#------------------------------------------------------------------------------
#$Date: 2017-10-13 13:42:48 +0200 (vie 13 de oct de 2017) $
#$Revision: 201982 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/71/4027135.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_4027135
loop_
_publ_author_name
'Christian Reus'
'Nai-Wei Liu'
'Michael Bolte'
'Hans-Wolfram Lerner'
'Matthias Wagner'
_publ_section_title
;
 Synthesis of Bromo-, Boryl-, and Stannyl-Functionalized
 1,2-Bis(trimethylsilyl)benzenes via Diels-Alder or C-H Activation
 Reactions
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3518
_journal_page_last               3523
_journal_paper_doi               10.1021/jo3002936
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C5 H3 Br O2'
_chemical_formula_sum            'C5 H3 Br O2'
_chemical_formula_weight         174.98
_chemical_name_systematic        ?
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 97.688(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.0278(6)
_cell_length_b                   6.1571(5)
_cell_length_c                   11.2580(7)
_cell_measurement_reflns_used    8723
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.3
_cell_measurement_theta_min      2.5
_cell_volume                     551.46(7)
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_collection       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_molecular_graphics    'XP (Sheldrick, 2008)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008) '
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008) '
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_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  0.0432
_diffrn_reflns_av_sigmaI/netI    0.0248
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5222
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.61
_diffrn_reflns_theta_min         3.34
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    7.344
_exptl_absorpt_correction_T_max  0.4055
_exptl_absorpt_correction_T_min  0.3077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'MULABS (Spek, 2003; Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.108
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     73
_refine_ls_number_reflns         1036
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0216
_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)+(0.0287P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0482
_refine_ls_wR_factor_ref         0.0496
_reflns_number_gt                917
_reflns_number_total             1036
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo3002936_si_002_1.cif
_cod_data_source_block           wa1187
_cod_database_code               4027135
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
Br1 Br 0.43930(3) 0.80862(4) 0.62729(2) 0.04812(11) Uani 1 1 d .
O1 O 0.1713(3) 0.4819(3) 0.34685(15) 0.0506(4) Uani 1 1 d .
O2 O 0.0272(3) 0.1753(3) 0.32675(19) 0.0613(5) Uani 1 1 d .
C1 C 0.1099(3) 0.2958(4) 0.3957(2) 0.0474(6) Uani 1 1 d .
C2 C 0.1529(3) 0.2689(4) 0.5235(2) 0.0464(6) Uani 1 1 d .
H2 H 0.1132 0.1453 0.5617 0.056 Uiso 1 1 calc R
C3 C 0.2483(3) 0.4158(4) 0.5891(2) 0.0439(5) Uani 1 1 d .
H3 H 0.2768 0.3947 0.6730 0.053 Uiso 1 1 calc R
C4 C 0.3067(3) 0.6033(4) 0.5332(2) 0.0418(5) Uani 1 1 d .
C5 C 0.2672(4) 0.6310(4) 0.4151(2) 0.0480(6) Uani 1 1 d .
H5 H 0.3063 0.7562 0.3780 0.058 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
Br1 0.05229(17) 0.04703(15) 0.04548(15) -0.00447(11) 0.00808(10) -0.00363(12)
O1 0.0550(11) 0.0608(11) 0.0347(8) 0.0007(7) 0.0012(8) 0.0024(8)
O2 0.0600(12) 0.0706(13) 0.0512(10) -0.0149(10) 0.0001(9) -0.0073(10)
C1 0.0449(14) 0.0539(14) 0.0428(12) -0.0035(11) 0.0040(10) 0.0055(12)
C2 0.0485(15) 0.0464(12) 0.0438(12) 0.0024(10) 0.0041(11) -0.0001(10)
C3 0.0452(14) 0.0503(13) 0.0357(11) 0.0030(10) 0.0040(10) 0.0027(11)
C4 0.0441(14) 0.0429(11) 0.0378(11) -0.0025(9) 0.0040(10) 0.0011(10)
C5 0.0506(15) 0.0518(13) 0.0419(12) 0.0030(10) 0.0068(11) 0.0012(11)
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'
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
C5 O1 C1 122.3(2)
O2 C1 O1 116.5(2)
O2 C1 C2 127.5(3)
O1 C1 C2 116.0(2)
C3 C2 C1 121.0(2)
C3 C2 H2 119.5
C1 C2 H2 119.5
C2 C3 C4 120.0(2)
C2 C3 H3 120.0
C4 C3 H3 120.0
C5 C4 C3 119.7(2)
C5 C4 Br1 121.0(2)
C3 C4 Br1 119.32(17)
C4 C5 O1 121.0(2)
C4 C5 H5 119.5
O1 C5 H5 119.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C4 1.885(2)
O1 C5 1.366(3)
O1 C1 1.390(3)
O2 C1 1.207(3)
C1 C2 1.444(4)
C2 C3 1.341(4)
C2 H2 0.9500
C3 C4 1.424(4)
C3 H3 0.9500
C4 C5 1.336(3)
C5 H5 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
C5 O1 C1 O2 -179.7(3)
C5 O1 C1 C2 0.2(4)
O2 C1 C2 C3 179.2(3)
O1 C1 C2 C3 -0.7(4)
C1 C2 C3 C4 0.9(4)
C2 C3 C4 C5 -0.5(4)
C2 C3 C4 Br1 179.6(2)
C3 C4 C5 O1 0.0(4)
Br1 C4 C5 O1 179.87(19)
C1 O1 C5 C4 0.1(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9281009
