#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/64/2016495.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_2016495
loop_
_publ_author_name
'Brahma, Sanjaya'
'Sachin, H. P.'
'Shivashankar, S. A.'
'Narasimhamurthy, T.'
'Rathore, R. S.'
_publ_section_title
;
 Adducts of bis(acetylacetonato)zinc(II) with 1,10-phenanthroline and
 2,2'-bipyridine
;
_journal_coeditor_code           GG3140
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              m140
_journal_page_last               m143
_journal_paper_doi               10.1107/S0108270108003818
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          '[Zn (C5 H7 O2)2 (C10 H8 N2)]'
_chemical_formula_moiety         'C20 H22 N2 O4 Zn'
_chemical_formula_sum            'C20 H22 N2 O4 Zn'
_chemical_formula_weight         419.77
_chemical_melting_point          503
_chemical_name_systematic
;
bis(acetylacetonato-κ²O,O')(2,2'-bipyridine-κ²N,N')zinc(II)
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.1594(3)
_cell_length_b                   15.3466(6)
_cell_length_c                   15.5582(6)
_cell_measurement_reflns_used    8341
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      28.02
_cell_measurement_theta_min      2.62
_cell_volume                     1948.18(13)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2003)'
_computing_molecular_graphics
'Diamond (Brandenburg & Berndt, 1999) and PLATON (Spek, 2003)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Version 6.1; Sheldrick, 2008)'
_diffrn_ambient_temperature      110(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-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  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0328
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15162
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    1.288
_exptl_absorpt_correction_T_max  0.799
_exptl_absorpt_correction_T_min  0.737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2003)'
_exptl_crystal_colour            'light pink'
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.168
_refine_ls_abs_structure_details 'Flack (1983), 1632 Friedel pairs'
_refine_ls_abs_structure_Flack   0.027(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3822
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0240
_refine_ls_R_factor_gt           0.0224
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0214P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0517
_refine_ls_wR_factor_ref         0.0525
_reflns_number_gt                3690
_reflns_number_total             3822
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gg3140.cif
_cod_data_source_block           II
_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               2016495
_cod_database_fobs_code          2016495
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, 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
Zn Zn1 0.71706(3) 0.608007(13) 0.196796(14) 0.01776(7) Uani d . 1
O O1 0.95077(16) 0.60929(10) 0.14546(9) 0.0256(3) Uani d . 1
O O2 0.73234(18) 0.47547(8) 0.20545(9) 0.0256(3) Uani d . 1
O O3 0.80033(17) 0.64553(8) 0.31557(8) 0.0245(3) Uani d . 1
O O4 0.48224(17) 0.59764(9) 0.24932(9) 0.0239(3) Uani d . 1
N N1 0.61829(19) 0.60529(11) 0.06548(9) 0.0179(3) Uani d . 1
N N2 0.6534(2) 0.74427(10) 0.16571(10) 0.0185(4) Uani d . 1
C C1 0.6216(3) 0.53525(13) 0.01494(13) 0.0228(5) Uani d . 1
H H1 0.6622 0.4833 0.0372 0.027 Uiso calc R 1
C C2 0.5671(3) 0.53631(14) -0.06934(14) 0.0253(5) Uani d . 1
H H2 0.5711 0.4864 -0.1031 0.030 Uiso calc R 1
C C3 0.5068(2) 0.61340(15) -0.10174(13) 0.0256(4) Uani d . 1
H H3 0.4672 0.6158 -0.1577 0.031 Uiso calc R 1
C C4 0.5052(3) 0.68679(13) -0.05126(13) 0.0230(5) Uani d . 1
H H4 0.4677 0.7396 -0.0730 0.028 Uiso calc R 1
C C5 0.5612(3) 0.68063(12) 0.03354(13) 0.0182(4) Uani d . 1
C C6 0.5645(2) 0.75621(12) 0.09333(12) 0.0185(4) Uani d . 1
C C7 0.4808(3) 0.83324(13) 0.07770(14) 0.0234(5) Uani d . 1
H H7 0.4201 0.8401 0.0276 0.028 Uiso calc R 1
C C8 0.4886(3) 0.89930(14) 0.13723(14) 0.0285(5) Uani d . 1
H H8 0.4320 0.9511 0.1279 0.034 Uiso calc R 1
C C9 0.5810(2) 0.88836(13) 0.21109(13) 0.0252(5) Uani d . 1
H H9 0.5889 0.9324 0.2519 0.030 Uiso calc R 1
C C10 0.6612(3) 0.80991(12) 0.22214(13) 0.0216(5) Uani d . 1
H H10 0.7239 0.8023 0.2715 0.026 Uiso calc R 1
C C11 1.0402(3) 0.54333(15) 0.13142(13) 0.0261(5) Uani d . 1
C C12 0.9994(3) 0.45638(15) 0.14958(14) 0.0302(5) Uani d . 1
H H12 1.0781 0.4144 0.1373 0.036 Uiso calc R 1
C C13 0.8522(3) 0.42739(13) 0.18417(13) 0.0234(5) Uani d . 1
C C14 1.2072(3) 0.56189(17) 0.09250(15) 0.0414(6) Uani d . 1
H H14A 1.2017 0.6141 0.0587 0.062 Uiso calc R 1
H H14B 1.2392 0.5140 0.0565 0.062 Uiso calc R 1
H H14C 1.2862 0.5693 0.1376 0.062 Uiso calc R 1
C C15 0.8256(3) 0.33046(13) 0.19778(16) 0.0348(6) Uani d . 1
H H15A 0.8097 0.3191 0.2579 0.052 Uiso calc R 1
H H15B 0.9198 0.2990 0.1777 0.052 Uiso calc R 1
H H15C 0.7305 0.3120 0.1664 0.052 Uiso calc R 1
C C16 0.7133(3) 0.66214(12) 0.38092(13) 0.0277(5) Uani d . 1
C C17 0.5441(3) 0.64982(14) 0.38782(15) 0.0333(6) Uani d . 1
H H17 0.4963 0.6644 0.4401 0.040 Uiso calc R 1
C C18 0.4394(3) 0.61777(13) 0.32415(14) 0.0269(5) Uani d . 1
C C19 0.8036(4) 0.70167(15) 0.45617(14) 0.0422(7) Uani d . 1
H H19A 0.8999 0.6679 0.4682 0.063 Uiso calc R 1
H H19B 0.7335 0.7019 0.5057 0.063 Uiso calc R 1
H H19C 0.8348 0.7603 0.4424 0.063 Uiso calc R 1
C C20 0.2601(3) 0.60405(15) 0.34555(17) 0.0424(6) Uani d . 1
H H20A 0.1934 0.6290 0.3011 0.064 Uiso calc R 1
H H20B 0.2354 0.6317 0.3993 0.064 Uiso calc R 1
H H20C 0.2380 0.5428 0.3498 0.064 Uiso calc R 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'
Zn Zn 0.2839 1.4301 '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
O1 Zn1 O2 88.78(6)
O1 Zn1 O3 92.28(6)
O1 Zn1 O4 176.16(6)
O2 Zn1 O3 101.54(6)
O2 Zn1 O4 87.38(6)
O3 Zn1 O4 88.44(6)
O1 Zn1 N1 88.81(6)
O2 Zn1 N1 93.72(6)
O3 Zn1 N1 164.72(5)
O4 Zn1 N1 91.48(6)
O1 Zn1 N2 97.08(6)
O2 Zn1 N2 166.39(6)
O3 Zn1 N2 90.54(5)
O4 Zn1 N2 86.68(6)
N1 Zn1 N2 74.21(6)
C11 O1 Zn1 126.16(13)
C13 O2 Zn1 127.51(13)
C16 O3 Zn1 126.44(14)
C18 O4 Zn1 126.88(14)
C10 N2 C6 118.03(17)
C10 N2 Zn1 123.93(13)
C6 N2 Zn1 115.91(12)
C1 N1 C5 118.93(17)
C1 N1 Zn1 123.84(14)
C5 N1 Zn1 117.09(13)
N2 C6 C7 121.72(18)
N2 C6 C5 115.13(17)
C7 C6 C5 123.14(19)
N1 C5 C4 121.38(18)
N1 C5 C6 115.74(17)
C4 C5 C6 122.87(18)
C4 C3 C2 119.92(19)
C4 C3 H3 120.0
C2 C3 H3 120.0
O3 C16 C17 126.1(2)
O3 C16 C19 115.4(2)
C17 C16 C19 118.5(2)
C10 C9 C8 117.84(19)
C10 C9 H9 121.1
C8 C9 H9 121.1
C13 C12 C11 125.9(2)
C13 C12 H12 117.0
C11 C12 H12 117.0
O2 C13 C12 125.53(19)
O2 C13 C15 115.0(2)
C12 C13 C15 119.43(19)
C3 C2 C1 118.13(19)
C3 C2 H2 120.9
C1 C2 H2 120.9
C13 C15 H15A 109.5
C13 C15 H15B 109.5
H15A C15 H15B 109.5
C13 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C8 C7 C6 119.2(2)
C8 C7 H7 120.4
C6 C7 H7 120.4
C3 C4 C5 118.73(19)
C3 C4 H4 120.6
C5 C4 H4 120.6
N2 C10 C9 123.53(19)
N2 C10 H10 118.2
C9 C10 H10 118.2
C7 C8 C9 119.66(19)
C7 C8 H8 120.2
C9 C8 H8 120.2
O1 C11 C12 126.1(2)
O1 C11 C14 115.83(19)
C12 C11 C14 118.1(2)
N1 C1 C2 122.89(19)
N1 C1 H1 118.6
C2 C1 H1 118.6
O4 C18 C17 125.0(2)
O4 C18 C20 116.0(2)
C17 C18 C20 118.9(2)
C16 C17 C18 126.7(2)
C16 C17 H17 116.7
C18 C17 H17 116.7
C11 C14 H14A 109.5
C11 C14 H14B 109.5
H14A C14 H14B 109.5
C11 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C16 C19 H19A 109.5
C16 C19 H19B 109.5
H19A C19 H19B 109.5
C16 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
C18 C20 H20A 109.5
C18 C20 H20B 109.5
H20A C20 H20B 109.5
C18 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Zn1 O1 2.0675(13)
Zn1 O2 2.0422(12)
Zn1 O3 2.0513(13)
Zn1 O4 2.0891(14)
Zn1 N1 2.1967(15)
Zn1 N2 2.2083(15)
O1 C11 1.267(2)
O2 C13 1.269(2)
O3 C16 1.266(2)
O4 C18 1.254(2)
N1 C1 1.332(2)
N1 C5 1.342(2)
N2 C6 1.352(2)
N2 C10 1.338(2)
C1 C2 1.385(3)
C1 H1 0.9300
C2 C3 1.377(3)
C2 H2 0.9300
C3 C4 1.373(3)
C3 H3 0.9300
C4 C5 1.399(3)
C4 H4 0.9300
C5 C6 1.487(3)
C6 C7 1.387(3)
C7 C8 1.375(3)
C7 H7 0.9300
C8 H8 0.9300
C8 C9 1.385(3)
C9 C10 1.381(3)
C9 H9 0.9300
C10 H10 0.9300
C11 C12 1.404(3)
C11 C14 1.518(3)
C12 C13 1.389(3)
C12 H12 0.9300
C13 C15 1.518(3)
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
C16 C17 1.397(3)
C16 C19 1.511(3)
C17 C18 1.398(3)
C17 H17 0.9300
C19 H19A 0.9600
C19 H19B 0.9600
C19 H19C 0.9600
C18 C20 1.515(3)
C20 H20A 0.9600
C20 H20B 0.9600
C20 H20C 0.9600
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C10 H10 O3 . 0.93 2.58 3.125(2) 118 y
C4 H4 O1 3_465 0.93 2.58 3.484(3) 164 y
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
C10 N2 C6 C7 -1.1(3)
Zn1 N2 C6 C7 163.03(16)
C10 N2 C6 C5 179.97(17)
Zn1 N2 C6 C5 -15.9(2)
C1 N1 C5 C4 0.1(3)
Zn1 N1 C5 C4 176.01(15)
C1 N1 C5 C6 -178.88(18)
Zn1 N1 C5 C6 -3.0(2)
N2 C6 C5 N1 12.6(2)
C7 C6 C5 N1 -166.34(19)
N2 C6 C5 C4 -166.40(19)
C7 C6 C5 C4 14.7(3)
Zn1 O3 C16 C17 6.9(3)
Zn1 O3 C16 C19 -170.93(13)
Zn1 O2 C13 C12 -0.4(3)
Zn1 O2 C13 C15 -179.53(13)
C11 C12 C13 O2 -0.7(4)
C11 C12 C13 C15 178.4(2)
C4 C3 C2 C1 1.4(3)
N2 C6 C7 C8 0.1(3)
C5 C6 C7 C8 178.99(19)
C2 C3 C4 C5 -1.8(3)
N1 C5 C4 C3 1.1(3)
C6 C5 C4 C3 -179.97(19)
C6 N2 C10 C9 1.2(3)
Zn1 N2 C10 C9 -161.52(16)
C8 C9 C10 N2 -0.3(3)
C6 C7 C8 C9 0.8(3)
C10 C9 C8 C7 -0.7(3)
Zn1 O1 C11 C12 -1.4(3)
Zn1 O1 C11 C14 179.55(13)
C13 C12 C11 O1 1.7(4)
C13 C12 C11 C14 -179.2(2)
C5 N1 C1 C2 -0.6(3)
Zn1 N1 C1 C2 -176.21(15)
C3 C2 C1 N1 -0.1(3)
Zn1 O4 C18 C17 -1.4(3)
Zn1 O4 C18 C20 179.70(13)
O3 C16 C17 C18 -0.6(4)
C19 C16 C17 C18 177.2(2)
O4 C18 C17 C16 -2.4(4)
C20 C18 C17 C16 176.5(2)
