11 128.52(12)
O2 C9 C11 117.66(11)
C8 C10 O2 107.06(10)
C8 C10 C12 136.39(11)
O2 C10 C12 116.55(10)
C9 C11 H11A 109.5
C9 C11 H11B 109.5
H11A C11 H11B 109.5
C9 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C17 C12 C13 118.45(12)
C17 C12 C10 120.59(11)
C13 C12 C10 120.96(12)
C14 C13 C12 120.58(14)
C14 C13 H13 119.7
C12 C13 H13 119.7
C15 C14 C13 120.34(14)
C15 C14 H14 119.8
C13 C14 H14 119.8
C14 C15 C16 119.87(13)
C14 C15 H15 120.1
C16 C15 H15 120.1
C17 C16 C15 120.21(14)
C17 C16 H16 119.9
C15 C16 H16 119.9
C16 C17 C12 120.55(13)
C16 C17 H17 119.7
C12 C17 H17 119.7
C9 N1 C8 105.23(10)
C7 O1 H1 108.0(12)
C9 O2 C10 104.97(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.3819(18)
C1 C6 1.3916(17)
C1 C7 1.5224(17)
C2 C3 1.390(2)
C2 H2 0.9300
C3 C4 1.379(3)
C3 H3 0.9300
C4 C5 1.368(3)
C4 H4 0.9300
C5 C6 1.375(2)
C5 H5 0.9300
C6 H6 0.9300
C7 O1 1.4185(15)
C7 C8 1.5083(15)
C7 H7 0.9800
C8 C10 1.3561(16)
C8 N1 1.3927(15)
C9 N1 1.2924(16)
C9 O2 1.3506(15)
C9 C11 1.4792(18)
C10 O2 1.3875(14)
C10 C12 1.4561(17)
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
C12 C17 1.3936(19)
C12 C13 1.3971(18)
C13 C14 1.379(2)
C13 H13 0.9300
C14 C15 1.376(2)
C14 H14 0.9300
C15 C16 1.383(2)
C15 H15 0.9300
C16 C17 1.3814(19)
C16 H16 0.9300
C17 H17 0.9300
O1 H1 0.841(9)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C3 H3 O1 0.93 2.47 3.3884(19) 171.4 1_565
O1 H1 N1 0.841(9) 2.039(10) 2.8641(15) 166.9(17) 2
