#------------------------------------------------------------------------------
#$Date: 2016-02-18 14:25:00 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176728 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/28/8102845.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_8102845
loop_
_publ_author_name
'Sheng-Li Liu'
'Jin-Liang Zhu'
'Tao Ouyang'
_publ_section_title
;
 Crystal structure of
 1,1'-(pyridin-2,6-diyl)bis-3-p-tolylpropane-1,3-dione, C25H21NO4
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              643
_journal_volume                  225
_journal_year                    2010
_chemical_formula_sum            'C25 H21 N O4'
_chemical_formula_weight         399.43
_chemical_name_systematic
; 
1,1'-(pyridin-2,6-diyl)bis-3-p-tolylpropane-1,3-dione,
C₂₅H₂₁NO₄
;
_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_creation_method           SHELXL-97
_audit_update_record
;
2010-07-27 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 100.831(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.2915(18)
_cell_length_b                   9.7207(11)
_cell_length_c                   11.1047(11)
_cell_measurement_reflns_used    1945
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.78
_cell_measurement_theta_min      2.36
_cell_volume                     2045.3(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL[5]'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)[4]'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)[3]'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0588
_diffrn_reflns_av_sigmaI/netI    0.0349
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7900
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9843
_exptl_absorpt_correction_T_min  0.9573
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.114
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.0057(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         1806
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0439
_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)+(0.0853P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1296
_refine_ls_wR_factor_ref         0.1451
_reflns_number_gt                1188
_reflns_number_total             1806
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-3177.cff
_cod_data_source_block           zjl13_0m
_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 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               8102845
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_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.28174(12) 0.4398(2) -0.0447(2) 0.1147(8) Uani 1 1 d . . .
H1A H 0.2728 0.4206 0.0358 0.172 Uiso 1 1 calc R . .
H1B H 0.3151 0.3745 -0.0648 0.172 Uiso 1 1 calc R . .
H1C H 0.2385 0.4331 -0.1034 0.172 Uiso 1 1 calc R . .
C2 C 0.31116(9) 0.5825(2) -0.04754(19) 0.0854(6) Uani 1 1 d . . .
C3 C 0.31461(11) 0.6472(3) -0.1565(2) 0.1000(7) Uani 1 1 d . . .
H3 H 0.2989 0.6004 -0.2296 0.120 Uiso 1 1 calc R . .
C4 C 0.34046(10) 0.7785(3) -0.16096(16) 0.0910(7) Uani 1 1 d . . .
H4 H 0.3413 0.8192 -0.2365 0.109 Uiso 1 1 calc R . .
C5 C 0.36536(8) 0.85082(19) -0.05377(13) 0.0693(5) Uani 1 1 d . . .
C6 C 0.36234(10) 0.78554(19) 0.05575(15) 0.0787(6) Uani 1 1 d . . .
H6 H 0.3785 0.8311 0.1293 0.094 Uiso 1 1 calc R . .
C7 C 0.33593(10) 0.6550(2) 0.05791(17) 0.0858(6) Uani 1 1 d . . .
H7 H 0.3347 0.6142 0.1332 0.103 Uiso 1 1 calc R . .
C8 C 0.39196(9) 0.9918(2) -0.05906(14) 0.0730(5) Uani 1 1 d . . .
C9 C 0.42457(8) 1.06490(18) 0.04639(14) 0.0693(5) Uani 1 1 d . . .
H9 H 0.4317 1.0217 0.1224 0.083 Uiso 1 1 calc R . .
C10 C 0.44593(9) 1.1993(2) 0.03831(16) 0.0751(5) Uani 1 1 d . . .
C11 C 0.47555(8) 1.27987(18) 0.14778(16) 0.0730(5) Uani 1 1 d . . .
C12 C 0.47593(10) 1.4231(2) 0.1439(2) 0.0952(7) Uani 1 1 d . . .
H12 H 0.4601 1.4695 0.0706 0.114 Uiso 1 1 calc R . .
C13 C 0.5000 1.4943(3) 0.2500 0.1056(10) Uani 1 2 d S . .
H13 H 0.5000 1.5900 0.2500 0.127 Uiso 1 2 calc SR . .
N1 N 0.5000 1.20951(19) 0.2500 0.0698(6) Uani 1 2 d S . .
O1 O 0.43890(9) 1.26387(15) -0.06545(13) 0.1049(6) Uani 1 1 d . . .
H1 H 0.4193 1.2135 -0.1208 0.157 Uiso 1 1 calc R . .
O2 O 0.38373(8) 1.05038(15) -0.16387(10) 0.1024(5) Uani 1 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 0.0033 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 C3 116.6(2) . . ?
C7 C2 C1 121.9(2) . . ?
C3 C2 C1 121.41(19) . . ?
C4 C3 C2 122.26(18) . . ?
C4 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
C3 C4 C5 120.58(19) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 117.17(19) . . ?
C6 C5 C8 122.43(15) . . ?
C4 C5 C8 120.38(16) . . ?
C7 C6 C5 121.20(16) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C2 122.13(19) . . ?
C6 C7 H7 118.9 . . ?
C2 C7 H7 118.9 . . ?
O2 C8 C9 119.35(18) . . ?
O2 C8 C5 117.88(16) . . ?
C9 C8 C5 122.75(14) . . ?
C10 C9 C8 121.01(16) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
O1 C10 C9 122.28(18) . . ?
O1 C10 C11 115.93(18) . . ?
C9 C10 C11 121.75(15) . . ?
N1 C11 C12 122.42(19) . . ?
N1 C11 C10 116.85(16) . . ?
C12 C11 C10 120.71(17) . . ?
C13 C12 C11 118.8(2) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C12 C13 C12 119.3(3) . 2_655 ?
C12 C13 H13 120.4 . . ?
C12 C13 H13 120.4 2_655 . ?
C11 N1 C11 118.3(2) . 2_655 ?
C10 O1 H1 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.501(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C7 1.373(2) . ?
C2 C3 1.376(3) . ?
C3 C4 1.375(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(2) . ?
C5 C8 1.468(3) . ?
C6 C7 1.369(2) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 O2 1.2786(19) . ?
C8 C9 1.413(2) . ?
C9 C10 1.378(2) . ?
C9 H9 0.9300 . ?
C10 O1 1.296(2) . ?
C10 C11 1.468(3) . ?
C11 N1 1.3333(19) . ?
C11 C12 1.393(3) . ?
C12 C13 1.371(2) . ?
C12 H12 0.9300 . ?
C13 C12 1.371(2) 2_655 ?
C13 H13 0.9300 . ?
N1 C11 1.3333(19) 2_655 ?
O1 H1 0.8200 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 C2 C3 C4 -0.9(3) . . . . ?
C1 C2 C3 C4 179.08(18) . . . . ?
C2 C3 C4 C5 1.0(3) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
C3 C4 C5 C8 -179.11(16) . . . . ?
C4 C5 C6 C7 0.1(3) . . . . ?
C8 C5 C6 C7 178.64(16) . . . . ?
C5 C6 C7 C2 -0.1(3) . . . . ?
C3 C2 C7 C6 0.5(3) . . . . ?
C1 C2 C7 C6 -179.53(17) . . . . ?
C6 C5 C8 O2 -170.48(16) . . . . ?
C4 C5 C8 O2 8.1(2) . . . . ?
C6 C5 C8 C9 8.2(2) . . . . ?
C4 C5 C8 C9 -173.26(14) . . . . ?
O2 C8 C9 C10 1.7(2) . . . . ?
C5 C8 C9 C10 -176.98(14) . . . . ?
C8 C9 C10 O1 -1.7(3) . . . . ?
C8 C9 C10 C11 175.82(14) . . . . ?
O1 C10 C11 N1 -163.31(14) . . . . ?
C9 C10 C11 N1 19.0(2) . . . . ?
O1 C10 C11 C12 18.3(2) . . . . ?
C9 C10 C11 C12 -159.40(15) . . . . ?
N1 C11 C12 C13 -2.4(2) . . . . ?
C10 C11 C12 C13 175.94(13) . . . . ?
C11 C12 C13 C12 1.12(11) . . . 2_655 ?
C12 C11 N1 C11 1.20(11) . . . 2_655 ?
C10 C11 N1 C11 -177.18(15) . . . 2_655 ?
