#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:18:01 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178429 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/50/4025049.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_4025049
loop_
_publ_author_name
'Jing Li'
'Wangqing Kong'
'Yihua Yu'
'Chunling Fu'
'Shengming Ma'
_publ_section_title
;
Studies on Electrophilic Reaction of Tertiary 2,3-Allenols with NBS in H2O
or Aqueous MeCN: An Efficient Selective Synthesis of 2-Bromoallylic
Ketones, 1,2-Allenyl Ketones, or 3-Bromo-2,5-dihydrofurans
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8733
_journal_page_last               8738
_journal_paper_doi               10.1021/jo9018717
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C13 H13 Br O'
_chemical_formula_weight         265.14
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 99.934(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.7860(4)
_cell_length_b                   6.0794(2)
_cell_length_c                   14.2698(4)
_cell_measurement_temperature    173(2)
_cell_volume                     1092.58(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0389
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9937
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    3.731
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.254839
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.764
_exptl_crystal_size_mid          0.702
_exptl_crystal_size_min          0.404
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.0176(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1922
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0216
_refine_ls_R_factor_gt           0.0204
_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)+(0.0206P)²+0.8397P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0516
_refine_ls_wR_factor_ref         0.0524
_reflns_number_gt                1831
_reflns_number_total             1922
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9018717_si_001.cif
_cod_data_source_block           z
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4025049
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.463255(15) 0.15708(3) 0.109257(13) 0.02253(11) Uani 1 1 d . . .
O1 O 0.25230(10) 0.3756(2) 0.22281(10) 0.0195(3) Uani 1 1 d . . .
C1 C 0.53550(13) 0.5001(3) 0.28543(13) 0.0153(4) Uani 1 1 d . . .
C2 C 0.61279(15) 0.6519(3) 0.27216(15) 0.0210(4) Uani 1 1 d . . .
H2A H 0.5948 0.7690 0.2283 0.025 Uiso 1 1 calc R . .
C3 C 0.71606(16) 0.6357(3) 0.32191(15) 0.0254(5) Uani 1 1 d . . .
H3A H 0.7682 0.7406 0.3120 0.030 Uiso 1 1 calc R . .
C4 C 0.74200(15) 0.4664(4) 0.38560(14) 0.0256(5) Uani 1 1 d . . .
H4A H 0.8123 0.4538 0.4199 0.031 Uiso 1 1 calc R . .
C5 C 0.66570(15) 0.3143(3) 0.39971(14) 0.0228(4) Uani 1 1 d . . .
H5A H 0.6846 0.1984 0.4440 0.027 Uiso 1 1 calc R . .
C6 C 0.56138(14) 0.3271(3) 0.35034(14) 0.0169(4) Uani 1 1 d . . .
C7 C 0.48042(15) 0.1613(3) 0.37008(14) 0.0202(4) Uani 1 1 d . . .
H7A H 0.5177 0.0386 0.4074 0.024 Uiso 1 1 calc R . .
H7B H 0.4436 0.1004 0.3089 0.024 Uiso 1 1 calc R . .
C8 C 0.39738(15) 0.2566(3) 0.42449(14) 0.0221(4) Uani 1 1 d . . .
H8A H 0.4316 0.2903 0.4906 0.027 Uiso 1 1 calc R . .
H8B H 0.3415 0.1453 0.4272 0.027 Uiso 1 1 calc R . .
C9 C 0.34607(14) 0.4672(3) 0.37724(13) 0.0193(4) Uani 1 1 d . . .
H9A H 0.2761 0.4910 0.3965 0.023 Uiso 1 1 calc R . .
H9B H 0.3917 0.5956 0.3985 0.023 Uiso 1 1 calc R . .
C10 C 0.33220(14) 0.4465(3) 0.27095(13) 0.0155(4) Uani 1 1 d . . .
C11 C 0.42503(13) 0.5291(3) 0.22555(12) 0.0140(4) Uani 1 1 d . . .
H11A H 0.4147 0.6920 0.2205 0.017 Uiso 1 1 calc R . .
C12 C 0.41767(13) 0.4521(3) 0.12443(13) 0.0156(4) Uani 1 1 d . . .
C13 C 0.38217(15) 0.5668(4) 0.04732(15) 0.0225(4) Uani 1 1 d . . .
H13B H 0.3785(17) 0.508(4) -0.0126(17) 0.024(6) Uiso 1 1 d . . .
H13A H 0.3631(18) 0.713(4) 0.0557(16) 0.026(6) 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.73(16) . . ?
C2 C1 C11 117.22(16) . . ?
C6 C1 C11 123.04(16) . . ?
C1 C2 C3 121.25(18) . . ?
C1 C2 H2A 119.4 . . ?
C3 C2 H2A 119.4 . . ?
C4 C3 C2 119.32(18) . . ?
C4 C3 H3A 120.3 . . ?
C2 C3 H3A 120.3 . . ?
C3 C4 C5 120.03(18) . . ?
C3 C4 H4A 120.0 . . ?
C5 C4 H4A 120.0 . . ?
C4 C5 C6 121.64(19) . . ?
C4 C5 H5A 119.2 . . ?
C6 C5 H5A 119.2 . . ?
C5 C6 C1 118.03(17) . . ?
C5 C6 C7 119.68(17) . . ?
C1 C6 C7 122.27(16) . . ?
C6 C7 C8 113.61(16) . . ?
C6 C7 H7A 108.8 . . ?
C8 C7 H7A 108.8 . . ?
C6 C7 H7B 108.8 . . ?
C8 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C7 C8 C9 111.85(15) . . ?
C7 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C10 C9 C8 109.84(15) . . ?
C10 C9 H9A 109.7 . . ?
C8 C9 H9A 109.7 . . ?
C10 C9 H9B 109.7 . . ?
C8 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
O1 C10 C9 123.04(16) . . ?
O1 C10 C11 121.17(17) . . ?
C9 C10 C11 115.76(15) . . ?
C12 C11 C1 113.50(14) . . ?
C12 C11 C10 112.26(14) . . ?
C1 C11 C10 115.73(15) . . ?
C12 C11 H11A 104.6 . . ?
C1 C11 H11A 104.6 . . ?
C10 C11 H11A 104.6 . . ?
C13 C12 C11 126.34(18) . . ?
C13 C12 Br1 118.11(15) . . ?
C11 C12 Br1 115.55(12) . . ?
C12 C13 H13B 121.6(14) . . ?
C12 C13 H13A 117.2(14) . . ?
H13B C13 H13A 121(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C12 1.9096(18) . ?
O1 C10 1.208(2) . ?
C1 C2 1.389(3) . ?
C1 C6 1.403(3) . ?
C1 C11 1.530(2) . ?
C2 C3 1.391(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.375(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.384(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.399(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.506(3) . ?
C7 C8 1.533(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.540(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.502(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.532(2) . ?
C11 C12 1.504(3) . ?
C11 H11A 1.0000 . ?
C12 C13 1.316(3) . ?
C13 H13B 0.92(2) . ?
C13 H13A 0.94(2) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.2(3) . . . . ?
C11 C1 C2 C3 -178.56(18) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C4 C5 C6 C1 -0.1(3) . . . . ?
C4 C5 C6 C7 -178.35(18) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
C11 C1 C6 C5 178.61(17) . . . . ?
C2 C1 C6 C7 178.12(17) . . . . ?
C11 C1 C6 C7 -3.2(3) . . . . ?
C5 C6 C7 C8 108.4(2) . . . . ?
C1 C6 C7 C8 -69.8(2) . . . . ?
C6 C7 C8 C9 51.2(2) . . . . ?
C7 C8 C9 C10 36.9(2) . . . . ?
C8 C9 C10 O1 91.6(2) . . . . ?
C8 C9 C10 C11 -90.52(18) . . . . ?
C2 C1 C11 C12 77.4(2) . . . . ?
C6 C1 C11 C12 -101.3(2) . . . . ?
C2 C1 C11 C10 -150.69(17) . . . . ?
C6 C1 C11 C10 30.6(2) . . . . ?
O1 C10 C11 C12 -16.5(2) . . . . ?
C9 C10 C11 C12 165.57(15) . . . . ?
O1 C10 C11 C1 -148.98(17) . . . . ?
C9 C10 C11 C1 33.1(2) . . . . ?
C1 C11 C12 C13 -126.96(19) . . . . ?
C10 C11 C12 C13 99.4(2) . . . . ?
C1 C11 C12 Br1 53.90(18) . . . . ?
C10 C11 C12 Br1 -79.69(16) . . . . ?
