#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/30/1503068.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_1503068
loop_
_publ_author_name
'Yang, Hua'
'Carter, Rich G.'
_publ_section_title
;
 Synthesis of all-carbon, quaternary center-containing cyclohexenones
 through an organocatalyzed, multicomponent coupling.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3108
_journal_page_last               3111
_journal_paper_doi               10.1021/ol1011955
_journal_volume                  12
_journal_year                    2010
_chemical_formula_sum            'C14 H15 Br O'
_chemical_formula_weight         279.17
_chemical_name_systematic
;

 ?

;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXLTL
_cell_angle_alpha                90.00
_cell_angle_beta                 98.015(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.240(3)
_cell_length_b                   7.706(3)
_cell_length_c                   12.861(5)
_cell_measurement_reflns_used    2200
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      22.35
_cell_measurement_theta_min      3.09
_cell_volume                     612.4(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Apex CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0374
_diffrn_reflns_av_sigmaI/netI    0.0573
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6842
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.60
_exptl_absorpt_coefficient_mu    3.332
_exptl_absorpt_correction_T_max  0.8251
_exptl_absorpt_correction_T_min  0.4347
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.034(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2647
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0327
_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)+(0.0143P)²+0.0850P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0638
_refine_ls_wR_factor_ref         0.0688
_reflns_number_gt                2393
_reflns_number_total             2647
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol1011955_si_004.cif
_cod_data_source_block           rc56
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1503068
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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 0.17465(5) 0.46703(6) 0.29663(2) 0.03829(12) Uani 1 1 d
O1 O 0.0938(4) 0.3667(3) 1.0519(2) 0.0378(6) Uani 1 1 d
C1 C 0.2442(5) 0.4627(7) 0.4452(2) 0.0287(6) Uani 1 1 d
C2 C 0.0978(6) 0.3893(5) 0.5050(3) 0.0334(8) Uani 1 1 d
C3 C 0.1521(6) 0.3827(5) 0.6135(3) 0.0309(8) Uani 1 1 d
C4 C 0.3503(5) 0.4449(5) 0.6633(2) 0.0249(7) Uani 1 1 d
C5 C 0.4921(6) 0.5169(4) 0.6002(3) 0.0317(9) Uani 1 1 d
C6 C 0.4394(6) 0.5263(4) 0.4925(3) 0.0331(9) Uani 1 1 d
C7 C 0.3983(5) 0.4362(4) 0.7830(2) 0.0238(8) Uani 1 1 d
C8 C 0.2778(6) 0.5867(5) 0.8308(3) 0.0253(8) Uani 1 1 d
C9 C 0.2743(6) 0.5605(5) 0.9483(3) 0.0283(8) Uani 1 1 d
C10 C 0.1823(6) 0.3880(5) 0.9735(3) 0.0262(8) Uani 1 1 d
C11 C 0.2128(6) 0.2440(5) 0.9026(3) 0.0276(7) Uani 1 1 d
C12 C 0.3148(6) 0.2648(5) 0.8197(3) 0.0255(8) Uani 1 1 d
C13 C 0.6438(5) 0.4408(7) 0.8222(3) 0.0318(9) Uani 1 1 d
C14 C 0.3614(8) 0.7655(6) 0.8115(4) 0.0352(10) Uani 1 1 d
H2 H -0.031(6) 0.345(5) 0.470(3) 0.029(10) Uiso 1 1 d
H3 H 0.059(6) 0.323(5) 0.664(3) 0.049(12) Uiso 1 1 d
H5 H 0.628(6) 0.561(5) 0.638(3) 0.038(10) Uiso 1 1 d
H6 H 0.527(6) 0.572(5) 0.445(3) 0.041(11) Uiso 1 1 d
H8 H 0.122(5) 0.585(4) 0.802(2) 0.022(9) Uiso 1 1 d
H9A H 0.190(5) 0.644(5) 0.980(3) 0.021(9) Uiso 1 1 d
H9B H 0.424(5) 0.561(4) 0.983(2) 0.015(8) Uiso 1 1 d
H11 H 0.163(5) 0.133(4) 0.929(2) 0.022(9) Uiso 1 1 d
H12 H 0.334(5) 0.177(4) 0.784(3) 0.006(9) Uiso 1 1 d
H13A H 0.673(5) 0.423(4) 0.905(2) 0.025(9) Uiso 1 1 d
H13B H 0.733(7) 0.344(6) 0.795(3) 0.043(13) Uiso 1 1 d
H13C H 0.697(5) 0.541(5) 0.804(2) 0.004(9) Uiso 1 1 d
H14A H 0.532(7) 0.786(5) 0.855(3) 0.055(12) Uiso 1 1 d
H14B H 0.259(6) 0.856(5) 0.846(3) 0.044(11) Uiso 1 1 d
H14C H 0.365(5) 0.787(4) 0.762(3) 0.009(10) 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
C6 C1 C2 120.7(3)
C6 C1 Br1 120.2(3)
C2 C1 Br1 119.1(3)
C3 C2 C1 118.8(3)
C3 C2 H2 123(2)
C1 C2 H2 118(2)
C2 C3 C4 121.6(3)
C2 C3 H3 124(2)
C4 C3 H3 114(2)
C5 C4 C3 117.6(3)
C5 C4 C7 123.5(3)
C3 C4 C7 118.9(3)
C6 C5 C4 121.5(3)
C6 C5 H5 123(2)
C4 C5 H5 115(2)
C1 C6 C5 119.8(3)
C1 C6 H6 114(2)
C5 C6 H6 126(2)
C12 C7 C4 108.9(3)
C12 C7 C13 106.6(3)
C4 C7 C13 112.0(3)
C12 C7 C8 108.7(3)
C4 C7 C8 109.2(3)
C13 C7 C8 111.4(3)
C14 C8 C9 109.8(3)
C14 C8 C7 114.8(3)
C9 C8 C7 111.5(3)
C14 C8 H8 107(2)
C9 C8 H8 102.7(18)
C7 C8 H8 110.0(19)
C10 C9 C8 113.0(3)
C10 C9 H9A 105(2)
C8 C9 H9A 115(2)
C10 C9 H9B 105.8(18)
C8 C9 H9B 108.2(18)
H9A C9 H9B 110(3)
O1 C10 C11 121.6(4)
O1 C10 C9 121.7(3)
C11 C10 C9 116.6(3)
C12 C11 C10 121.9(3)
C12 C11 H11 126.4(18)
C10 C11 H11 111.4(18)
C11 C12 C7 125.4(3)
C11 C12 H12 118(2)
C7 C12 H12 117(2)
C7 C13 H13A 110.2(17)
C7 C13 H13B 116(2)
H13A C13 H13B 103(3)
C7 C13 H13C 109(2)
H13A C13 H13C 112(3)
H13B C13 H13C 108(3)
C8 C14 H14A 111(2)
C8 C14 H14B 107(2)
H14A C14 H14B 106(3)
C8 C14 H14C 117(3)
H14A C14 H14C 106(4)
H14B C14 H14C 109(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1 1.900(3)
O1 C10 1.226(5)
C1 C6 1.374(5)
C1 C2 1.393(5)
C2 C3 1.390(5)
C2 H2 0.93(4)
C3 C4 1.396(5)
C3 H3 1.04(4)
C4 C5 1.396(4)
C4 C7 1.528(4)
C5 C6 1.381(5)
C5 H5 0.98(4)
C6 H6 0.94(4)
C7 C12 1.519(5)
C7 C13 1.545(5)
C7 C8 1.555(5)
C8 C14 1.506(6)
C8 C9 1.527(5)
C8 H8 0.99(3)
C9 C10 1.502(5)
C9 H9A 0.96(3)
C9 H9B 0.98(3)
C10 C11 1.465(5)
C11 C12 1.326(5)
C11 H11 0.99(3)
C12 H12 0.84(4)
C13 H13A 1.06(3)
C13 H13B 1.02(4)
C13 H13C 0.89(3)
C14 H14A 1.14(4)
C14 H14B 1.08(4)
C14 H14C 0.66(3)
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
C6 C1 C2 C3 0.5(7)
Br1 C1 C2 C3 178.4(3)
C1 C2 C3 C4 -1.1(6)
C2 C3 C4 C5 0.9(6)
C2 C3 C4 C7 179.1(3)
C3 C4 C5 C6 -0.1(5)
C7 C4 C5 C6 -178.2(3)
C2 C1 C6 C5 0.3(7)
Br1 C1 C6 C5 -177.6(3)
C4 C5 C6 C1 -0.5(6)
C5 C4 C7 C12 -141.8(4)
C3 C4 C7 C12 40.1(4)
C5 C4 C7 C13 -24.2(5)
C3 C4 C7 C13 157.8(4)
C5 C4 C7 C8 99.7(4)
C3 C4 C7 C8 -78.3(4)
C12 C7 C8 C14 173.3(4)
C4 C7 C8 C14 -68.0(4)
C13 C7 C8 C14 56.1(4)
C12 C7 C8 C9 47.7(4)
C4 C7 C8 C9 166.4(3)
C13 C7 C8 C9 -69.5(4)
C14 C8 C9 C10 177.1(3)
C7 C8 C9 C10 -54.5(4)
C8 C9 C10 O1 -152.7(4)
C8 C9 C10 C11 30.2(5)
O1 C10 C11 C12 -177.7(3)
C9 C10 C11 C12 -0.5(5)
C10 C11 C12 C7 -4.3(6)
C4 C7 C12 C11 -138.7(4)
C13 C7 C12 C11 100.3(4)
C8 C7 C12 C11 -19.9(4)
