#------------------------------------------------------------------------------
#$Date: 2016-03-25 22:23:42 +0200 (Fri, 25 Mar 2016) $
#$Revision: 180010 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/04/7030432.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_7030432
loop_
_publ_author_name
'Burns, Michael J.'
'Thatcher, Robert J.'
'Taylor, Richard J. K.'
'Fairlamb, Ian J. S.'
_publ_section_title
;
 Pd-catalysed regioselective C-H functionalisation of 2-pyrones.
;
_journal_issue                   43
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              10391
_journal_page_last               10400
_journal_paper_doi               10.1039/c0dt00421a
_journal_volume                  39
_journal_year                    2010
_chemical_formula_moiety         'C11 H6 O3'
_chemical_formula_sum            'C11 H6 O3'
_chemical_formula_weight         186.16
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 105.787(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.1190(16)
_cell_length_b                   8.2091(12)
_cell_length_c                   18.856(3)
_cell_measurement_reflns_used    3453
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      3.13
_cell_volume                     1656.2(4)
_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, 1997)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0175
_diffrn_reflns_av_sigmaI/netI    0.0149
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            8041
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         2.24
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.800
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.10 (Sheldrick)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Shard
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2057
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0373
_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)+(0.0571P)²+0.9674P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1024
_reflns_number_gt                1765
_reflns_number_total             2057
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0dt00421a.txt
_cod_data_source_block           ijf0934m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/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_sg_symbol_H-M      C2/c
_cod_database_code               7030432
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
C1 C 0.06541(10) 0.26444(14) 0.55902(6) 0.0214(2) Uani 1 1 d .
C2 C 0.03945(11) 0.35284(15) 0.61759(7) 0.0255(3) Uani 1 1 d .
H2 H -0.0209 0.4376 0.6096 0.031 Uiso 1 1 calc R
C3 C 0.10630(11) 0.30814(15) 0.68524(7) 0.0275(3) Uani 1 1 d .
H3 H 0.0930 0.3654 0.7262 0.033 Uiso 1 1 calc R
C4 C 0.21995(10) 0.09436(15) 0.64273(6) 0.0240(2) Uani 1 1 d .
C5 C 0.15101(10) 0.14039(13) 0.56995(6) 0.0201(2) Uani 1 1 d .
C6 C 0.15265(10) 0.08235(13) 0.49811(6) 0.0201(2) Uani 1 1 d .
C7 C 0.21758(10) -0.03716(14) 0.47109(6) 0.0237(2) Uani 1 1 d .
H7 H 0.2771 -0.1050 0.5036 0.028 Uiso 1 1 calc R
C8 C 0.19264(11) -0.05413(15) 0.39510(7) 0.0279(3) Uani 1 1 d .
H8 H 0.2354 -0.1353 0.3755 0.033 Uiso 1 1 calc R
C9 C 0.10598(11) 0.04595(16) 0.34717(6) 0.0289(3) Uani 1 1 d .
H9 H 0.0923 0.0325 0.2955 0.035 Uiso 1 1 calc R
C10 C 0.03901(11) 0.16500(15) 0.37288(6) 0.0270(3) Uani 1 1 d .
H10 H -0.0209 0.2323 0.3404 0.032 Uiso 1 1 calc R
C11 C 0.06518(10) 0.17927(13) 0.44869(6) 0.0216(2) Uani 1 1 d .
O1 O 0.01080(7) 0.29158(10) 0.48602(4) 0.0240(2) Uani 1 1 d .
O2 O 0.19246(8) 0.18498(11) 0.69877(4) 0.0280(2) Uani 1 1 d .
O3 O 0.29777(8) -0.01200(12) 0.66034(5) 0.0337(2) Uani 1 1 d .
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
C1 0.0192(5) 0.0228(5) 0.0216(5) -0.0005(4) 0.0047(4) -0.0029(4)
C2 0.0220(5) 0.0265(6) 0.0291(6) -0.0061(5) 0.0086(4) -0.0007(4)
C3 0.0247(6) 0.0327(6) 0.0275(6) -0.0070(5) 0.0113(5) -0.0032(5)
C4 0.0239(5) 0.0283(6) 0.0207(5) 0.0010(4) 0.0078(4) -0.0012(4)
C5 0.0193(5) 0.0206(5) 0.0208(5) -0.0005(4) 0.0061(4) -0.0020(4)
C6 0.0187(5) 0.0201(5) 0.0214(5) -0.0004(4) 0.0056(4) -0.0039(4)
C7 0.0226(5) 0.0219(5) 0.0269(6) -0.0018(4) 0.0073(4) -0.0015(4)
C8 0.0271(6) 0.0286(6) 0.0301(6) -0.0086(5) 0.0112(5) -0.0057(5)
C9 0.0293(6) 0.0369(7) 0.0205(5) -0.0061(5) 0.0068(4) -0.0094(5)
C10 0.0247(5) 0.0316(6) 0.0221(5) 0.0012(5) 0.0021(4) -0.0042(5)
C11 0.0197(5) 0.0216(5) 0.0232(5) -0.0017(4) 0.0053(4) -0.0025(4)
O1 0.0226(4) 0.0251(4) 0.0229(4) -0.0001(3) 0.0038(3) 0.0031(3)
O2 0.0284(4) 0.0360(5) 0.0200(4) -0.0009(3) 0.0072(3) 0.0014(3)
O3 0.0353(5) 0.0399(5) 0.0253(4) 0.0085(4) 0.0072(4) 0.0129(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
O1 C1 C5 111.94(9)
O1 C1 C2 125.09(10)
C5 C1 C2 122.97(10)
C3 C2 C1 115.09(11)
C3 C2 H2 122.5
C1 C2 H2 122.5
C2 C3 O2 123.95(11)
C2 C3 H3 118.0
O2 C3 H3 118.0
O3 C4 O2 117.72(10)
O3 C4 C5 127.66(11)
O2 C4 C5 114.62(10)
C1 C5 C4 120.67(10)
C1 C5 C6 106.87(9)
C4 C5 C6 132.45(10)
C7 C6 C11 119.50(10)
C7 C6 C5 135.78(10)
C11 C6 C5 104.72(10)
C8 C7 C6 117.99(11)
C8 C7 H7 121.0
C6 C7 H7 121.0
C7 C8 C9 121.17(11)
C7 C8 H8 119.4
C9 C8 H8 119.4
C10 C9 C8 121.87(11)
C10 C9 H9 119.1
C8 C9 H9 119.1
C11 C10 C9 115.89(11)
C11 C10 H10 122.1
C9 C10 H10 122.1
C10 C11 O1 125.41(10)
C10 C11 C6 123.57(11)
O1 C11 C6 111.01(9)
C1 O1 C11 105.46(8)
C3 O2 C4 122.70(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.3631(13)
C1 C5 1.3707(15)
C1 C2 1.4154(16)
C2 C3 1.3410(17)
C2 H2 0.9500
C3 O2 1.3682(15)
C3 H3 0.9500
C4 O3 1.2105(14)
C4 O2 1.3926(14)
C4 C5 1.4287(15)
C5 C6 1.4407(15)
C6 C7 1.3940(15)
C6 C11 1.3980(15)
C7 C8 1.3905(16)
C7 H7 0.9500
C8 C9 1.3951(18)
C8 H8 0.9500
C9 C10 1.3932(18)
C9 H9 0.9500
C10 C11 1.3841(16)
C10 H10 0.9500
C11 O1 1.3937(13)
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
O1 C1 C2 C3 -178.46(10)
C5 C1 C2 C3 0.93(17)
C1 C2 C3 O2 -1.06(17)
O1 C1 C5 C4 179.12(9)
C2 C1 C5 C4 -0.34(17)
O1 C1 C5 C6 0.24(12)
C2 C1 C5 C6 -179.22(10)
O3 C4 C5 C1 179.99(12)
O2 C4 C5 C1 -0.16(15)
O3 C4 C5 C6 -1.5(2)
O2 C4 C5 C6 178.39(11)
C1 C5 C6 C7 179.41(12)
C4 C5 C6 C7 0.7(2)
C1 C5 C6 C11 -0.07(12)
C4 C5 C6 C11 -178.76(11)
C11 C6 C7 C8 0.41(16)
C5 C6 C7 C8 -179.00(12)
C6 C7 C8 C9 0.45(17)
C7 C8 C9 C10 -1.17(18)
C8 C9 C10 C11 0.94(17)
C9 C10 C11 O1 178.89(10)
C9 C10 C11 C6 -0.06(17)
C7 C6 C11 C10 -0.62(17)
C5 C6 C11 C10 178.96(10)
C7 C6 C11 O1 -179.70(9)
C5 C6 C11 O1 -0.13(12)
C5 C1 O1 C11 -0.31(12)
C2 C1 O1 C11 179.14(10)
C10 C11 O1 C1 -178.79(11)
C6 C11 O1 C1 0.27(11)
C2 C3 O2 C4 0.62(18)
O3 C4 O2 C3 179.92(10)
C5 C4 O2 C3 0.05(15)
