#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:53:44 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180321 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/35/7153567.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_7153567
loop_
_publ_author_name
'Lone, Ali Mohd'
'Bhat, Bilal Ahmad'
_publ_section_title
;
 Metal free stereoselective synthesis of functionalized enamides.
;
_journal_issue                   2
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              242
_journal_page_last               246
_journal_paper_doi               10.1039/c3ob41847b
_journal_volume                  12
_journal_year                    2014
_chemical_formula_sum            'C7 H5 Br N2 O2'
_chemical_formula_weight         229.04
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.8346(13)
_cell_length_b                   7.4175(9)
_cell_length_c                   17.3968(16)
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.0850
_cell_measurement_theta_min      3.3770
_cell_volume                     1656.2(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.870
_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  0.0347
_diffrn_reflns_av_sigmaI/netI    0.0443
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4895
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.02
_diffrn_reflns_theta_min         3.17
_exptl_absorpt_coefficient_mu    4.921
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46913
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.837
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.787
_refine_diff_density_min         -1.011
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         1921
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0437
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0402P)²+2.2597P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0936
_refine_ls_wR_factor_ref         0.1071
_reflns_number_gt                1324
_reflns_number_total             1921
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob41847b.txt
_cod_data_source_block           gm5
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               7153567
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'
'-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
C7 C 0.9117(4) 0.2160(6) 0.5815(2) 0.0359(10) Uani 1 1 d .
N2 N 0.9889(3) 0.2340(6) 0.5551(2) 0.0556(11) Uani 1 1 d .
H5 H 0.722(3) 0.109(6) 0.697(2) 0.035(11) Uiso 1 1 d .
Br1 Br 0.70195(4) 0.17905(6) 0.53891(3) 0.04529(18) Uani 1 1 d .
C6 C 0.8096(3) 0.1821(5) 0.6119(2) 0.0309(9) Uani 1 1 d .
C4 C 0.9201(3) 0.3135(5) 0.7601(2) 0.0310(9) Uani 1 1 d .
N1 N 0.8551(2) 0.1656(4) 0.74656(18) 0.0276(7) Uani 1 1 d .
C5 C 0.7875(3) 0.1488(5) 0.6847(2) 0.0316(9) Uani 1 1 d .
O1 O 0.9371(2) 0.4290(4) 0.71350(17) 0.0431(7) Uani 1 1 d .
O2 O 0.7812(3) -0.0602(5) 0.8150(2) 0.0611(10) Uani 1 1 d .
C2 C 0.8996(3) 0.1459(6) 0.8764(2) 0.0400(10) Uani 1 1 d .
H2A H 0.9476 0.0580 0.8976 0.048 Uiso 1 1 calc R
H2B H 0.8543 0.1886 0.9172 0.048 Uiso 1 1 calc R
C1 C 0.8381(3) 0.0663(6) 0.8135(2) 0.0361(10) Uani 1 1 d .
C3 C 0.9582(4) 0.3010(6) 0.8404(3) 0.0420(11) Uani 1 1 d .
H3A H 0.9444 0.4121 0.8679 0.050 Uiso 1 1 calc R
H3B H 1.0326 0.2782 0.8413 0.050 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C7 0.040(2) 0.042(3) 0.026(2) 0.0021(18) -0.0054(19) 0.005(2)
N2 0.042(2) 0.077(3) 0.048(3) 0.000(2) 0.005(2) 0.005(2)
Br1 0.0430(3) 0.0589(3) 0.0339(2) 0.0040(2) -0.0116(2) -0.0098(2)
C6 0.027(2) 0.038(2) 0.0280(19) -0.0001(18) -0.0044(17) -0.0041(17)
C4 0.0235(19) 0.036(2) 0.033(2) -0.0043(19) -0.0015(17) 0.0019(18)
N1 0.0257(17) 0.0318(17) 0.0254(15) -0.0005(14) -0.0014(13) -0.0013(14)
C5 0.028(2) 0.034(2) 0.033(2) 0.0004(17) -0.0028(18) -0.0059(18)
O1 0.0415(18) 0.0447(17) 0.0432(17) 0.0063(15) -0.0006(14) -0.0127(14)
O2 0.075(2) 0.061(2) 0.047(2) 0.0179(17) -0.0122(18) -0.034(2)
C2 0.043(2) 0.049(3) 0.028(2) -0.004(2) -0.005(2) 0.007(2)
C1 0.034(2) 0.044(3) 0.030(2) 0.0039(19) -0.0021(18) 0.000(2)
C3 0.042(2) 0.041(3) 0.043(2) -0.004(2) -0.013(2) -0.003(2)
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'
Br Br -0.2901 2.4595 '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
N2 C7 C6 175.8(5)
C5 C6 C7 125.5(4)
C5 C6 Br1 119.3(3)
C7 C6 Br1 115.2(3)
O1 C4 N1 123.7(4)
O1 C4 C3 128.5(4)
N1 C4 C3 107.9(3)
C5 N1 C1 120.2(3)
C5 N1 C4 125.0(3)
C1 N1 C4 111.5(3)
C6 C5 N1 126.4(4)
C1 C2 C3 105.3(3)
O2 C1 N1 122.1(4)
O2 C1 C2 129.0(4)
N1 C1 C2 109.0(4)
C4 C3 C2 105.9(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C7 N2 1.101(6)
C7 C6 1.435(6)
Br1 C6 1.876(4)
C6 C5 1.322(6)
C4 O1 1.199(5)
C4 N1 1.399(5)
C4 C3 1.482(6)
N1 C5 1.387(5)
N1 C1 1.394(5)
O2 C1 1.189(5)
C2 C1 1.473(6)
C2 C3 1.511(6)
