#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:43:29 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180274 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/60/7116042.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_7116042
loop_
_publ_author_name
'Mieko Arisawa'
'Saori Tanii'
'Masahiko Yamaguchi'
_publ_section_title
;
 A palladium-catalyzed addition reaction of aroyl/heteroaroyl acid
 anhydrides to norbornenes
;
_journal_name_full               Chem.Commun.
_journal_page_first              15267
_journal_paper_doi               10.1039/C4cc07759H
_journal_volume                  50
_journal_year                    2014
_chemical_formula_sum            'C21 H18 O3'
_chemical_formula_weight         318.35
_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                 103.618(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.8452(15)
_cell_length_b                   16.351(3)
_cell_length_c                   10.564(2)
_cell_measurement_reflns_used    4562
_cell_measurement_temperature    373(2)
_cell_measurement_theta_max      27.41
_cell_measurement_theta_min      3.19
_cell_volume                     1652.8(5)
_computing_molecular_graphics
'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material
'Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      373(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Rigaku R-AXIS'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'seald X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_av_sigmaI/netI    0.0573
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14893
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.19
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9750
_exptl_absorpt_correction_T_min  0.9750
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.119
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3723
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.1244
_refine_ls_R_factor_gt           0.0662
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1384P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1619
_refine_ls_wR_factor_ref         0.2334
_reflns_number_gt                2031
_reflns_number_total             3723
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc07759h2.cif
_cod_data_source_block           ydkr
_cod_original_cell_volume        1652.7(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7116042
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
C1 C -0.07155(16) 0.34029(12) 0.02762(13) 0.0471(7) Uani 1 1 d G
H1 H -0.1383 0.3231 -0.0452 0.057 Uiso 1 1 calc R
C2 C -0.08856(14) 0.32282(10) 0.15174(15) 0.0358(6) Uani 1 1 d G
C3 C 0.01121(17) 0.34847(11) 0.26064(12) 0.0447(7) Uani 1 1 d G
H2 H -0.0002 0.3368 0.3437 0.054 Uiso 1 1 calc R
C4 C 0.12799(15) 0.39160(11) 0.24543(15) 0.0510(7) Uani 1 1 d G
H3 H 0.1947 0.4088 0.3183 0.061 Uiso 1 1 calc R
C5 C 0.14501(16) 0.40907(12) 0.12132(18) 0.0567(8) Uani 1 1 d G
H4 H 0.2231 0.4379 0.1111 0.068 Uiso 1 1 calc R
C6 C 0.04524(19) 0.38342(13) 0.01241(14) 0.0583(8) Uani 1 1 d G
H5 H 0.0566 0.3951 -0.0706 0.070 Uiso 1 1 calc R
C7 C -0.74057(18) 0.31507(7) -0.23885(18) 0.0489(7) Uani 1 1 d G
H6 H -0.7287 0.2588 -0.2290 0.059 Uiso 1 1 calc R
C8 C -0.66598(16) 0.36763(9) -0.14419(15) 0.0406(6) Uani 1 1 d G
C9 C -0.68366(17) 0.45171(9) -0.15892(16) 0.0469(7) Uani 1 1 d G
H7 H -0.6338 0.4869 -0.0956 0.056 Uiso 1 1 calc R
C10 C -0.77593(18) 0.48324(8) -0.26832(19) 0.0546(8) Uani 1 1 d G
H8 H -0.7878 0.5395 -0.2782 0.066 Uiso 1 1 calc R
C11 C -0.85053(18) 0.43068(12) -0.36298(16) 0.0606(9) Uani 1 1 d G
H9 H -0.9123 0.4518 -0.4362 0.073 Uiso 1 1 calc R
C12 C -0.83285(18) 0.34660(11) -0.34825(16) 0.0610(9) Uani 1 1 d G
H10 H -0.8828 0.3114 -0.4116 0.073 Uiso 1 1 calc R
O1 O -0.23512(19) 0.27786(13) 0.28355(16) 0.0497(5) Uani 1 1 d .
O2 O -0.56211(16) 0.25409(10) -0.02251(17) 0.0413(5) Uani 1 1 d .
O3 O -0.4929(2) 0.37832(12) 0.0561(2) 0.0599(6) Uani 1 1 d .
C13 C -0.2137(2) 0.27863(15) 0.1742(2) 0.0363(6) Uani 1 1 d .
C14 C -0.4584(2) 0.21786(15) 0.0839(2) 0.0368(6) Uani 1 1 d .
H11 H -0.4683 0.2375 0.1689 0.044 Uiso 1 1 calc R
C15 C -0.3095(2) 0.23222(15) 0.0651(2) 0.0336(6) Uani 1 1 d .
H12 H -0.3159 0.2619 -0.0167 0.040 Uiso 1 1 calc R
C16 C -0.5656(3) 0.33627(16) -0.0264(3) 0.0433(7) Uani 1 1 d .
C17 C -0.2588(2) 0.14238(15) 0.0488(2) 0.0389(6) Uani 1 1 d .
H13 H -0.1767 0.1371 0.0119 0.047 Uiso 1 1 calc R
C18 C -0.3959(3) 0.10629(17) -0.0332(3) 0.0443(7) Uani 1 1 d .
H14 H -0.4312 0.1357 -0.1140 0.053 Uiso 1 1 calc R
H15 H -0.3893 0.0483 -0.0501 0.053 Uiso 1 1 calc R
C19 C -0.2499(3) 0.09951(16) 0.1773(3) 0.0467(7) Uani 1 1 d .
H16 H -0.1685 0.0835 0.2363 0.056 Uiso 1 1 calc R
C20 C -0.4781(3) 0.12465(16) 0.0706(3) 0.0442(7) Uani 1 1 d .
H17 H -0.5747 0.1048 0.0521 0.053 Uiso 1 1 calc R
C21 C -0.3790(3) 0.08892(16) 0.1902(3) 0.0505(8) Uani 1 1 d .
H18 H -0.4046 0.0640 0.2602 0.061 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C6 120.0
C3 C2 C1 120.0
C3 C2 C13 117.55(13)
C1 C2 C13 122.43(13)
C2 C3 C4 120.0
C5 C4 C3 120.0
C4 C5 C6 120.0
C5 C6 C1 120.0
C8 C7 C12 120.0
C7 C8 C9 120.0
C7 C8 C16 121.57(15)
C9 C8 C16 118.42(15)
C10 C9 C8 120.0
C9 C10 C11 120.0
C12 C11 C10 120.0
C11 C12 C7 120.0
C16 O2 C14 116.02(19)
O1 C13 C2 119.2(2)
O1 C13 C15 120.0(2)
C2 C13 C15 120.75(19)
O2 C14 C20 106.4(2)
O2 C14 C15 110.73(18)
C20 C14 C15 104.03(19)
C13 C15 C14 114.8(2)
C13 C15 C17 113.3(2)
C14 C15 C17 101.97(18)
O3 C16 O2 122.8(2)
O3 C16 C8 125.0(2)
O2 C16 C8 112.2(2)
C19 C17 C18 100.7(2)
C19 C17 C15 106.71(19)
C18 C17 C15 99.25(19)
C20 C18 C17 93.6(2)
C21 C19 C17 107.5(2)
C21 C20 C18 100.1(2)
C21 C20 C14 105.2(2)
C18 C20 C14 100.48(19)
C19 C21 C20 108.0(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.3900
C1 C6 1.3900
C2 C3 1.3900
C2 C13 1.495(3)
C3 C4 1.3900
C4 C5 1.3900
C5 C6 1.3900
C7 C8 1.3900
C7 C12 1.3900
C8 C9 1.3900
C8 C16 1.486(3)
C9 C10 1.3900
C10 C11 1.3900
C11 C12 1.3900
O1 C13 1.222(3)
O2 C16 1.345(3)
O2 C14 1.455(3)
O3 C16 1.204(3)
C13 C15 1.511(3)
C14 C20 1.539(4)
C14 C15 1.543(3)
C15 C17 1.574(3)
C17 C19 1.511(4)
C17 C18 1.540(3)
C18 C20 1.538(4)
C19 C21 1.321(4)
C20 C21 1.520(4)
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
C6 C1 C2 C3 0.0
C6 C1 C2 C13 178.35(18)
C1 C2 C3 C4 0.0
C13 C2 C3 C4 -178.43(17)
C2 C3 C4 C5 0.0
C3 C4 C5 C6 0.0
C4 C5 C6 C1 0.0
C2 C1 C6 C5 0.0
C12 C7 C8 C9 0.0
C12 C7 C8 C16 -179.52(18)
C7 C8 C9 C10 0.0
C16 C8 C9 C10 179.54(18)
C8 C9 C10 C11 0.0
C9 C10 C11 C12 0.0
C10 C11 C12 C7 0.0
C8 C7 C12 C11 0.0
C3 C2 C13 O1 11.4(3)
C1 C2 C13 O1 -167.02(18)
C3 C2 C13 C15 -165.96(17)
C1 C2 C13 C15 15.7(3)
C16 O2 C14 C20 177.99(19)
C16 O2 C14 C15 -69.6(3)
O1 C13 C15 C14 24.7(3)
C2 C13 C15 C14 -158.0(2)
O1 C13 C15 C17 -91.9(3)
C2 C13 C15 C17 85.5(3)
O2 C14 C15 C13 120.8(2)
C20 C14 C15 C13 -125.2(2)
O2 C14 C15 C17 -116.3(2)
C20 C14 C15 C17 -2.3(2)
C14 O2 C16 O3 -3.7(4)
C14 O2 C16 C8 175.13(18)
C7 C8 C16 O3 176.4(2)
C9 C8 C16 O3 -3.2(3)
C7 C8 C16 O2 -2.5(3)
C9 C8 C16 O2 178.01(14)
C13 C15 C17 C19 58.5(3)
C14 C15 C17 C19 -65.4(2)
C13 C15 C17 C18 162.69(19)
C14 C15 C17 C18 38.8(2)
C19 C17 C18 C20 49.9(2)
C15 C17 C18 C20 -59.2(2)
C18 C17 C19 C21 -33.2(3)
C15 C17 C19 C21 70.0(3)
C17 C18 C20 C21 -49.5(2)
C17 C18 C20 C14 58.2(2)
O2 C14 C20 C21 -174.42(18)
C15 C14 C20 C21 68.6(2)
O2 C14 C20 C18 82.0(2)
C15 C14 C20 C18 -35.0(2)
C17 C19 C21 C20 -0.1(3)
C18 C20 C21 C19 33.3(3)
C14 C20 C21 C19 -70.6(3)
