#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/90/2209039.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_2209039
loop_
_publ_author_name
'Qiu, Xiao-Yang'
'Liu, Wei-Sheng'
'Zhu, Hai-Liang'
_publ_section_title
;
 1,5-Bis(4-chlorophenyl)-3-(4-pyridyl)pentane-1,5-dione
;
_journal_coeditor_code           WN2015
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1826
_journal_page_last               o1827
_journal_paper_doi               10.1107/S1600536806012694
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C22 H17 Cl2 N O2'
_chemical_formula_moiety         'C22 H17 Cl2 N O2'
_chemical_formula_sum            'C22 H17 Cl2 N O2'
_chemical_formula_weight         398.27
_chemical_name_systematic
;
1,5-Bis(4-chlorophenyl)-3-(4-pyridyl)pentane-1,5-dione
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.6553(11)
_cell_length_b                   15.754(3)
_cell_length_c                   21.191(4)
_cell_measurement_reflns_used    2564
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      12.5
_cell_measurement_theta_min      5.0
_cell_volume                     1888.0(6)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART APEX area-detector'
_diffrn_measurement_method       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  0.0538
_diffrn_reflns_av_sigmaI/netI    0.0826
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            17030
_diffrn_reflns_theta_full        28.20
_diffrn_reflns_theta_max         28.20
_diffrn_reflns_theta_min         1.92
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.361
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_correction_T_min  0.941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.182
_refine_ls_abs_structure_details 'Flack (1983), with 1918 Friedel pairs'
_refine_ls_abs_structure_Flack   0.01(7)
_refine_ls_extinction_coef       0.0066(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997a)'
_refine_ls_goodness_of_fit_ref   0.757
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4606
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.757
_refine_ls_R_factor_all          0.1252
_refine_ls_R_factor_gt           0.0372
_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)+(0.0544P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.1020
_reflns_number_gt                1774
_reflns_number_total             4606
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wn2015.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 'Orthorhombic' changed to
'orthorhombic' 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_database_code               2209039
_cod_database_fobs_code          2209039
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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
C C1 1.0968(6) 0.14064(16) -0.00139(13) 0.0673(7) Uani d . 1
C C2 0.8826(6) 0.10070(17) -0.01273(14) 0.0732(8) Uani d . 1
H H2 0.8252 0.0948 -0.0536 0.088 Uiso calc R 1
C C3 0.7574(6) 0.07015(16) 0.03763(13) 0.0653(7) Uani d . 1
H H3 0.6141 0.0428 0.0306 0.078 Uiso calc R 1
C C4 0.8401(5) 0.07916(15) 0.09936(12) 0.0585(7) Uani d . 1
C C5 1.0550(5) 0.11963(16) 0.10880(13) 0.0641(7) Uani d . 1
H H5 1.1137 0.1258 0.1495 0.077 Uiso calc R 1
C C6 1.1827(5) 0.15079(17) 0.05831(13) 0.0703(8) Uani d . 1
H H6 1.3258 0.1784 0.0649 0.084 Uiso calc R 1
C C7 0.6929(5) 0.04654(17) 0.15195(13) 0.0639(7) Uani d . 1
C C8 0.7561(5) 0.06909(16) 0.21835(11) 0.0646(7) Uani d . 1
H H8A 0.7763 0.1301 0.2211 0.078 Uiso calc R 1
H H8B 0.9065 0.0430 0.2287 0.078 Uiso calc R 1
C C9 0.5722(5) 0.04133(16) 0.26742(12) 0.0635(7) Uani d . 1
H H9A 0.4150 0.0564 0.2515 0.076 Uiso calc R 1
C C10 0.6124(5) 0.08820(16) 0.32854(12) 0.0672(8) Uani d . 1
H H10A 0.7602 0.0688 0.3468 0.081 Uiso calc R 1
H H10B 0.6295 0.1482 0.3193 0.081 Uiso calc R 1
C C11 0.4196(5) 0.07753(16) 0.37676(13) 0.0621(7) Uani d . 1
C C12 0.4676(5) 0.10638(15) 0.44257(13) 0.0576(7) Uani d . 1
C C13 0.3044(5) 0.08878(16) 0.48980(14) 0.0662(8) Uani d . 1
H H13 0.1671 0.0593 0.4797 0.079 Uiso calc R 1
C C14 0.3414(5) 0.11388(18) 0.55086(14) 0.0727(9) Uani d . 1
H H14 0.2296 0.1021 0.5818 0.087 Uiso calc R 1
C C15 0.5479(5) 0.15720(17) 0.56613(12) 0.0657(7) Uani d . 1
C C16 0.7119(5) 0.17494(18) 0.52041(13) 0.0685(8) Uani d . 1
H H16 0.8489 0.2046 0.5306 0.082 Uiso calc R 1
C C17 0.6728(5) 0.14869(16) 0.45959(13) 0.0629(7) Uani d . 1
H H17 0.7868 0.1595 0.4290 0.076 Uiso calc R 1
C C18 0.5809(5) -0.05525(16) 0.27675(11) 0.0597(7) Uani d . 1
C C19 0.4000(5) -0.10674(19) 0.25609(12) 0.0669(8) Uani d . 1
H H19 0.2680 -0.0830 0.2368 0.080 Uiso calc R 1
C C20 0.4144(6) -0.1926(2) 0.26393(13) 0.0781(9) Uani d . 1
H H20 0.2883 -0.2252 0.2496 0.094 Uiso calc R 1
C C21 0.7672(6) -0.1836(2) 0.31066(13) 0.0759(8) Uani d . 1
H H21 0.8964 -0.2093 0.3300 0.091 Uiso calc R 1
C C22 0.7689(6) -0.09574(18) 0.30506(12) 0.0677(8) Uani d . 1
H H22 0.8961 -0.0645 0.3203 0.081 Uiso calc R 1
N N1 0.5945(6) -0.23314(15) 0.29042(11) 0.0793(7) Uani d . 1
O O1 0.5145(4) 0.00522(13) 0.14023(9) 0.0899(7) Uani d . 1
O O2 0.2290(4) 0.04825(14) 0.36310(9) 0.0895(6) Uani d . 1
Cl Cl1 1.25397(18) 0.17991(6) -0.06528(4) 0.1027(3) Uani d . 1
Cl Cl2 0.59811(19) 0.18941(6) 0.64306(3) 0.1063(3) Uani d . 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 0.0000 0.0000 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
C6 C1 C2 121.7(3)
C6 C1 Cl1 120.0(3)
C2 C1 Cl1 118.3(2)
C3 C2 C1 118.5(3)
C3 C2 H2 120.8
C1 C2 H2 120.8
C2 C3 C4 121.4(3)
C2 C3 H3 119.3
C4 C3 H3 119.3
C5 C4 C3 118.4(3)
C5 C4 C7 122.9(3)
C3 C4 C7 118.7(3)
C6 C5 C4 120.6(3)
C6 C5 H5 119.7
C4 C5 H5 119.7
C1 C6 C5 119.4(3)
C1 C6 H6 120.3
C5 C6 H6 120.3
O1 C7 C4 119.6(3)
O1 C7 C8 120.9(3)
C4 C7 C8 119.4(3)
C7 C8 C9 114.1(2)
C7 C8 H8A 108.7
C9 C8 H8A 108.7
C7 C8 H8B 108.7
C9 C8 H8B 108.7
H8A C8 H8B 107.6
C10 C9 C8 109.9(2)
C10 C9 C18 111.7(2)
C8 C9 C18 110.4(2)
C10 C9 H9A 108.3
C8 C9 H9A 108.3
C18 C9 H9A 108.3
C11 C10 C9 114.8(2)
C11 C10 H10A 108.6
C9 C10 H10A 108.6
C11 C10 H10B 108.6
C9 C10 H10B 108.6
H10A C10 H10B 107.5
O2 C11 C12 120.2(2)
O2 C11 C10 121.8(3)
C12 C11 C10 118.0(3)
C17 C12 C13 117.7(3)
C17 C12 C11 122.8(3)
C13 C12 C11 119.5(2)
C14 C13 C12 121.5(3)
C14 C13 H13 119.3
C12 C13 H13 119.3
C13 C14 C15 119.3(3)
C13 C14 H14 120.3
C15 C14 H14 120.3
C16 C15 C14 120.3(3)
C16 C15 Cl2 119.7(2)
C14 C15 Cl2 120.1(2)
C15 C16 C17 119.6(3)
C15 C16 H16 120.2
C17 C16 H16 120.2
C16 C17 C12 121.6(3)
C16 C17 H17 119.2
C12 C17 H17 119.2
C19 C18 C22 116.1(2)
C19 C18 C9 121.3(3)
C22 C18 C9 122.7(3)
C20 C19 C18 120.0(3)
C20 C19 H19 120.0
C18 C19 H19 120.0
N1 C20 C19 125.1(3)
N1 C20 H20 117.5
C19 C20 H20 117.5
N1 C21 C22 124.5(3)
N1 C21 H21 117.8
C22 C21 H21 117.8
C18 C22 C21 119.6(3)
C18 C22 H22 120.2
C21 C22 H22 120.2
C21 N1 C20 114.8(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.365(3)
C1 C2 1.386(4)
C1 Cl1 1.734(3)
C2 C3 1.368(4)
C2 H2 0.9300
C3 C4 1.396(3)
C3 H3 0.9300
C4 C5 1.387(4)
C4 C7 1.483(4)
C5 C6 1.381(3)
C5 H5 0.9300
C6 H6 0.9300
C7 O1 1.226(3)
C7 C8 1.494(4)
C8 C9 1.534(4)
C8 H8A 0.9700
C8 H8B 0.9700
C9 C10 1.508(3)
C9 C18 1.535(3)
C9 H9A 0.9800
C10 C11 1.504(4)
C10 H10A 0.9700
C10 H10B 0.9700
C11 O2 1.208(3)
C11 C12 1.491(4)
C12 C17 1.386(3)
C12 C13 1.389(4)
C13 C14 1.369(4)
C13 H13 0.9300
C14 C15 1.391(4)
C14 H14 0.9300
C15 C16 1.370(4)
C15 Cl2 1.731(3)
C16 C17 1.372(3)
C16 H16 0.9300
C17 H17 0.9300
C18 C19 1.377(4)
C18 C22 1.378(4)
C19 C20 1.365(4)
C19 H19 0.9300
C20 N1 1.327(4)
C20 H20 0.9300
C21 N1 1.322(4)
C21 C22 1.389(4)
C21 H21 0.9300
C22 H22 0.9300
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
C6 C1 C2 C3 -0.8(4)
Cl1 C1 C2 C3 -179.6(2)
C1 C2 C3 C4 0.6(4)
C2 C3 C4 C5 -0.5(4)
C2 C3 C4 C7 178.5(2)
C3 C4 C5 C6 0.5(4)
C7 C4 C5 C6 -178.3(2)
C2 C1 C6 C5 0.9(4)
Cl1 C1 C6 C5 179.6(2)
C4 C5 C6 C1 -0.7(4)
C5 C4 C7 O1 -174.0(2)
C3 C4 C7 O1 7.1(4)
C5 C4 C7 C8 9.8(4)
C3 C4 C7 C8 -169.1(2)
O1 C7 C8 C9 -3.8(4)
C4 C7 C8 C9 172.3(2)
C7 C8 C9 C10 -163.3(2)
C7 C8 C9 C18 73.1(3)
C8 C9 C10 C11 170.2(2)
C18 C9 C10 C11 -66.9(3)
C9 C10 C11 O2 -14.0(4)
C9 C10 C11 C12 167.5(2)
O2 C11 C12 C17 -172.9(3)
C10 C11 C12 C17 5.6(4)
O2 C11 C12 C13 8.8(4)
C10 C11 C12 C13 -172.7(2)
C17 C12 C13 C14 1.5(4)
C11 C12 C13 C14 179.9(2)
C12 C13 C14 C15 -0.7(4)
C13 C14 C15 C16 0.4(4)
C13 C14 C15 Cl2 -180.0(2)
C14 C15 C16 C17 -0.9(4)
Cl2 C15 C16 C17 179.4(2)
C15 C16 C17 C12 1.8(4)
C13 C12 C17 C16 -2.0(4)
C11 C12 C17 C16 179.6(2)
C10 C9 C18 C19 127.3(3)
C8 C9 C18 C19 -110.1(3)
C10 C9 C18 C22 -53.7(4)
C8 C9 C18 C22 68.9(3)
C22 C18 C19 C20 -0.3(4)
C9 C18 C19 C20 178.7(2)
C18 C19 C20 N1 -0.4(5)
C19 C18 C22 C21 0.5(4)
C9 C18 C22 C21 -178.5(3)
N1 C21 C22 C18 0.0(4)
C22 C21 N1 C20 -0.6(4)
C19 C20 N1 C21 0.9(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21128276
