#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/50/4025050.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_4025050
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            'C12 H12 O'
_chemical_formula_weight         172.22
_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                 93.7300(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.5594(3)
_cell_length_b                   13.6697(5)
_cell_length_c                   9.4364(3)
_cell_measurement_temperature    173(2)
_cell_volume                     973.04(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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0170
_diffrn_reflns_av_sigmaI/netI    0.0108
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11007
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.63
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.867411
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.627
_exptl_crystal_size_mid          0.622
_exptl_crystal_size_min          0.591
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         1704
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0373
_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)+(0.0463P)²+0.3342P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1044
_reflns_number_gt                1535
_reflns_number_total             1704
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9018717_si_002.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               4025050
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
O1 O 0.21744(14) 0.55399(7) 0.34281(12) 0.0479(3) Uani 1 1 d . . .
C1 C 0.1640(2) 0.60442(11) 0.10349(16) 0.0471(4) Uani 1 1 d . . .
H1A H 0.2126 0.5399 0.0827 0.071 Uiso 1 1 calc R . .
H1B H 0.2377 0.6554 0.0642 0.071 Uiso 1 1 calc R . .
H1C H 0.0427 0.6095 0.0605 0.071 Uiso 1 1 calc R . .
C2 C 0.16212(17) 0.61743(10) 0.26156(15) 0.0356(3) Uani 1 1 d . . .
C3 C 0.09224(17) 0.71150(9) 0.31521(14) 0.0312(3) Uani 1 1 d . . .
C4 C 0.08031(16) 0.72686(9) 0.47067(14) 0.0312(3) Uani 1 1 d . . .
C5 C 0.01622(18) 0.65454(10) 0.55813(15) 0.0368(3) Uani 1 1 d . . .
H5A H -0.0215 0.5934 0.5190 0.044 Uiso 1 1 calc R . .
C6 C 0.0077(2) 0.67205(11) 0.70175(16) 0.0422(4) Uani 1 1 d . . .
H6A H -0.0355 0.6226 0.7612 0.051 Uiso 1 1 calc R . .
C7 C 0.06169(19) 0.76091(11) 0.75975(15) 0.0417(4) Uani 1 1 d . . .
H7A H 0.0562 0.7716 0.8589 0.050 Uiso 1 1 calc R . .
C8 C 0.12387(18) 0.83482(10) 0.67505(15) 0.0369(3) Uani 1 1 d . . .
C9 C 0.13256(17) 0.81611(10) 0.53083(14) 0.0335(3) Uani 1 1 d . . .
H9A H 0.1755 0.8658 0.4715 0.040 Uiso 1 1 calc R . .
C10 C 0.1776(2) 0.93263(11) 0.73659(17) 0.0482(4) Uani 1 1 d . . .
H10A H 0.1628 0.9324 0.8390 0.072 Uiso 1 1 calc R . .
H10B H 0.1029 0.9838 0.6912 0.072 Uiso 1 1 calc R . .
H10C H 0.3020 0.9454 0.7197 0.072 Uiso 1 1 calc R . .
C11 C 0.05053(16) 0.78232(9) 0.22403(14) 0.0326(3) Uani 1 1 d . . .
C12 C 0.0127(2) 0.85319(10) 0.13699(15) 0.0379(3) Uani 1 1 d . . .
H12B H -0.104(2) 0.8610(11) 0.0926(17) 0.044(4) Uiso 1 1 d . . .
H12A H 0.106(2) 0.9009(13) 0.1156(18) 0.052(5) 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'
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 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 121.12(13) . . ?
O1 C2 C1 121.15(12) . . ?
C3 C2 C1 117.73(12) . . ?
C11 C3 C4 120.74(11) . . ?
C11 C3 C2 119.08(12) . . ?
C4 C3 C2 120.07(11) . . ?
C9 C4 C5 118.70(12) . . ?
C9 C4 C3 119.42(12) . . ?
C5 C4 C3 121.88(12) . . ?
C6 C5 C4 119.84(13) . . ?
C6 C5 H5A 120.1 . . ?
C4 C5 H5A 120.1 . . ?
C5 C6 C7 120.60(14) . . ?
C5 C6 H6A 119.7 . . ?
C7 C6 H6A 119.7 . . ?
C6 C7 C8 120.89(13) . . ?
C6 C7 H7A 119.6 . . ?
C8 C7 H7A 119.6 . . ?
C7 C8 C9 117.95(13) . . ?
C7 C8 C10 121.18(13) . . ?
C9 C8 C10 120.86(13) . . ?
C8 C9 C4 122.02(13) . . ?
C8 C9 H9A 119.0 . . ?
C4 C9 H9A 119.0 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C3 178.37(14) . . ?
C11 C12 H12B 121.4(9) . . ?
C11 C12 H12A 119.5(10) . . ?
H12B C12 H12A 119.1(14) . . ?
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
O1 C2 1.2137(17) . ?
C1 C2 1.503(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.4912(18) . ?
C3 C11 1.3197(19) . ?
C3 C4 1.4905(19) . ?
C4 C9 1.3919(18) . ?
C4 C5 1.3947(19) . ?
C5 C6 1.382(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.383(2) . ?
C6 H6A 0.9500 . ?
C7 C8 1.389(2) . ?
C7 H7A 0.9500 . ?
C8 C9 1.3905(19) . ?
C8 C10 1.503(2) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.290(2) . ?
C12 H12B 0.958(17) . ?
C12 H12A 0.992(18) . ?
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
O1 C2 C3 C11 173.06(13) . . . . ?
C1 C2 C3 C11 -6.13(19) . . . . ?
O1 C2 C3 C4 -3.32(19) . . . . ?
C1 C2 C3 C4 177.49(12) . . . . ?
C11 C3 C4 C9 -39.38(18) . . . . ?
C2 C3 C4 C9 136.94(12) . . . . ?
C11 C3 C4 C5 139.91(14) . . . . ?
C2 C3 C4 C5 -43.77(18) . . . . ?
C9 C4 C5 C6 -0.8(2) . . . . ?
C3 C4 C5 C6 179.94(12) . . . . ?
C4 C5 C6 C7 0.2(2) . . . . ?
C5 C6 C7 C8 0.6(2) . . . . ?
C6 C7 C8 C9 -0.9(2) . . . . ?
C6 C7 C8 C10 178.14(13) . . . . ?
C7 C8 C9 C4 0.38(19) . . . . ?
C10 C8 C9 C4 -178.69(12) . . . . ?
C5 C4 C9 C8 0.46(19) . . . . ?
C3 C4 C9 C8 179.77(12) . . . . ?
C4 C3 C11 C12 51(5) . . . . ?
C2 C3 C11 C12 -125(5) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659089
