#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/66/1506668.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_1506668
loop_
_publ_author_name
'Kopp, Felix'
'Sklute, Genia'
'Polborn, Kurt'
'Marek, Ilan'
'Knochel, Paul'
_publ_contact_author
;
 Paul Knochel 
 Department Chemie
 Universität München
 Butenandtstr. 5-13
 D-81377 München
 Germany  
;
_publ_section_title
;
 Stereoselective functionalization of cyclopropane derivatives using
 bromine/magnesium and sulfoxide/magnesium exchange reactions.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              3789
_journal_page_last               3791
_journal_paper_doi               10.1021/ol051452p
_journal_volume                  7
_journal_year                    2005
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H11 Br O2'
_chemical_formula_sum            'C12 H11 Br O2'
_chemical_formula_weight         267.12
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             14-06-05
_audit_creation_method           SHELXL
_audit_update_record             ' ?'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.0914(14)
_cell_length_b                   24.615(5)
_cell_length_c                   6.3857(13)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      18
_cell_measurement_theta_min      9
_cell_volume                     1114.7(4)
_computing_cell_refinement       'CAD4 Operation Manual, Nonius, 1994'
_computing_data_collection       'CAD4 Operation Manual, Nonius, 1994'
_computing_data_reduction        OpenMolEN(Nonius,_1997)
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  Nonius_MACH3
_diffrn_measurement_method       ο-scan
_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  0.0153
_diffrn_reflns_av_sigmaI/netI    0.0296
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            2370
_diffrn_reflns_theta_full        26.28
_diffrn_reflns_theta_max         26.28
_diffrn_reflns_theta_min         2.99
_diffrn_standards_decay_%        3.4
_diffrn_standards_interval_time  7200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    3.664
_exptl_absorpt_correction_T_max  0.9980
_exptl_absorpt_correction_T_min  0.7025
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   OpenMolEN(Nonius,_1997)
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.529
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.012(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2206
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0340
_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)+(0.0516P)²+0.1809P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0780
_refine_ls_wR_factor_ref         0.0916
_reflns_number_gt                1709
_reflns_number_total             2206
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol051452psi20050622_082233.cif
_cod_data_source_block           kopp1
_cod_database_code               1506668
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, 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 1.14970(7) 0.334458(17) 0.00408(7) 0.05859(17) Uani 1 1 d .
O1 O 0.8646(4) 0.45269(12) 0.3065(5) 0.0418(7) Uani 1 1 d .
O2 O 1.0531(5) 0.52460(12) 0.3303(5) 0.0549(9) Uani 1 1 d .
C1 C 1.0803(6) 0.38452(16) 0.2171(6) 0.0354(9) Uani 1 1 d .
C2 C 1.1885(7) 0.3898(2) 0.4129(8) 0.0476(11) Uani 1 1 d .
H2A H 1.3038 0.3689 0.4262 0.057 Uiso 1 1 calc R
H2B H 1.1186 0.3947 0.5421 0.057 Uiso 1 1 calc R
C3 C 1.1854(6) 0.43621(18) 0.2536(7) 0.0415(10) Uani 1 1 d .
C4 C 1.0364(7) 0.47684(18) 0.2996(7) 0.0412(10) Uani 1 1 d .
C5 C 0.8713(5) 0.39764(15) 0.2296(6) 0.0323(9) Uani 1 1 d .
H5 H 0.8173 0.3965 0.0884 0.039 Uiso 1 1 calc R
C6 C 1.3601(7) 0.4548(2) 0.1449(9) 0.0576(14) Uani 1 1 d .
H6A H 1.4487 0.4254 0.1381 0.069 Uiso 1 1 calc R
H6B H 1.4147 0.4845 0.2210 0.069 Uiso 1 1 calc R
H6C H 1.3291 0.4665 0.0056 0.069 Uiso 1 1 calc R
C7 C 0.7573(6) 0.36089(18) 0.3718(7) 0.0351(10) Uani 1 1 d .
C8 C 0.7164(7) 0.3750(2) 0.5751(7) 0.0448(12) Uani 1 1 d .
H8 H 0.7580 0.4081 0.6278 0.054 Uiso 1 1 calc R
C9 C 0.6135(7) 0.3401(2) 0.7023(8) 0.0514(13) Uani 1 1 d .
H9 H 0.5836 0.3504 0.8385 0.062 Uiso 1 1 calc R
C10 C 0.5560(7) 0.2907(2) 0.6272(9) 0.0513(14) Uani 1 1 d .
H10 H 0.4886 0.2670 0.7125 0.062 Uiso 1 1 calc R
C11 C 0.5988(8) 0.2766(2) 0.4260(9) 0.0521(14) Uani 1 1 d .
H11 H 0.5608 0.2429 0.3754 0.063 Uiso 1 1 calc R
C12 C 0.6971(7) 0.31123(19) 0.2961(7) 0.0440(11) Uani 1 1 d .
H12 H 0.7227 0.3013 0.1585 0.053 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 0.0643(3) 0.0502(2) 0.0613(3) -0.0030(3) 0.0225(3) 0.0098(2)
O1 0.0383(17) 0.0330(15) 0.0542(18) -0.0006(13) 0.0083(14) -0.0008(13)
O2 0.069(2) 0.0385(18) 0.058(2) -0.0032(16) 0.0134(18) -0.0121(17)
C1 0.032(2) 0.035(2) 0.039(2) 0.0052(17) 0.0056(17) 0.0038(18)
C2 0.036(3) 0.057(3) 0.050(2) 0.016(2) -0.0065(18) 0.006(2)
C3 0.036(2) 0.043(2) 0.046(2) 0.0062(19) -0.0038(18) -0.0052(19)
C4 0.045(3) 0.042(2) 0.036(2) 0.0035(19) 0.004(2) -0.006(2)
C5 0.030(2) 0.033(2) 0.0344(19) -0.0014(16) -0.0010(16) 0.0022(17)
C6 0.037(3) 0.065(3) 0.071(4) 0.018(3) -0.003(2) -0.006(2)
C7 0.026(2) 0.043(2) 0.037(2) 0.0037(19) -0.0038(17) 0.0028(19)
C8 0.037(3) 0.048(3) 0.049(3) -0.0037(19) 0.0013(19) -0.011(2)
C9 0.046(3) 0.072(4) 0.036(2) 0.005(2) 0.004(2) -0.012(3)
C10 0.033(3) 0.049(3) 0.071(4) 0.018(3) 0.009(2) -0.005(2)
C11 0.048(3) 0.035(3) 0.073(3) -0.002(2) 0.006(2) -0.002(2)
C12 0.040(3) 0.038(2) 0.053(3) -0.010(2) 0.006(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'
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
C4 O1 C5 111.8(3)
C2 C1 C3 62.1(3)
C2 C1 C5 116.4(4)
C3 C1 C5 107.3(3)
C2 C1 Br1 122.0(3)
C3 C1 Br1 122.4(3)
C5 C1 Br1 115.4(3)
C1 C2 C3 59.6(3)
C4 C3 C6 118.5(4)
C4 C3 C1 104.4(3)
C6 C3 C1 127.1(4)
C4 C3 C2 112.4(4)
C6 C3 C2 121.8(4)
C1 C3 C2 58.3(3)
O2 C4 O1 120.9(4)
O2 C4 C3 128.6(5)
O1 C4 C3 110.5(4)
O1 C5 C7 109.9(3)
O1 C5 C1 104.4(3)
C7 C5 C1 115.2(3)
C8 C7 C12 119.2(5)
C8 C7 C5 121.9(4)
C12 C7 C5 118.9(4)
C7 C8 C9 120.5(5)
C10 C9 C8 120.0(5)
C11 C10 C9 119.3(5)
C10 C11 C12 121.4(5)
C11 C12 C7 119.6(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1 1.900(4)
O1 C4 1.356(5)
O1 C5 1.442(4)
O2 C4 1.198(5)
C1 C2 1.473(6)
C1 C3 1.493(6)
C1 C5 1.519(5)
C2 C3 1.529(6)
C3 C4 1.484(6)
C3 C6 1.492(6)
C5 C7 1.515(6)
C7 C8 1.374(6)
C7 C12 1.382(6)
C8 C9 1.388(7)
C9 C10 1.371(7)
C10 C11 1.365(7)
C11 C12 1.379(7)
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 C1 C2 C3 -96.5(4)
Br1 C1 C2 C3 112.5(4)
C2 C1 C3 C4 -107.7(4)
C5 C1 C3 C4 3.5(4)
Br1 C1 C3 C4 140.3(3)
C2 C1 C3 C6 108.0(5)
C5 C1 C3 C6 -140.8(4)
Br1 C1 C3 C6 -4.0(6)
C5 C1 C3 C2 111.2(4)
Br1 C1 C3 C2 -112.0(4)
C1 C2 C3 C4 93.6(4)
C1 C2 C3 C6 -116.8(5)
C5 O1 C4 O2 169.8(4)
C5 O1 C4 C3 -10.8(5)
C6 C3 C4 O2 -28.5(7)
C1 C3 C4 O2 -176.6(5)
C2 C3 C4 O2 122.2(5)
C6 C3 C4 O1 152.2(4)
C1 C3 C4 O1 4.2(5)
C2 C3 C4 O1 -57.1(5)
C4 O1 C5 C7 136.6(4)
C4 O1 C5 C1 12.5(4)
C2 C1 C5 O1 57.5(4)
C3 C1 C5 O1 -9.4(4)
Br1 C1 C5 O1 -149.6(3)
C2 C1 C5 C7 -63.1(5)
C3 C1 C5 C7 -129.9(4)
Br1 C1 C5 C7 89.8(4)
O1 C5 C7 C8 -21.3(6)
C1 C5 C7 C8 96.3(5)
O1 C5 C7 C12 160.4(4)
C1 C5 C7 C12 -82.0(5)
C12 C7 C8 C9 -0.9(7)
C5 C7 C8 C9 -179.2(5)
C7 C8 C9 C10 1.7(8)
C8 C9 C10 C11 -0.9(8)
C9 C10 C11 C12 -0.6(8)
C10 C11 C12 C7 1.4(8)
C8 C7 C12 C11 -0.6(7)
C5 C7 C12 C11 177.8(5)
