#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:19:43 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178778 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/32/4103236.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_4103236
loop_
_publ_author_name
'Scott A. Snyder'
'Daniel S. Treitler'
'Alexandria P. Brucks'
_publ_section_title
;
 Simple Reagents for Direct Halonium-Induced Polyene Cyclizations
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14303
_journal_page_last               14314
_journal_paper_doi               10.1021/ja106813s
_journal_volume                  132
_journal_year                    2010
_chemical_formula_sum            'C12 H21 Br O3'
_chemical_formula_weight         293.20
_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                97.1190(10)
_cell_angle_beta                 98.8340(10)
_cell_angle_gamma                109.6280(10)
_cell_formula_units_Z            2
_cell_length_a                   6.5204(3)
_cell_length_b                   7.5841(3)
_cell_length_c                   14.6753(7)
_cell_measurement_reflns_used    7192
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      32.24
_cell_measurement_theta_min      2.86
_cell_volume                     663.32(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.928
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0171
_diffrn_reflns_av_sigmaI/netI    0.0202
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11494
_diffrn_reflns_theta_full        32.68
_diffrn_reflns_theta_max         32.68
_diffrn_reflns_theta_min         1.43
_exptl_absorpt_coefficient_mu    3.090
_exptl_absorpt_correction_T_max  0.5769
_exptl_absorpt_correction_T_min  0.3712
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.746
_refine_diff_density_min         -0.530
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         4517
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0281
_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)+(0.0338P)²+0.1943P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0680
_refine_ls_wR_factor_ref         0.0721
_reflns_number_gt                3708
_reflns_number_total             4517
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja106813s_si_003.cif
_cod_data_source_block           dt58s10
_cod_database_code               4103236
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
Br Br 0.88235(3) 0.67087(3) 0.542798(10) 0.04418(6) Uani 1 1 d .
O1 O 0.79541(18) 1.12911(15) 0.80131(8) 0.0376(2) Uani 1 1 d .
H1A H 0.8587 1.2455 0.8250 0.056 Uiso 1 1 calc R
O2 O 1.06706(17) 0.83250(13) 0.92853(7) 0.0306(2) Uani 1 1 d .
O3 O 0.9982(2) 0.52413(17) 0.88266(11) 0.0582(4) Uani 1 1 d .
C1 C 0.6703(2) 0.7646(2) 0.59987(10) 0.0335(3) Uani 1 1 d .
H1B H 0.5191 0.6994 0.5584 0.040 Uiso 1 1 calc R
C2 C 0.7399(3) 0.9765(2) 0.59877(11) 0.0416(3) Uani 1 1 d .
H2A H 0.6228 1.0221 0.6159 0.050 Uiso 1 1 calc R
H2B H 0.7543 0.9978 0.5345 0.050 Uiso 1 1 calc R
C3 C 0.9591(3) 1.0903(2) 0.66648(11) 0.0383(3) Uani 1 1 d .
H3A H 0.9949 1.2276 0.6655 0.046 Uiso 1 1 calc R
H3B H 1.0788 1.0538 0.6454 0.046 Uiso 1 1 calc R
C4 C 0.9530(2) 1.05781(18) 0.76715(9) 0.0285(2) Uani 1 1 d .
C5 C 0.8737(2) 0.84182(17) 0.77065(8) 0.0239(2) Uani 1 1 d .
H5A H 0.9942 0.7971 0.7550 0.029 Uiso 1 1 calc R
C6 C 0.6565(2) 0.71511(19) 0.69806(9) 0.0278(2) Uani 1 1 d .
C7 C 1.1845(2) 1.1652(2) 0.82917(11) 0.0355(3) Uani 1 1 d .
H7A H 1.2365 1.2983 0.8211 0.053 Uiso 1 1 calc R
H7B H 1.2881 1.1057 0.8111 0.053 Uiso 1 1 calc R
H7C H 1.1773 1.1602 0.8951 0.053 Uiso 1 1 calc R
C8 C 0.8543(2) 0.8109(2) 0.87064(9) 0.0284(2) Uani 1 1 d .
H8A H 0.7964 0.9038 0.9002 0.034 Uiso 1 1 calc R
H8B H 0.7461 0.6813 0.8678 0.034 Uiso 1 1 calc R
C9 C 1.1187(2) 0.6771(2) 0.92782(10) 0.0320(3) Uani 1 1 d .
C10 C 1.3417(3) 0.7187(3) 0.98905(12) 0.0424(3) Uani 1 1 d .
H10A H 1.3728 0.6008 0.9879 0.064 Uiso 1 1 calc R
H10B H 1.3415 0.7708 1.0536 0.064 Uiso 1 1 calc R
H10C H 1.4567 0.8118 0.9657 0.064 Uiso 1 1 calc R
C11 C 0.4459(2) 0.7437(3) 0.72187(12) 0.0403(3) Uani 1 1 d .
H11A H 0.3155 0.6618 0.6737 0.061 Uiso 1 1 calc R
H11B H 0.4617 0.8773 0.7238 0.061 Uiso 1 1 calc R
H11C H 0.4269 0.7101 0.7832 0.061 Uiso 1 1 calc R
C12 C 0.6196(3) 0.5024(2) 0.69398(11) 0.0387(3) Uani 1 1 d .
H12A H 0.5018 0.4260 0.6396 0.058 Uiso 1 1 calc R
H12B H 0.5756 0.4641 0.7516 0.058 Uiso 1 1 calc R
H12C H 0.7580 0.4818 0.6882 0.058 Uiso 1 1 calc R
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
C9 O2 C8 116.95(11)
C2 C1 C6 113.94(12)
C2 C1 Br 107.51(11)
C6 C1 Br 111.75(10)
C1 C2 C3 111.78(13)
C2 C3 C4 112.33(13)
O1 C4 C3 109.18(12)
O1 C4 C7 109.46(11)
C3 C4 C7 108.96(12)
O1 C4 C5 107.04(11)
C3 C4 C5 111.05(11)
C7 C4 C5 111.10(11)
C8 C5 C4 110.46(10)
C8 C5 C6 111.32(11)
C4 C5 C6 114.95(11)
C1 C6 C12 109.67(11)
C1 C6 C11 106.23(12)
C12 C6 C11 107.00(12)
C1 C6 C5 110.28(11)
C12 C6 C5 110.38(11)
C11 C6 C5 113.12(11)
O2 C8 C5 112.31(11)
O3 C9 O2 122.82(14)
O3 C9 C10 125.49(15)
O2 C9 C10 111.69(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br C1 1.9969(15)
O1 C4 1.4365(17)
O2 C9 1.3296(17)
O2 C8 1.4576(16)
O3 C9 1.1996(19)
C1 C2 1.519(2)
C1 C6 1.5417(19)
C2 C3 1.516(2)
C3 C4 1.532(2)
C4 C7 1.529(2)
C4 C5 1.5535(18)
C5 C8 1.5319(18)
C5 C6 1.5596(17)
C6 C12 1.541(2)
C6 C11 1.544(2)
C9 C10 1.497(2)
