#------------------------------------------------------------------------------
#$Date: 2016-02-18 14:25:00 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176728 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/25/8102577.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_8102577
loop_
_publ_author_name
'Xiu-Yan Wang'
'Ming Wang'
'Wan-Qiu Yu'
'Ya-Ming Sun'
_publ_section_title
;
 Crystal structure of
 [(2-(2-chloro-6-fluorophenyl)-1H-imidazo-[4,5-f][1,10]phenanthroline-k2N,N')]-(m2-adipato)lead(II),
 Pb(C19H10N4FCl)(C6H8O4)
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              74
_journal_volume                  225
_journal_year                    2010
_chemical_formula_moiety         'C25 H18 Cl F N4 O4 Pb'
_chemical_formula_sum            'C25 H18 Cl F N4 O4 Pb'
_chemical_formula_weight         700.07
_chemical_name_systematic
;
[[(2-(2-chloro-6-fluorophenyl)-1H-imidazo[4,5-f][1,10]phenanthroline-
κ²N,N')lead(II)]-μ₂-adipicato], 
[Pb(C₁₉H₁₀N₄FCl)(C₆H₈O₄)]
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.682(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.056(2)
_cell_length_b                   9.2897(15)
_cell_length_c                   19.126(3)
_cell_measurement_reflns_used    4460
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      0.341
_cell_measurement_theta_min      0.225
_cell_volume                     2279.5(6)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL-PLUS (Sheldrick, 1990)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX diffractometer'
_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  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0272
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12234
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         1.59
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    7.569
_exptl_absorpt_correction_T_max  0.341
_exptl_absorpt_correction_T_min  0.225
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.040
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         2.207
_refine_diff_density_min         -1.717
_refine_diff_density_rms         0.166
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         4460
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0398
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0705P)²+9.3565P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1213
_reflns_number_gt                3879
_reflns_number_total             4460
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            1267-2795.cff
_cod_data_source_block           wang3
_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      'P 21/c'
_cod_database_code               8102577
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_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 0.6260(5) 1.2113(9) -0.0756(4) 0.0501(18) Uani 1 1 d . . .
H1 H 0.5589 1.1793 -0.0742 0.060 Uiso 1 1 calc R . .
C2 C 0.6391(5) 1.3113(8) -0.1276(4) 0.0478(17) Uani 1 1 d . . .
H2 H 0.5821 1.3436 -0.1604 0.057 Uiso 1 1 calc R . .
C3 C 0.7369(5) 1.3609(7) -0.1296(4) 0.0406(15) Uani 1 1 d . . .
H3A H 0.7475 1.4278 -0.1637 0.049 Uiso 1 1 calc R . .
C4 C 0.8210(4) 1.3098(7) -0.0795(3) 0.0363(14) Uani 1 1 d . . .
C5 C 0.8016(5) 1.2063(7) -0.0296(4) 0.0367(14) Uani 1 1 d . . .
C6 C 0.8865(5) 1.1484(7) 0.0241(3) 0.0349(13) Uani 1 1 d . . .
C7 C 0.9909(5) 1.1908(7) 0.0247(4) 0.0364(13) Uani 1 1 d . . .
C8 C 1.0687(5) 1.1292(7) 0.0764(4) 0.0400(15) Uani 1 1 d . . .
H8 H 1.1382 1.1545 0.0785 0.048 Uiso 1 1 calc R . .
C9 C 1.0423(6) 1.0325(8) 0.1234(4) 0.0454(17) Uani 1 1 d . . .
H9 H 1.0935 0.9909 0.1578 0.054 Uiso 1 1 calc R . .
C10 C 0.9381(6) 0.9964(7) 0.1197(4) 0.0449(17) Uani 1 1 d . . .
H10 H 0.9210 0.9304 0.1523 0.054 Uiso 1 1 calc R . .
C11 C 1.0076(5) 1.2940(7) -0.0278(4) 0.0369(14) Uani 1 1 d . . .
C12 C 0.9276(5) 1.3530(7) -0.0762(4) 0.0377(14) Uani 1 1 d . . .
C13 C 1.0670(5) 1.4509(7) -0.0961(4) 0.0385(14) Uani 1 1 d . . .
C14 C 1.1383(5) 1.5454(7) -0.1273(4) 0.0405(15) Uani 1 1 d . . .
C15 C 1.2439(6) 1.5575(8) -0.1005(4) 0.0481(17) Uani 1 1 d . . .
C16 C 1.3106(6) 1.6428(10) -0.1299(5) 0.063(2) Uani 1 1 d . . .
H16 H 1.3812 1.6465 -0.1103 0.075 Uiso 1 1 calc R . .
C17 C 1.2694(8) 1.7239(10) -0.1898(5) 0.067(2) Uani 1 1 d . . .
H17 H 1.3130 1.7814 -0.2114 0.080 Uiso 1 1 calc R . .
C18 C 1.1640(8) 1.7187(9) -0.2172(5) 0.062(2) Uani 1 1 d . . .
H18 H 1.1359 1.7736 -0.2568 0.075 Uiso 1 1 calc R . .
C19 C 1.1010(6) 1.6318(9) -0.1855(4) 0.0487(17) Uani 1 1 d . . .
C20 C 0.6977(6) 0.7641(11) 0.1868(5) 0.061(2) Uani 1 1 d . . .
C21 C 0.7259(6) 0.6792(10) 0.2565(4) 0.060(2) Uani 1 1 d . . .
H21A H 0.7711 0.6001 0.2489 0.072 Uiso 1 1 calc R . .
H21B H 0.7654 0.7418 0.2922 0.072 Uiso 1 1 calc R . .
C22 C 0.6367(7) 0.6198(10) 0.2851(5) 0.061(2) Uani 1 1 d . . .
H22A H 0.6635 0.5516 0.3224 0.074 Uiso 1 1 calc R . .
H22B H 0.5926 0.5667 0.2474 0.074 Uiso 1 1 calc R . .
C23 C 0.5696(6) 0.7279(11) 0.3149(5) 0.065(2) Uani 1 1 d . . .
H23A H 0.5059 0.6804 0.3215 0.078 Uiso 1 1 calc R . .
H23B H 0.5504 0.8036 0.2800 0.078 Uiso 1 1 calc R . .
C24 C 0.6203(7) 0.7967(10) 0.3854(5) 0.060(2) Uani 1 1 d . . .
H24A H 0.6901 0.8276 0.3818 0.072 Uiso 1 1 calc R . .
H24B H 0.5808 0.8817 0.3933 0.072 Uiso 1 1 calc R . .
C25 C 0.6269(5) 0.6979(8) 0.4490(4) 0.0420(15) Uani 1 1 d . . .
N1 N 0.7036(4) 1.1597(6) -0.0283(3) 0.0418(13) Uani 1 1 d . . .
N2 N 0.8619(4) 1.0517(6) 0.0718(3) 0.0406(12) Uani 1 1 d . . .
N3 N 1.0973(4) 1.3563(6) -0.0411(3) 0.0393(12) Uani 1 1 d . . .
H3 H 1.1599 1.3395 -0.0193 0.047 Uiso 1 1 calc R . .
N4 N 0.9650(4) 1.4508(6) -0.1185(3) 0.0412(13) Uani 1 1 d . . .
O1 O 0.7655(9) 0.8033(13) 0.1548(6) 0.049(3) Uani 0.50 1 d PU . .
O3 O 0.7148(4) 0.6849(6) 0.4905(3) 0.0488(12) Uani 1 1 d . . .
O4 O 0.5484(4) 0.6336(6) 0.4601(3) 0.0556(14) Uani 1 1 d . . .
Cl1 Cl 0.9865(6) 1.6531(10) -0.2229(4) 0.225(3) Uani 1 1 d . . .
F1 F 1.2860(4) 1.4811(5) -0.0409(3) 0.0653(14) Uani 1 1 d . . .
Pb1 Pb 0.669463(18) 0.98309(3) 0.073179(14) 0.04149(13) Uani 1 1 d . . .
O1' O 0.7679(11) 0.8516(16) 0.1755(7) 0.065(4) Uani 0.50 1 d PU . .
O2 O 0.6070(6) 0.7618(8) 0.1519(4) 0.0830(19) Uani 1 1 d U . .
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'
F F 0.0171 0.0103 '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'
Pb Pb -3.3944 10.1111 '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
N1 C1 C2 123.5(7) . . ?
N1 C1 H1 118.2 . . ?
C2 C1 H1 118.2 . . ?
C3 C2 C1 118.9(7) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 119.1(7) . . ?
C2 C3 H3A 120.4 . . ?
C4 C3 H3A 120.4 . . ?
C3 C4 C5 118.5(6) . . ?
C3 C4 C12 124.5(6) . . ?
C5 C4 C12 117.0(6) . . ?
N1 C5 C4 121.3(6) . . ?
N1 C5 C6 117.6(6) . . ?
C4 C5 C6 121.1(5) . . ?
N2 C6 C7 121.6(6) . . ?
N2 C6 C5 118.0(5) . . ?
C7 C6 C5 120.3(6) . . ?
C8 C7 C6 117.6(6) . . ?
C8 C7 C11 125.6(6) . . ?
C6 C7 C11 116.8(6) . . ?
C9 C8 C7 119.8(6) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 119.4(7) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
N2 C10 C9 122.9(7) . . ?
N2 C10 H10 118.5 . . ?
C9 C10 H10 118.5 . . ?
N3 C11 C12 106.0(6) . . ?
N3 C11 C7 131.1(6) . . ?
C12 C11 C7 122.8(6) . . ?
N4 C12 C11 110.7(6) . . ?
N4 C12 C4 127.4(6) . . ?
C11 C12 C4 121.8(6) . . ?
N4 C13 N3 112.3(6) . . ?
N4 C13 C14 122.7(6) . . ?
N3 C13 C14 125.1(6) . . ?
C15 C14 C19 115.4(7) . . ?
C15 C14 C13 123.7(7) . . ?
C19 C14 C13 120.9(6) . . ?
F1 C15 C16 117.0(7) . . ?
F1 C15 C14 119.0(6) . . ?
C16 C15 C14 124.0(8) . . ?
C15 C16 C17 118.2(8) . . ?
C15 C16 H16 120.9 . . ?
C17 C16 H16 120.9 . . ?
C18 C17 C16 119.9(8) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C19 C18 C17 119.4(8) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C18 C19 C14 123.1(8) . . ?
C18 C19 Cl1 109.1(7) . . ?
C14 C19 Cl1 127.7(7) . . ?
O1 C20 O2 116.2(9) . . ?
O1 C20 O1' 27.5(7) . . ?
O2 C20 O1' 124.2(10) . . ?
O1 C20 C21 120.6(8) . . ?
O2 C20 C21 120.5(8) . . ?
O1' C20 C21 114.3(9) . . ?
C22 C21 C20 115.7(7) . . ?
C22 C21 H21A 108.4 . . ?
C20 C21 H21A 108.4 . . ?
C22 C21 H21B 108.4 . . ?
C20 C21 H21B 108.4 . . ?
H21A C21 H21B 107.4 . . ?
C21 C22 C23 116.2(8) . . ?
C21 C22 H22A 108.2 . . ?
C23 C22 H22A 108.2 . . ?
C21 C22 H22B 108.2 . . ?
C23 C22 H22B 108.2 . . ?
H22A C22 H22B 107.4 . . ?
C22 C23 C24 115.1(7) . . ?
C22 C23 H23A 108.5 . . ?
C24 C23 H23A 108.5 . . ?
C22 C23 H23B 108.5 . . ?
C24 C23 H23B 108.5 . . ?
H23A C23 H23B 107.5 . . ?
C25 C24 C23 113.9(7) . . ?
C25 C24 H24A 108.8 . . ?
C23 C24 H24A 108.8 . . ?
C25 C24 H24B 108.8 . . ?
C23 C24 H24B 108.8 . . ?
H24A C24 H24B 107.7 . . ?
O4 C25 O3 121.7(7) . . ?
O4 C25 C24 120.4(7) . . ?
O3 C25 C24 117.9(7) . . ?
C1 N1 C5 118.7(6) . . ?
C1 N1 Pb1 121.2(5) . . ?
C5 N1 Pb1 120.0(4) . . ?
C10 N2 C6 118.7(6) . . ?
C10 N2 Pb1 120.0(5) . . ?
C6 N2 Pb1 121.2(4) . . ?
C11 N3 C13 106.1(5) . . ?
C11 N3 H3 127.0 . . ?
C13 N3 H3 127.0 . . ?
C13 N4 C12 104.9(6) . . ?
O1' O1 C20 81(2) . . ?
O1' O1 Pb1 82(2) . . ?
C20 O1 Pb1 100.8(7) . . ?
C25 O3 Pb1 99.8(4) . 4_576 ?
C25 O4 Pb1 87.2(4) . 4_576 ?
O3 Pb1 O1' 92.6(4) 4_575 . ?
O3 Pb1 O1 79.4(3) 4_575 . ?
O1' Pb1 O1 13.9(4) . . ?
O3 Pb1 N2 78.07(18) 4_575 . ?
O1' Pb1 N2 76.5(3) . . ?
O1 Pb1 N2 78.1(3) . . ?
O3 Pb1 N1 79.74(19) 4_575 . ?
O1' Pb1 N1 139.4(3) . . ?
O1 Pb1 N1 138.7(3) . . ?
N2 Pb1 N1 62.91(17) . . ?
O3 Pb1 O4 51.28(15) 4_575 4_575 ?
O1' Pb1 O4 126.1(4) . 4_575 ?
O1 Pb1 O4 113.2(3) . 4_575 ?
N2 Pb1 O4 121.42(17) . 4_575 ?
N1 Pb1 O4 79.15(18) . 4_575 ?
O3 Pb1 O2 90.5(2) 4_575 . ?
O1' Pb1 O2 50.1(4) . . ?
O1 Pb1 O2 46.9(3) . . ?
N2 Pb1 O2 124.9(2) . . ?
N1 Pb1 O2 166.1(2) . . ?
O4 Pb1 O2 87.1(2) 4_575 . ?
O1 O1' C20 71(2) . . ?
O1 O1' Pb1 84(2) . . ?
C20 O1' Pb1 99.5(8) . . ?
C20 O2 Pb1 86.1(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 N1 1.317(9) . ?
C1 C2 1.396(11) . ?
C1 H1 0.9300 . ?
C2 C3 1.365(10) . ?
C2 H2 0.9300 . ?
C3 C4 1.400(9) . ?
C3 H3A 0.9300 . ?
C4 C5 1.411(9) . ?
C4 C12 1.438(8) . ?
C5 N1 1.355(8) . ?
C5 C6 1.467(9) . ?
C6 N2 1.360(8) . ?
C6 C7 1.417(8) . ?
C7 C8 1.402(9) . ?
C7 C11 1.434(10) . ?
C8 C9 1.361(10) . ?
C8 H8 0.9300 . ?
C9 C10 1.391(10) . ?
C9 H9 0.9300 . ?
C10 N2 1.325(9) . ?
C10 H10 0.9300 . ?
C11 N3 1.371(8) . ?
C11 C12 1.375(9) . ?
C12 N4 1.366(8) . ?
C13 N4 1.322(9) . ?
C13 N3 1.371(9) . ?
C13 C14 1.484(9) . ?
C14 C15 1.384(10) . ?
C14 C19 1.385(10) . ?
C15 F1 1.369(10) . ?
C15 C16 1.371(11) . ?
C16 C17 1.394(13) . ?
C16 H16 0.9300 . ?
C17 C18 1.380(13) . ?
C17 H17 0.9300 . ?
C18 C19 1.371(11) . ?
C18 H18 0.9300 . ?
C19 Cl1 1.546(10) . ?
C20 O1 1.222(14) . ?
C20 O2 1.246(10) . ?
C20 O1' 1.273(16) . ?
C20 C21 1.534(11) . ?
C21 C22 1.483(12) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.511(12) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.528(13) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.513(11) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 O4 1.237(8) . ?
C25 O3 1.275(8) . ?
N1 Pb1 2.642(6) . ?
N2 Pb1 2.597(5) . ?
N3 H3 0.8600 . ?
O1 O1' 0.596(15) . ?
O1 Pb1 2.464(11) . ?
O3 Pb1 2.374(5) 4_576 ?
O4 Pb1 2.662(5) 4_576 ?
Pb1 O3 2.374(5) 4_575 ?
Pb1 O1' 2.458(14) . ?
Pb1 O4 2.662(5) 4_575 ?
Pb1 O2 2.759(7) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3 O3 0.86 2.17 2.934(7) 147.9 2_755
N3 H3 F1 0.86 2.21 2.722(7) 118.5 .
