#------------------------------------------------------------------------------
#$Date: 2019-11-10 20:20:56 +0200 (Sun, 10 Nov 2019) $
#$Revision: 226168 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/61/4516177.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_4516177
loop_
_publ_author_name
'Grolleau, Jérémie'
'Petrov, Ravil'
'Allain, Magali'
'Skene, William G.'
'Frère, Pierre'
_publ_section_title
;
 Solid-State Emission Enhancement via Molecular Engineering of Benzofuran
 Derivatives.
;
_journal_issue                   12
_journal_name_full               'ACS omega'
_journal_page_first              18542
_journal_page_last               18552
_journal_paper_doi               10.1021/acsomega.8b02384
_journal_volume                  3
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C18 H12 O2'
_chemical_formula_sum            'C18 H12 O2'
_chemical_formula_weight         260.28
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_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             2016-06-08T10:11:59-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 100.161(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.4009(2)
_cell_length_b                   7.3211(3)
_cell_length_c                   13.9114(6)
_cell_measurement_reflns_used    2604
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      75.938
_cell_measurement_theta_min      3.19
_cell_volume                     641.69(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_molecular_graphics    'DIAMOND 3.2k (Crystal Impact GbR, 2014)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector_area_resol_mean 5.199
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'SuperNova, Single source at offset, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3840
_diffrn_reflns_theta_full        74
_diffrn_reflns_theta_max         76.19
_diffrn_reflns_theta_min         3.23
_exptl_absorpt_coefficient_mu    0.696
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.9137
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.172
_exptl_crystal_size_mid          0.083
_exptl_crystal_size_min          0.046
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.159
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2178
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.06
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0326
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0593P)²+0.0566P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0922
_refine_ls_wR_factor_ref         0.0934
_reflns_number_gt                2075
_reflns_number_total             2178
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ao8b02384_si_002.cif
_cod_data_source_block           jg276-150k
_cod_database_code               4516177
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-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_refinement_flags
C1 C 0.7857(2) 0.2883(2) 0.37859(12) 0.0328(3) Uani 1 d .
C2 C 0.7160(3) 0.3411(2) 0.28344(12) 0.0366(4) Uani 1 d .
H2 H 0.5779 0.3815 0.2619 0.044 Uiso 1 calc R
C3 C 0.8634(3) 0.3307(2) 0.22108(12) 0.0391(4) Uani 1 d .
H3 H 0.8241 0.3656 0.1561 0.047 Uiso 1 calc R
C4 C 1.0704(3) 0.2685(3) 0.25490(13) 0.0401(4) Uani 1 d .
H4 H 1.1658 0.2634 0.2117 0.048 Uiso 1 calc R
C5 C 1.1364(2) 0.2145(3) 0.35038(13) 0.0378(4) Uani 1 d .
H5 H 1.2745 0.1741 0.3719 0.045 Uiso 1 calc R
C6 C 0.9899(2) 0.2223(2) 0.41422(12) 0.0335(3) Uani 1 d .
C7 C 0.9932(3) 0.1826(2) 0.51484(13) 0.0356(4) Uani 1 d .
H7 H 1.1066 0.1341 0.5584 0.043 Uiso 1 calc R
C8 C 0.8010(2) 0.2284(3) 0.53520(12) 0.0352(3) Uani 1 d .
C9 C 0.7184(3) 0.2245(3) 0.62475(12) 0.0362(4) Uani 1 d .
H9 H 0.799 0.1665 0.6782 0.043 Uiso 1 calc R
C10 C 0.5327(3) 0.2990(3) 0.63647(12) 0.0367(4) Uani 1 d .
H10 H 0.4538 0.3589 0.5832 0.044 Uiso 1 calc R
C11 C 0.4467(2) 0.2931(2) 0.72494(12) 0.0335(3) Uani 1 d .
C12 C 0.2571(3) 0.3499(2) 0.74456(13) 0.0349(4) Uani 1 d .
H12 H 0.153 0.4136 0.7025 0.042 Uiso 1 calc R
C13 C 0.2473(2) 0.2935(2) 0.84206(12) 0.0326(3) Uani 1 d .
C14 C 0.0946(2) 0.2992(3) 0.90291(12) 0.0377(4) Uani 1 d .
H14 H -0.036 0.3553 0.8825 0.045 Uiso 1 calc R
C15 C 0.1433(3) 0.2193(3) 0.99391(13) 0.0405(4) Uani 1 d .
H15 H 0.0425 0.2202 1.0345 0.049 Uiso 1 calc R
C16 C 0.3401(3) 0.1372(3) 1.02678(13) 0.0413(4) Uani 1 d .
H16 H 0.3686 0.0872 1.0892 0.05 Uiso 1 calc R
C17 C 0.4940(3) 0.1290(2) 0.96769(13) 0.0375(4) Uani 1 d .
H17 H 0.6251 0.074 0.9885 0.045 Uiso 1 calc R
C18 C 0.4410(2) 0.2068(2) 0.87662(11) 0.0320(3) Uani 1 d .
O1 O 0.66835(16) 0.29354(17) 0.45244(8) 0.0351(3) Uani 1 d .
O2 O 0.56576(16) 0.20692(17) 0.80526(8) 0.0342(3) Uani 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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C2 C1 O1 125.70(14)
C2 C1 C6 124.18(15)
O1 C1 C6 110.11(14)
C1 C2 C3 116.36(15)
C1 C2 H2 121.8
C3 C2 H2 121.8
C2 C3 C4 120.86(16)
C2 C3 H3 119.6
C4 C3 H3 119.6
C5 C4 C3 121.85(15)
C5 C4 H4 119.1
C3 C4 H4 119.1
C4 C5 C6 118.24(15)
C4 C5 H5 120.9
C6 C5 H5 120.9
C1 C6 C5 118.48(15)
C1 C6 C7 105.61(14)
C5 C6 C7 135.88(16)
C8 C7 C6 107.36(15)
C8 C7 H7 126.3
C6 C7 H7 126.3
C7 C8 O1 110.95(14)
C7 C8 C9 131.59(16)
O1 C8 C9 117.44(14)
C10 C9 C8 124.45(15)
C10 C9 H9 117.8
C8 C9 H9 117.8
C9 C10 C11 124.98(16)
C9 C10 H10 117.5
C11 C10 H10 117.5
C12 C11 O2 111.18(14)
C12 C11 C10 131.00(16)
O2 C11 C10 117.71(14)
C11 C12 C13 107.04(15)
C11 C12 H12 126.5
C13 C12 H12 126.5
C18 C13 C14 118.39(15)
C18 C13 C12 105.80(14)
C14 C13 C12 135.74(15)
C15 C14 C13 118.21(15)
C15 C14 H14 120.9
C13 C14 H14 120.9
C14 C15 C16 121.84(15)
C14 C15 H15 119.1
C16 C15 H15 119.1
C17 C16 C15 121.08(16)
C17 C16 H16 119.5
C15 C16 H16 119.5
C18 C17 C16 116.16(15)
C18 C17 H17 121.9
C16 C17 H17 121.9
C17 C18 O2 125.64(14)
C17 C18 C13 124.29(14)
O2 C18 C13 110.05(13)
C1 O1 C8 105.95(12)
C18 O2 C11 105.91(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.375(2)
C1 O1 1.3760(18)
C1 C6 1.400(2)
C2 C3 1.392(2)
C2 H2 0.93
C3 C4 1.401(2)
C3 H3 0.93
C4 C5 1.379(3)
C4 H4 0.93
C5 C6 1.402(2)
C5 H5 0.93
C6 C7 1.426(2)
C7 C8 1.352(2)
C7 H7 0.93
C8 O1 1.389(2)
C8 C9 1.437(2)
C9 C10 1.344(2)
C9 H9 0.93
C10 C11 1.435(2)
C10 H10 0.93
C11 C12 1.356(2)
C11 O2 1.388(2)
C12 C13 1.430(2)
C12 H12 0.93
C13 C18 1.400(2)
C13 C14 1.402(2)
C14 C15 1.379(2)
C14 H14 0.93
C15 C16 1.398(3)
C15 H15 0.93
C16 C17 1.391(2)
C16 H16 0.93
C17 C18 1.376(2)
C17 H17 0.93
C18 O2 1.3795(17)
