#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:00:49 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180327 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/41/7154121.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_7154121
loop_
_publ_author_name
'Yeh, Chien-Hung'
'Chen, Wei-Chen'
'Gandeepan, Parthasarathy'
'Hong, Ya-Chun'
'Shih, Cheng-Hung'
'Cheng, Chien-Hong'
_publ_section_title
;
 Rh(III)-catalyzed dual directing group assisted sterically hindered C-H
 bond activation: a unique route to meta and ortho substituted
 benzofurans.
;
_journal_issue                   45
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              9105
_journal_page_last               9108
_journal_paper_doi               10.1039/c4ob01876a
_journal_volume                  12
_journal_year                    2014
_chemical_formula_sum            'C44 H30 N2 O4'
_chemical_formula_weight         650.70
_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                 101.271(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   25.919(3)
_cell_length_b                   11.2554(14)
_cell_length_c                   11.6261(14)
_cell_measurement_reflns_used    2150
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.3069
_cell_measurement_theta_min      2.5589
_cell_volume                     3326.3(7)
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0487
_diffrn_reflns_av_sigmaI/netI    0.0424
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13500
_diffrn_reflns_theta_full        26.48
_diffrn_reflns_theta_max         26.48
_diffrn_reflns_theta_min         1.60
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9486
_exptl_absorpt_correction_T_min  0.8035
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Lump
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.835
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3428
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0494
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0707P)²+2.5441P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1252
_refine_ls_wR_factor_ref         0.1394
_reflns_number_gt                2535
_reflns_number_total             3428
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob01876a2.cif
_cod_data_source_block           mo_130940lt_0m
_cod_depositor_comments
;Adding full bibliography for 7154119--7154121.cif.

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               7154121
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
O1 O 0.18654(5) 0.14585(12) 0.39458(11) 0.0235(3) Uani 1 1 d .
O2 O 0.01972(5) 0.36779(13) -0.01938(12) 0.0292(3) Uani 1 1 d .
N1 N 0.04993(7) 0.33383(14) 0.08710(14) 0.0246(4) Uani 1 1 d .
C1 C 0.33602(8) -0.01766(18) 0.23811(19) 0.0306(5) Uani 1 1 d .
H1A H 0.3685 -0.0529 0.2308 0.037 Uiso 1 1 calc R
C2 C 0.33382(8) 0.0607(2) 0.3282(2) 0.0315(5) Uani 1 1 d .
H2 H 0.3650 0.0797 0.3831 0.038 Uiso 1 1 calc R
C3 C 0.28641(8) 0.11195(19) 0.33915(18) 0.0275(5) Uani 1 1 d .
H3 H 0.2854 0.1663 0.4012 0.033 Uiso 1 1 calc R
C4 C 0.24027(7) 0.08461(17) 0.26006(17) 0.0225(4) Uani 1 1 d .
C5 C 0.18985(8) 0.13414(17) 0.27720(16) 0.0223(4) Uani 1 1 d .
C6 C 0.14451(7) 0.16692(17) 0.20494(17) 0.0211(4) Uani 1 1 d .
C7 C 0.10851(7) 0.20061(16) 0.28064(16) 0.0201(4) Uani 1 1 d .
C8 C 0.05582(7) 0.23930(16) 0.26691(16) 0.0189(4) Uani 1 1 d .
C9 C 0.02364(7) 0.27610(15) 0.15294(16) 0.0192(4) Uani 1 1 d .
C10 C 0.03298(7) 0.24679(16) 0.36724(16) 0.0200(4) Uani 1 1 d .
C11 C 0.24273(8) 0.00561(18) 0.16865(18) 0.0289(5) Uani 1 1 d .
H11 H 0.2117 -0.0138 0.1136 0.035 Uiso 1 1 calc R
C12 C 0.29052(9) -0.0445(2) 0.1584(2) 0.0337(5) Uani 1 1 d .
H12 H 0.2920 -0.0980 0.0959 0.040 Uiso 1 1 calc R
C13 C 0.13645(7) 0.18293(16) 0.39496(17) 0.0215(4) Uani 1 1 d .
C14 C 0.13485(8) 0.16077(17) 0.07512(17) 0.0241(4) Uani 1 1 d .
C15 C 0.16991(9) 0.2135(2) 0.0131(2) 0.0360(5) Uani 1 1 d .
H15 H 0.1992 0.2574 0.0539 0.043 Uiso 1 1 calc R
C16 C 0.16204(11) 0.2020(2) -0.1077(2) 0.0481(7) Uani 1 1 d .
H16 H 0.1861 0.2373 -0.1495 0.058 Uiso 1 1 calc R
C17 C 0.11947(12) 0.1395(3) -0.1674(2) 0.0489(7) Uani 1 1 d .
H17 H 0.1145 0.1312 -0.2501 0.059 Uiso 1 1 calc R
C18 C 0.08392(10) 0.0887(2) -0.1074(2) 0.0403(6) Uani 1 1 d .
H18 H 0.0541 0.0472 -0.1490 0.048 Uiso 1 1 calc R
C19 C 0.09185(8) 0.09852(18) 0.01391(18) 0.0276(5) Uani 1 1 d .
H19 H 0.0678 0.0625 0.0552 0.033 Uiso 1 1 calc R
C20 C 0.06325(7) 0.22518(17) 0.48014(17) 0.0222(4) Uani 1 1 d .
H20 H 0.0473 0.2316 0.5468 0.027 Uiso 1 1 calc R
C21 C 0.11574(8) 0.19481(17) 0.49500(17) 0.0233(4) Uani 1 1 d .
H21 H 0.1367 0.1826 0.5708 0.028 Uiso 1 1 calc R
C22 C 0.05308(9) 0.4305(2) -0.08402(19) 0.0328(5) Uani 1 1 d .
H22A H 0.0653 0.5045 -0.0431 0.049 Uiso 1 1 calc R
H22B H 0.0333 0.4490 -0.1627 0.049 Uiso 1 1 calc R
H22C H 0.0835 0.3809 -0.0903 0.049 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'
N N 0.0061 0.0033 '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
C13 O1 C5 105.86(14) . .
N1 O2 C22 108.10(15) . .
C9 N1 O2 113.36(16) . .
C2 C1 C12 119.48(19) . .
C2 C1 H1A 120.3 . .
C12 C1 H1A 120.3 . .
C1 C2 C3 120.3(2) . .
C1 C2 H2 119.8 . .
C3 C2 H2 119.8 . .
C2 C3 C4 120.67(19) . .
C2 C3 H3 119.7 . .
C4 C3 H3 119.7 . .
C3 C4 C11 118.81(18) . .
C3 C4 C5 119.88(18) . .
C11 C4 C5 121.25(18) . .
C6 C5 O1 111.74(16) . .
C6 C5 C4 134.86(18) . .
O1 C5 C4 113.33(16) . .
C5 C6 C7 106.10(16) . .
C5 C6 C14 124.87(17) . .
C7 C6 C14 128.93(17) . .
C13 C7 C8 117.46(17) . .
C13 C7 C6 105.32(16) . .
C8 C7 C6 137.17(18) . .
C10 C8 C7 118.55(17) . .
C10 C8 C9 118.01(16) . .
C7 C8 C9 123.41(16) . .
N1 C9 C10 129.75(17) . 2
N1 C9 C8 113.57(16) . .
C10 C9 C8 116.62(15) 2 .
C8 C10 C20 120.79(17) . .
C8 C10 C9 116.52(16) . 2
C20 C10 C9 122.69(16) . 2
C12 C11 C4 119.9(2) . .
C12 C11 H11 120.0 . .
C4 C11 H11 120.0 . .
C1 C12 C11 120.8(2) . .
C1 C12 H12 119.6 . .
C11 C12 H12 119.6 . .
O1 C13 C21 124.03(17) . .
O1 C13 C7 110.91(16) . .
C21 C13 C7 124.98(18) . .
C19 C14 C15 119.2(2) . .
C19 C14 C6 120.27(17) . .
C15 C14 C6 120.51(19) . .
C16 C15 C14 120.1(2) . .
C16 C15 H15 120.0 . .
C14 C15 H15 120.0 . .
C17 C16 C15 120.3(2) . .
C17 C16 H16 119.9 . .
C15 C16 H16 119.9 . .
C16 C17 C18 120.3(2) . .
C16 C17 H17 119.9 . .
C18 C17 H17 119.9 . .
C17 C18 C19 119.9(2) . .
C17 C18 H18 120.1 . .
C19 C18 H18 120.1 . .
C18 C19 C14 120.3(2) . .
C18 C19 H19 119.8 . .
C14 C19 H19 119.8 . .
C21 C20 C10 120.91(17) . .
C21 C20 H20 119.5 . .
C10 C20 H20 119.5 . .
C13 C21 C20 117.06(18) . .
C13 C21 H21 121.5 . .
C20 C21 H21 121.5 . .
O2 C22 H22A 109.5 . .
O2 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
O2 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C13 1.365(2) .
O1 C5 1.390(2) .
O2 N1 1.383(2) .
O2 C22 1.437(2) .
N1 C9 1.295(2) .
C1 C2 1.380(3) .
C1 C12 1.383(3) .
C1 H1A 0.9500 .
C2 C3 1.385(3) .
C2 H2 0.9500 .
C3 C4 1.393(3) .
C3 H3 0.9500 .
C4 C11 1.397(3) .
C4 C5 1.470(3) .
C5 C6 1.355(3) .
C6 C7 1.453(3) .
C6 C14 1.482(3) .
C7 C13 1.398(3) .
C7 C8 1.412(3) .
C8 C10 1.410(3) .
C8 C9 1.480(3) .
C9 C10 1.478(3) 2
C10 C20 1.412(3) .
C10 C9 1.477(3) 2
C11 C12 1.387(3) .
C11 H11 0.9500 .
C12 H12 0.9500 .
C13 C21 1.379(3) .
C14 C19 1.389(3) .
C14 C15 1.398(3) .
C15 C16 1.385(3) .
C15 H15 0.9500 .
C16 C17 1.376(4) .
C16 H16 0.9500 .
C17 C18 1.383(4) .
C17 H17 0.9500 .
C18 C19 1.389(3) .
C18 H18 0.9500 .
C19 H19 0.9500 .
C20 C21 1.381(3) .
C20 H20 0.9500 .
C21 H21 0.9500 .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
