#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:28:02 +0100 (lun 21 de mar de 2016) $
#$Revision: 178470 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/91/4029186.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_4029186
loop_
_publ_author_name
'Lin, Mei-Huey'
'Huang, Yen-Chih'
'Kuo, Chung-Kai'
'Tsai, Chang-Hsien'
'Li, Yi-Syuan'
'Hu, Ting-Chia'
'Chuang, Tsung-Hsun'
_publ_section_title
;
 γ-Halo-enones: A Method for their Synthesis from Arylacyl Halides and
 Their Application to the Preparation of Five-Membered Ring Heterocycles.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2751
_journal_page_last               2757
_journal_paper_doi               10.1021/jo5001274
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C11 H9 Cl3 O'
_chemical_formula_weight         263.53
_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                 118.36(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.463(3)
_cell_length_b                   12.044(4)
_cell_length_c                   10.740(4)
_cell_measurement_reflns_used    1993
_cell_measurement_temperature    250(2)
_cell_measurement_theta_max      23.822
_cell_measurement_theta_min      2.740
_cell_volume                     1191.0(7)
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      250(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       /w
_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  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0397
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            7145
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.24
_exptl_absorpt_coefficient_mu    0.738
_exptl_absorpt_correction_T_max  0.9711
_exptl_absorpt_correction_T_min  0.9298
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.890
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2867
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.890
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0397
_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)+(0.1000P)²+0.0400P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1241
_refine_ls_wR_factor_ref         0.1543
_reflns_number_gt                1761
_reflns_number_total             2867
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5001274_si_001.cif
_cod_data_source_block           hyjii1330202
_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 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_cell_volume        1191.1(7)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4029186
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
Cl1 Cl 0.27342(8) 0.03409(7) 0.67732(7) 0.0696(3) Uani 1 1 d .
Cl3 Cl -0.14776(8) -0.05636(7) 0.71792(8) 0.0736(3) Uani 1 1 d .
Cl2 Cl 0.56887(8) -0.26937(6) 1.07602(9) 0.0780(3) Uani 1 1 d .
C1 C 0.2989(3) -0.0372(2) 0.8285(2) 0.0485(6) Uani 1 1 d .
C6 C 0.2131(2) -0.0125(2) 0.8911(2) 0.0478(6) Uani 1 1 d .
C9 C -0.0095(3) 0.2452(2) 0.8830(3) 0.0568(6) Uani 1 1 d .
C7 C 0.0928(3) 0.0709(2) 0.8347(2) 0.0477(5) Uani 1 1 d .
C8 C 0.1007(2) 0.1580(2) 0.9141(2) 0.0508(6) Uani 1 1 d .
H8 H 0.1859 0.1648 0.9995 0.061 Uiso 1 1 calc R
C3 C 0.4317(3) -0.1713(2) 1.0042(3) 0.0559(6) Uani 1 1 d .
C2 C 0.4079(3) -0.1150(2) 0.8836(3) 0.0548(6) Uani 1 1 d .
H2 H 0.4646 -0.1294 0.8401 0.066 Uiso 1 1 calc R
C11 C -0.0361(3) 0.0448(2) 0.6938(2) 0.0569(6) Uani 1 1 d .
H11A H -0.0033 0.0162 0.6294 0.068 Uiso 1 1 calc R
H11B H -0.0918 0.1118 0.6531 0.068 Uiso 1 1 calc R
C5 C 0.2420(3) -0.0706(2) 1.0130(3) 0.0596(7) Uani 1 1 d .
H5 H 0.1868 -0.0554 1.0580 0.071 Uiso 1 1 calc R
O1 O -0.1202(2) 0.25347(19) 0.7720(2) 0.0885(7) Uani 1 1 d .
C4 C 0.3494(3) -0.1502(2) 1.0704(3) 0.0625(7) Uani 1 1 d .
H4 H 0.3657 -0.1886 1.1518 0.075 Uiso 1 1 calc R
C10 C 0.0231(4) 0.3253(3) 1.0002(4) 0.0998(12) Uani 1 1 d .
H10A H -0.0536 0.3791 0.9701 0.150 Uiso 1 1 calc R
H10B H 0.1132 0.3623 1.0247 0.150 Uiso 1 1 calc R
H10C H 0.0306 0.2860 1.0811 0.150 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
Cl1 0.0689(5) 0.0955(6) 0.0489(4) 0.0037(3) 0.0316(3) -0.0074(4)
Cl3 0.0631(5) 0.0833(5) 0.0745(5) -0.0157(4) 0.0328(4) -0.0225(4)
Cl2 0.0692(5) 0.0597(4) 0.1006(6) 0.0011(4) 0.0367(4) 0.0144(3)
C1 0.0491(13) 0.0557(13) 0.0398(12) -0.0079(10) 0.0204(10) -0.0085(11)
C6 0.0472(13) 0.0526(13) 0.0420(12) -0.0047(10) 0.0198(10) -0.0047(11)
C9 0.0506(14) 0.0607(15) 0.0572(15) 0.0037(11) 0.0242(12) 0.0034(12)
C7 0.0421(12) 0.0595(13) 0.0387(11) 0.0027(10) 0.0170(9) -0.0049(11)
C8 0.0420(12) 0.0589(14) 0.0458(13) -0.0012(11) 0.0162(10) -0.0004(11)
C3 0.0554(14) 0.0491(13) 0.0594(15) -0.0071(11) 0.0241(12) -0.0012(12)
C2 0.0495(14) 0.0610(15) 0.0550(14) -0.0170(12) 0.0258(11) -0.0080(12)
C11 0.0510(14) 0.0657(15) 0.0447(13) -0.0001(11) 0.0152(11) -0.0043(12)
C5 0.0681(17) 0.0660(16) 0.0549(14) 0.0071(12) 0.0377(12) 0.0108(13)
O1 0.0670(13) 0.1134(18) 0.0618(12) -0.0020(11) 0.0117(11) 0.0347(12)
C4 0.0685(17) 0.0646(16) 0.0588(16) 0.0099(13) 0.0339(13) 0.0075(14)
C10 0.082(2) 0.085(2) 0.096(2) -0.0294(19) 0.0127(19) 0.0228(19)
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'
Cl Cl 0.1484 0.1585 '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
C2 C1 C6 122.3(2)
C2 C1 Cl1 117.75(19)
C6 C1 Cl1 119.96(19)
C1 C6 C5 116.7(2)
C1 C6 C7 124.2(2)
C5 C6 C7 119.1(2)
O1 C9 C8 124.2(2)
O1 C9 C10 120.4(3)
C8 C9 C10 115.4(2)
C8 C7 C6 119.1(2)
C8 C7 C11 124.2(2)
C6 C7 C11 116.5(2)
C7 C8 C9 127.7(2)
C2 C3 C4 121.2(2)
C2 C3 Cl2 119.8(2)
C4 C3 Cl2 119.0(2)
C1 C2 C3 118.9(2)
C7 C11 Cl3 109.36(17)
C4 C5 C6 122.6(2)
C3 C4 C5 118.3(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.742(2)
Cl3 C11 1.789(3)
Cl2 C3 1.732(3)
C1 C2 1.374(3)
C1 C6 1.385(3)
C6 C5 1.386(3)
C6 C7 1.496(3)
C9 O1 1.209(3)
C9 C8 1.476(3)
C9 C10 1.491(4)
C7 C8 1.330(3)
C7 C11 1.506(3)
C3 C2 1.375(4)
C3 C4 1.377(4)
C5 C4 1.379(4)
