#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/91/2009168.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_2009168
loop_
_publ_author_name
'Pulkkinen, Juha T.'
'Ahlgrén, Markku J.'
_publ_section_title
;
 1,5-Diphenylpentane-2,4-dione and 1,5-bis(2-naphthyl)pentane-2,4-dione
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              IUC9900142
_journal_paper_doi               10.1107/S0108270199098546
_journal_volume                  55
_journal_year                    1999
_chemical_formula_sum            'C25 H20 O2'
_chemical_formula_weight         352.41
_chemical_name_systematic
;
1,5-Di-(2-naphtyl)pentane-2,4-dione
;
_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'
_audit_creation_method           'SHELXL-97 (Sheldrick, 1997)'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.09(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   37.501(8)
_cell_length_b                   5.8050(10)
_cell_length_c                   8.313(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      7
_cell_volume                     1809.7(7)
_computing_cell_refinement       'P3/PC (Siemens 1989)'
_computing_data_collection       'P3/PC (Siemens 1989)'
_computing_data_reduction        'P3/PC (Siemens 1989)'
_computing_molecular_graphics    'SHELXTL-Plus (Sheldrick, 1990a)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990b)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.450
_diffrn_measured_fraction_theta_max 0.450
_diffrn_measurement_device       'Nicolet R3m'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_sigmaI/netI    0.0638
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2987
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.17
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.191
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     123
_refine_ls_number_reflns         1577
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0441
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0300P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0931
_reflns_number_gt                893
_reflns_number_total             1577
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            qa0181.cif
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2009168
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_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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 .02610(4) -.0324(3) .3432(2) .0723(5) Uani d . 1 . . O
C1 .0000 .3079(5) .2500 .0568(9) Uani d S 1 . . C
H1 .0000 .4681 .2500 .080 Uiso calc SR 1 . . H
C2 .02497(6) .1918(4) .3413(3) .0568(6) Uani d . 1 . . C
C3 .05190(5) .3137(4) .4440(3) .0652(7) Uani d . 1 . . C
H3A .0481 .2718 .5556 .080 Uiso calc R 1 . . H
H3B .0483 .4786 .4344 .080 Uiso calc R 1 . . H
C4 .08982(5) .2567(3) .3985(3) .0461(6) Uani d . 1 . . C
C5 .10554(6) .0477(4) .4503(3) .0499(6) Uani d . 1 . . C
H5 .0923 -.0538 .5127 .080 Uiso calc R 1 . . H
C6 .13951(6) -.0072(3) .4110(2) .0462(6) Uani d . 1 . . C
H6 .1491 -.1460 .4462 .080 Uiso calc R 1 . . H
C7 .16052(5) .1430(3) .3172(2) .0379(5) Uani d . 1 . . C
C8 .14532(5) .3532(3) .2638(2) .0375(5) Uani d . 1 . . C
C9 .10988(5) .4041(3) .3070(3) .0457(5) Uani d . 1 . . C
H9 .0998 .5418 .2724 .080 Uiso calc R 1 . . H
C10 .16649(6) .5030(3) .1703(2) .0475(6) Uani d . 1 . . C
H10 .1569 .6418 .1350 .080 Uiso calc R 1 . . H
C11 .20046(6) .4487(4) .1309(3) .0566(6) Uani d . 1 . . C
H11 .2139 .5494 .0686 .080 Uiso calc R 1 . . H
C12 .21542(6) .2400(4) .1842(3) .0569(6) Uani d . 1 . . C
H12 .2388 .2033 .1573 .080 Uiso calc R 1 . . H
C13 .19592(5) .0919(3) .2747(3) .0477(6) Uani d . 1 . . C
H13 .2061 -.0456 .3092 .080 Uiso calc R 1 . . H
H2 .0000 -.0686 .2500 .080 Uiso d S 1 . . H
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C2 O1 H2 . . 97.68(15)
C2 C1 C2 . 2 121.6(3)
C2 C1 H1 . . 119.2
C2 C1 H1 2 . 119.2
O1 C2 C1 . . 121.1(2)
O1 C2 C3 . . 116.3(2)
C1 C2 C3 . . 122.6(2)
C2 C3 C4 . . 112.85(18)
C2 C3 H3A . . 109.0
C4 C3 H3A . . 109.0
C2 C3 H3B . . 109.0
C4 C3 H3B . . 109.0
H3A C3 H3B . . 107.8
C9 C4 C5 . . 118.38(19)
C9 C4 C3 . . 121.4(2)
C5 C4 C3 . . 120.2(2)
C6 C5 C4 . . 121.3(2)
C6 C5 H5 . . 119.3
C4 C5 H5 . . 119.3
C5 C6 C7 . . 120.98(19)
C5 C6 H6 . . 119.5
C7 C6 H6 . . 119.5
C13 C7 C6 . . 122.48(18)
C13 C7 C8 . . 118.83(17)
C6 C7 C8 . . 118.69(18)
C9 C8 C10 . . 122.90(19)
C9 C8 C7 . . 118.66(17)
C10 C8 C7 . . 118.44(18)
C4 C9 C8 . . 121.99(19)
C4 C9 H9 . . 119.0
C8 C9 H9 . . 119.0
C11 C10 C8 . . 121.4(2)
C11 C10 H10 . . 119.3
C8 C10 H10 . . 119.3
C10 C11 C12 . . 120.0(2)
C10 C11 H11 . . 120.0
C12 C11 H11 . . 120.0
C13 C12 C11 . . 120.4(2)
C13 C12 H12 . . 119.8
C11 C12 H12 . . 119.8
C12 C13 C7 . . 121.04(19)
C12 C13 H13 . . 119.5
C7 C13 H13 . . 119.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 . 1.302(2) ?
O1 H2 . 1.2647(17) ?
C1 C2 . 1.380(3) ?
C1 C2 2 1.380(3) ?
C1 H1 . .9300 ?
C2 C3 . 1.499(3) ?
C3 C4 . 1.508(3) ?
C3 H3A . .9700 ?
C3 H3B . .9700 ?
C4 C9 . 1.370(3) ?
C4 C5 . 1.416(3) ?
C5 C6 . 1.354(3) ?
C5 H5 . .9300 ?
C6 C7 . 1.411(3) ?
C6 H6 . .9300 ?
C7 C13 . 1.406(3) ?
C7 C8 . 1.418(2) ?
C8 C9 . 1.409(3) ?
C8 C10 . 1.412(3) ?
C9 H9 . .9300 ?
C10 C11 . 1.353(3) ?
C10 H10 . .9300 ?
C11 C12 . 1.407(3) ?
C11 H11 . .9300 ?
C12 C13 . 1.357(3) ?
C12 H12 . .9300 ?
C13 H13 . .9300 ?
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_site_symmetry_1
_geom_torsion
C2 C1 C2 O1 2 0.74(16)
C2 C1 C2 C3 2 -178.8(2)
O1 C2 C3 C4 . 59.6(3)
C1 C2 C3 C4 . -120.9(2)
C2 C3 C4 C9 . 100.7(2)
C2 C3 C4 C5 . -79.4(3)
C9 C4 C5 C6 . -0.1(3)
C3 C4 C5 C6 . 179.97(19)
C4 C5 C6 C7 . 0.3(3)
C5 C6 C7 C13 . 179.72(19)
C5 C6 C7 C8 . -0.3(3)
C13 C7 C8 C9 . -179.82(19)
C6 C7 C8 C9 . 0.2(2)
C13 C7 C8 C10 . -0.2(2)
C6 C7 C8 C10 . 179.88(18)
C5 C4 C9 C8 . 0.0(3)
C3 C4 C9 C8 . 179.93(18)
C10 C8 C9 C4 . -179.72(19)
C7 C8 C9 C4 . -0.1(3)
C9 C8 C10 C11 . 180.0(2)
C7 C8 C10 C11 . 0.4(3)
C8 C10 C11 C12 . -0.4(3)
C10 C11 C12 C13 . 0.2(3)
C11 C12 C13 C7 . 0.0(3)
C6 C7 C13 C12 . 179.94(19)
C8 C7 C13 C12 . 0.0(3)
