#------------------------------------------------------------------------------
#$Date: 2016-03-21 05:34:46 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178485 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/06/4030638.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_4030638
loop_
_publ_author_name
'Fan, Yu-Shiou'
'Das, Utpal'
'Hsiao, Ming-Yu'
'Liu, Meng-Hsien'
'Lin, Wenwei'
_publ_section_title
;
 Chemoselective intramolecular Wittig reactions for the synthesis of
 oxazoles and benzofurans.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11567
_journal_page_last               11582
_journal_paper_doi               10.1021/jo502232q
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C27 H24 Br N O4'
_chemical_formula_sum            'C27 H24 Br N O4'
_chemical_formula_weight         506.38
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                83.822(3)
_cell_angle_beta                 67.724(3)
_cell_angle_gamma                72.660(3)
_cell_formula_units_Z            2
_cell_length_a                   10.5165(6)
_cell_length_b                   11.0302(6)
_cell_length_c                   11.7920(6)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     1208.23(12)
_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-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_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  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0650
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10577
_diffrn_reflns_theta_full        25.22
_diffrn_reflns_theta_max         25.22
_diffrn_reflns_theta_min         1.87
_exptl_absorpt_coefficient_mu    1.734
_exptl_absorpt_correction_T_max  0.5821
_exptl_absorpt_correction_T_min  0.5159
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4284
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.1175
_refine_ls_R_factor_gt           0.0506
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0917P)²+0.1196P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.1721
_reflns_number_gt                2325
_reflns_number_total             4284
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo502232q_si_002.cif
_cod_data_source_block           ch15698
_cod_original_cell_volume        1208.23(11)
_cod_database_code               4030638
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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 0.4299(6) -0.1078(4) 0.8726(5) 0.0639(12) Uani 1 1 d .
C2 C 0.2874(6) -0.0437(4) 0.9237(4) 0.0679(13) Uani 1 1 d .
H2 H 0.2421 -0.0356 1.0083 0.082 Uiso 1 1 calc R
C3 C 0.2121(5) 0.0085(4) 0.8487(4) 0.0625(12) Uani 1 1 d .
H3 H 0.1157 0.0523 0.8835 0.075 Uiso 1 1 calc R
C4 C 0.2767(5) -0.0025(4) 0.7228(4) 0.0538(11) Uani 1 1 d .
C5 C 0.4203(5) -0.0716(4) 0.6738(4) 0.0645(12) Uani 1 1 d .
H5 H 0.4652 -0.0824 0.5893 0.077 Uiso 1 1 calc R
C6 C 0.4963(5) -0.1235(5) 0.7469(5) 0.0722(14) Uani 1 1 d .
H6 H 0.5921 -0.1692 0.7126 0.087 Uiso 1 1 calc R
C7 C 0.1990(5) 0.0556(4) 0.6427(4) 0.0528(11) Uani 1 1 d .
C8 C 0.0978(4) 0.1656(4) 0.6452(3) 0.0485(10) Uani 1 1 d .
C9 C 0.0663(5) 0.1731(4) 0.5359(4) 0.0511(11) Uani 1 1 d .
C10 C -0.0273(5) 0.2596(4) 0.4885(4) 0.0572(12) Uani 1 1 d .
H10 H -0.0881 0.3342 0.5304 0.069 Uiso 1 1 calc R
C11 C -0.0272(5) 0.2314(5) 0.3771(4) 0.0657(13) Uani 1 1 d .
C12 C -0.1314(8) 0.3031(7) 0.2235(6) 0.118(2) Uani 1 1 d .
H12A H -0.2035 0.3728 0.2086 0.177 Uiso 1 1 calc R
H12B H -0.1553 0.2253 0.2252 0.177 Uiso 1 1 calc R
H12C H -0.0404 0.2989 0.1594 0.177 Uiso 1 1 calc R
C13 C 0.0626(6) 0.1200(6) 0.3153(4) 0.0734(15) Uani 1 1 d .
H13 H 0.0595 0.1030 0.2410 0.088 Uiso 1 1 calc R
C14 C 0.1563(5) 0.0336(5) 0.3602(4) 0.0719(14) Uani 1 1 d .
H14 H 0.2170 -0.0409 0.3180 0.086 Uiso 1 1 calc R
C15 C 0.1560(5) 0.0630(5) 0.4715(4) 0.0553(11) Uani 1 1 d .
C16 C -0.1151(5) 0.2911(4) 0.8005(4) 0.0563(11) Uani 1 1 d .
C17 C -0.2044(4) 0.4279(4) 0.8418(4) 0.0568(12) Uani 1 1 d .
C18 C -0.3366(6) 0.4525(6) 0.8092(6) 0.0977(18) Uani 1 1 d .
H18A H -0.3963 0.5373 0.8335 0.147 Uiso 1 1 calc R
H18B H -0.3890 0.3928 0.8510 0.147 Uiso 1 1 calc R
H18C H -0.3080 0.4431 0.7223 0.147 Uiso 1 1 calc R
C19 C -0.2560(6) 0.4354(6) 0.9821(5) 0.0978(18) Uani 1 1 d .
H19A H -0.1750 0.4191 1.0063 0.147 Uiso 1 1 calc R
H19B H -0.3069 0.3732 1.0180 0.147 Uiso 1 1 calc R
H19C H -0.3184 0.5187 1.0095 0.147 Uiso 1 1 calc R
C20 C -0.1283(6) 0.5278(5) 0.7820(6) 0.0994(19) Uani 1 1 d .
H20A H -0.0443 0.5126 0.8019 0.149 Uiso 1 1 calc R
H20B H -0.1911 0.6103 0.8115 0.149 Uiso 1 1 calc R
H20C H -0.1009 0.5238 0.6948 0.149 Uiso 1 1 calc R
C21 C 0.1228(5) 0.3013(4) 0.7821(4) 0.0580(12) Uani 1 1 d .
C22 C 0.2650(5) 0.3076(4) 0.6939(5) 0.0602(12) Uani 1 1 d .
C23 C 0.2873(5) 0.3496(5) 0.5756(5) 0.0696(14) Uani 1 1 d .
H23 H 0.2125 0.3714 0.5467 0.083 Uiso 1 1 calc R
C24 C 0.4223(7) 0.3592(6) 0.4995(6) 0.0943(18) Uani 1 1 d .
H24 H 0.4383 0.3891 0.4199 0.113 Uiso 1 1 calc R
C25 C 0.5324(6) 0.3238(6) 0.5440(9) 0.108(2) Uani 1 1 d .
H25 H 0.6235 0.3283 0.4935 0.129 Uiso 1 1 calc R
C26 C 0.5082(8) 0.2825(6) 0.6609(10) 0.110(2) Uani 1 1 d .
H26 H 0.5831 0.2595 0.6898 0.132 Uiso 1 1 calc R
C27 C 0.3774(6) 0.2745(5) 0.7358(6) 0.0824(16) Uani 1 1 d .
H27 H 0.3625 0.2466 0.8159 0.099 Uiso 1 1 calc R
N1 N 0.0358(3) 0.2632(3) 0.7362(3) 0.0481(9) Uani 1 1 d .
O1 O 0.2407(3) -0.0097(3) 0.5335(3) 0.0613(8) Uani 1 1 d .
O2 O -0.1240(4) 0.3214(4) 0.3373(3) 0.0845(11) Uani 1 1 d .
O3 O -0.1702(4) 0.2087(4) 0.8079(3) 0.0907(12) Uani 1 1 d .
O4 O 0.0812(4) 0.3276(4) 0.8895(3) 0.0850(11) Uani 1 1 d .
Br1 Br 0.53518(7) -0.17696(5) 0.97455(6) 0.0960(3) 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'
Br Br -0.2901 2.4595 '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 120.4(5)
C2 C1 Br1 119.8(4)
C6 C1 Br1 119.8(4)
C1 C2 C3 119.5(4)
C1 C2 H2 120.3
C3 C2 H2 120.3
C2 C3 C4 121.4(5)
C2 C3 H3 119.3
C4 C3 H3 119.3
C3 C4 C5 117.8(4)
C3 C4 C7 121.7(4)
C5 C4 C7 120.5(4)
C6 C5 C4 121.4(4)
C6 C5 H5 119.3
C4 C5 H5 119.3
C5 C6 C1 119.4(5)
C5 C6 H6 120.3
C1 C6 H6 120.3
C8 C7 O1 109.7(4)
C8 C7 C4 134.4(4)
O1 C7 C4 115.7(4)
C7 C8 N1 127.0(3)
C7 C8 C9 108.6(4)
N1 C8 C9 124.3(4)
C15 C9 C10 119.9(4)
C15 C9 C8 104.7(4)
C10 C9 C8 135.4(4)
C11 C10 C9 118.0(5)
C11 C10 H10 121.0
C9 C10 H10 121.0
O2 C11 C10 114.2(5)
O2 C11 C13 124.9(4)
C10 C11 C13 120.9(5)
O2 C12 H12A 109.5
O2 C12 H12B 109.5
H12A C12 H12B 109.5
O2 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C14 C13 C11 122.1(4)
C14 C13 H13 119.0
C11 C13 H13 119.0
C13 C14 C15 116.6(5)
C13 C14 H14 121.7
C15 C14 H14 121.7
O1 C15 C14 126.4(5)
O1 C15 C9 111.0(3)
C14 C15 C9 122.5(5)
O3 C16 N1 117.7(4)
O3 C16 C17 121.6(4)
N1 C16 C17 120.2(4)
C20 C17 C18 109.0(4)
C20 C17 C19 111.0(4)
C18 C17 C19 107.1(4)
C20 C17 C16 114.4(4)
C18 C17 C16 106.3(4)
C19 C17 C16 108.7(4)
C17 C18 H18A 109.5
C17 C18 H18B 109.5
H18A C18 H18B 109.5
C17 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
C17 C19 H19A 109.5
C17 C19 H19B 109.5
H19A C19 H19B 109.5
C17 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
C17 C20 H20A 109.5
C17 C20 H20B 109.5
H20A C20 H20B 109.5
C17 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
O4 C21 N1 120.4(4)
O4 C21 C22 122.5(4)
N1 C21 C22 117.1(4)
C23 C22 C27 119.7(5)
C23 C22 C21 122.6(4)
C27 C22 C21 117.6(5)
C22 C23 C24 119.6(5)
C22 C23 H23 120.2
C24 C23 H23 120.2
C25 C24 C23 119.1(6)
C25 C24 H24 120.5
C23 C24 H24 120.5
C26 C25 C24 120.4(6)
C26 C25 H25 119.8
C24 C25 H25 119.8
C27 C26 C25 121.0(6)
C27 C26 H26 119.5
C25 C26 H26 119.5
C26 C27 C22 120.3(6)
C26 C27 H27 119.9
C22 C27 H27 119.9
C21 N1 C16 121.3(3)
C21 N1 C8 120.0(3)
C16 N1 C8 116.3(3)
C15 O1 C7 105.9(3)
C11 O2 C12 119.0(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.373(6)
C1 C6 1.383(7)
C1 Br1 1.888(5)
C2 C3 1.374(6)
C2 H2 0.9300
C3 C4 1.381(6)
C3 H3 0.9300
C4 C5 1.394(6)
C4 C7 1.454(6)
C5 C6 1.362(6)
C5 H5 0.9300
C6 H6 0.9300
C7 C8 1.349(6)
C7 O1 1.397(5)
C8 N1 1.426(5)
C8 C9 1.435(5)
C9 C15 1.384(6)
C9 C10 1.391(6)
C10 C11 1.381(6)
C10 H10 0.9300
C11 O2 1.379(6)
C11 C13 1.383(7)
C12 O2 1.412(6)
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 0.9600
C13 C14 1.374(7)
C13 H13 0.9300
C14 C15 1.384(6)
C14 H14 0.9300
C15 O1 1.382(5)
C16 O3 1.195(5)
C16 N1 1.426(5)
C16 C17 1.537(6)
C17 C20 1.511(7)
C17 C18 1.521(7)
C17 C19 1.536(6)
C18 H18A 0.9600
C18 H18B 0.9600
C18 H18C 0.9600
C19 H19A 0.9600
C19 H19B 0.9600
C19 H19C 0.9600
C20 H20A 0.9600
C20 H20B 0.9600
C20 H20C 0.9600
C21 O4 1.210(5)
C21 N1 1.401(5)
C21 C22 1.480(6)
C22 C23 1.376(7)
C22 C27 1.386(6)
C23 C24 1.391(7)
C23 H23 0.9300
C24 C25 1.385(9)
C24 H24 0.9300
C25 C26 1.357(9)
C25 H25 0.9300
C26 C27 1.347(9)
C26 H26 0.9300
C27 H27 0.9300
