#------------------------------------------------------------------------------
#$Date: 2017-10-13 13:42:48 +0200 (vie 13 de oct de 2017) $
#$Revision: 201982 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/21/4022116.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_4022116
loop_
_publ_author_name
'Manab Chakravarty'
'K. C. Kumara Swamy'
_publ_section_title
;
 Palladium-Catalyzed Coupling of Allenylphosphonates, Phenylallenes,
 and Allenyl Esters: Remarkable Salt Effect and Routes to Novel
 Benzofurans and Isocoumarins
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9128
_journal_page_last               9138
_journal_paper_doi               10.1021/jo061525y
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C13 H12 O4'
_chemical_formula_weight         232.23
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 102.455(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.994(5)
_cell_length_b                   5.1441(16)
_cell_length_c                   14.520(5)
_cell_measurement_reflns_used    1539
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      25.01
_cell_measurement_theta_min      2.61
_cell_volume                     1166.5(6)
_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      273(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_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  0.0401
_diffrn_reflns_av_sigmaI/netI    0.0457
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5488
_diffrn_reflns_theta_full        26.03
_diffrn_reflns_theta_max         26.03
_diffrn_reflns_theta_min         2.61
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.9883
_exptl_absorpt_correction_T_min  0.9692
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   'empirical sadabs'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2270
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.956
_refine_ls_R_factor_all          0.1214
_refine_ls_R_factor_gt           0.0660
_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)+(0.1165P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1900
_refine_ls_wR_factor_ref         0.2185
_reflns_number_gt                1076
_reflns_number_total             2270
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo061525ysi20060722_122107_14.cif
_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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4022116
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O1 O 0.14548(19) -0.0937(6) 1.08512(16) 0.1363(11) Uani 1 1 d .
O2 O 0.23781(16) -0.2486(5) 1.00733(16) 0.1019(8) Uani 1 1 d .
O3 O 0.37499(13) 0.2605(4) 0.82049(16) 0.0904(7) Uani 1 1 d .
O4 O 0.37136(15) 0.0897(5) 0.68067(16) 0.1056(9) Uani 1 1 d .
C1 C 0.1738(2) -0.0810(8) 1.0147(2) 0.0913(10) Uani 1 1 d .
C2 C 0.2728(2) -0.2524(7) 0.9291(2) 0.0832(9) Uani 1 1 d .
H2 H 0.3158 -0.3731 0.9276 0.100 Uiso 1 1 calc R
C3 C 0.24989(17) -0.0975(5) 0.8560(2) 0.0647(8) Uani 1 1 d .
C4 C 0.18162(16) 0.0893(5) 0.85656(18) 0.0589(7) Uani 1 1 d .
C5 C 0.15154(18) 0.2595(5) 0.78305(19) 0.0676(8) Uani 1 1 d .
H5 H 0.1754 0.2588 0.7300 0.081 Uiso 1 1 calc R
C6 C 0.0866(2) 0.4291(6) 0.7883(2) 0.0863(10) Uani 1 1 d .
H6 H 0.0665 0.5424 0.7385 0.104 Uiso 1 1 calc R
C7 C 0.0508(2) 0.4333(7) 0.8668(3) 0.0952(11) Uani 1 1 d .
H7 H 0.0069 0.5499 0.8696 0.114 Uiso 1 1 calc R
C8 C 0.0789(2) 0.2695(7) 0.9392(2) 0.0892(10) Uani 1 1 d .
H8 H 0.0543 0.2726 0.9917 0.107 Uiso 1 1 calc R
C9 C 0.14463(18) 0.0960(6) 0.93561(19) 0.0698(8) Uani 1 1 d .
C10 C 0.29139(19) -0.1233(5) 0.7731(2) 0.0747(9) Uani 1 1 d .
H10A H 0.3240 -0.2837 0.7792 0.090 Uiso 1 1 calc R
H10B H 0.2471 -0.1352 0.7159 0.090 Uiso 1 1 calc R
C11 C 0.34966(18) 0.0986(6) 0.7636(2) 0.0700(8) Uani 1 1 d .
C12 C 0.4298(3) 0.2916(9) 0.6622(3) 0.1314(16) Uani 1 1 d .
H12A H 0.4019 0.4597 0.6599 0.158 Uiso 1 1 calc R
H12B H 0.4802 0.2950 0.7131 0.158 Uiso 1 1 calc R
C13 C 0.4531(3) 0.2480(12) 0.5806(3) 0.172(2) Uani 1 1 d .
H13A H 0.4785 0.0786 0.5819 0.258 Uiso 1 1 calc R
H13B H 0.4939 0.3772 0.5716 0.258 Uiso 1 1 calc R
H13C H 0.4036 0.2569 0.5297 0.258 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
O1 0.151(2) 0.196(3) 0.0713(17) 0.0177(18) 0.0451(16) 0.012(2)
O2 0.1057(18) 0.1148(18) 0.0842(16) 0.0298(13) 0.0184(14) 0.0193(16)
O3 0.0944(16) 0.0735(14) 0.1048(17) -0.0207(13) 0.0248(12) -0.0205(12)
O4 0.1153(18) 0.1179(19) 0.0949(17) -0.0189(14) 0.0474(14) -0.0426(16)
C1 0.095(2) 0.114(3) 0.065(2) 0.002(2) 0.0178(19) -0.003(2)
C2 0.074(2) 0.082(2) 0.093(2) 0.0105(19) 0.0180(17) 0.0099(17)
C3 0.0671(18) 0.0553(15) 0.0728(19) -0.0089(15) 0.0176(14) -0.0022(14)
C4 0.0593(16) 0.0572(15) 0.0590(16) -0.0067(13) 0.0105(13) -0.0073(13)
C5 0.0657(17) 0.0687(18) 0.0670(18) 0.0003(15) 0.0111(14) -0.0037(15)
C6 0.077(2) 0.082(2) 0.093(2) 0.0078(18) 0.0004(18) 0.0062(18)
C7 0.073(2) 0.097(3) 0.112(3) -0.013(2) 0.012(2) 0.0220(19)
C8 0.081(2) 0.107(3) 0.084(2) -0.016(2) 0.0281(18) 0.008(2)
C9 0.0718(19) 0.0762(19) 0.0618(18) -0.0075(15) 0.0150(14) -0.0010(16)
C10 0.0760(19) 0.0622(17) 0.091(2) -0.0151(15) 0.0297(17) -0.0057(15)
C11 0.0659(19) 0.0642(19) 0.082(2) -0.0051(17) 0.0213(16) 0.0020(16)
C12 0.142(4) 0.147(4) 0.121(3) -0.009(3) 0.063(3) -0.061(3)
C13 0.201(6) 0.205(6) 0.118(4) -0.002(4) 0.054(4) -0.092(4)
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
C1 O2 C2 121.6(3)
C11 O4 C12 116.5(3)
O1 C1 O2 117.4(3)
O1 C1 C9 125.8(4)
O2 C1 C9 116.8(3)
C3 C2 O2 124.6(3)
C3 C2 H2 117.7
O2 C2 H2 117.7
C2 C3 C4 118.4(3)
C2 C3 C10 120.0(3)
C4 C3 C10 121.6(3)
C5 C4 C9 118.6(3)
C5 C4 C3 123.4(3)
C9 C4 C3 118.0(2)
C6 C5 C4 120.1(3)
C6 C5 H5 120.0
C4 C5 H5 120.0
C5 C6 C7 120.6(3)
C5 C6 H6 119.7
C7 C6 H6 119.7
C8 C7 C6 120.4(3)
C8 C7 H7 119.8
C6 C7 H7 119.8
C7 C8 C9 120.0(3)
C7 C8 H8 120.0
C9 C8 H8 120.0
C8 C9 C4 120.2(3)
C8 C9 C1 119.1(3)
C4 C9 C1 120.6(3)
C11 C10 C3 113.4(2)
C11 C10 H10A 108.9
C3 C10 H10A 108.9
C11 C10 H10B 108.9
C3 C10 H10B 108.9
H10A C10 H10B 107.7
O3 C11 O4 122.9(3)
O3 C11 C10 126.8(3)
O4 C11 C10 110.3(3)
C13 C12 O4 110.8(4)
C13 C12 H12A 109.5
O4 C12 H12A 109.5
C13 C12 H12B 109.5
O4 C12 H12B 109.5
H12A C12 H12B 108.1
C12 C13 H13A 109.5
C12 C13 H13B 109.5
H13A C13 H13B 109.5
C12 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.206(4)
O2 C1 1.360(4)
O2 C2 1.370(4)
O3 C11 1.182(3)
O4 C11 1.324(3)
O4 C12 1.460(4)
C1 C9 1.461(4)
C2 C3 1.315(4)
C2 H2 0.9300
C3 C4 1.456(4)
C3 C10 1.501(4)
C4 C5 1.384(4)
C4 C9 1.401(3)
C5 C6 1.370(4)
C5 H5 0.9300
C6 C7 1.383(4)
C6 H6 0.9300
C7 C8 1.347(4)
C7 H7 0.9300
C8 C9 1.389(4)
C8 H8 0.9300
C10 C11 1.499(4)
C10 H10A 0.9700
C10 H10B 0.9700
C12 C13 1.336(5)
C12 H12A 0.9700
C12 H12B 0.9700
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10167765
