#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/55/1505545.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_1505545
loop_
_publ_author_name
'Ko, Changhong'
'Hsung, Richard P.'
'Al-Rashid, Ziyad F'
'Feltenberger, John B.'
'Lu, Ting'
'Yang, Jin-Haek'
'Wei, Yonggang'
'Zificsak, Craig A.'
_publ_section_title
;
 A stereoselective intramolecular halo-etherification of chiral enamides
 in the synthesis of halogenated cyclic ethers.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              4459
_journal_page_last               4462
_journal_paper_doi               10.1021/ol701768n
_journal_volume                  9
_journal_year                    2007
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C13 H14 Br N O3'
_chemical_formula_sum            'C13 H14 Br N O3'
_chemical_formula_weight         312.16
_chemical_name_common            07112a
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 115.333(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.682(4)
_cell_length_b                   5.9165(10)
_cell_length_c                   11.670(2)
_cell_measurement_reflns_used    1656
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.67
_cell_measurement_theta_min      3.48
_cell_volume                     1290.7(4)
_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  'Bruker SHELXTL'
_computing_structure_solution    SIR-2002
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0645
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6044
_diffrn_reflns_theta_full        27.06
_diffrn_reflns_theta_max         27.06
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    3.185
_exptl_absorpt_correction_T_max  0.6823
_exptl_absorpt_correction_T_min  0.3283
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (G. Sheldrick, 2003)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.794
_refine_diff_density_min         -0.486
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.021(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2744
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0352
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0340P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0791
_refine_ls_wR_factor_ref         0.0830
_reflns_number_gt                2344
_reflns_number_total             2744
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol701768n-file004.cif
_cod_data_source_block           07112a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1290.6(4)
_cod_original_sg_symbol_H-M      'C2   '
_cod_database_code               1505545
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-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
Br1 Br 0.580522(16) 0.49735(8) 0.63622(3) 0.03977(13) Uani 1 1 d .
C1 C 0.68530(15) 0.5204(8) 0.7242(3) 0.0229(7) Uani 1 1 d .
H1A H 0.7012 0.6007 0.8072 0.027 Uiso 1 1 calc R
C2 C 0.71299(19) 0.6348(6) 0.6377(3) 0.0273(8) Uani 1 1 d .
H2A H 0.6802 0.7559 0.5871 0.033 Uiso 1 1 calc R
H2B H 0.7612 0.6997 0.6867 0.033 Uiso 1 1 calc R
C3 C 0.7154(2) 0.4430(5) 0.5539(3) 0.0332(10) Uani 1 1 d .
H3A H 0.6700 0.4348 0.4759 0.040 Uiso 1 1 calc R
H3B H 0.7553 0.4645 0.5294 0.040 Uiso 1 1 calc R
O1 O 0.72587(14) 0.2387(4) 0.6286(2) 0.0292(6) Uani 1 1 d .
C4 C 0.71693(19) 0.2830(6) 0.7404(3) 0.0239(7) Uani 1 1 d .
H4A H 0.6815 0.1731 0.7453 0.029 Uiso 1 1 calc R
N1 N 0.78387(14) 0.2583(5) 0.8533(2) 0.0227(6) Uani 1 1 d .
C5 C 0.7942(2) 0.0800(6) 0.9319(3) 0.0276(8) Uani 1 1 d .
O2 O 0.75429(17) -0.0797(4) 0.9161(3) 0.0376(7) Uani 1 1 d .
O3 O 0.85726(14) 0.0954(4) 1.0338(2) 0.0334(6) Uani 1 1 d .
C6 C 0.8874(2) 0.3186(7) 1.0368(4) 0.0371(9) Uani 1 1 d .
H6A H 0.9381 0.3069 1.0517 0.044 Uiso 1 1 calc R
H6B H 0.8845 0.4117 1.1050 0.044 Uiso 1 1 calc R
C7 C 0.84199(18) 0.4241(5) 0.9057(3) 0.0242(8) Uani 1 1 d .
H7A H 0.8221 0.5719 0.9173 0.029 Uiso 1 1 calc R
C8 C 0.88437(17) 0.4610(6) 0.8286(3) 0.0230(8) Uani 1 1 d .
C9 C 0.91968(19) 0.6666(6) 0.8409(4) 0.0346(9) Uani 1 1 d .
H9A H 0.9153 0.7809 0.8944 0.042 Uiso 1 1 calc R
C10 C 0.9610(2) 0.7056(7) 0.7758(4) 0.0425(10) Uani 1 1 d .
H10A H 0.9858 0.8448 0.7861 0.051 Uiso 1 1 calc R
C11 C 0.9662(2) 0.5419(8) 0.6960(4) 0.0404(11) Uani 1 1 d .
H11A H 0.9936 0.5701 0.6496 0.048 Uiso 1 1 calc R
C12 C 0.9319(2) 0.3379(7) 0.6834(4) 0.0340(8) Uani 1 1 d .
H12A H 0.9363 0.2243 0.6296 0.041 Uiso 1 1 calc R
C13 C 0.8909(2) 0.2979(6) 0.7493(3) 0.0290(8) Uani 1 1 d .
H13A H 0.8671 0.1572 0.7398 0.035 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 0.0000 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 C4 103.3(3)
C2 C1 Br1 109.2(2)
C4 C1 Br1 108.6(3)
C2 C1 H1A 111.8
C4 C1 H1A 111.8
Br1 C1 H1A 111.8
C3 C2 C1 102.8(3)
C3 C2 H2A 111.2
C1 C2 H2A 111.2
C3 C2 H2B 111.2
C1 C2 H2B 111.2
H2A C2 H2B 109.1
O1 C3 C2 105.9(3)
O1 C3 H3A 110.6
C2 C3 H3A 110.6
O1 C3 H3B 110.6
C2 C3 H3B 110.6
H3A C3 H3B 108.7
C4 O1 C3 110.7(2)
O1 C4 N1 111.5(3)
O1 C4 C1 105.9(3)
N1 C4 C1 113.3(3)
O1 C4 H4A 108.7
N1 C4 H4A 108.7
C1 C4 H4A 108.7
C5 N1 C4 120.3(3)
C5 N1 C7 112.1(3)
C4 N1 C7 127.1(3)
O2 C5 O3 121.8(3)
O2 C5 N1 127.1(4)
O3 C5 N1 111.1(3)
C5 O3 C6 109.1(3)
O3 C6 C7 105.7(3)
O3 C6 H6A 110.6
C7 C6 H6A 110.6
O3 C6 H6B 110.6
C7 C6 H6B 110.6
H6A C6 H6B 108.7
N1 C7 C8 115.3(3)
N1 C7 C6 100.7(3)
C8 C7 C6 112.7(3)
N1 C7 H7A 109.3
C8 C7 H7A 109.3
C6 C7 H7A 109.3
C13 C8 C9 118.7(3)
C13 C8 C7 122.9(3)
C9 C8 C7 118.4(3)
C10 C9 C8 120.5(4)
C10 C9 H9A 119.7
C8 C9 H9A 119.7
C11 C10 C9 119.9(4)
C11 C10 H10A 120.0
C9 C10 H10A 120.0
C12 C11 C10 120.1(3)
C12 C11 H11A 119.9
C10 C11 H11A 119.9
C11 C12 C13 120.0(4)
C11 C12 H12A 120.0
C13 C12 H12A 120.0
C8 C13 C12 120.7(3)
C8 C13 H13A 119.7
C12 C13 H13A 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1 1.966(3)
C1 C2 1.517(5)
C1 C4 1.526(5)
C1 H1A 1.0000
C2 C3 1.512(5)
C2 H2A 0.9900
C2 H2B 0.9900
C3 O1 1.451(4)
C3 H3A 0.9900
C3 H3B 0.9900
O1 C4 1.418(4)
C4 N1 1.454(4)
C4 H4A 1.0000
N1 C5 1.354(4)
N1 C7 1.467(4)
C5 O2 1.215(4)
C5 O3 1.340(5)
O3 C6 1.455(5)
C6 C7 1.543(5)
C6 H6A 0.9900
C6 H6B 0.9900
C7 C8 1.516(4)
C7 H7A 1.0000
C8 C13 1.384(5)
C8 C9 1.394(5)
C9 C10 1.385(5)
C9 H9A 0.9500
C10 C11 1.380(6)
C10 H10A 0.9500
C11 C12 1.376(6)
C11 H11A 0.9500
C12 C13 1.387(5)
C12 H12A 0.9500
C13 H13A 0.9500
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
C4 C1 C2 C3 33.5(3)
Br1 C1 C2 C3 -81.9(3)
C1 C2 C3 O1 -27.7(4)
C2 C3 O1 C4 10.8(4)
C3 O1 C4 N1 -112.9(3)
C3 O1 C4 C1 10.8(4)
C2 C1 C4 O1 -27.9(3)
Br1 C1 C4 O1 88.0(2)
C2 C1 C4 N1 94.7(3)
Br1 C1 C4 N1 -149.4(2)
O1 C4 N1 C5 -108.1(3)
C1 C4 N1 C5 132.6(3)
O1 C4 N1 C7 80.6(4)
C1 C4 N1 C7 -38.8(4)
C4 N1 C5 O2 5.0(5)
C7 N1 C5 O2 177.6(3)
C4 N1 C5 O3 -176.3(3)
C7 N1 C5 O3 -3.8(4)
O2 C5 O3 C6 -171.0(3)
N1 C5 O3 C6 10.3(4)
C5 O3 C6 C7 -12.3(4)
C5 N1 C7 C8 117.7(3)
C4 N1 C7 C8 -70.4(4)
C5 N1 C7 C6 -3.8(3)
C4 N1 C7 C6 168.1(3)
O3 C6 C7 N1 9.3(3)
O3 C6 C7 C8 -114.1(3)
N1 C7 C8 C13 -26.3(5)
C6 C7 C8 C13 88.5(4)
N1 C7 C8 C9 155.3(3)
C6 C7 C8 C9 -89.9(4)
C13 C8 C9 C10 -0.6(6)
C7 C8 C9 C10 177.8(4)
C8 C9 C10 C11 1.4(6)
C9 C10 C11 C12 -1.7(6)
C10 C11 C12 C13 1.2(6)
C9 C8 C13 C12 0.1(5)
C7 C8 C13 C12 -178.2(3)
C11 C12 C13 C8 -0.4(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30651637
