#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/86/1508623.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_1508623
loop_
_publ_author_name
'Zhou, Wei'
'Xie, Chen'
'Han, Jianlin'
'Pan, Yi'
_publ_section_title
;
 Catalyst-free intramolecular oxidative cyclization of N-allylbenzamides:
 a new route to 2,5-substituted oxazoles.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4766
_journal_page_last               4769
_journal_paper_doi               10.1021/ol302031z
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C10 H7 Br Cl N O'
_chemical_formula_sum            'C10 H7 Br Cl N O'
_chemical_formula_weight         272.53
_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                91.074(3)
_cell_angle_beta                 99.011(2)
_cell_angle_gamma                102.439(3)
_cell_formula_units_Z            2
_cell_length_a                   5.7402(11)
_cell_length_b                   7.5688(13)
_cell_length_c                   12.262(2)
_cell_measurement_reflns_used    1792
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      28.00
_cell_measurement_theta_min      3.31
_cell_volume                     513.05(16)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker Smart Apex CCD'
_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  0.0796
_diffrn_reflns_av_sigmaI/netI    0.0608
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3218
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.15
_exptl_absorpt_coefficient_mu    4.229
_exptl_absorpt_correction_T_max  0.605
_exptl_absorpt_correction_T_min  0.494
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'
_exptl_crystal_density_diffrn    1.764
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.573
_refine_diff_density_min         -0.564
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       0.274(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2090
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0412
_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)+(0.06P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1047
_reflns_number_gt                1696
_reflns_number_total             2090
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol302031z_si_002.cif
_cod_data_source_block           20120307a_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        513.06(16)
_cod_original_sg_symbol_H-M      'P-1   '
_cod_database_code               1508623
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
Br1 Br 0.02230(6) 0.24221(5) 0.06146(2) 0.0669(2) Uani 1 1 d .
C1 C 0.2547(5) 0.3254(4) 0.5442(2) 0.0462(7) Uani 1 1 d .
H1 H 0.3237 0.3848 0.4874 0.055 Uiso 1 1 calc R
C2 C 0.3956(5) 0.3237(4) 0.6466(3) 0.0525(7) Uani 1 1 d .
H2 H 0.5583 0.3816 0.6591 0.063 Uiso 1 1 calc R
C3 C 0.2914(5) 0.2357(4) 0.7288(2) 0.0478(7) Uani 1 1 d .
C4 C 0.0505(6) 0.1489(4) 0.7129(2) 0.0482(7) Uani 1 1 d .
H4 H -0.0170 0.0899 0.7701 0.058 Uiso 1 1 calc R
C5 C -0.0891(5) 0.1508(4) 0.6105(2) 0.0442(6) Uani 1 1 d .
H5 H -0.2517 0.0923 0.5984 0.053 Uiso 1 1 calc R
C6 C 0.0128(4) 0.2398(3) 0.5255(2) 0.0372(6) Uani 1 1 d .
C7 C -0.1345(5) 0.2419(3) 0.4178(2) 0.0394(6) Uani 1 1 d .
C8 C -0.4094(6) 0.2166(5) 0.2783(3) 0.0549(8) Uani 1 1 d .
H8 H -0.5601 0.1868 0.2334 0.066 Uiso 1 1 calc R
C9 C -0.2057(6) 0.3054(4) 0.2464(2) 0.0489(7) Uani 1 1 d .
C10 C -0.1445(7) 0.3864(5) 0.1445(3) 0.0614(8) Uani 1 1 d .
H10A H -0.0419 0.5063 0.1627 0.074 Uiso 1 1 calc R
H10B H -0.2917 0.4001 0.0979 0.074 Uiso 1 1 calc R
Cl1 Cl 0.47203(18) 0.23084(14) 0.85660(7) 0.0732(3) Uani 1 1 d .
N1 N -0.3629(4) 0.1753(3) 0.3883(2) 0.0501(6) Uani 1 1 d .
O1 O -0.0233(4) 0.3240(3) 0.33584(16) 0.0442(5) Uani 1 1 d .
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
Br1 0.0791(3) 0.0927(4) 0.0360(2) 0.01300(16) 0.01119(17) 0.0327(2)
C1 0.0395(15) 0.0575(16) 0.0382(16) 0.0060(12) 0.0112(12) -0.0004(13)
C2 0.0399(15) 0.0634(18) 0.0495(18) -0.0054(14) 0.0043(13) 0.0039(14)
C3 0.0488(16) 0.0540(16) 0.0395(16) -0.0012(12) 0.0021(13) 0.0126(13)
C4 0.0527(17) 0.0555(16) 0.0376(15) 0.0088(12) 0.0135(13) 0.0094(14)
C5 0.0394(14) 0.0497(15) 0.0424(16) 0.0046(12) 0.0118(12) 0.0033(12)
C6 0.0389(13) 0.0405(13) 0.0323(13) 0.0004(10) 0.0095(11) 0.0067(11)
C7 0.0400(15) 0.0428(14) 0.0358(14) 0.0023(11) 0.0110(11) 0.0065(11)
C8 0.0449(16) 0.069(2) 0.0472(18) 0.0023(15) -0.0013(14) 0.0111(15)
C9 0.0545(17) 0.0569(17) 0.0359(15) 0.0029(12) 0.0019(13) 0.0178(14)
C10 0.083(2) 0.0659(19) 0.0394(17) 0.0121(14) 0.0073(16) 0.0264(18)
Cl1 0.0747(6) 0.0958(7) 0.0423(5) 0.0000(4) -0.0102(4) 0.0184(5)
N1 0.0377(12) 0.0606(15) 0.0483(15) 0.0045(11) 0.0059(11) 0.0036(11)
O1 0.0454(10) 0.0523(10) 0.0333(10) 0.0068(8) 0.0079(8) 0.0058(9)
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'
Cl Cl 0.1484 0.1585 '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
C6 C1 C2 120.6(3)
C6 C1 H1 119.7
C2 C1 H1 119.7
C3 C2 C1 118.9(3)
C3 C2 H2 120.6
C1 C2 H2 120.6
C2 C3 C4 121.9(3)
C2 C3 Cl1 118.4(2)
C4 C3 Cl1 119.7(2)
C3 C4 C5 119.0(3)
C3 C4 H4 120.5
C5 C4 H4 120.5
C4 C5 C6 120.1(3)
C4 C5 H5 119.9
C6 C5 H5 119.9
C1 C6 C5 119.4(3)
C1 C6 C7 120.5(2)
C5 C6 C7 120.1(2)
N1 C7 O1 114.1(2)
N1 C7 C6 128.1(2)
O1 C7 C6 117.7(2)
C9 C8 N1 110.0(3)
C9 C8 H8 125.0
N1 C8 H8 125.0
C8 C9 O1 107.5(3)
C8 C9 C10 134.8(3)
O1 C9 C10 117.6(3)
C9 C10 Br1 113.1(2)
C9 C10 H10A 109.0
Br1 C10 H10A 109.0
C9 C10 H10B 109.0
Br1 C10 H10B 109.0
H10A C10 H10B 107.8
C7 N1 C8 104.1(3)
C7 O1 C9 104.2(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C10 1.964(3)
C1 C6 1.381(4)
C1 C2 1.385(4)
C1 H1 0.9300
C2 C3 1.364(4)
C2 H2 0.9300
C3 C4 1.379(4)
C3 Cl1 1.744(3)
C4 C5 1.382(4)
C4 H4 0.9300
C5 C6 1.389(4)
C5 H5 0.9300
C6 C7 1.455(4)
C7 N1 1.290(4)
C7 O1 1.362(3)
C8 C9 1.337(5)
C8 N1 1.389(4)
C8 H8 0.9300
C9 O1 1.375(3)
C9 C10 1.460(4)
C10 H10A 0.9700
C10 H10B 0.9700
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
C6 C1 C2 C3 0.1(5)
C1 C2 C3 C4 -0.1(5)
C1 C2 C3 Cl1 178.8(2)
C2 C3 C4 C5 0.2(4)
Cl1 C3 C4 C5 -178.7(2)
C3 C4 C5 C6 -0.3(4)
C2 C1 C6 C5 -0.2(4)
C2 C1 C6 C7 -180.0(3)
C4 C5 C6 C1 0.3(4)
C4 C5 C6 C7 -179.9(2)
C1 C6 C7 N1 -177.0(3)
C5 C6 C7 N1 3.2(4)
C1 C6 C7 O1 2.7(4)
C5 C6 C7 O1 -177.1(2)
N1 C8 C9 O1 -0.3(4)
N1 C8 C9 C10 -177.7(3)
C8 C9 C10 Br1 -105.0(4)
O1 C9 C10 Br1 77.7(3)
O1 C7 N1 C8 -0.4(3)
C6 C7 N1 C8 179.4(3)
C9 C8 N1 C7 0.4(3)
N1 C7 O1 C9 0.2(3)
C6 C7 O1 C9 -179.6(2)
C8 C9 O1 C7 0.1(3)
C10 C9 O1 C7 178.0(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652024
