#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2202602.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_2202602
loop_
_publ_author_name
'Sakai, Ken'
'Okamoto, Ken'
'Takahashi, Satoru'
'Yokokawa, Kazuo'
_publ_section_title
;
 <i>N</i>-Methyl-<i>N</i>'-(3-phthalimidopropyl)-4,4'-bipyridinium
 diiodide
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o917
_journal_page_last               o918
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C22 H21 N3 O2 2+, 2I 1-'
_chemical_formula_moiety         'C22 H21 N3 O2 2+, 2I 1-'
_chemical_formula_sum            'C22 H21 I2 N3 O2'
_chemical_formula_weight         613.22
_chemical_name_systematic
;
N-Methyl-N'-(3-phthalimidopropyl)-4,4'-bipyridinium diiodide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                83.7150(10)
_cell_angle_beta                 88.570(2)
_cell_angle_gamma                82.2230(10)
_cell_formula_units_Z            2
_cell_length_a                   6.0535(5)
_cell_length_b                   7.4674(6)
_cell_length_c                   25.776(2)
_cell_measurement_reflns_used    3414
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.17
_cell_measurement_theta_min      2.77
_cell_volume                     1147.46(16)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'KENX (Sakai, 2002)'
_computing_publication_material
;
SHELXL97 (Sheldrick, 1997), TEXSAN (Molecular Structure Corporation, 2001),
KENX (Sakai, 2002) and ORTEPII (Johnson, 1976)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.925
_diffrn_measured_fraction_theta_max 0.925
_diffrn_measurement_device       'Bruker SMART APEX CCD-detector'
_diffrn_measurement_method       \w
_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  0.0189
_diffrn_reflns_av_sigmaI/netI    0.0381
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            6983
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.38
_diffrn_standards_decay_%        0.265
_diffrn_standards_interval_time  330
_diffrn_standards_number         134
_exptl_absorpt_coefficient_mu    2.763
_exptl_absorpt_correction_T_max  0.871
_exptl_absorpt_correction_T_min  0.586
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.775
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.267
_refine_diff_density_min         -0.443
_refine_ls_extinction_expression not_refined
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4883
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.048P)^2^+0.5905P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0968
_refine_ls_wR_factor_ref         0.1017
_reflns_number_gt                4060
_reflns_number_total             4883
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    dn6076.cif
_[local]_cod_data_source_block   I
_cod_original_cell_volume        1147.45(16)
_cod_database_code               2202602
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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_type_symbol
I1 0.19500(5) 0.72933(4) 0.254201(15) 0.06628(13) Uani d . 1 I
I2 0.84565(5) 0.74396(4) 0.065322(12) 0.05327(11) Uani d . 1 I
O1 0.4876(5) 0.2479(5) 0.44316(13) 0.0672(9) Uani d . 1 O
O2 -0.1257(6) 0.3202(5) 0.34073(14) 0.0749(10) Uani d . 1 O
N1 0.1978(6) 0.2446(5) 0.38681(13) 0.0492(8) Uani d . 1 N
N2 0.5727(5) 0.2105(4) 0.24093(12) 0.0377(7) Uani d . 1 N
N3 1.4807(5) 0.2657(4) 0.06983(12) 0.0398(7) Uani d . 1 N
C1 0.3138(7) 0.3200(6) 0.42332(16) 0.0499(10) Uani d . 1 C
C2 0.1766(7) 0.4947(6) 0.43191(16) 0.0489(10) Uani d . 1 C
C3 0.2117(8) 0.6203(6) 0.46498(18) 0.0586(11) Uani d . 1 C
H3 0.3390 0.6064 0.4853 0.070 Uiso calc R 1 H
C4 0.0484(10) 0.7685(7) 0.4666(2) 0.0697(14) Uani d . 1 C
H4 0.0648 0.8558 0.4889 0.084 Uiso calc R 1 H
C5 -0.1378(10) 0.7887(8) 0.4359(2) 0.0776(16) Uani d . 1 C
H5 -0.2434 0.8909 0.4373 0.093 Uiso calc R 1 H
C6 -0.1721(9) 0.6599(8) 0.4028(2) 0.0715(14) Uani d . 1 C
H6 -0.2990 0.6727 0.3824 0.086 Uiso calc R 1 H
C7 -0.0104(7) 0.5141(6) 0.40176(17) 0.0527(10) Uani d . 1 C
C8 0.0021(7) 0.3550(7) 0.37156(17) 0.0552(11) Uani d . 1 C
C9 0.2768(8) 0.0703(6) 0.36789(16) 0.0530(11) Uani d . 1 C
H9A 0.1530 0.0257 0.3525 0.064 Uiso calc R 1 H
H9B 0.3287 -0.0163 0.3973 0.064 Uiso calc R 1 H
C10 0.4626(7) 0.0793(5) 0.32801(15) 0.0465(9) Uani d . 1 C
H10A 0.5837 0.1301 0.3425 0.056 Uiso calc R 1 H
H10B 0.5191 -0.0427 0.3201 0.056 Uiso calc R 1 H
C11 0.3849(6) 0.1939(5) 0.27838(15) 0.0434(9) Uani d . 1 C
H11A 0.2703 0.1391 0.2626 0.052 Uiso calc R 1 H
H11B 0.3203 0.3139 0.2864 0.052 Uiso calc R 1 H
C12 0.6752(7) 0.3591(5) 0.23621(15) 0.0433(9) Uani d . 1 C
H12 0.6250 0.4538 0.2560 0.052 Uiso calc R 1 H
C13 0.8524(6) 0.3747(5) 0.20284(16) 0.0420(9) Uani d . 1 C
H13 0.9205 0.4798 0.1997 0.050 Uiso calc R 1 H
C14 0.9306(6) 0.2327(5) 0.17358(14) 0.0345(7) Uani d . 1 C
C15 0.8192(6) 0.0811(5) 0.17903(15) 0.0420(9) Uani d . 1 C
H15 0.8659 -0.0154 0.1597 0.050 Uiso calc R 1 H
C16 0.6415(7) 0.0722(5) 0.21254(16) 0.0453(9) Uani d . 1 C
H16 0.5679 -0.0300 0.2157 0.054 Uiso calc R 1 H
C17 1.3702(7) 0.1209(6) 0.07274(17) 0.0503(10) Uani d . 1 C
H17 1.4133 0.0294 0.0514 0.060 Uiso calc R 1 H
C18 1.1957(7) 0.1061(5) 0.10658(17) 0.0478(10) Uani d . 1 C
H18 1.1224 0.0037 0.1086 0.057 Uiso calc R 1 H
C19 1.1264(6) 0.2432(5) 0.13816(14) 0.0361(8) Uani d . 1 C
C20 1.2465(7) 0.3901(5) 0.13447(15) 0.0425(9) Uani d . 1 C
H20 1.2072 0.4838 0.1553 0.051 Uiso calc R 1 H
C21 1.4225(6) 0.3974(5) 0.10025(15) 0.0417(9) Uani d . 1 C
H21 1.5025 0.4958 0.0983 0.050 Uiso calc R 1 H
C22 1.6680(7) 0.2759(6) 0.03166(17) 0.0495(10) Uani d . 1 C
H22A 1.6097 0.3005 -0.0031 0.074 Uiso calc R 1 H
H22B 1.7645 0.1622 0.0347 0.074 Uiso calc R 1 H
H22C 1.7506 0.3714 0.0387 0.074 Uiso calc R 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
I1 0.0654(2) 0.03703(17) 0.1002(3) -0.01153(14) -0.01225(18) -0.01576(15)
I2 0.05358(18) 0.03899(16) 0.0708(2) -0.01621(12) -0.00222(14) -0.00893(13)
O1 0.062(2) 0.074(2) 0.066(2) 0.0056(17) -0.0165(17) -0.0240(17)
O2 0.066(2) 0.090(3) 0.075(2) -0.0285(19) -0.0166(18) -0.0111(19)
N1 0.052(2) 0.056(2) 0.0440(19) -0.0184(17) -0.0002(16) -0.0115(16)
N2 0.0386(16) 0.0334(16) 0.0407(17) -0.0050(13) 0.0008(13) -0.0016(13)
N3 0.0373(16) 0.0357(16) 0.0467(18) -0.0064(13) -0.0003(14) -0.0041(13)
C1 0.054(2) 0.058(3) 0.041(2) -0.014(2) 0.0009(19) -0.0103(18)
C2 0.053(2) 0.051(2) 0.043(2) -0.0112(19) 0.0062(19) -0.0053(18)
C3 0.068(3) 0.054(3) 0.055(3) -0.009(2) 0.003(2) -0.010(2)
C4 0.094(4) 0.051(3) 0.063(3) -0.009(3) 0.011(3) -0.007(2)
C5 0.081(4) 0.064(3) 0.080(4) 0.006(3) 0.019(3) 0.004(3)
C6 0.062(3) 0.081(4) 0.065(3) -0.003(3) -0.002(2) 0.011(3)
C7 0.051(2) 0.057(3) 0.050(2) -0.011(2) 0.0036(19) 0.002(2)
C8 0.052(3) 0.070(3) 0.047(2) -0.025(2) 0.000(2) -0.001(2)
C9 0.068(3) 0.052(2) 0.044(2) -0.026(2) 0.001(2) -0.0043(18)
C10 0.052(2) 0.041(2) 0.049(2) -0.0124(18) -0.0018(19) -0.0051(17)
C11 0.043(2) 0.040(2) 0.048(2) -0.0071(17) 0.0019(17) -0.0038(16)
C12 0.049(2) 0.037(2) 0.045(2) -0.0068(17) -0.0011(18) -0.0115(16)
C13 0.042(2) 0.0325(18) 0.055(2) -0.0131(16) 0.0019(17) -0.0110(16)
C14 0.0359(18) 0.0293(17) 0.0384(19) -0.0046(14) -0.0029(15) -0.0033(14)
C15 0.046(2) 0.0301(18) 0.050(2) -0.0065(16) 0.0041(18) -0.0079(16)
C16 0.054(2) 0.0302(18) 0.053(2) -0.0114(17) 0.0057(19) -0.0052(16)
C17 0.047(2) 0.045(2) 0.065(3) -0.0169(18) 0.009(2) -0.0222(19)
C18 0.049(2) 0.039(2) 0.062(3) -0.0173(18) 0.007(2) -0.0207(18)
C19 0.0368(18) 0.0293(17) 0.042(2) -0.0052(14) -0.0060(15) -0.0023(14)
C20 0.051(2) 0.0305(18) 0.048(2) -0.0105(16) 0.0002(18) -0.0067(15)
C21 0.046(2) 0.0293(18) 0.051(2) -0.0118(16) -0.0008(18) -0.0027(16)
C22 0.045(2) 0.048(2) 0.057(3) -0.0128(18) 0.0096(19) -0.0081(19)
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'
I I -0.4742 1.8119 '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
C8 N1 C1 111.9(4)
C8 N1 C9 125.2(4)
C1 N1 C9 122.9(4)
C12 N2 C16 120.5(3)
C12 N2 C11 120.5(3)
C16 N2 C11 119.1(3)
C21 N3 C17 120.5(3)
C21 N3 C22 121.0(3)
C17 N3 C22 118.5(3)
O1 C1 N1 124.3(4)
O1 C1 C2 130.2(4)
N1 C1 C2 105.5(4)
C7 C2 C3 122.1(5)
C7 C2 C1 108.4(4)
C3 C2 C1 129.5(4)
C2 C3 C4 116.8(5)
C2 C3 H3 121.6
C4 C3 H3 121.6
C5 C4 C3 121.0(5)
C5 C4 H4 119.5
C3 C4 H4 119.5
C4 C5 C6 121.6(5)
C4 C5 H5 119.2
C6 C5 H5 119.2
C7 C6 C5 116.7(5)
C7 C6 H6 121.7
C5 C6 H6 121.7
C6 C7 C2 121.8(5)
C6 C7 C8 129.9(5)
C2 C7 C8 108.3(4)
O2 C8 N1 124.5(5)
O2 C8 C7 129.6(5)
N1 C8 C7 105.8(4)
N1 C9 C10 113.5(3)
N1 C9 H9A 108.9
C10 C9 H9A 108.9
N1 C9 H9B 108.9
C10 C9 H9B 108.9
H9A C9 H9B 107.7
C11 C10 C9 111.7(3)
C11 C10 H10A 109.3
C9 C10 H10A 109.3
C11 C10 H10B 109.3
C9 C10 H10B 109.3
H10A C10 H10B 107.9
N2 C11 C10 110.9(3)
N2 C11 H11A 109.5
C10 C11 H11A 109.5
N2 C11 H11B 109.5
C10 C11 H11B 109.5
H11A C11 H11B 108.0
N2 C12 C13 121.2(3)
N2 C12 H12 119.4
C13 C12 H12 119.4
C12 C13 C14 119.8(3)
C12 C13 H13 120.1
C14 C13 H13 120.1
C15 C14 C13 117.5(3)
C15 C14 C19 121.4(3)
C13 C14 C19 121.1(3)
C16 C15 C14 120.7(3)
C16 C15 H15 119.7
C14 C15 H15 119.7
N2 C16 C15 120.3(3)
N2 C16 H16 119.8
C15 C16 H16 119.8
N3 C17 C18 120.9(4)
N3 C17 H17 119.6
C18 C17 H17 119.6
C17 C18 C19 120.3(4)
C17 C18 H18 119.8
C19 C18 H18 119.8
C20 C19 C18 117.2(3)
C20 C19 C14 121.9(3)
C18 C19 C14 120.9(3)
C21 C20 C19 120.2(4)
C21 C20 H20 119.9
C19 C20 H20 119.9
N3 C21 C20 121.0(3)
N3 C21 H21 119.5
C20 C21 H21 119.5
N3 C22 H22A 109.5
N3 C22 H22B 109.5
H22A C22 H22B 109.5
N3 C22 H22C 109.5
H22A C22 H22C 109.5
H22B C22 H22C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.213(5)
O2 C8 1.195(5)
N1 C8 1.387(6)
N1 C1 1.397(5)
N1 C9 1.456(5)
N2 C12 1.336(5)
N2 C16 1.345(5)
N2 C11 1.482(5)
N3 C21 1.329(5)
N3 C17 1.341(5)
N3 C22 1.486(5)
C1 C2 1.483(6)
C2 C7 1.372(6)
C2 C3 1.375(6)
C3 C4 1.384(7)
C3 H3 0.9300
C4 C5 1.375(8)
C4 H4 0.9300
C5 C6 1.393(8)
C5 H5 0.9300
C6 C7 1.364(7)
C6 H6 0.9300
C7 C8 1.483(6)
C9 C10 1.508(5)
C9 H9A 0.9700
C9 H9B 0.9700
C10 C11 1.507(5)
C10 H10A 0.9700
C10 H10B 0.9700
C11 H11A 0.9700
C11 H11B 0.9700
C12 C13 1.367(5)
C12 H12 0.9300
C13 C14 1.392(5)
C13 H13 0.9300
C14 C15 1.386(5)
C14 C19 1.483(5)
C15 C16 1.367(5)
C15 H15 0.9300
C16 H16 0.9300
C17 C18 1.362(6)
C17 H17 0.9300
C18 C19 1.392(5)
C18 H18 0.9300
C19 C20 1.389(5)
C20 C21 1.369(5)
C20 H20 0.9300
C21 H21 0.9300
C22 H22A 0.9600
C22 H22B 0.9600
C22 H22C 0.9600
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
C8 N1 C1 O1 178.8(4)
C9 N1 C1 O1 -1.1(7)
C8 N1 C1 C2 0.2(5)
C9 N1 C1 C2 -179.6(3)
O1 C1 C2 C7 -177.6(5)
N1 C1 C2 C7 0.8(5)
O1 C1 C2 C3 -0.2(8)
N1 C1 C2 C3 178.2(4)
C7 C2 C3 C4 0.1(7)
C1 C2 C3 C4 -177.0(4)
C2 C3 C4 C5 -0.9(7)
C3 C4 C5 C6 1.3(8)
C4 C5 C6 C7 -0.9(8)
C5 C6 C7 C2 0.2(7)
C5 C6 C7 C8 179.4(4)
C3 C2 C7 C6 0.2(7)
C1 C2 C7 C6 177.9(4)
C3 C2 C7 C8 -179.1(4)
C1 C2 C7 C8 -1.5(5)
C1 N1 C8 O2 180.0(4)
C9 N1 C8 O2 -0.2(7)
C1 N1 C8 C7 -1.1(5)
C9 N1 C8 C7 178.7(3)
C6 C7 C8 O2 1.1(8)
C2 C7 C8 O2 -179.6(5)
C6 C7 C8 N1 -177.7(4)
C2 C7 C8 N1 1.6(5)
C8 N1 C9 C10 103.0(5)
C1 N1 C9 C10 -77.2(5)
N1 C9 C10 C11 -65.6(5)
C12 N2 C11 C10 -99.4(4)
C16 N2 C11 C10 79.2(4)
C9 C10 C11 N2 176.5(3)
C16 N2 C12 C13 -0.3(6)
C11 N2 C12 C13 178.3(4)
N2 C12 C13 C14 -0.8(6)
C12 C13 C14 C15 1.4(6)
C12 C13 C14 C19 -178.3(4)
C13 C14 C15 C16 -0.9(6)
C19 C14 C15 C16 178.8(4)
C12 N2 C16 C15 0.9(6)
C11 N2 C16 C15 -177.8(4)
C14 C15 C16 N2 -0.3(6)
C21 N3 C17 C18 0.4(6)
C22 N3 C17 C18 -179.2(4)
N3 C17 C18 C19 1.2(7)
C17 C18 C19 C20 -1.8(6)
C17 C18 C19 C14 177.4(4)
C15 C14 C19 C20 -176.5(3)
C13 C14 C19 C20 3.2(6)
C15 C14 C19 C18 4.3(6)
C13 C14 C19 C18 -176.0(4)
C18 C19 C20 C21 1.0(6)
C14 C19 C20 C21 -178.2(4)
C17 N3 C21 C20 -1.2(6)
C22 N3 C21 C20 178.3(4)
C19 C20 C21 N3 0.5(6)