#------------------------------------------------------------------------------
#$Date: 2016-03-25 22:23:42 +0200 (Fri, 25 Mar 2016) $
#$Revision: 180010 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/04/7030431.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_7030431
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         'C12 H8 O3'
_chemical_formula_sum            'C12 H8 O3'
_chemical_formula_weight         200.18
_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                69.7600(10)
_cell_angle_beta                 81.8920(10)
_cell_angle_gamma                75.2200(10)
_cell_formula_units_Z            2
_cell_length_a                   7.1467(5)
_cell_length_b                   7.3546(5)
_cell_length_c                   9.3252(6)
_cell_measurement_reflns_used    4450
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.35
_cell_measurement_theta_min      2.33
_cell_volume                     443.91(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, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0124
_diffrn_reflns_av_sigmaI/netI    0.0124
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6084
_diffrn_reflns_theta_full        28.35
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         2.33
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.13 (Sheldrick)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             208
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2211
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0352
_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)+(0.0628P)²+0.0958P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1023
_reflns_number_gt                2081
_reflns_number_total             2211
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0dt00421a.txt
_cod_data_source_block           ijf0925m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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      P-1
_cod_database_code               7030431
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
C1 C -0.04997(13) 0.55646(13) 0.21453(10) 0.01846(19) Uani 1 1 d .
C2 C 0.01747(12) 0.67816(13) 0.07049(10) 0.01757(19) Uani 1 1 d .
C3 C -0.07940(13) 0.81841(13) -0.06290(10) 0.0181(2) Uani 1 1 d .
C4 C -0.27071(13) 0.89311(14) -0.10585(11) 0.0214(2) Uani 1 1 d .
H4 H -0.3727 0.8489 -0.0407 0.026 Uiso 1 1 calc R
C5 C -0.30405(15) 1.03589(15) -0.24944(12) 0.0248(2) Uani 1 1 d .
H5 H -0.4305 1.0879 -0.2799 0.030 Uiso 1 1 calc R
C6 C -0.15193(15) 1.10283(15) -0.34879(11) 0.0248(2) Uani 1 1 d .
H6 H -0.1792 1.1979 -0.4440 0.030 Uiso 1 1 calc R
C7 C 0.03971(15) 1.02973(14) -0.30771(11) 0.0232(2) Uani 1 1 d .
H7 H 0.1419 1.0731 -0.3730 0.028 Uiso 1 1 calc R
C8 C 0.06943(13) 0.88914(13) -0.16440(10) 0.0192(2) Uani 1 1 d .
C9 C 0.21165(13) 0.67617(13) 0.04085(10) 0.01778(19) Uani 1 1 d .
C10 C 0.35408(13) 0.55994(13) 0.14668(10) 0.01894(19) Uani 1 1 d .
H10 H 0.4849 0.5610 0.1243 0.023 Uiso 1 1 calc R
C11 C 0.28734(13) 0.44709(13) 0.28282(10) 0.01871(19) Uani 1 1 d .
C12 C 0.40791(14) 0.31764(14) 0.41321(11) 0.0237(2) Uani 1 1 d .
H12A H 0.5399 0.3303 0.3875 0.036 Uiso 1 1 calc R
H12B H 0.4017 0.1819 0.4344 0.036 Uiso 1 1 calc R
H12C H 0.3602 0.3570 0.5020 0.036 Uiso 1 1 calc R
O1 O 0.09506(9) 0.44335(10) 0.31570(7) 0.01984(17) Uani 1 1 d .
O2 O -0.21517(10) 0.54064(11) 0.25804(8) 0.02521(18) Uani 1 1 d .
O3 O 0.24928(9) 0.80190(10) -0.10127(7) 0.02019(17) Uani 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
O2 C1 O1 117.28(8)
O2 C1 C2 128.10(8)
O1 C1 C2 114.62(8)
C9 C2 C1 119.99(8)
C9 C2 C3 106.81(8)
C1 C2 C3 133.18(8)
C4 C3 C8 119.15(8)
C4 C3 C2 136.20(8)
C8 C3 C2 104.64(8)
C5 C4 C3 117.91(9)
C5 C4 H4 121.0
C3 C4 H4 121.0
C4 C5 C6 121.59(9)
C4 C5 H5 119.2
C6 C5 H5 119.2
C7 C6 C5 121.20(9)
C7 C6 H6 119.4
C5 C6 H6 119.4
C8 C7 C6 116.26(9)
C8 C7 H7 121.9
C6 C7 H7 121.9
C7 C8 O3 124.89(9)
C7 C8 C3 123.89(9)
O3 C8 C3 111.22(8)
O3 C9 C2 111.95(8)
O3 C9 C10 124.36(8)
C2 C9 C10 123.68(8)
C11 C10 C9 115.48(8)
C11 C10 H10 122.3
C9 C10 H10 122.3
C10 C11 O1 122.46(8)
C10 C11 C12 125.33(8)
O1 C11 C12 112.20(8)
C11 C12 H12A 109.5
C11 C12 H12B 109.5
H12A C12 H12B 109.5
C11 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C11 O1 C1 123.76(7)
C9 O3 C8 105.37(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O2 1.2142(11)
C1 O1 1.3962(10)
C1 C2 1.4295(12)
C2 C9 1.3736(12)
C2 C3 1.4426(12)
C3 C4 1.3966(12)
C3 C8 1.3984(12)
C4 C5 1.3935(13)
C4 H4 0.9300
C5 C6 1.3986(15)
C5 H5 0.9300
C6 C7 1.3934(14)
C6 H6 0.9300
C7 C8 1.3827(13)
C7 H7 0.9300
C8 O3 1.3935(11)
C9 O3 1.3646(10)
C9 C10 1.4130(12)
C10 C11 1.3529(12)
C10 H10 0.9300
C11 O1 1.3702(11)
C11 C12 1.4844(12)
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 0.9600
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
O2 C1 C2 C9 -179.68(9)
O1 C1 C2 C9 0.37(13)
O2 C1 C2 C3 1.67(17)
O1 C1 C2 C3 -178.28(9)
C9 C2 C3 C4 -178.04(10)
C1 C2 C3 C4 0.74(18)
C9 C2 C3 C8 0.51(10)
C1 C2 C3 C8 179.28(9)
C8 C3 C4 C5 0.07(13)
C2 C3 C4 C5 178.45(10)
C3 C4 C5 C6 0.31(14)
C4 C5 C6 C7 -0.28(15)
C5 C6 C7 C8 -0.13(14)
C6 C7 C8 O3 -178.46(8)
C6 C7 C8 C3 0.53(14)
C4 C3 C8 C7 -0.50(14)
C2 C3 C8 C7 -179.35(9)
C4 C3 C8 O3 178.61(7)
C2 C3 C8 O3 -0.24(10)
C1 C2 C9 O3 -179.59(7)
C3 C2 C9 O3 -0.62(10)
C1 C2 C9 C10 -0.65(14)
C3 C2 C9 C10 178.31(8)
O3 C9 C10 C11 178.88(8)
C2 C9 C10 C11 0.07(14)
C9 C10 C11 O1 0.79(13)
C9 C10 C11 C12 -178.17(8)
C10 C11 O1 C1 -1.10(14)
C12 C11 O1 C1 177.97(8)
O2 C1 O1 C11 -179.48(8)
C2 C1 O1 C11 0.47(12)
C2 C9 O3 C8 0.47(10)
C10 C9 O3 C8 -178.46(8)
C7 C8 O3 C9 178.98(9)
C3 C8 O3 C9 -0.12(10)
