#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/06/2220687.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_2220687
loop_
_publ_author_name
'Chen, Ming-Hua'
'Zhang, Yun-Qian'
'Zhu, Qian-Jiang'
'Xue, Sai-Feng'
'Tao, Zhu'
_publ_section_title
;
 2-(2-Furyl)-1H-imidazo[4,5-f][1,10]phenanthroline-3,7-diium
 dichloride monohydrate
;
_journal_coeditor_code           AT2707
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o341
_journal_paper_doi               10.1107/S1600536809001160
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C17 H12 N4 O 2+, 2Cl -, H2 O'
_chemical_formula_moiety         'C17 H12 N4 O 2+, 2(Cl -), H2 O'
_chemical_formula_sum            'C17 H14 Cl2 N4 O2'
_chemical_formula_weight         377.22
_chemical_name_systematic
;
2-(2-Furyl)-1H-imidazo[4,5-f][1,10]phenanthroline-
3,7-diium dichloride monohydrate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 92.060(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.768(3)
_cell_length_b                   17.897(10)
_cell_length_c                   19.241(11)
_cell_measurement_reflns_used    2859
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      1.55
_cell_volume                     1640.8(17)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0580
_diffrn_reflns_av_sigmaI/netI    0.0591
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10782
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.55
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.415
_exptl_absorpt_correction_T_max  0.9403
_exptl_absorpt_correction_T_min  0.9105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            red-brown
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.258
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2859
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0470
_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)+(0.0514P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1031
_refine_ls_wR_factor_ref         0.1149
_reflns_number_gt                1886
_reflns_number_total             2859
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2707.cif
_cod_data_source_block           I
_cod_original_cell_volume        1641.0(16)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2220687
_cod_database_fobs_code          2220687
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.2549(7) 0.5257(2) 0.91899(18) 0.0595(10) Uani d . 1 . .
H H1 0.1981 0.5270 0.9647 0.071 Uiso calc R 1 . .
C C2 0.1543(7) 0.57043(18) 0.86872(17) 0.0491(9) Uani d . 1 . .
H H2 0.0184 0.6073 0.8728 0.059 Uiso calc R 1 . .
C C3 0.2960(6) 0.55060(16) 0.80743(16) 0.0439(8) Uani d . 1 . .
H H3 0.2711 0.5718 0.7635 0.053 Uiso calc R 1 . .
C C4 0.4742(6) 0.49469(16) 0.82609(15) 0.0366(7) Uani d . 1 . .
C C5 0.6721(6) 0.45050(15) 0.78964(15) 0.0356(7) Uani d . 1 . .
C C6 0.9978(6) 0.36694(15) 0.76729(14) 0.0334(7) Uani d . 1 . .
C C7 1.2049(6) 0.30919(15) 0.77145(14) 0.0331(7) Uani d . 1 . .
C C8 1.2878(6) 0.26901(16) 0.83160(16) 0.0405(8) Uani d . 1 . .
H H8 1.2062 0.2786 0.8739 0.049 Uiso calc R 1 . .
C C9 1.4924(6) 0.21529(17) 0.82645(16) 0.0465(8) Uani d . 1 . .
H H9 1.5506 0.1877 0.8653 0.056 Uiso calc R 1 . .
C C10 1.6108(6) 0.20276(16) 0.76279(17) 0.0453(8) Uani d . 1 . .
H H10 1.7500 0.1665 0.7607 0.054 Uiso calc R 1 . .
C C11 1.3351(6) 0.29168(15) 0.70909(14) 0.0328(7) Uani d . 1 . .
C C12 1.2531(6) 0.33026(15) 0.64536(14) 0.0320(7) Uani d . 1 . .
C C13 1.3161(6) 0.34323(16) 0.52471(15) 0.0417(8) Uani d . 1 . .
H H13 1.4109 0.3287 0.4855 0.050 Uiso calc R 1 . .
C C14 1.1068(6) 0.39700(16) 0.51891(15) 0.0420(8) Uani d . 1 . .
H H14 1.0577 0.4177 0.4758 0.050 Uiso calc R 1 . .
C C15 0.9734(6) 0.41932(15) 0.57711(14) 0.0376(7) Uani d . 1 . .
H H15 0.8349 0.4559 0.5741 0.045 Uiso calc R 1 . .
C C16 1.0477(6) 0.38639(15) 0.64198(14) 0.0322(7) Uani d . 1 . .
C C17 0.9259(6) 0.40383(15) 0.70643(14) 0.0319(7) Uani d . 1 . .
N N3 1.5391(5) 0.23910(13) 0.70414(13) 0.0412(6) Uani d . 1 . .
N N4 1.3821(5) 0.31224(12) 0.58612(12) 0.0359(6) Uani d . 1 . .
H H4 1.5130 0.2792 0.5882 0.043 Uiso calc R 1 . .
N N1 0.8358(5) 0.39716(13) 0.81854(11) 0.0348(6) Uani d . 1 . .
H H1A 0.8394 0.3840 0.8615 0.042 Uiso calc R 1 . .
N N2 0.7228(5) 0.45605(12) 0.72179(12) 0.0345(6) Uani d . 1 . .
H H2A 0.6432 0.4867 0.6928 0.041 Uiso calc R 1 . .
O O1 0.4528(5) 0.47741(12) 0.89489(11) 0.0550(6) Uani d . 1 . .
Cl Cl1 0.44997(17) 0.56432(4) 0.62293(4) 0.0514(3) Uani d . 1 . .
Cl Cl2 0.83425(17) 0.20341(5) 0.53339(5) 0.0579(3) Uani d . 1 . .
O O1W 0.8356(5) 0.35229(14) 0.94806(11) 0.0703(8) Uani d . 1 . .
H H1WA 0.9993 0.3370 0.9803 0.084 Uiso d R 1 . .
H H1WB 0.6840 0.3400 0.9751 0.084 Uiso d 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 O1 . . 111.5(3) ?
C2 C1 H1 . . 124.2 ?
O1 C1 H1 . . 124.2 ?
C1 C2 C3 . . 106.4(3) ?
C1 C2 H2 . . 126.8 ?
C3 C2 H2 . . 126.8 ?
C4 C3 C2 . . 106.1(3) ?
C4 C3 H3 . . 127.0 ?
C2 C3 H3 . . 127.0 ?
C3 C4 O1 . . 110.9(3) ?
C3 C4 C5 . . 134.1(3) ?
O1 C4 C5 . . 115.0(3) ?
N2 C5 N1 . . 109.5(3) ?
N2 C5 C4 . . 125.5(3) ?
N1 C5 C4 . . 125.0(3) ?
C17 C6 N1 . . 106.9(2) ?
C17 C6 C7 . . 123.0(3) ?
N1 C6 C7 . . 130.1(3) ?
C11 C7 C8 . . 117.9(3) ?
C11 C7 C6 . . 116.0(2) ?
C8 C7 C6 . . 126.1(3) ?
C9 C8 C7 . . 118.5(3) ?
C9 C8 H8 . . 120.8 ?
C7 C8 H8 . . 120.8 ?
C8 C9 C10 . . 119.3(3) ?
C8 C9 H9 . . 120.3 ?
C10 C9 H9 . . 120.3 ?
N3 C10 C9 . . 124.6(3) ?
N3 C10 H10 . . 117.7 ?
C9 C10 H10 . . 117.7 ?
N3 C11 C7 . . 123.6(3) ?
N3 C11 C12 . . 116.3(3) ?
C7 C11 C12 . . 120.1(3) ?
N4 C12 C16 . . 118.0(3) ?
N4 C12 C11 . . 118.8(3) ?
C16 C12 C11 . . 123.2(3) ?
N4 C13 C14 . . 120.4(3) ?
N4 C13 H13 . . 119.8 ?
C14 C13 H13 . . 119.8 ?
C15 C14 C13 . . 119.4(3) ?
C15 C14 H14 . . 120.3 ?
C13 C14 H14 . . 120.3 ?
C14 C15 C16 . . 119.5(3) ?
C14 C15 H15 . . 120.3 ?
C16 C15 H15 . . 120.3 ?
C12 C16 C15 . . 119.5(3) ?
C12 C16 C17 . . 115.0(2) ?
C15 C16 C17 . . 125.5(3) ?
C6 C17 N2 . . 107.3(2) ?
C6 C17 C16 . . 122.6(3) ?
N2 C17 C16 . . 130.1(2) ?
C10 N3 C11 . . 116.1(3) ?
C13 N4 C12 . . 123.2(3) ?
C13 N4 H4 . . 118.4 ?
C12 N4 H4 . . 118.4 ?
C5 N1 C6 . . 108.3(2) ?
C5 N1 H1A . . 125.8 ?
C6 N1 H1A . . 125.8 ?
C5 N2 C17 . . 108.1(2) ?
C5 N2 H2A . . 126.0 ?
C17 N2 H2A . . 126.0 ?
C4 O1 C1 . . 105.1(2) ?
H1WA O1W H1WB . . 100.9 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.332(4) ?
C1 O1 . 1.373(4) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.425(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.353(4) ?
C3 H3 . 0.9300 ?
C4 O1 . 1.367(3) ?
C4 C5 . 1.434(4) ?
C5 N2 . 1.340(3) ?
C5 N1 . 1.341(3) ?
C6 C17 . 1.377(4) ?
C6 N1 . 1.384(3) ?
C6 C7 . 1.429(4) ?
C7 C11 . 1.406(4) ?
C7 C8 . 1.407(4) ?
C8 C9 . 1.376(4) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.385(4) ?
C9 H9 . 0.9300 ?
C10 N3 . 1.336(4) ?
C10 H10 . 0.9300 ?
C11 N3 . 1.359(3) ?
C11 C12 . 1.449(4) ?
C12 N4 . 1.353(3) ?
C12 C16 . 1.403(4) ?
C13 N4 . 1.333(3) ?
C13 C14 . 1.388(4) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.367(4) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.414(4) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.423(4) ?
C17 N2 . 1.385(3) ?
N4 H4 . 0.8600 ?
N1 H1A . 0.8600 ?
N2 H2A . 0.8600 ?
O1W H1WA . 1.0173 ?
O1W H1WB . 0.9323 ?
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
N1 H1A O1W . 0.86 1.76 2.618(3) 176.6
N2 H2A Cl1 . 0.86 2.12 2.981(3) 178.7
N4 H4 Cl2 1_655 0.86 2.33 3.103(3) 150.3
O1W H1WA Cl2 4_666 1.02 2.00 3.011(3) 172.0
O1W H1WB Cl2 4_566 0.93 2.19 3.112(3) 172.7
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 C2 C3 . . . . -0.3(4) ?
C1 C2 C3 C4 . . . . -0.2(4) ?
C2 C3 C4 O1 . . . . 0.5(3) ?
C2 C3 C4 C5 . . . . 179.6(3) ?
C3 C4 C5 N2 . . . . -0.9(5) ?
O1 C4 C5 N2 . . . . 178.1(3) ?
C3 C4 C5 N1 . . . . 178.9(3) ?
O1 C4 C5 N1 . . . . -2.0(4) ?
C17 C6 C7 C11 . . . . 0.2(4) ?
N1 C6 C7 C11 . . . . -179.5(3) ?
C17 C6 C7 C8 . . . . -179.7(3) ?
N1 C6 C7 C8 . . . . 0.6(5) ?
C11 C7 C8 C9 . . . . 0.4(4) ?
C6 C7 C8 C9 . . . . -179.6(3) ?
C7 C8 C9 C10 . . . . 0.4(4) ?
C8 C9 C10 N3 . . . . -0.6(5) ?
C8 C7 C11 N3 . . . . -1.1(4) ?
C6 C7 C11 N3 . . . . 179.0(2) ?
C8 C7 C11 C12 . . . . 178.7(2) ?
C6 C7 C11 C12 . . . . -1.3(4) ?
N3 C11 C12 N4 . . . . -0.2(4) ?
C7 C11 C12 N4 . . . . 180.0(2) ?
N3 C11 C12 C16 . . . . -179.4(2) ?
C7 C11 C12 C16 . . . . 0.8(4) ?
N4 C13 C14 C15 . . . . 1.6(4) ?
C13 C14 C15 C16 . . . . -1.0(4) ?
N4 C12 C16 C15 . . . . 3.0(4) ?
C11 C12 C16 C15 . . . . -177.8(2) ?
N4 C12 C16 C17 . . . . -178.5(2) ?
C11 C12 C16 C17 . . . . 0.8(4) ?
C14 C15 C16 C12 . . . . -1.3(4) ?
C14 C15 C16 C17 . . . . -179.7(3) ?
N1 C6 C17 N2 . . . . 0.3(3) ?
C7 C6 C17 N2 . . . . -179.4(2) ?
N1 C6 C17 C16 . . . . -178.8(2) ?
C7 C6 C17 C16 . . . . 1.4(4) ?
C12 C16 C17 C6 . . . . -1.9(4) ?
C15 C16 C17 C6 . . . . 176.6(3) ?
C12 C16 C17 N2 . . . . 179.2(3) ?
C15 C16 C17 N2 . . . . -2.3(5) ?
C9 C10 N3 C11 . . . . 0.0(4) ?
C7 C11 N3 C10 . . . . 0.9(4) ?
C12 C11 N3 C10 . . . . -178.9(2) ?
C14 C13 N4 C12 . . . . 0.2(4) ?
C16 C12 N4 C13 . . . . -2.5(4) ?
C11 C12 N4 C13 . . . . 178.2(2) ?
N2 C5 N1 C6 . . . . -0.2(3) ?
C4 C5 N1 C6 . . . . 179.9(3) ?
C17 C6 N1 C5 . . . . -0.1(3) ?
C7 C6 N1 C5 . . . . 179.6(3) ?
N1 C5 N2 C17 . . . . 0.4(3) ?
C4 C5 N2 C17 . . . . -179.7(3) ?
C6 C17 N2 C5 . . . . -0.4(3) ?
C16 C17 N2 C5 . . . . 178.6(3) ?
C3 C4 O1 C1 . . . . -0.7(3) ?
C5 C4 O1 C1 . . . . -180.0(3) ?
C2 C1 O1 C4 . . . . 0.6(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655702
