#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/22/1512208.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_1512208
loop_
_publ_author_name
'Rout, Saroj Kumar'
'Guin, Srimanta'
'Banerjee, Arghya'
'Khatun, Nilufa'
'Gogoi, Anupal'
'Patel, Bhisma K.'
_publ_section_title
;
 Directing group assisted copper-catalyzed chemoselective o-aroylation of
 phenols and enols using alkylbenzenes.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              4106
_journal_page_last               4109
_journal_paper_doi               10.1021/ol401682a
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C15 H12 O3'
_chemical_formula_sum            'C15 H12 O3'
_chemical_formula_weight         240.25
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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            4
_cell_length_a                   22.827(2)
_cell_length_b                   4.0137(4)
_cell_length_c                   13.1725(12)
_cell_measurement_temperature    298(2)
_cell_volume                     1206.87(19)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0464
_diffrn_reflns_av_sigmaI/netI    0.0298
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16257
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.78
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.118
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.6(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2130
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.979
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0418
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1287
_reflns_number_gt                1828
_reflns_number_total             2130
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol401682a_si_002.cif
_cod_data_source_block           1b
_cod_original_formula_sum        '     C15 H12 O3'
_cod_database_code               1512208
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'
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 0.14163(7) 0.8071(5) 0.19428(12) 0.0607(4) Uani 1 1 d .
O2 O 0.05344(8) 1.0546(5) 0.20280(13) 0.0734(5) Uani 1 1 d .
O3 O 0.27810(10) 1.4165(7) 0.15188(19) 0.0890(7) Uani 1 1 d .
C9 C 0.08775(10) 0.7509(6) 0.34615(17) 0.0487(5) Uani 1 1 d .
C1 C 0.15107(10) 0.9191(6) 0.09524(16) 0.0529(6) Uani 1 1 d .
C10 C 0.13418(10) 0.5763(6) 0.38949(17) 0.0525(6) Uani 1 1 d .
H10 H 0.1675 0.5307 0.3513 0.063 Uiso 1 1 calc R
C8 C 0.08995(9) 0.8877(6) 0.24237(19) 0.0524(5) Uani 1 1 d .
C11 C 0.13089(12) 0.4713(6) 0.48862(19) 0.0595(6) Uani 1 1 d .
H11 H 0.1621 0.3550 0.5170 0.071 Uiso 1 1 calc R
C14 C 0.03789(10) 0.8123(6) 0.40365(19) 0.0576(6) Uani 1 1 d .
H14 H 0.0064 0.9256 0.3751 0.069 Uiso 1 1 calc R
C13 C 0.03501(11) 0.7059(7) 0.50265(19) 0.0602(6) Uani 1 1 d .
H13 H 0.0014 0.7482 0.5403 0.072 Uiso 1 1 calc R
C12 C 0.08114(10) 0.5372(6) 0.54747(18) 0.0573(6) Uani 1 1 d .
C5 C 0.21358(12) 1.2018(7) -0.02155(19) 0.0653(7) Uani 1 1 d .
H5 H 0.2465 1.3314 -0.0348 0.078 Uiso 1 1 calc R
C15 C 0.07918(14) 0.4250(8) 0.6564(2) 0.0782(8) Uani 1 1 d .
H15A H 0.0435 0.5012 0.6872 0.117 Uiso 1 1 calc R
H15B H 0.1121 0.5161 0.6923 0.117 Uiso 1 1 calc R
H15C H 0.0807 0.1862 0.6591 0.117 Uiso 1 1 calc R
C6 C 0.20064(10) 1.1088(6) 0.07839(18) 0.0542(6) Uani 1 1 d .
C4 C 0.17832(14) 1.1036(9) -0.0997(2) 0.0754(8) Uani 1 1 d .
H4 H 0.1876 1.1636 -0.1660 0.090 Uiso 1 1 calc R
C3 C 0.12922(14) 0.9168(9) -0.0806(2) 0.0787(9) Uani 1 1 d .
H3 H 0.1053 0.8526 -0.1344 0.094 Uiso 1 1 calc R
C7 C 0.23857(11) 1.2204(7) 0.1617(2) 0.0615(6) Uani 1 1 d .
H7 H 0.2316 1.1342 0.2261 0.074 Uiso 1 1 calc R
C2 C 0.11461(13) 0.8220(8) 0.0171(2) 0.0685(7) Uani 1 1 d .
H2 H 0.0812 0.6964 0.0298 0.082 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
C8 O1 C1 119.09(18)
C10 C9 C14 119.3(2)
C10 C9 C8 122.8(2)
C14 C9 C8 117.9(2)
C6 C1 C2 122.0(2)
C6 C1 O1 117.00(19)
C2 C1 O1 120.8(2)
C11 C10 C9 120.2(2)
O2 C8 O1 122.1(2)
O2 C8 C9 126.3(2)
O1 C8 C9 111.61(19)
C10 C11 C12 120.8(2)
C13 C14 C9 120.1(2)
C14 C13 C12 121.4(2)
C13 C12 C11 118.3(2)
C13 C12 C15 122.0(2)
C11 C12 C15 119.7(2)
C4 C5 C6 120.5(3)
C1 C6 C5 118.1(2)
C1 C6 C7 122.1(2)
C5 C6 C7 119.8(2)
C3 C4 C5 120.1(3)
C4 C3 C2 121.2(3)
O3 C7 C6 124.1(3)
C1 C2 C3 118.1(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C8 1.377(3)
O1 C1 1.397(3)
O2 C8 1.190(3)
O3 C7 1.204(3)
C9 C10 1.393(3)
C9 C14 1.389(3)
C9 C8 1.474(3)
C1 C6 1.382(4)
C1 C2 1.380(4)
C10 C11 1.374(3)
C11 C12 1.400(4)
C14 C13 1.374(4)
C13 C12 1.384(4)
C12 C15 1.504(4)
C5 C4 1.365(4)
C5 C6 1.400(3)
C6 C7 1.468(4)
C4 C3 1.372(5)
C3 C2 1.383(4)
