#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:35:49 +0100 (lun 21 de mar de 2016) $
#$Revision: 178486 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/07/4030753.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_4030753
loop_
_publ_author_name
'Lin, Mei-Huey'
'Li, Yi-Syuan'
'Kuo, Chung-Kai'
'Chen, Chung-Hao'
'Huang, Yen-Chih'
'Liang, Kung-Yu'
'Chen, Yu-Chun'
'Tsai, Chang-Hsien'
'Chuang, Tsung-Hsun'
_publ_section_title
;
 Synthesis of Hexahydro-1H-isoindole Derivatives from Arylacyl Bromides
 via Homoallenic Bromohydrins.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2462
_journal_page_last               2466
_journal_paper_doi               10.1021/acs.joc.5b00072
_journal_volume                  80
_journal_year                    2015
_chemical_formula_sum            'C12 H12 Br2 O'
_chemical_formula_weight         332.04
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 92.316(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.9526(6)
_cell_length_b                   5.4114(2)
_cell_length_c                   16.5276(6)
_cell_measurement_reflns_used    2359
_cell_measurement_temperature    270(2)
_cell_measurement_theta_max      22.91
_cell_measurement_theta_min      3.75
_cell_volume                     1246.87(8)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'DIAMOND (Brandenburg, 2006)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      270(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_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  0.0400
_diffrn_reflns_av_sigmaI/netI    0.0397
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12850
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.82
_exptl_absorpt_coefficient_mu    6.473
_exptl_absorpt_correction_T_max  0.6255
_exptl_absorpt_correction_T_min  0.5105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2.10 (Sheldrick, 2003)'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.769
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.607
_refine_diff_density_min         -0.795
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         3078
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0372
_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)+(0.0428P)²+0.3489P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0852
_refine_ls_wR_factor_ref         0.0967
_reflns_number_gt                1958
_reflns_number_total             3078
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b00072_si_001.cif
_cod_data_source_block           lys
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3086 2015-02-26 13:12:21Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4030753
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Br2 Br 0.64894(4) 0.16584(9) 0.51520(2) 0.07910(18) Uani 1 1 d .
Br1 Br 0.61352(3) -0.14463(6) 0.85381(2) 0.05947(15) Uani 1 1 d .
O1 O 1.06964(17) 0.2454(5) 0.93732(14) 0.0570(6) Uani 1 1 d .
C11 C 0.6572(3) -0.0361(7) 0.6106(2) 0.0521(8) Uani 1 1 d .
C10 C 0.7380(2) 0.0316(6) 0.66432(19) 0.0471(8) Uani 1 1 d .
H12 H 0.7984 0.0294 0.6425 0.056 Uiso 1 1 calc R
C8 C 0.7338(2) 0.0965(5) 0.74207(19) 0.0410(7) Uani 1 1 d .
C4 C 0.8220(2) 0.1349(5) 0.79330(19) 0.0389(7) Uani 1 1 d .
C3 C 0.8340(2) 0.3357(5) 0.8455(2) 0.0424(7) Uani 1 1 d .
H4 H 0.7848 0.4505 0.8491 0.051 Uiso 1 1 calc R
C2 C 0.9164(2) 0.3674(5) 0.8914(2) 0.0451(8) Uani 1 1 d .
H3 H 0.9229 0.5041 0.9253 0.054 Uiso 1 1 calc R
C1 C 0.9906(2) 0.1974(5) 0.8881(2) 0.0414(7) Uani 1 1 d .
C7 C 1.1422(3) 0.0614(7) 0.9434(2) 0.0643(10) Uani 1 1 d .
H5 H 1.1701 0.0404 0.8917 0.096 Uiso 1 1 calc R
H7 H 1.1145 -0.0920 0.9600 0.096 Uiso 1 1 calc R
H6 H 1.1909 0.1115 0.9827 0.096 Uiso 1 1 calc R
C12 C 0.5955(3) -0.2157(8) 0.6185(3) 0.0770(12) Uani 1 1 d .
H10 H 0.6006 -0.3197 0.6633 0.092 Uiso 1 1 calc R
H11 H 0.5466 -0.2395 0.5794 0.092 Uiso 1 1 calc R
C9 C 0.6402(2) 0.1339(5) 0.7811(2) 0.0474(8) Uani 1 1 d .
H8 H 0.5891 0.1470 0.7397 0.057 Uiso 1 1 calc R
H9 H 0.6421 0.2867 0.8118 0.057 Uiso 1 1 calc R
C6 C 0.9816(2) -0.0015(6) 0.83613(19) 0.0444(8) Uani 1 1 d .
H1 H 1.0313 -0.1147 0.8323 0.053 Uiso 1 1 calc R
C5 C 0.8984(2) -0.0298(5) 0.79035(19) 0.0437(8) Uani 1 1 d .
H2 H 0.8926 -0.1650 0.7558 0.052 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
Br2 0.0828(4) 0.1034(4) 0.0499(3) 0.0081(2) -0.0129(2) -0.0240(3)
Br1 0.0567(3) 0.0570(2) 0.0661(3) 0.00395(17) 0.01945(19) 0.00199(17)
O1 0.0432(15) 0.0653(14) 0.0615(16) -0.0079(12) -0.0106(12) 0.0058(12)
C11 0.044(2) 0.067(2) 0.0453(19) -0.0051(17) 0.0010(16) -0.0045(17)
C10 0.043(2) 0.0513(17) 0.047(2) -0.0022(15) 0.0034(16) -0.0075(15)
C8 0.043(2) 0.0357(15) 0.0446(19) 0.0019(13) 0.0032(15) 0.0009(12)
C4 0.0376(18) 0.0376(14) 0.0420(17) 0.0020(13) 0.0069(14) 0.0019(13)
C3 0.0389(19) 0.0388(15) 0.0499(19) -0.0046(14) 0.0057(15) 0.0070(13)
C2 0.047(2) 0.0428(16) 0.0454(19) -0.0069(14) 0.0009(16) 0.0036(15)
C1 0.039(2) 0.0431(16) 0.0422(18) 0.0036(13) 0.0012(15) -0.0010(13)
C7 0.048(2) 0.077(2) 0.068(3) 0.008(2) -0.007(2) 0.009(2)
C12 0.065(3) 0.087(3) 0.079(3) 0.005(2) -0.009(2) -0.026(2)
C9 0.045(2) 0.0439(16) 0.053(2) 0.0022(14) 0.0015(16) 0.0055(14)
C6 0.0394(19) 0.0428(16) 0.0511(19) 0.0003(14) 0.0047(16) 0.0076(14)
C5 0.047(2) 0.0396(15) 0.0454(18) -0.0086(14) 0.0067(16) 0.0001(14)
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
C1 O1 C7 117.6(3)
C12 C11 C10 128.5(4)
C12 C11 Br2 119.2(3)
C10 C11 Br2 112.2(2)
C8 C10 C11 126.2(3)
C8 C10 H12 116.9
C11 C10 H12 116.9
C10 C8 C4 121.3(3)
C10 C8 C9 121.6(3)
C4 C8 C9 117.1(3)
C5 C4 C3 116.6(3)
C5 C4 C8 120.7(3)
C3 C4 C8 122.7(3)
C2 C3 C4 121.4(3)
C2 C3 H4 119.3
C4 C3 H4 119.3
C3 C2 C1 120.6(3)
C3 C2 H3 119.7
C1 C2 H3 119.7
O1 C1 C6 124.8(3)
O1 C1 C2 115.8(3)
C6 C1 C2 119.4(3)
O1 C7 H5 109.5
O1 C7 H7 109.5
H5 C7 H7 109.5
O1 C7 H6 109.5
H5 C7 H6 109.5
H7 C7 H6 109.5
C11 C12 H10 120.0
C11 C12 H11 120.0
H10 C12 H11 120.0
C8 C9 Br1 110.4(2)
C8 C9 H8 109.6
Br1 C9 H8 109.6
C8 C9 H9 109.6
Br1 C9 H9 109.6
H8 C9 H9 108.1
C5 C6 C1 119.1(3)
C5 C6 H1 120.5
C1 C6 H1 120.5
C6 C5 C4 122.9(3)
C6 C5 H2 118.6
C4 C5 H2 118.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br2 C11 1.918(4)
Br1 C9 1.972(3)
O1 C1 1.368(4)
O1 C7 1.420(4)
C11 C12 1.309(5)
C11 C10 1.453(5)
C10 C8 1.336(4)
C10 H12 0.9300
C8 C4 1.480(5)
C8 C9 1.494(4)
C4 C5 1.391(4)
C4 C3 1.394(4)
C3 C2 1.362(5)
C3 H4 0.9300
C2 C1 1.388(4)
C2 H3 0.9300
C1 C6 1.379(4)
C7 H5 0.9600
C7 H7 0.9600
C7 H6 0.9600
C12 H10 0.9300
C12 H11 0.9300
C9 H8 0.9700
C9 H9 0.9700
C6 C5 1.368(5)
C6 H1 0.9300
C5 H2 0.9300
