#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/75/4027519.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_4027519
loop_
_publ_author_name
'Nayyef Aljaar'
'Chandi C. Malakar'
'Jürgen Conrad'
'Sabine Strobel'
'Thomas Schleid'
'Uwe Beifuss'
_publ_section_title
;
 Cu-Catalyzed Reaction of 1,2-Dihalobenzenes with 1,3-Cyclohexanediones
 for the Synthesis of 3,4-Dihydrodibenzo[b,d]furan-1(2H)-ones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7793
_journal_page_last               7803
_journal_paper_doi               10.1021/jo3014275
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C13 H12 O2'
_chemical_formula_sum            'C13 H12 O2'
_chemical_formula_weight         200.23
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.0264(3)
_cell_length_b                   12.8797(3)
_cell_length_c                   14.4734(3)
_cell_measurement_reflns_used    2741
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      0.41
_cell_volume                     2055.46(9)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_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  0.0179
_diffrn_reflns_av_sigmaI/netI    0.0241
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4536
_diffrn_reflns_theta_full        28.20
_diffrn_reflns_theta_max         28.20
_diffrn_reflns_theta_min         8.18
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9983
_exptl_absorpt_correction_T_min  0.9949
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Scalepack (W. Minor & Z. Otwinowski)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_description       platelet
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2450
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0617
_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)+(0.0695P)²+0.8642P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1560
_refine_ls_wR_factor_ref         0.1716
_reflns_number_gt                1943
_reflns_number_total             2450
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3014275_si_001.cif
_cod_data_source_block           c:\crystal\x-red\beijul11
_cod_database_code               4027519
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, 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 0.08026(19) 1.21102(15) 0.08577(15) 0.0518(5) Uani 1 1 d .
C2 C 0.2137(2) 1.23683(18) 0.08200(19) 0.0638(6) Uani 1 1 d .
H2B H 0.2242 1.3091 0.0992 0.077 Uiso 1 1 calc R
H2A H 0.2414 1.2292 0.0187 0.077 Uiso 1 1 calc R
C3 C 0.2934(2) 1.1705(2) 0.14391(19) 0.0660(6) Uani 1 1 d .
H3B H 0.2768 1.1881 0.2079 0.079 Uiso 1 1 calc R
H3A H 0.3777 1.1870 0.1316 0.079 Uiso 1 1 calc R
C4 C 0.27430(16) 1.05478(16) 0.13057(14) 0.0493(5) Uani 1 1 d .
H4B H 0.3107 1.0324 0.0729 0.059 Uiso 1 1 calc R
H4A H 0.3118 1.0166 0.1807 0.059 Uiso 1 1 calc R
C4A C 0.14218(16) 1.03507(14) 0.12907(12) 0.0415(4) Uani 1 1 d .
C5A C -0.02809(16) 0.94806(14) 0.14284(13) 0.0421(4) Uani 1 1 d .
C6 C -0.11085(19) 0.86993(15) 0.15899(16) 0.0525(5) Uani 1 1 d .
H6 H -0.0868 0.8030 0.1747 0.063 Uiso 1 1 calc R
C7 C -0.23216(18) 0.89690(16) 0.15050(14) 0.0520(5) Uani 1 1 d .
H7A H -0.2908 0.8463 0.1608 0.062 Uiso 1 1 calc R
C8 C -0.26967(16) 0.99735(16) 0.12703(12) 0.0464(4) Uani 1 1 d .
C8' C -0.40249(18) 1.0226(2) 0.12020(17) 0.0607(6) Uani 1 1 d .
H8'C H -0.4493 0.9614 0.1332 0.073 Uiso 1 1 calc R
H8'B H -0.4206 1.0466 0.0590 0.073 Uiso 1 1 calc R
H8'A H -0.4224 1.0758 0.1641 0.073 Uiso 1 1 calc R
C9A C -0.06055(16) 1.04905(13) 0.11906(12) 0.0395(4) Uani 1 1 d .
C9 C -0.18331(16) 1.07335(15) 0.11111(12) 0.0444(4) Uani 1 1 d .
H9 H -0.2071 1.1403 0.0952 0.053 Uiso 1 1 calc R
C9B C 0.05285(15) 1.10441(14) 0.11068(12) 0.0408(4) Uani 1 1 d .
O O 0.00154(18) 1.27352(13) 0.06571(17) 0.0856(6) Uani 1 1 d .
O5 O 0.09741(11) 0.93888(10) 0.14775(10) 0.0471(4) 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
O C1 C9B 122.38(19)
O C1 C2 122.69(19)
C9B C1 C2 114.86(18)
C1 C2 C3 114.77(18)
C1 C2 H2B 108.6
C3 C2 H2B 108.6
C1 C2 H2A 108.6
C3 C2 H2A 108.6
H2B C2 H2A 107.6
C2 C3 C4 113.40(19)
C2 C3 H3B 108.9
C4 C3 H3B 108.9
C2 C3 H3A 108.9
C4 C3 H3A 108.9
H3B C3 H3A 107.7
C4A C4 C3 107.87(17)
C4A C4 H4B 110.1
C3 C4 H4B 110.1
C4A C4 H4A 110.1
C3 C4 H4A 110.1
H4B C4 H4A 108.4
C9B C4A O5 112.03(15)
C9B C4A C4 127.26(17)
O5 C4A C4 120.71(16)
C6 C5A O5 126.02(16)
C6 C5A C9A 123.63(17)
O5 C5A C9A 110.35(15)
C5A C6 C7 116.13(18)
C5A C6 H6 121.9
C7 C6 H6 121.9
C6 C7 C8 122.52(18)
C6 C7 H7A 118.7
C8 C7 H7A 118.7
C9 C8 C7 119.37(17)
C9 C8 C8' 120.42(19)
C7 C8 C8' 120.21(19)
C8 C8' H8'C 109.5
C8 C8' H8'B 109.5
H8'C C8' H8'B 109.5
C8 C8' H8'A 109.5
H8'C C8' H8'A 109.5
H8'B C8' H8'A 109.5
C5A C9A C9 118.67(17)
C5A C9A C9B 105.04(15)
C9 C9A C9B 136.28(17)
C8 C9 C9A 119.68(17)
C8 C9 H9 120.2
C9A C9 H9 120.2
C4A C9B C9A 106.69(15)
C4A C9B C1 121.36(17)
C9A C9B C1 131.92(16)
C4A O5 C5A 105.87(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O 1.219(3)
C1 C9B 1.452(3)
C1 C2 1.509(3)
C2 C3 1.518(4)
C2 H2B 0.9700
C2 H2A 0.9700
C3 C4 1.518(3)
C3 H3B 0.9700
C3 H3A 0.9700
C4 C4A 1.479(3)
C4 H4B 0.9700
C4 H4A 0.9700
C4A C9B 1.356(2)
C4A O5 1.361(2)
C5A C6 1.378(3)
C5A O5 1.391(2)
C5A C9A 1.392(2)
C6 C7 1.387(3)
C6 H6 0.9300
C7 C8 1.400(3)
C7 H7A 0.9300
C8 C9 1.385(3)
C8 C8' 1.503(3)
C8' H8'C 0.9600
C8' H8'B 0.9600
C8' H8'A 0.9600
C9A C9 1.394(2)
C9A C9B 1.444(2)
C9 H9 0.9300
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 8417379
