#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:31:46 +0200 (vie 13 de oct de 2017) $
#$Revision: 201979 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/67/2236757.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2236757
loop_
_publ_author_name
'Matos, Maria J.'
'Santana, Lourdes'
'Uriarte, Eugenio'
_publ_section_title
;
 3-Phenylcoumarin
;
_journal_coeditor_code           ZJ2091
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2645
_journal_paper_doi               10.1107/S1600536812034277
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C15 H10 O2'
_chemical_formula_moiety         'C15 H10 O2'
_chemical_formula_sum            'C15 H10 O2'
_chemical_formula_weight         222.23
_chemical_name_systematic
;
3-Phenylcoumarin
;
_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_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 99.079(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.469(4)
_cell_length_b                   5.9596(12)
_cell_length_c                   19.274(4)
_cell_measurement_reflns_used    1813
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.22
_cell_measurement_theta_min      2.84
_cell_volume                     2094.9(8)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD 1000'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            9021
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.14
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.8763
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.256
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1924
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.057
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0528P)²+1.3579P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.1042
_reflns_number_gt                1492
_reflns_number_total             1924
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zj2091.cif
_cod_data_source_block           I
_cod_original_cell_volume        2094.9(7)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2236757
_cod_database_fobs_code          2236757
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
C C1 0.21370(8) 0.2410(3) 0.36971(8) 0.0168(4) Uani d . 1 1
H H1 0.219 0.3712 0.3985 0.02 Uiso calc R 1 1
C C2 0.15672(9) 0.2280(3) 0.31395(8) 0.0184(4) Uani d . 1 1
H H2 0.1223 0.3472 0.3054 0.022 Uiso calc R 1 1
C C3 0.14979(9) 0.0409(3) 0.27041(8) 0.0192(4) Uani d . 1 1
H H3 0.1115 0.0337 0.2313 0.023 Uiso calc R 1 1
C C4 0.19876(9) -0.1348(3) 0.28427(8) 0.0188(4) Uani d . 1 1
H H4 0.1939 -0.263 0.2546 0.023 Uiso calc R 1 1
C C5 0.25492(9) -0.1254(3) 0.34124(8) 0.0166(4) Uani d . 1 1
H H5 0.2876 -0.2485 0.3511 0.02 Uiso calc R 1 1
C C6 0.26348(8) 0.0646(3) 0.38409(8) 0.0145(4) Uani d . 1 1
C C7 0.32522(8) 0.0774(3) 0.44333(8) 0.0146(3) Uani d . 1 1
C C8 0.34288(8) -0.0903(3) 0.49004(8) 0.0145(3) Uani d . 1 1
H H8 0.3139 -0.2228 0.4858 0.017 Uiso calc R 1 1
C C9 0.40398(8) -0.0744(3) 0.54588(8) 0.0145(4) Uani d . 1 1
C C10 0.42315(8) -0.2408(3) 0.59681(8) 0.0168(4) Uani d . 1 1
H H10 0.3949 -0.3744 0.5955 0.02 Uiso calc R 1 1
C C11 0.48286(9) -0.2116(3) 0.64877(8) 0.0201(4) Uani d . 1 1
H H11 0.4954 -0.3246 0.6834 0.024 Uiso calc R 1 1
C C12 0.52497(9) -0.0168(3) 0.65072(8) 0.0206(4) Uani d . 1 1
H H12 0.5664 0.001 0.6863 0.025 Uiso calc R 1 1
C C13 0.50708(9) 0.1506(3) 0.60137(8) 0.0190(4) Uani d . 1 1
H H13 0.5357 0.2835 0.6026 0.023 Uiso calc R 1 1
C C14 0.44646(8) 0.1196(3) 0.55016(8) 0.0152(4) Uani d . 1 1
C C15 0.37106(8) 0.2799(3) 0.44882(8) 0.0161(4) Uani d . 1 1
O O1 0.42953(6) 0.29055(18) 0.50224(5) 0.0177(3) Uani d . 1 1
O O2 0.36238(6) 0.43926(18) 0.40948(6) 0.0220(3) Uani d . 1 1
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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 C6 120.61(15)
C2 C1 H1 119.7
C6 C1 H1 119.7
C1 C2 C3 120.03(15)
C1 C2 H2 120
C3 C2 H2 120
C4 C3 C2 119.76(15)
C4 C3 H3 120.1
C2 C3 H3 120.1
C3 C4 C5 120.48(15)
C3 C4 H4 119.8
C5 C4 H4 119.8
C4 C5 C6 120.11(15)
C4 C5 H5 119.9
C6 C5 H5 119.9
C1 C6 C5 118.96(14)
C1 C6 C7 121.09(14)
C5 C6 C7 119.94(14)
C8 C7 C15 118.97(14)
C8 C7 C6 123.41(14)
C15 C7 C6 117.56(14)
C7 C8 C9 122.02(15)
C7 C8 H8 119
C9 C8 H8 119
C14 C9 C10 117.94(14)
C14 C9 C8 117.93(14)
C10 C9 C8 124.13(15)
C11 C10 C9 120.29(15)
C11 C10 H10 119.9
C9 C10 H10 119.9
C10 C11 C12 120.22(15)
C10 C11 H11 119.9
C12 C11 H11 119.9
C13 C12 C11 120.71(15)
C13 C12 H12 119.6
C11 C12 H12 119.6
C12 C13 C14 118.25(15)
C12 C13 H13 120.9
C14 C13 H13 120.9
O1 C14 C13 116.88(14)
O1 C14 C9 120.55(14)
C13 C14 C9 122.57(14)
O2 C15 O1 116.41(14)
O2 C15 C7 125.59(15)
O1 C15 C7 117.99(14)
C15 O1 C14 122.53(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.382(2)
C1 C6 1.395(2)
C1 H1 0.95
C2 C3 1.390(2)
C2 H2 0.95
C3 C4 1.382(2)
C3 H3 0.95
C4 C5 1.387(2)
C4 H4 0.95
C5 C6 1.396(2)
C5 H5 0.95
C6 C7 1.483(2)
C7 C8 1.350(2)
C7 C15 1.468(2)
C8 C9 1.434(2)
C8 H8 0.95
C9 C14 1.392(2)
C9 C10 1.401(2)
C10 C11 1.379(2)
C10 H10 0.95
C11 C12 1.395(2)
C11 H11 0.95
C12 C13 1.382(2)
C12 H12 0.95
C13 C14 1.383(2)
C13 H13 0.95
C14 O1 1.3776(18)
C15 O2 1.2102(19)
C15 O1 1.3709(19)
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
C6 C1 C2 C3 -1.8(2)
C1 C2 C3 C4 1.9(2)
C2 C3 C4 C5 -0.2(2)
C3 C4 C5 C6 -1.6(2)
C2 C1 C6 C5 0.0(2)
C2 C1 C6 C7 179.41(14)
C4 C5 C6 C1 1.6(2)
C4 C5 C6 C7 -177.73(14)
C1 C6 C7 C8 133.05(16)
C5 C6 C7 C8 -47.6(2)
C1 C6 C7 C15 -49.86(19)
C5 C6 C7 C15 129.50(15)
C15 C7 C8 C9 1.5(2)
C6 C7 C8 C9 178.59(14)
C7 C8 C9 C14 -1.3(2)
C7 C8 C9 C10 178.02(14)
C14 C9 C10 C11 -0.6(2)
C8 C9 C10 C11 -179.96(14)
C9 C10 C11 C12 -0.5(2)
C10 C11 C12 C13 0.8(2)
C11 C12 C13 C14 0.0(2)
C12 C13 C14 O1 179.25(13)
C12 C13 C14 C9 -1.2(2)
C10 C9 C14 O1 -178.93(13)
C8 C9 C14 O1 0.4(2)
C10 C9 C14 C13 1.5(2)
C8 C9 C14 C13 -179.15(13)
C8 C7 C15 O2 178.09(15)
C6 C7 C15 O2 0.9(2)
C8 C7 C15 O1 -0.9(2)
C6 C7 C15 O1 -178.17(12)
O2 C15 O1 C14 -179.01(13)
C7 C15 O1 C14 0.1(2)
C13 C14 O1 C15 179.72(13)
C9 C14 O1 C15 0.1(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 63565
