#------------------------------------------------------------------------------
#$Date: 2018-09-26 06:29:44 +0300 (Wed, 26 Sep 2018) $
#$Revision: 211175 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/25/8102537.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_8102537
loop_
_publ_author_name
'Zhan-Lin Xu'
'Xiao-Yuan Ma'
'Xiu-Yan Wang'
_publ_section_title
;
 Crystal structure of
 aqua[bis[2-(2-chloro-6-fluorophenyl)imidazo[4,5-f][1,10]phenanthroline]zinc(II)]]
 monohydrate, Zn(H2O)(C19H9N4FCl)2 · H2O
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              661
_journal_volume                  224
_journal_year                    2009
_chemical_formula_moiety         'C38 H20 Cl2 F2 N8 O Zn, H2 O'
_chemical_formula_sum            'C38 H22 Cl2 F2 N8 O2 Zn'
_chemical_formula_weight         796.91
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 104.7360(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.1806(13)
_cell_length_b                   18.9875(19)
_cell_length_c                   13.5282(13)
_cell_measurement_reflns_used    3239
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.05
_cell_measurement_theta_min      3.01
_cell_volume                     3274.3(6)
_computing_cell_refinement       'SMART (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1998)'
_computing_publication_material  'SHELXTL (Bruker, 1998)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX 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  0.0194
_diffrn_reflns_av_sigmaI/netI    0.0221
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9111
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.05
_diffrn_reflns_theta_min         1.92
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.976
_exptl_absorpt_correction_T_max  0.62
_exptl_absorpt_correction_T_min  0.45
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.900
_refine_diff_density_min         -0.746
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3239
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0473
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0857P)²+6.0522P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1430
_refine_ls_wR_factor_ref         0.1490
_reflns_number_gt                2813
_reflns_number_total             3239
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            1267-2749.cff
_cod_data_source_block           wang4
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               8102537
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 -0.2489(2) 0.19474(16) 0.1789(2) 0.0339(7) Uani 1 1 d . . .
H1 H -0.2459 0.2088 0.2454 0.041 Uiso 1 1 calc R . .
C2 C -0.3445(2) 0.19966(17) 0.1057(2) 0.0344(7) Uani 1 1 d . . .
H2 H -0.4041 0.2156 0.1237 0.041 Uiso 1 1 calc R . .
C3 C -0.3498(2) 0.18071(15) 0.0066(2) 0.0318(6) Uani 1 1 d . . .
H3 H -0.4128 0.1842 -0.0433 0.038 Uiso 1 1 calc R . .
C4 C -0.2592(2) 0.15604(14) -0.0188(2) 0.0274(6) Uani 1 1 d . . .
C5 C -0.1665(2) 0.15119(15) 0.0601(2) 0.0276(6) Uani 1 1 d . . .
C6 C -0.0695(2) 0.12513(15) 0.0403(2) 0.0276(6) Uani 1 1 d . . .
C7 C 0.1039(2) 0.09305(18) 0.1075(3) 0.0388(7) Uani 1 1 d . . .
H7 H 0.1614 0.0884 0.1635 0.047 Uiso 1 1 calc R . .
C8 C 0.1128(2) 0.07027(19) 0.0121(3) 0.0408(8) Uani 1 1 d . . .
H8 H 0.1753 0.0505 0.0053 0.049 Uiso 1 1 calc R . .
C9 C 0.0292(2) 0.07712(18) -0.0715(2) 0.0379(7) Uani 1 1 d . . .
H9 H 0.0349 0.0636 -0.1359 0.046 Uiso 1 1 calc R . .
C10 C -0.0655(2) 0.10500(16) -0.0583(2) 0.0306(6) Uani 1 1 d . . .
C11 C -0.1596(2) 0.11353(16) -0.1383(2) 0.0314(6) Uani 1 1 d . . .
C12 C -0.2523(2) 0.13709(15) -0.1193(2) 0.0290(6) Uani 1 1 d . . .
C13 C -0.2749(2) 0.11995(18) -0.2785(2) 0.0366(7) Uani 1 1 d . . .
C14 C -0.3258(2) 0.1109(2) -0.3890(2) 0.0439(8) Uani 1 1 d . A .
C15 C -0.3493(3) 0.0434(3) -0.4299(3) 0.0552(10) Uani 1 1 d . . .
C16 C -0.3918(12) 0.0433(6) -0.5389(11) 0.041(3) Uani 0.50 1 d P A 1
H16 H -0.4109 0.0005 -0.5720 0.049 Uiso 0.50 1 calc PR A 1
C17 C -0.4054(5) 0.1053(6) -0.5974(6) 0.0378(16) Uani 0.50 1 d P A 1
H17 H -0.4324 0.1015 -0.6677 0.045 Uiso 0.50 1 calc PR A 1
C18 C -0.3808(6) 0.1724(5) -0.5559(6) 0.0411(18) Uani 0.50 1 d P A 1
H18 H -0.3878 0.2142 -0.5927 0.049 Uiso 0.50 1 calc PR A 1
C19 C -0.3471(4) 0.1667(3) -0.4587(3) 0.0687(14) Uani 1 1 d . . .
N1 N -0.1620(2) 0.17094(12) 0.15799(19) 0.0297(5) Uani 1 1 d . . .
N2 N 0.01630(19) 0.12113(13) 0.12140(19) 0.0314(5) Uani 1 1 d . . .
N3 N -0.1735(2) 0.10275(16) -0.2412(2) 0.0398(6) Uani 1 1 d . . .
N4 N -0.32792(19) 0.14096(14) -0.21055(19) 0.0318(5) Uani 1 1 d . . .
O1W O 0.0000 0.27661(17) 0.2500 0.0416(8) Uani 1 2 d S . .
O2W O 0.0000 0.2119(3) -0.2500 0.0624(11) Uani 1 2 d S . .
F1 F -0.3339(2) 0.23758(9) -0.42595(16) 0.0531(6) Uani 1 1 d . A .
Cl1 Cl -0.32879(11) -0.02331(6) -0.35418(11) 0.0802(4) Uani 1 1 d . A .
Zn1 Zn 0.0000 0.17259(3) 0.2500 0.03159(19) Uani 1 2 d S . .
C18' C -0.3894(8) 0.1418(7) -0.5698(8) 0.046(3) Uani 0.50 1 d PU A 2
H18' H -0.4051 0.1754 -0.6215 0.055 Uiso 0.50 1 calc PR A 2
C17' C -0.4053(8) 0.0698(7) -0.5966(10) 0.051(3) Uani 0.50 1 d PU A 2
H17' H -0.4301 0.0588 -0.6655 0.061 Uiso 0.50 1 calc PR A 2
C16' C -0.3864(14) 0.0139(7) -0.5266(14) 0.057(3) Uani 0.50 1 d P A 2
H16' H -0.3966 -0.0337 -0.5418 0.068 Uiso 0.50 1 calc PR A 2
HW11 H -0.061(4) 0.308(3) 0.241(4) 0.085 Uiso 1 1 d . . .
HW21 H 0.047(4) 0.183(2) -0.240(5) 0.079(18) Uiso 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'
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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 123.0(3) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
C3 C2 C1 119.2(3) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 119.5(3) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 117.6(3) . . ?
C3 C4 C12 125.4(3) . . ?
C5 C4 C12 116.9(3) . . ?
N1 C5 C4 122.3(3) . . ?
N1 C5 C6 116.7(3) . . ?
C4 C5 C6 121.0(3) . . ?
N2 C6 C10 121.7(3) . . ?
N2 C6 C5 117.3(3) . . ?
C10 C6 C5 121.0(3) . . ?
N2 C7 C8 122.5(3) . . ?
N2 C7 H7 118.7 . . ?
C8 C7 H7 118.7 . . ?
C9 C8 C7 119.7(3) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C9 C10 119.0(3) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
C6 C10 C9 118.2(3) . . ?
C6 C10 C11 116.9(3) . . ?
C9 C10 C11 124.9(3) . . ?
N3 C11 C12 109.9(3) . . ?
N3 C11 C10 127.9(3) . . ?
C12 C11 C10 122.2(3) . . ?
N4 C12 C11 108.8(3) . . ?
N4 C12 C4 129.2(3) . . ?
C11 C12 C4 121.9(3) . . ?
N3 C13 N4 117.0(3) . . ?
N3 C13 C14 120.1(3) . . ?
N4 C13 C14 122.7(3) . . ?
C15 C14 C19 116.2(4) . . ?
C15 C14 C13 120.2(3) . . ?
C19 C14 C13 123.5(4) . . ?
C16' C15 C14 136.9(7) . . ?
C16' C15 C16 23.7(5) . . ?
C14 C15 C16 113.4(6) . . ?
C16' C15 Cl1 104.0(7) . . ?
C14 C15 Cl1 119.0(3) . . ?
C16 C15 Cl1 127.6(6) . . ?
C17 C16 C15 122.4(10) . . ?
C17 C16 H16 118.8 . . ?
C15 C16 H16 118.8 . . ?
C18 C17 C16 123.7(9) . . ?
C18 C17 H17 118.1 . . ?
C16 C17 H17 118.1 . . ?
C19 C18 C17 108.7(7) . . ?
C19 C18 H18 125.7 . . ?
C17 C18 H18 125.7 . . ?
C18 C19 C14 135.5(7) . . ?
C18 C19 F1 103.0(6) . . ?
C14 C19 F1 121.5(4) . . ?
C18 C19 C18' 22.8(5) . . ?
C14 C19 C18' 112.7(6) . . ?
F1 C19 C18' 125.7(6) . . ?
C1 N1 C5 118.3(3) . . ?
C1 N1 Zn1 130.3(2) . . ?
C5 N1 Zn1 110.64(19) . . ?
C7 N2 C6 118.8(3) . . ?
C7 N2 Zn1 126.4(2) . . ?
C6 N2 Zn1 114.26(19) . . ?
C13 N3 C11 102.0(3) . . ?
C13 N4 C12 102.3(2) . . ?
Zn1 O1W HW11 127(3) . . ?
O1W Zn1 N2 118.41(7) . . ?
O1W Zn1 N2 118.41(7) . 2 ?
N2 Zn1 N2 123.17(14) . 2 ?
O1W Zn1 N1 90.82(6) . . ?
N2 Zn1 N1 78.93(9) . . ?
N2 Zn1 N1 100.27(9) 2 . ?
O1W Zn1 N1 90.82(6) . 2 ?
N2 Zn1 N1 100.27(9) . 2 ?
N2 Zn1 N1 78.93(9) 2 2 ?
N1 Zn1 N1 178.35(13) . 2 ?
C17' C18' C19 122.7(10) . . ?
C17' C18' H18' 118.7 . . ?
C19 C18' H18' 118.7 . . ?
C16' C17' C18' 124.6(12) . . ?
C16' C17' H17' 117.7 . . ?
C18' C17' H17' 117.7 . . ?
C15 C16' C17' 106.8(11) . . ?
C15 C16' H16' 126.6 . . ?
C17' C16' H16' 126.6 . . ?
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 1.327(4) . ?
C1 C2 1.393(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.372(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.405(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.406(4) . ?
C4 C12 1.431(4) . ?
C5 N1 1.363(4) . ?
C5 C6 1.457(4) . ?
C6 N2 1.363(4) . ?
C6 C10 1.403(4) . ?
C7 N2 1.328(4) . ?
C7 C8 1.394(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.370(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.408(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.432(4) . ?
C11 N3 1.373(4) . ?
C11 C12 1.385(4) . ?
C12 N4 1.377(4) . ?
C13 N3 1.343(4) . ?
C13 N4 1.349(4) . ?
C13 C14 1.486(4) . ?
C14 C15 1.397(6) . ?
C14 C19 1.399(6) . ?
C15 C16' 1.392(18) . ?
C15 C16 1.438(15) . ?
C15 Cl1 1.609(5) . ?
C16 C17 1.405(13) . ?
C16 H16 0.9300 . ?
C17 C18 1.396(12) . ?
C17 H17 0.9300 . ?
C18 C19 1.281(9) . ?
C18 H18 0.9300 . ?
C19 F1 1.414(6) . ?
C19 C18' 1.538(13) . ?
N1 Zn1 2.181(3) . ?
N2 Zn1 2.054(3) . ?
O1W Zn1 1.975(3) . ?
O1W HW11 0.99(5) . ?
O2W HW21 0.80(5) . ?
Zn1 N2 2.054(3) 2 ?
Zn1 N1 2.181(3) 2 ?
C18' C17' 1.417(14) . ?
C18' H18' 0.9300 . ?
C17' C16' 1.402(16) . ?
C17' H17' 0.9300 . ?
C16' H16' 0.9300 . ?
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
O1W HW11 N4 0.99(5) 1.71(5) 2.695(3) 173(5) 7_455
O2W HW21 N3 0.80(5) 2.33(5) 3.111(4) 165(6) 2_554
