#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:52:34 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180320 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/34/7153424.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_7153424
loop_
_publ_author_name
'Ravelli, Davide'
'Zema, Michele'
'Mella, Mariella'
'Fagnoni, Maurizio'
'Albini, Angelo'
_publ_section_title
;
 Benzoyl radicals from (hetero)aromatic aldehydes. Decatungstate
 photocatalyzed synthesis of substituted aromatic ketones.
;
_journal_issue                   18
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4158
_journal_page_last               4164
_journal_paper_doi               10.1039/c0ob00066c
_journal_volume                  8
_journal_year                    2010
_chemical_formula_moiety         'C16 H18 O3'
_chemical_formula_sum            'C16 H18 O3'
_chemical_formula_weight         258.30
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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                 93.2240(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.0252(6)
_cell_length_b                   6.6763(4)
_cell_length_c                   20.0548(12)
_cell_measurement_reflns_used    2216
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.7
_cell_measurement_theta_min      2.8
_cell_measurement_wavelength     0.71073
_cell_volume                     1340.17(14)
_computing_cell_refinement       'GLOBAL (Bruker)'
_computing_data_collection       'Bruker-AXS SMART APEX'
_computing_data_reduction        'SAINTPLUS (Bruker)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publ routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device_type  'Bruker-AXS SMART APEX'
_diffrn_measurement_method       'ω scan'
_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  0.0485
_diffrn_reflns_av_sigmaI/netI    0.0432
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            14597
_diffrn_reflns_theta_full        29.99
_diffrn_reflns_theta_max         29.99
_diffrn_reflns_theta_min         2.03
_diffrn_standards_decay_%        0.0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sheldrick, 2004'
_exptl_crystal_colour            'pale green'
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3906
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.1102
_refine_ls_R_factor_gt           0.0581
_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)+(0.0646P)²+0.1037P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1253
_refine_ls_wR_factor_ref         0.1469
_reflns_number_gt                2207
_reflns_number_total             3906
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ob00066c.txt
_cod_data_source_block           fagn2
_cod_database_code               7153424
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_calc_flag
O1 O 0.49575(12) 0.63915(19) 0.79417(7) 0.0652(4) Uani 1 d
O2 O 0.09843(12) 0.32357(19) 0.89234(6) 0.0649(4) Uani 1 d
O3 O 0.32643(14) -0.4701(2) 1.02607(7) 0.0763(4) Uani 1 d
C1 C 0.31581(18) 0.7137(3) 0.71143(9) 0.0560(5) Uani 1 d
C2 C 0.37932(16) 0.6344(2) 0.77571(8) 0.0476(4) Uani 1 d
C3 C 0.26764(16) 0.5368(2) 0.81281(8) 0.0461(4) Uani 1 d
C4 C 0.15132(17) 0.5500(3) 0.75986(9) 0.0542(4) Uani 1 d
C5 C 0.1789(2) 0.4181(3) 0.70057(10) 0.0661(5) Uani 1 d
C6 C 0.2918(2) 0.5270(3) 0.66769(10) 0.0648(5) Uani 1 d
C7 C 0.17451(19) 0.7602(3) 0.73178(11) 0.0606(5) Uani 1 d
C8 C 0.30910(18) 0.3383(3) 0.84387(9) 0.0488(4) Uani 1 d
C9 C 0.20612(16) 0.2440(2) 0.88598(7) 0.0452(4) Uani 1 d
C10 C 0.23912(15) 0.0509(2) 0.92036(7) 0.0418(4) Uani 1 d
C11 C 0.13798(17) -0.0538(3) 0.94951(8) 0.0493(4) Uani 1 d
C12 C 0.16210(18) -0.2275(3) 0.98516(9) 0.0527(4) Uani 1 d
C13 C 0.29052(17) -0.3004(3) 0.99163(8) 0.0514(4) Uani 1 d
C14 C 0.39284(18) -0.2020(3) 0.96180(9) 0.0566(5) Uani 1 d
C15 C 0.36686(17) -0.0288(3) 0.92658(8) 0.0503(4) Uani 1 d
C16 C 0.2283(3) -0.5725(4) 1.06118(14) 0.0794(7) Uani 1 d
H1 H 0.3643(18) 0.816(3) 0.6912(9) 0.065(5) Uiso 1 d
H3 H 0.2461(17) 0.630(3) 0.8490(9) 0.057(5) Uiso 1 d
H4 H 0.0680(18) 0.538(3) 0.7774(9) 0.055(5) Uiso 1 d
H6A H 0.368(2) 0.443(4) 0.6663(11) 0.086(7) Uiso 1 d
H6B H 0.2618(19) 0.568(3) 0.6209(11) 0.075(6) Uiso 1 d
H5A H 0.098(2) 0.409(3) 0.6713(12) 0.090(7) Uiso 1 d
H5B H 0.201(2) 0.277(4) 0.7145(11) 0.087(7) Uiso 1 d
H7A H 0.173(2) 0.868(3) 0.7648(11) 0.076(6) Uiso 1 d
H7B H 0.1122(19) 0.786(3) 0.6918(10) 0.068(6) Uiso 1 d
H8A H 0.3363(17) 0.243(3) 0.8072(10) 0.065(5) Uiso 1 d
H8B H 0.389(2) 0.361(3) 0.8740(10) 0.067(6) Uiso 1 d
H11 H 0.0519(19) -0.004(3) 0.9457(9) 0.060(5) Uiso 1 d
H12 H 0.0919(19) -0.295(3) 1.0049(9) 0.063(5) Uiso 1 d
H14 H 0.4772(19) -0.259(3) 0.9667(9) 0.066(5) Uiso 1 d
H15 H 0.4360(18) 0.036(3) 0.9067(9) 0.057(5) Uiso 1 d
H16A H 0.186(2) -0.484(4) 1.0921(13) 0.101(8) Uiso 1 d
H16B H 0.280(3) -0.671(5) 1.0848(15) 0.125(10) Uiso 1 d
H16C H 0.158(3) -0.632(4) 1.0304(14) 0.108(9) Uiso 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
C13 O3 C16 118.75(17)
C2 C1 C7 101.37(15)
C2 C1 C6 104.43(15)
C7 C1 C6 101.50(16)
C2 C1 H1 114.9(11)
C7 C1 H1 118.4(11)
C6 C1 H1 114.2(11)
O1 C2 C1 127.66(16)
O1 C2 C3 125.91(15)
C1 C2 C3 106.38(14)
C8 C3 C2 112.51(14)
C8 C3 C4 121.04(15)
C2 C3 C4 100.83(13)
C8 C3 H3 108.3(10)
C2 C3 H3 106.6(10)
C4 C3 H3 106.5(10)
C5 C4 C7 101.83(16)
C5 C4 C3 110.13(16)
C7 C4 C3 100.46(14)
C5 C4 H4 116.9(11)
C7 C4 H4 112.2(11)
C3 C4 H4 113.5(11)
C4 C5 C6 103.55(16)
C4 C5 H5A 109.1(14)
C6 C5 H5A 112.3(13)
C4 C5 H5B 111.9(13)
C6 C5 H5B 114.2(12)
H5A C5 H5B 105.9(18)
C5 C6 C1 103.66(16)
C5 C6 H6A 110.5(14)
C1 C6 H6A 113.2(14)
C5 C6 H6B 110.0(11)
C1 C6 H6B 110.0(12)
H6A C6 H6B 109.3(18)
C1 C7 C4 94.26(14)
C1 C7 H7A 112.2(13)
C4 C7 H7A 114.6(12)
C1 C7 H7B 111.5(11)
C4 C7 H7B 110.4(11)
H7A C7 H7B 112.6(17)
C9 C8 C3 114.55(14)
C9 C8 H8A 111.3(10)
C3 C8 H8A 109.1(10)
C9 C8 H8B 106.1(11)
C3 C8 H8B 108.2(11)
H8A C8 H8B 107.2(15)
O2 C9 C10 120.30(14)
O2 C9 C8 121.08(15)
C10 C9 C8 118.62(13)
C15 C10 C11 117.52(15)
C15 C10 C9 123.62(14)
C11 C10 C9 118.83(14)
C12 C11 C10 122.14(16)
C12 C11 H11 119.0(11)
C10 C11 H11 118.8(11)
C13 C12 C11 118.89(16)
C13 C12 H12 120.6(11)
C11 C12 H12 120.5(11)
O3 C13 C12 124.08(16)
O3 C13 C14 115.62(16)
C12 C13 C14 120.29(16)
C15 C14 C13 119.94(17)
C15 C14 H14 123.0(12)
C13 C14 H14 117.1(12)
C14 C15 C10 121.17(16)
C14 C15 H15 119.2(11)
C10 C15 H15 119.6(11)
O3 C16 H16A 111.4(15)
O3 C16 H16B 102.2(18)
H16A C16 H16B 111(2)
O3 C16 H16C 112.0(15)
H16A C16 H16C 108(2)
H16B C16 H16C 112(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.2051(19)
O2 C9 1.2164(18)
O3 C13 1.364(2)
O3 C16 1.418(3)
C1 C2 1.502(2)
C1 C7 1.528(3)
C1 C6 1.536(3)
C1 H1 0.944(19)
C2 C3 1.525(2)
C3 C8 1.513(2)
C3 C4 1.535(2)
C3 H3 0.989(18)
C4 C5 1.517(3)
C4 C7 1.534(3)
C4 H4 0.928(18)
C5 C6 1.526(3)
C5 H5A 0.97(2)
C5 H5B 1.00(2)
C6 H6A 0.95(2)
C6 H6B 1.01(2)
C7 H7A 0.98(2)
C7 H7B 1.00(2)
C8 C9 1.508(2)
C8 H8A 1.020(19)
C8 H8B 0.99(2)
C9 C10 1.491(2)
C10 C15 1.386(2)
C10 C11 1.388(2)
C11 C12 1.376(2)
C11 H11 0.925(19)
C12 C13 1.376(2)
C12 H12 0.942(19)
C13 C14 1.382(2)
C14 C15 1.372(3)
C14 H14 0.927(19)
C15 H15 0.925(19)
C16 H16A 0.97(3)
C16 H16B 0.95(3)
C16 H16C 0.99(3)
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
C7 C1 C2 O1 -152.55(18)
C6 C1 C2 O1 102.3(2)
C7 C1 C2 C3 29.77(18)
C6 C1 C2 C3 -75.41(16)
O1 C2 C3 C8 -40.8(2)
C1 C2 C3 C8 136.98(16)
O1 C2 C3 C4 -171.12(17)
C1 C2 C3 C4 6.61(17)
C8 C3 C4 C5 -58.4(2)
C2 C3 C4 C5 66.33(17)
C8 C3 C4 C7 -165.27(15)
C2 C3 C4 C7 -40.51(16)
C7 C4 C5 C6 35.6(2)
C3 C4 C5 C6 -70.3(2)
C4 C5 C6 C1 -0.9(2)
C2 C1 C6 C5 70.85(19)
C7 C1 C6 C5 -34.23(19)
C2 C1 C7 C4 -53.13(17)
C6 C1 C7 C4 54.35(17)
C5 C4 C7 C1 -55.37(18)
C3 C4 C7 C1 57.97(17)
C2 C3 C8 C9 175.12(14)
C4 C3 C8 C9 -65.7(2)
C3 C8 C9 O2 1.3(2)
C3 C8 C9 C10 -178.26(14)
O2 C9 C10 C15 -166.81(16)
C8 C9 C10 C15 12.8(2)
O2 C9 C10 C11 11.4(2)
C8 C9 C10 C11 -169.03(15)
C15 C10 C11 C12 1.9(2)
C9 C10 C11 C12 -176.45(15)
C10 C11 C12 C13 -0.5(3)
C16 O3 C13 C12 -4.2(3)
C16 O3 C13 C14 176.4(2)
C11 C12 C13 O3 179.57(17)
C11 C12 C13 C14 -1.0(3)
O3 C13 C14 C15 -179.37(17)
C12 C13 C14 C15 1.2(3)
C13 C14 C15 C10 0.2(3)
C11 C10 C15 C14 -1.7(2)
C9 C10 C15 C14 176.53(16)
