#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/42/4024231.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_4024231
loop_
_publ_author_name
'Li Lu'
'Xue-Yuan Liu'
'Xing-Zhong Shu'
'Ke Yang'
'Ke-Gong Ji'
'Yong-Min Liang'
_publ_section_title
;
Platinum-Catalyzed Cycloisomerization Reaction of 1,6-Enyne Coupling with
Rearrangement of Propargylic Esters
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              474
_journal_page_last               477
_journal_paper_doi               10.1021/jo802043z
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C15 H11 Cl O2'
_chemical_formula_weight         258.69
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.105(7)
_cell_angle_beta                 94.926(8)
_cell_angle_gamma                90.416(7)
_cell_formula_units_Z            2
_cell_length_a                   6.212(3)
_cell_length_b                   7.420(4)
_cell_length_c                   13.040(6)
_cell_measurement_reflns_used    2310
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.10
_cell_measurement_theta_min      2.75
_cell_volume                     598.8(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  '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  0.0143
_diffrn_reflns_av_sigmaI/netI    0.0237
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3087
_diffrn_reflns_theta_full        25.48
_diffrn_reflns_theta_max         25.48
_diffrn_reflns_theta_min         1.57
_exptl_absorpt_coefficient_mu    0.308
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.934
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.571
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2195
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.571
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0404
_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)+(0.1000P)²+1.0817P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1164
_reflns_number_gt                1947
_reflns_number_total             2195
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo802043z_si_001.cif
_cod_data_source_block           p-1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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      P-1
_cod_database_code               4024231
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.08162(11) 0.11639(9) 0.88457(4) 0.0677(2) Uani 1 1 d . . .
C7 C 0.5216(3) 0.2583(2) 0.49598(14) 0.0388(4) Uani 1 1 d . . .
C4 C 0.7188(3) 0.2370(3) 0.77711(14) 0.0439(4) Uani 1 1 d . . .
H4 H 0.6690 0.2654 0.8404 0.053 Uiso 1 1 calc R . .
C8 C 0.6083(3) 0.2806(2) 0.39319(13) 0.0349(4) Uani 1 1 d . . .
C2 C 0.9987(3) 0.1176(2) 0.67900(14) 0.0420(4) Uani 1 1 d . . .
H2 H 1.1338 0.0651 0.6770 0.050 Uiso 1 1 calc R . .
C9 C 0.8085(3) 0.3618(2) 0.38109(14) 0.0391(4) Uani 1 1 d . . .
H9 H 0.8978 0.3955 0.4389 0.047 Uiso 1 1 calc R . .
C6 C 0.6688(3) 0.2301(2) 0.59125(13) 0.0349(4) Uani 1 1 d . . .
C3 C 0.9204(3) 0.1600(2) 0.77159(14) 0.0420(4) Uani 1 1 d . . .
C11 C 0.7412(3) 0.3406(2) 0.19886(14) 0.0423(4) Uani 1 1 d . . .
C1 C 0.8729(3) 0.1546(2) 0.58925(14) 0.0389(4) Uani 1 1 d . . .
H1 H 0.9254 0.1285 0.5262 0.047 Uiso 1 1 calc R . .
C5 C 0.5936(3) 0.2703(2) 0.68653(14) 0.0409(4) Uani 1 1 d . . .
H5 H 0.4573 0.3202 0.6890 0.049 Uiso 1 1 calc R . .
O1 O 0.3268(2) 0.2605(3) 0.50168(11) 0.0638(5) Uani 1 1 d . . .
C13 C 0.4758(3) 0.2279(2) 0.30637(14) 0.0397(4) Uani 1 1 d . . .
H13 H 0.3423 0.1740 0.3134 0.048 Uiso 1 1 calc R . .
C12 C 0.5446(3) 0.2565(3) 0.21024(14) 0.0418(4) Uani 1 1 d . . .
C10 C 0.8749(3) 0.3924(3) 0.28399(15) 0.0433(4) Uani 1 1 d . . .
H10 H 1.0077 0.4470 0.2762 0.052 Uiso 1 1 calc R . .
O2 O 0.5846(3) 0.2715(3) 0.03480(11) 0.0743(5) Uani 1 1 d . . .
C15 C 0.7671(4) 0.3601(3) 0.08554(17) 0.0597(6) Uani 1 1 d . . .
H15A H 0.7702 0.4862 0.0663 0.072 Uiso 1 1 calc R . .
H15B H 0.8998 0.3041 0.0680 0.072 Uiso 1 1 calc R . .
C14 C 0.4384(4) 0.2143(4) 0.10535(16) 0.0621(6) Uani 1 1 d . . .
H14A H 0.4100 0.0860 0.0982 0.075 Uiso 1 1 calc R . .
H14B H 0.3027 0.2780 0.0937 0.075 Uiso 1 1 calc R . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C7 C6 119.49(16) . . ?
O1 C7 C8 119.21(17) . . ?
C6 C7 C8 121.29(15) . . ?
C5 C4 C3 118.50(17) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C9 C8 C13 119.53(16) . . ?
C9 C8 C7 122.65(16) . . ?
C13 C8 C7 117.69(16) . . ?
C3 C2 C1 118.70(17) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C10 C9 C8 120.70(17) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C1 C6 C5 118.61(16) . . ?
C1 C6 C7 122.50(15) . . ?
C5 C6 C7 118.76(16) . . ?
C2 C3 C4 122.00(17) . . ?
C2 C3 Cl1 118.51(16) . . ?
C4 C3 Cl1 119.49(15) . . ?
C10 C11 C12 120.62(17) . . ?
C10 C11 C15 130.90(19) . . ?
C12 C11 C15 108.48(18) . . ?
C2 C1 C6 121.20(16) . . ?
C2 C1 H1 119.4 . . ?
C6 C1 H1 119.4 . . ?
C4 C5 C6 120.98(17) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C12 C13 C8 119.34(17) . . ?
C12 C13 H13 120.3 . . ?
C8 C13 H13 120.3 . . ?
C13 C12 C11 120.75(17) . . ?
C13 C12 C14 130.83(18) . . ?
C11 C12 C14 108.41(17) . . ?
C11 C10 C9 119.03(17) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
C14 O2 C15 111.40(17) . . ?
O2 C15 C11 105.34(18) . . ?
O2 C15 H15A 110.7 . . ?
C11 C15 H15A 110.7 . . ?
O2 C15 H15B 110.7 . . ?
C11 C15 H15B 110.7 . . ?
H15A C15 H15B 108.8 . . ?
O2 C14 C12 106.07(18) . . ?
O2 C14 H14A 110.5 . . ?
C12 C14 H14A 110.5 . . ?
O2 C14 H14B 110.5 . . ?
C12 C14 H14B 110.5 . . ?
H14A C14 H14B 108.7 . . ?
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
Cl1 C3 1.741(2) . ?
C7 O1 1.218(2) . ?
C7 C6 1.494(3) . ?
C7 C8 1.496(2) . ?
C4 C5 1.381(3) . ?
C4 C3 1.388(3) . ?
C4 H4 0.9300 . ?
C8 C9 1.399(3) . ?
C8 C13 1.395(3) . ?
C2 C3 1.377(3) . ?
C2 C1 1.379(3) . ?
C2 H2 0.9300 . ?
C9 C10 1.384(3) . ?
C9 H9 0.9300 . ?
C6 C1 1.393(3) . ?
C6 C5 1.397(2) . ?
C11 C10 1.380(3) . ?
C11 C12 1.387(3) . ?
C11 C15 1.507(3) . ?
C1 H1 0.9300 . ?
C5 H5 0.9300 . ?
C13 C12 1.375(3) . ?
C13 H13 0.9300 . ?
C12 C14 1.498(3) . ?
C10 H10 0.9300 . ?
O2 C14 1.411(3) . ?
O2 C15 1.419(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
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 C7 C8 C9 149.21(19) . . . . ?
C6 C7 C8 C9 -31.9(3) . . . . ?
O1 C7 C8 C13 -26.6(3) . . . . ?
C6 C7 C8 C13 152.32(17) . . . . ?
C13 C8 C9 C10 0.8(3) . . . . ?
C7 C8 C9 C10 -174.90(17) . . . . ?
O1 C7 C6 C1 153.25(19) . . . . ?
C8 C7 C6 C1 -25.7(3) . . . . ?
O1 C7 C6 C5 -22.5(3) . . . . ?
C8 C7 C6 C5 158.58(16) . . . . ?
C1 C2 C3 C4 0.6(3) . . . . ?
C1 C2 C3 Cl1 -179.00(14) . . . . ?
C5 C4 C3 C2 0.4(3) . . . . ?
C5 C4 C3 Cl1 -179.96(14) . . . . ?
C3 C2 C1 C6 -1.2(3) . . . . ?
C5 C6 C1 C2 0.7(3) . . . . ?
C7 C6 C1 C2 -175.02(16) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
C1 C6 C5 C4 0.3(3) . . . . ?
C7 C6 C5 C4 176.26(16) . . . . ?
C9 C8 C13 C12 0.1(3) . . . . ?
C7 C8 C13 C12 176.06(16) . . . . ?
C8 C13 C12 C11 -1.5(3) . . . . ?
C8 C13 C12 C14 179.9(2) . . . . ?
C10 C11 C12 C13 2.0(3) . . . . ?
C15 C11 C12 C13 -177.50(18) . . . . ?
C10 C11 C12 C14 -179.14(19) . . . . ?
C15 C11 C12 C14 1.4(2) . . . . ?
C12 C11 C10 C9 -1.0(3) . . . . ?
C15 C11 C10 C9 178.3(2) . . . . ?
C8 C9 C10 C11 -0.4(3) . . . . ?
C14 O2 C15 C11 5.6(3) . . . . ?
C10 C11 C15 O2 176.4(2) . . . . ?
C12 C11 C15 O2 -4.2(2) . . . . ?
C15 O2 C14 C12 -4.9(3) . . . . ?
C13 C12 C14 O2 -179.3(2) . . . . ?
C11 C12 C14 O2 2.0(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658860
