#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:31:30 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180303 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/17/7151751.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_7151751
loop_
_publ_author_name
'Ponce González, Julia'
'Edgar, Mark'
'Elsegood, Mark R. J.'
'Weaver, George W.'
_publ_section_title
;
 Synthesis of fluorinated fused benzofurans and benzothiophenes:
 Smiles-type rearrangement and cyclisation of perfluoro(het)aryl ethers
 and sulfides.
;
_journal_issue                   7
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2294
_journal_page_last               2305
_journal_paper_doi               10.1039/c0ob00790k
_journal_volume                  9
_journal_year                    2011
_chemical_formula_moiety         'C18 H8 F2 O2'
_chemical_formula_sum            'C18 H8 F2 O2'
_chemical_formula_weight         294.24
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   'all non-H atoms found by direct methods'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.211(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.198(2)
_cell_length_b                   6.525(2)
_cell_length_c                   15.416(5)
_cell_measurement_reflns_used    519
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      23.55
_cell_measurement_theta_min      3.32
_cell_volume                     618.5(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX 2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX 2 CCD diffractometer'
_diffrn_measurement_method       'ω rotation with narrow frames'
_diffrn_radiation_monochromator  'silicon 111'
_diffrn_radiation_source         'Daresbury SRS station 9.8'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.6942
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_sigmaI/netI    0.0634
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            2656
_diffrn_reflns_theta_full        22.99
_diffrn_reflns_theta_max         22.99
_diffrn_reflns_theta_min         3.32
_diffrn_standards_decay_%        4
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1, Sheldrick, G.M., (2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.974
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       0.8(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         907
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.1365
_refine_ls_R_factor_gt           0.0949
_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)+(0.1905P)²+0.7738P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2480
_refine_ls_wR_factor_ref         0.2902
_reflns_number_gt                588
_reflns_number_total             907
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c0ob00790k.txt
_cod_data_source_block           22
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7151751
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3000(7) 0.2143(7) 0.6197(3) 0.0524(15) Uani 1 1 d . . .
C2 C 0.4431(10) 0.3776(10) 0.6368(4) 0.0476(18) Uani 1 1 d . . .
C3 C 0.4151(11) 0.5308(11) 0.6944(4) 0.054(2) Uani 1 1 d . . .
H3 H 0.2932 0.5348 0.7261 0.065 Uiso 1 1 calc R . .
C4 C 0.5743(13) 0.6798(10) 0.7040(4) 0.060(2) Uani 1 1 d . . .
H4 H 0.5616 0.7901 0.7432 0.072 Uiso 1 1 calc R . .
C5 C 0.7529(11) 0.6731(11) 0.6577(5) 0.057(2) Uani 1 1 d . . .
H5 H 0.8597 0.7781 0.6661 0.068 Uiso 1 1 calc R . .
C6 C 0.7772(10) 0.5174(10) 0.6002(4) 0.0504(19) Uani 1 1 d . . .
H6 H 0.8990 0.5124 0.5685 0.061 Uiso 1 1 calc R . .
C7 C 0.6180(10) 0.3677(9) 0.5899(4) 0.0480(19) Uani 1 1 d . . .
C8 C 0.5862(9) 0.1777(9) 0.5372(4) 0.0428(17) Uani 1 1 d . . .
C9 C 0.6941(9) 0.0819(10) 0.4779(4) 0.0454(18) Uani 1 1 d . . .
F1 F 0.8815(5) 0.1611(6) 0.4546(2) 0.0546(14) Uani 1 1 d . . .
C10 C 0.3932(10) 0.0946(9) 0.5589(4) 0.0442(18) Uani 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.056(3) 0.044(3) 0.059(3) -0.006(2) 0.012(2) -0.004(2)
C2 0.048(4) 0.036(4) 0.056(4) 0.007(3) -0.009(3) -0.007(3)
C3 0.056(4) 0.056(5) 0.048(4) 0.008(3) 0.002(3) 0.009(3)
C4 0.091(5) 0.042(4) 0.041(4) -0.008(3) -0.016(4) 0.016(4)
C5 0.054(4) 0.040(4) 0.069(5) 0.008(3) -0.019(3) -0.012(3)
C6 0.051(4) 0.050(4) 0.048(4) 0.013(3) 0.000(3) 0.003(3)
C7 0.062(4) 0.035(4) 0.042(4) 0.002(3) -0.010(3) 0.010(3)
C8 0.042(3) 0.035(4) 0.047(4) 0.004(3) -0.009(3) -0.003(3)
C9 0.032(3) 0.042(4) 0.062(4) 0.016(3) 0.006(3) -0.008(3)
F1 0.046(2) 0.045(2) 0.074(3) 0.0042(18) 0.0130(17) -0.0054(16)
C10 0.054(4) 0.040(4) 0.040(3) 0.003(3) 0.006(3) 0.017(3)
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'
F F 0.0171 0.0103 '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
_geom_angle_publ_flag
C2 O1 C10 104.3(5) . . ?
C3 C2 C7 123.3(6) . . ?
C3 C2 O1 123.8(6) . . ?
C7 C2 O1 112.9(6) . . ?
C2 C3 C4 116.0(6) . . ?
C3 C4 C5 121.8(6) . . ?
C6 C5 C4 121.0(6) . . ?
C5 C6 C7 117.6(6) . . ?
C2 C7 C6 120.2(6) . . ?
C2 C7 C8 105.5(6) . . ?
C6 C7 C8 134.3(6) . . ?
C9 C8 C10 119.7(5) . . ?
C9 C8 C7 135.6(6) . . ?
C10 C8 C7 104.7(5) . . ?
C8 C9 F1 121.0(6) . . ?
C8 C9 C10 117.8(5) . 3_656 ?
F1 C9 C10 121.2(6) . 3_656 ?
C9 C10 C8 122.5(5) 3_656 . ?
C9 C10 O1 125.0(5) 3_656 . ?
C8 C10 O1 112.5(5) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.391(7) . ?
O1 C10 1.400(7) . ?
C2 C3 1.362(9) . ?
C2 C7 1.378(9) . ?
C3 C4 1.380(10) . ?
C4 C5 1.391(11) . ?
C5 C6 1.368(10) . ?
C6 C7 1.384(9) . ?
C7 C8 1.481(9) . ?
C8 C9 1.352(8) . ?
C8 C10 1.391(8) . ?
C9 F1 1.360(6) . ?
C9 C10 1.366(9) 3_656 ?
C10 C9 1.366(9) 3_656 ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 O1 C2 C3 -179.0(5) . . . . ?
C10 O1 C2 C7 0.6(6) . . . . ?
C7 C2 C3 C4 -0.1(9) . . . . ?
O1 C2 C3 C4 179.4(6) . . . . ?
C2 C3 C4 C5 -0.2(9) . . . . ?
C3 C4 C5 C6 0.2(9) . . . . ?
C4 C5 C6 C7 0.0(9) . . . . ?
C3 C2 C7 C6 0.4(9) . . . . ?
O1 C2 C7 C6 -179.2(5) . . . . ?
C3 C2 C7 C8 179.1(5) . . . . ?
O1 C2 C7 C8 -0.4(7) . . . . ?
C5 C6 C7 C2 -0.3(9) . . . . ?
C5 C6 C7 C8 -178.6(6) . . . . ?
C2 C7 C8 C9 178.9(7) . . . . ?
C6 C7 C8 C9 -2.6(12) . . . . ?
C2 C7 C8 C10 0.1(6) . . . . ?
C6 C7 C8 C10 178.6(6) . . . . ?
C10 C8 C9 F1 179.0(5) . . . . ?
C7 C8 C9 F1 0.4(10) . . . . ?
C10 C8 C9 C10 0.2(9) . . . 3_656 ?
C7 C8 C9 C10 -178.4(6) . . . 3_656 ?
C9 C8 C10 C9 -0.2(10) . . . 3_656 ?
C7 C8 C10 C9 178.8(5) . . . 3_656 ?
C9 C8 C10 O1 -178.8(5) . . . . ?
C7 C8 C10 O1 0.2(6) . . . . ?
C2 O1 C10 C9 -179.0(6) . . . 3_656 ?
C2 O1 C10 C8 -0.5(6) . . . . ?
