#------------------------------------------------------------------------------
#$Date: 2015-09-22 09:57:49 +0200 (mar 22 de sep de 2015) $
#$Revision: 158214 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/77/7117798.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_7117798
loop_
_publ_author_name
'Beom Shin Cho'
'Young Keun Chung'
_publ_section_title
;
 Palladium-catalyzed bisarylation of 3-alkylbenzofurans to
 3-arylalkyl-2-arylbenzofurans on water: tandem C(sp3)-H and C(sp2)-H
 activation reactions of 3-alkylbenzofurans
;
_journal_name_full               Chem.Commun.
_journal_page_first              14543
_journal_paper_doi               10.1039/C5cc04052C
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C25 H18 O'
_chemical_formula_sum            'C25 H18 O'
_chemical_formula_weight         334.39
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-01-19
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_audit_update_record
;
2015-01-24 deposited with the CCDC.
2015-08-07 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 103.1477(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.2582(2)
_cell_length_b                   6.2091(2)
_cell_length_c                   17.8371(5)
_cell_measurement_reflns_used    9971
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      2.35
_cell_volume                     890.64(4)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      223.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            31392
_diffrn_reflns_theta_full        28.41
_diffrn_reflns_theta_max         28.41
_diffrn_reflns_theta_min         2.35
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.9926
_exptl_absorpt_correction_T_min  0.9824
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.4(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4438
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0405
_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)+(0.0340P)²+0.1670P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0833
_refine_ls_wR_factor_ref         0.0958
_reflns_number_gt                3479
_reflns_number_total             4438
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc04052c2.cif
_cod_data_source_block           no1
_cod_database_code               7117798
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C9(H9), C12(H12), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O -0.98315(13) -0.43300(18) -0.25200(6) 0.0302(3) Uani 1 d . . .
C2 C -0.82171(19) -0.4148(3) -0.11916(10) 0.0312(4) Uani 1 d . . .
H2 H -0.7728 -0.5510 -0.1207 0.037 Uiso 1 calc . . R
C3 C -0.93398(19) -0.3361(3) -0.18060(9) 0.0279(4) Uani 1 d . . .
C4 C -1.09181(19) -0.2887(3) -0.29875(10) 0.0301(4) Uani 1 d . . .
C5 C -0.8591(2) -0.0775(3) -0.05212(10) 0.0347(4) Uani 1 d . . .
C6 C -0.7812(2) -0.2843(3) -0.05272(10) 0.0327(4) Uani 1 d . . .
C7 C -1.38173(18) 0.1117(2) -0.27846(9) 0.0274(3) Uani 1 d . . .
C8 C -1.15316(19) -0.3586(3) -0.37822(10) 0.0320(4) Uani 1 d . . .
C9 C -0.97567(19) -0.0051(3) -0.11761(10) 0.0333(4) Uani 1 d . . .
H9 H -1.0279 0.1292 -0.1172 0.040 Uiso 1 calc . . R
C10 C -1.01252(18) -0.1333(3) -0.18246(9) 0.0280(3) Uani 1 d . . .
C11 C -1.20523(19) 0.0936(3) -0.28924(11) 0.0334(4) Uani 1 d . . .
H11A H -1.2088 0.1047 -0.3444 0.040 Uiso 1 calc . . R
H11B H -1.1418 0.2173 -0.2639 0.040 Uiso 1 calc . . R
C12 C -0.6628(2) -0.3508(3) 0.01433(11) 0.0401(4) Uani 1 d . . .
H12 H -0.6105 -0.4854 0.0148 0.048 Uiso 1 calc . . R
C13 C -1.11225(18) -0.1073(3) -0.25933(10) 0.0295(4) Uani 1 d . . .
C14 C -1.4642(2) 0.3073(3) -0.29340(10) 0.0337(4) Uani 1 d . . .
H14 H -1.4096 0.4250 -0.3099 0.040 Uiso 1 calc . . R
C15 C -0.8151(2) 0.0506(3) 0.01560(11) 0.0455(5) Uani 1 d . . .
H15 H -0.8653 0.1859 0.0171 0.055 Uiso 1 calc . . R
C16 C -1.4654(2) -0.0589(3) -0.25453(10) 0.0341(4) Uani 1 d . . .
H16 H -1.4122 -0.1930 -0.2442 0.041 Uiso 1 calc . . R
C17 C -1.0685(2) -0.5143(3) -0.41054(11) 0.0384(4) Uani 1 d . . .
H17 H -0.9716 -0.5773 -0.3807 0.046 Uiso 1 calc . . R
C18 C -1.6269(2) -0.0340(3) -0.24554(11) 0.0401(4) Uani 1 d . . .
H18 H -1.6820 -0.1513 -0.2292 0.048 Uiso 1 calc . . R
C19 C -1.6250(2) 0.3320(3) -0.28443(11) 0.0387(4) Uani 1 d . . .
H19 H -1.6787 0.4658 -0.2948 0.046 Uiso 1 calc . . R
C20 C -1.7071(2) 0.1612(3) -0.26037(11) 0.0392(4) Uani 1 d . . .
H20 H -1.8165 0.1777 -0.2542 0.047 Uiso 1 calc . . R
C21 C -0.7006(3) -0.0211(4) 0.07856(12) 0.0538(6) Uani 1 d . . .
H21 H -0.6728 0.0656 0.1228 0.065 Uiso 1 calc . . R
C22 C -0.6241(2) -0.2226(4) 0.07786(11) 0.0495(5) Uani 1 d . . .
H22 H -0.5454 -0.2694 0.1216 0.059 Uiso 1 calc . . R
C23 C -1.2680(3) -0.4853(4) -0.53134(12) 0.0553(6) Uani 1 d . . .
H23 H -1.3057 -0.5264 -0.5831 0.066 Uiso 1 calc . . R
C24 C -1.2981(2) -0.2718(3) -0.42382(11) 0.0438(5) Uani 1 d . . .
H24 H -1.3590 -0.1698 -0.4027 0.053 Uiso 1 calc . . R
C25 C -1.1262(3) -0.5767(3) -0.48642(12) 0.0492(5) Uani 1 d . . .
H25 H -1.0683 -0.6824 -0.5076 0.059 Uiso 1 calc . . R
C26 C -1.3531(3) -0.3336(4) -0.49958(12) 0.0555(6) Uani 1 d . . .
H26 H -1.4500 -0.2713 -0.5298 0.067 Uiso 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C3 O1 C4 106.51(12) . .
C3 C2 C6 117.37(15) . .
O1 C3 C10 109.19(13) . .
C2 C3 O1 126.24(15) . .
C2 C3 C10 124.48(15) . .
O1 C4 C8 114.97(14) . .
C13 C4 O1 111.11(14) . .
C13 C4 C8 133.87(16) . .
C9 C5 C6 120.12(16) . .
C9 C5 C15 121.36(17) . .
C15 C5 C6 118.52(17) . .
C2 C6 C5 119.86(15) . .
C2 C6 C12 121.72(16) . .
C12 C6 C5 118.41(16) . .
C14 C7 C11 118.93(14) . .
C16 C7 C11 122.94(14) . .
C16 C7 C14 118.12(14) . .
C17 C8 C4 120.84(15) . .
C17 C8 C24 118.19(17) . .
C24 C8 C4 120.97(16) . .
C10 C9 C5 119.36(15) . .
C3 C10 C13 106.41(14) . .
C9 C10 C3 118.79(15) . .
C9 C10 C13 134.69(15) . .
C13 C11 C7 116.48(13) . .
C22 C12 C6 121.10(19) . .
C4 C13 C10 106.78(14) . .
C4 C13 C11 128.32(16) . .
C10 C13 C11 124.65(15) . .
C19 C14 C7 121.14(16) . .
C21 C15 C5 120.68(19) . .
C7 C16 C18 120.71(15) . .
C25 C17 C8 120.38(18) . .
C20 C18 C16 120.58(16) . .
C20 C19 C14 120.30(16) . .
C18 C20 C19 119.15(15) . .
C15 C21 C22 120.8(2) . .
C12 C22 C21 120.49(19) . .
C26 C23 C25 119.3(2) . .
C26 C24 C8 120.82(19) . .
C23 C25 C17 120.7(2) . .
C23 C26 C24 120.67(19) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C3 1.3833(19) .
O1 C4 1.4010(18) .
C2 C3 1.355(2) .
C2 C6 1.412(2) .
C3 C10 1.413(2) .
C4 C8 1.459(2) .
C4 C13 1.359(2) .
C5 C6 1.438(2) .
C5 C9 1.408(2) .
C5 C15 1.423(2) .
C6 C12 1.422(2) .
C7 C11 1.517(2) .
C7 C14 1.388(2) .
C7 C16 1.384(2) .
C8 C17 1.393(2) .
C8 C24 1.393(2) .
C9 C10 1.380(2) .
C10 C13 1.439(2) .
C11 C13 1.498(2) .
C12 C22 1.362(3) .
C14 C19 1.382(2) .
C15 C21 1.368(3) .
C16 C18 1.387(2) .
C17 C25 1.384(3) .
C18 C20 1.378(3) .
C19 C20 1.379(3) .
C21 C22 1.403(3) .
C23 C25 1.382(3) .
C23 C26 1.372(3) .
C24 C26 1.379(3) .
