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#$Date: 2016-03-21 18:11:13 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178804 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/58/4105874.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_4105874
loop_
_publ_author_name
'Jørn H. Hansen'
'Timothy M. Gregg'
'Stephanie R. Ovalles'
'Yajing Lian'
'Jochen Autschbach'
'Huw M. L. Davies'
_publ_section_title
;
 On the Mechanism and Selectivity of the Combined C-H Activation/Cope
 Rearrangement
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5076
_journal_page_last               5085
_journal_paper_doi               10.1021/ja111408v
_journal_volume                  133
_journal_year                    2011
_chemical_formula_sum            'C16 H15 Br O2'
_chemical_formula_weight         319.19
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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            4
_cell_length_a                   5.9374(4)
_cell_length_b                   8.0353(5)
_cell_length_c                   28.7626(19)
_cell_measurement_reflns_used    74
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      27.00
_cell_measurement_theta_min      3.00
_cell_volume                     1372.23(16)
_computing_cell_refinement       SMART
_computing_data_collection       SMART
_computing_data_reduction        SAINT
_computing_molecular_graphics    XP
_computing_publication_material  XCIF
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.941
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_device_type  'SMART CCD'
_diffrn_measurement_method       'omega oscillation'
_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  0.0612
_diffrn_reflns_av_sigmaI/netI    0.0738
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            8566
_diffrn_reflns_theta_full        28.75
_diffrn_reflns_theta_max         28.75
_diffrn_reflns_theta_min         2.63
_exptl_absorpt_coefficient_mu    2.990
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_description       needle
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.004(10)
_refine_ls_extinction_coef       0.0076(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.927
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3239
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.927
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0337
_refine_ls_shift/su_max          0.136
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0200P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0594
_refine_ls_wR_factor_ref         0.0629
_reflns_number_gt                2682
_reflns_number_total             3239
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja111408v_si_003.cif
_cod_data_source_block           a1
_cod_database_code               4105874
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'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
Br1 Br 0.55155(6) -0.17453(4) 1.063419(12) 0.02451(11) Uani 1 1 d
O1 O 0.5726(4) 0.5650(3) 0.83894(7) 0.0246(5) Uani 1 1 d
C3 C 0.6713(5) 0.0467(4) 0.93615(13) 0.0187(6) Uani 1 1 d
O2 O 0.6119(4) 0.4534(3) 0.76786(8) 0.0248(6) Uani 1 1 d
C8 C 0.8409(5) 0.3270(4) 0.87666(10) 0.0169(6) Uani 1 1 d
C2 C 0.5716(6) -0.0399(4) 0.97225(11) 0.0180(7) Uani 1 1 d
C15 C 0.6596(5) 0.4564(4) 0.80876(11) 0.0200(7) Uani 1 1 d
C12 C 0.8219(5) 0.3396(4) 0.83073(10) 0.0164(6) Uani 1 1 d
C11 C 0.9545(6) 0.2210(3) 0.79946(11) 0.0191(7) Uani 1 1 d
C1 C 0.6861(6) -0.0546(4) 1.01384(11) 0.0193(7) Uani 1 1 d
C14 C 0.9264(6) -0.0250(4) 0.84064(11) 0.0187(7) Uani 1 1 d
C5 C 0.9931(5) 0.1031(4) 0.98361(12) 0.0179(8) Uani 1 1 d
C4 C 0.8851(4) 0.1170(3) 0.94110(12) 0.0155(7) Uani 1 1 d
C6 C 0.8951(5) 0.0162(4) 1.02008(12) 0.0186(8) Uani 1 1 d
C13 C 0.8450(5) 0.0499(4) 0.80375(12) 0.0199(7) Uani 1 1 d
C10 C 1.1819(5) 0.1884(5) 0.82306(12) 0.0210(7) Uani 1 1 d
C16 C 0.4060(7) 0.6779(6) 0.81979(16) 0.0340(9) Uani 1 1 d
C7 C 0.9973(5) 0.2042(4) 0.90035(11) 0.0178(7) Uani 1 1 d
C9 C 1.1033(5) 0.0829(4) 0.86440(12) 0.0187(7) Uani 1 1 d
H2 H 0.439(5) -0.084(3) 0.9673(9) 0.004(7) Uiso 1 1 d
H3 H 0.599(4) 0.058(3) 0.9081(9) 0.000(7) Uiso 1 1 d
H6 H 0.958(5) 0.002(3) 1.0486(10) 0.018(9) Uiso 1 1 d
H11 H 0.962(5) 0.270(3) 0.7676(9) 0.009(7) Uiso 1 1 d
H5 H 1.137(5) 0.146(4) 0.9866(11) 0.017(9) Uiso 1 1 d
H16A H 0.364(7) 0.747(5) 0.8418(14) 0.049(14) Uiso 1 1 d
H16B H 0.269(6) 0.611(4) 0.8078(12) 0.033(11) Uiso 1 1 d
H8 H 0.753(4) 0.396(3) 0.8981(10) 0.004(7) Uiso 1 1 d
H10A H 1.258(5) 0.285(4) 0.8320(10) 0.016(9) Uiso 1 1 d
H14 H 0.885(5) -0.130(4) 0.8537(10) 0.014(8) Uiso 1 1 d
H16C H 0.455(7) 0.723(4) 0.7934(14) 0.046(12) Uiso 1 1 d
H13 H 0.728(5) 0.016(4) 0.7809(11) 0.027(10) Uiso 1 1 d
H10B H 1.273(5) 0.129(4) 0.8016(10) 0.010(8) Uiso 1 1 d
H9 H 1.227(6) 0.023(5) 0.8809(12) 0.038(11) Uiso 1 1 d
H7 H 1.129(5) 0.272(4) 0.9130(11) 0.022(9) Uiso 1 1 d
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
C15 O1 C16 115.2(3)
C2 C3 C4 121.1(3)
C12 C8 C7 123.2(3)
C1 C2 C3 118.9(3)
O2 C15 O1 123.7(3)
O2 C15 C12 123.6(3)
O1 C15 C12 112.8(3)
C8 C12 C15 121.7(3)
C8 C12 C11 119.6(3)
C15 C12 C11 118.5(3)
C13 C11 C12 107.1(3)
C13 C11 C10 100.7(3)
C12 C11 C10 107.4(3)
C6 C1 C2 121.4(3)
C6 C1 Br1 119.4(3)
C2 C1 Br1 119.2(2)
C13 C14 C9 110.9(3)
C4 C5 C6 120.9(3)
C5 C4 C3 118.6(3)
C5 C4 C7 121.0(3)
C3 C4 C7 120.4(3)
C1 C6 C5 119.1(3)
C14 C13 C11 108.7(3)
C9 C10 C11 99.8(2)
C8 C7 C4 112.2(2)
C8 C7 C9 110.9(3)
C4 C7 C9 113.7(2)
C14 C9 C10 100.1(3)
C14 C9 C7 112.1(2)
C10 C9 C7 107.0(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1 1.897(3)
O1 C15 1.335(4)
O1 C16 1.451(4)
C3 C2 1.383(5)
C3 C4 1.397(4)
O2 C15 1.210(4)
C8 C12 1.330(4)
C8 C7 1.517(4)
C2 C1 1.381(4)
C15 C12 1.486(4)
C12 C11 1.529(4)
C11 C13 1.526(4)
C11 C10 1.533(4)
C1 C6 1.377(4)
C14 C13 1.312(4)
C14 C9 1.524(4)
C5 C4 1.385(4)
C5 C6 1.388(5)
C4 C7 1.519(4)
C10 C9 1.533(5)
C7 C9 1.554(4)
