#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/77/2207761.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_2207761
loop_
_publ_author_name
'Xian-Qiang Huang'
'Da-Qi Wang'
'Jian-Min Dou'
'Jin-Xian Wang'
_publ_section_title
;
 1,5-Diphenyl-3-(2-pyridyl)pentane-1,5-dione
;
_journal_coeditor_code           CV6614
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o60
_journal_page_last               o61
_journal_paper_doi               10.1107/S1600536805040080
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C22 H19 N O2'
_chemical_formula_moiety         'C22 H19 N O2'
_chemical_formula_sum            'C22 H19 N O2'
_chemical_formula_weight         329.38
_chemical_name_systematic
;
1,5-Diphenyl-3-(2-pyridyl)pentane-1,5-dione
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.213(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.519(2)
_cell_length_b                   18.162(3)
_cell_length_c                   8.640(3)
_cell_measurement_reflns_used    2451
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.681
_cell_measurement_theta_min      2.611
_cell_volume                     1807.5(8)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0520
_diffrn_reflns_av_sigmaI/netI    0.0514
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9346
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.09
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9646
_exptl_absorpt_correction_T_min  0.9587
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.47
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.157
_refine_ls_extinction_coef       0.049(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXTL (Bruker, 1997)'
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3189
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0887
_refine_ls_R_factor_gt           0.0449
_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)+(0.0423P)²+0.5691P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.1279
_reflns_number_gt                1889
_reflns_number_total             3189
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv6614.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1807.5(7)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2207761
_cod_database_fobs_code          2207761
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_type_symbol
N1 0.64986(16) 0.06597(10) 1.0878(2) 0.0607(5) Uani d . 1 N
O1 0.71688(14) 0.13498(9) 0.73392(19) 0.0693(5) Uani d . 1 O
O2 0.34654(13) 0.21340(9) 0.76615(19) 0.0672(5) Uani d . 1 O
C1 0.7208(2) 0.05815(14) 1.2104(3) 0.0749(8) Uani d . 1 C
H1 0.7534 0.0121 1.2282 0.090 Uiso calc R 1 H
C2 0.7478(2) 0.11372(16) 1.3105(3) 0.0714(7) Uani d . 1 C
H2 0.7969 0.1054 1.3944 0.086 Uiso calc R 1 H
C3 0.7014(2) 0.18165(16) 1.2847(3) 0.0704(7) Uani d . 1 C
H3 0.7189 0.2208 1.3501 0.085 Uiso calc R 1 H
C4 0.6288(2) 0.19114(13) 1.1615(3) 0.0611(6) Uani d . 1 C
H4 0.5961 0.2371 1.1420 0.073 Uiso calc R 1 H
C5 0.60384(17) 0.13239(11) 1.0655(2) 0.0446(5) Uani d . 1 C
C6 0.52172(17) 0.14184(11) 0.9310(2) 0.0444(5) Uani d . 1 C
H6 0.5382 0.1895 0.8827 0.053 Uiso calc R 1 H
C7 0.53681(18) 0.08244(11) 0.8084(2) 0.0520(6) Uani d . 1 C
H7A 0.5207 0.0349 0.8547 0.062 Uiso calc R 1 H
H7B 0.4801 0.0904 0.7268 0.062 Uiso calc R 1 H
C8 0.65629(19) 0.08037(12) 0.7376(2) 0.0504(5) Uani d . 1 C
C9 0.6982(2) 0.01021(13) 0.6683(2) 0.0590(6) Uani d . 1 C
C10 0.6231(3) -0.04686(14) 0.6304(3) 0.0753(8) Uani d . 1 C
H10 0.5443 -0.0423 0.6509 0.090 Uiso calc R 1 H
C11 0.6650(4) -0.11063(16) 0.5621(3) 0.1046(12) Uani d . 1 C
H11 0.6142 -0.1486 0.5366 0.125 Uiso calc R 1 H
C12 0.7808(5) -0.1177(2) 0.5325(4) 0.1209(16) Uani d . 1 C
H12 0.8085 -0.1604 0.4861 0.145 Uiso calc R 1 H
C13 0.8569(4) -0.0623(2) 0.5706(4) 0.1095(12) Uani d . 1 C
H13 0.9357 -0.0678 0.5510 0.131 Uiso calc R 1 H
C14 0.8160(3) 0.00239(15) 0.6386(3) 0.0812(8) Uani d . 1 C
H14 0.8674 0.0401 0.6638 0.097 Uiso calc R 1 H
C15 0.39591(17) 0.14319(12) 0.9882(2) 0.0508(6) Uani d . 1 C
H15A 0.3713 0.0931 1.0089 0.061 Uiso calc R 1 H
H15B 0.3930 0.1702 1.0850 0.061 Uiso calc R 1 H
C16 0.31204(18) 0.17754(11) 0.8762(2) 0.0485(5) Uani d . 1 C
C17 0.18484(18) 0.16906(12) 0.9047(2) 0.0511(6) Uani d . 1 C
C18 0.1408(2) 0.12207(15) 1.0154(3) 0.0780(8) Uani d . 1 C
H18 0.1913 0.0944 1.0760 0.094 Uiso calc R 1 H
C19 0.0221(2) 0.1156(2) 1.0373(4) 0.1039(11) Uani d . 1 C
H19 -0.0064 0.0839 1.1127 0.125 Uiso calc R 1 H
C20 -0.0520(2) 0.1552(2) 0.9497(4) 0.1022(11) Uani d . 1 C
H20 -0.1316 0.1505 0.9640 0.123 Uiso calc R 1 H
C21 -0.0103(2) 0.20237(19) 0.8394(4) 0.0938(10) Uani d . 1 C
H21 -0.0617 0.2298 0.7794 0.113 Uiso calc R 1 H
C22 0.1079(2) 0.20944(14) 0.8170(3) 0.0697(7) Uani d . 1 C
H22 0.1356 0.2417 0.7421 0.084 Uiso calc R 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'
N N 0.0061 0.0033 '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_publ_flag
C5 N1 C1 116.8(2) ?
N1 C1 C2 123.9(2) ?
N1 C1 H1 118.0 ?
C2 C1 H1 118.0 ?
C3 C2 C1 118.6(2) ?
C3 C2 H2 120.7 ?
C1 C2 H2 120.7 ?
C4 C3 C2 118.8(2) ?
C4 C3 H3 120.6 ?
C2 C3 H3 120.6 ?
C3 C4 C5 119.8(2) ?
C3 C4 H4 120.1 ?
C5 C4 H4 120.1 ?
N1 C5 C4 122.1(2) ?
N1 C5 C6 117.61(18) ?
C4 C5 C6 120.28(19) ?
C5 C6 C7 112.54(17) yes
C5 C6 C15 110.17(16) yes
C7 C6 C15 110.25(17) yes
C5 C6 H6 107.9 ?
C7 C6 H6 107.9 ?
C15 C6 H6 107.9 ?
C8 C7 C6 113.99(17) ?
C8 C7 H7A 108.8 ?
C6 C7 H7A 108.8 ?
C8 C7 H7B 108.8 ?
C6 C7 H7B 108.8 ?
H7A C7 H7B 107.6 ?
O1 C8 C9 120.1(2) ?
O1 C8 C7 121.05(19) ?
C9 C8 C7 118.8(2) ?
C10 C9 C14 119.2(2) ?
C10 C9 C8 122.1(2) ?
C14 C9 C8 118.7(2) ?
C11 C10 C9 120.5(3) ?
C11 C10 H10 119.8 ?
C9 C10 H10 119.8 ?
C12 C11 C10 120.0(4) ?
C12 C11 H11 120.0 ?
C10 C11 H11 120.0 ?
C11 C12 C13 120.6(3) ?
C11 C12 H12 119.7 ?
C13 C12 H12 119.7 ?
C12 C13 C14 120.1(4) ?
C12 C13 H13 119.9 ?
C14 C13 H13 119.9 ?
C9 C14 C13 119.7(3) ?
C9 C14 H14 120.2 ?
C13 C14 H14 120.2 ?
C16 C15 C6 113.95(17) ?
C16 C15 H15A 108.8 ?
C6 C15 H15A 108.8 ?
C16 C15 H15B 108.8 ?
C6 C15 H15B 108.8 ?
H15A C15 H15B 107.7 ?
O2 C16 C17 120.4(2) ?
O2 C16 C15 120.90(19) ?
C17 C16 C15 118.68(18) ?
C22 C17 C18 118.2(2) ?
C22 C17 C16 119.0(2) ?
C18 C17 C16 122.8(2) ?
C17 C18 C19 120.9(3) ?
C17 C18 H18 119.6 ?
C19 C18 H18 119.6 ?
C20 C19 C18 120.1(3) ?
C20 C19 H19 120.0 ?
C18 C19 H19 120.0 ?
C19 C20 C21 120.1(3) ?
C19 C20 H20 119.9 ?
C21 C20 H20 119.9 ?
C20 C21 C22 120.3(3) ?
C20 C21 H21 119.9 ?
C22 C21 H21 119.9 ?
C17 C22 C21 120.4(3) ?
C17 C22 H22 119.8 ?
C21 C22 H22 119.8 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C5 1.331(3) ?
N1 C1 1.343(3) ?
O1 C8 1.213(2) yes
O2 C16 1.220(2) yes
C1 C2 1.364(3) ?
C1 H1 0.9300 ?
C2 C3 1.363(3) ?
C2 H2 0.9300 ?
C3 C4 1.362(3) ?
C3 H3 0.9300 ?
C4 C5 1.381(3) ?
C4 H4 0.9300 ?
C5 C6 1.506(3) ?
C6 C7 1.522(3) yes
C6 C15 1.533(3) yes
C6 H6 0.9800 ?
C7 C8 1.509(3) ?
C7 H7A 0.9700 ?
C7 H7B 0.9700 ?
C8 C9 1.489(3) ?
C9 C10 1.388(3) ?
C9 C14 1.390(3) ?
C10 C11 1.387(4) ?
C10 H10 0.9300 ?
C11 C12 1.366(5) ?
C11 H11 0.9300 ?
C12 C13 1.374(5) ?
C12 H12 0.9300 ?
C13 C14 1.396(4) ?
C13 H13 0.9300 ?
C14 H14 0.9300 ?
C15 C16 1.501(3) ?
C15 H15A 0.9700 ?
C15 H15B 0.9700 ?
C16 C17 1.495(3) ?
C17 C22 1.376(3) ?
C17 C18 1.380(3) ?
C18 C19 1.385(3) ?
C18 H18 0.9300 ?
C19 C20 1.347(4) ?
C19 H19 0.9300 ?
C20 C21 1.370(4) ?
C20 H20 0.9300 ?
C21 C22 1.381(4) ?
C21 H21 0.9300 ?
C22 H22 0.9300 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 190220
