#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/74/2207492.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_2207492
loop_
_publ_author_name
'Lin-Hai Jing'
'Da-Bin Qin'
'Huan-Xia Zhang'
'Shao-Jin Gu'
'Zhi-Hua Mao'
_publ_section_title
;
 3,3'-(1,4-Naphthalenedimethylene)bis(1-methylimidazolium) diiodide
 monohydrate
;
_journal_coeditor_code           CI6689
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3992
_journal_page_last               o3993
_journal_paper_doi               10.1107/S1600536805035518
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C20 H22 N4 2+, 2I -, H2 O'
_chemical_formula_moiety         'C20 H22 N4 2+, 2I -, H2 O'
_chemical_formula_sum            'C20 H24 I2 N4 O'
_chemical_formula_weight         590.23
_chemical_name_systematic
;3,3'-(1,4-Naphthalenedimethylene)bis(1-methylimidazolium) diiodide
 monohydrate
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                102.97(3)
_cell_angle_beta                 103.66(3)
_cell_angle_gamma                98.24(3)
_cell_formula_units_Z            2
_cell_length_a                   8.563(3)
_cell_length_b                   9.572(3)
_cell_length_c                   14.684(6)
_cell_measurement_reflns_used    18
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      7.35
_cell_measurement_theta_min      4.42
_cell_volume                     1114.9(7)
_computing_cell_refinement       DIFRAC
_computing_data_collection       'DIFRAC (Gabe & White, 1993)'
_computing_data_reduction        'NRCVAX (Gabe et al.,  1989)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia,1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0164
_diffrn_reflns_av_sigmaI/netI    0.0335
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -2
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3927
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.48
_diffrn_standards_decay_%        2.061
_diffrn_standards_interval_count 300
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.837
_exptl_absorpt_correction_T_max  0.797
_exptl_absorpt_correction_T_min  0.583
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.758
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.512
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3900
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0315
_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/[σ²(Fo²)+(0.05P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0769
_refine_ls_wR_factor_ref         0.0834
_reflns_number_gt                2850
_reflns_number_total             3900
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci6689.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 'Triclinic' changed to 'triclinic'
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               2207492
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
N1 0.4114(4) 0.7267(4) 0.2456(3) 0.0378(8) Uani d . 1 N
N2 0.3266(4) 0.6030(4) 0.3368(2) 0.0383(8) Uani d . 1 N
N3 0.0560(4) 0.8516(4) -0.2294(2) 0.0346(8) Uani d . 1 N
N4 0.1375(4) 0.8710(4) -0.3542(3) 0.0396(9) Uani d . 1 N
C1 0.3350(5) 0.8589(4) 0.1186(3) 0.0343(9) Uani d . 1 C
C2 0.2037(5) 0.7473(5) 0.0667(3) 0.0410(10) Uani d . 1 C
H2 0.1875 0.6628 0.0876 0.049 Uiso calc R 1 H
C3 0.0922(6) 0.7582(5) -0.0181(3) 0.0435(11) Uani d . 1 C
H3 0.0037 0.6807 -0.0515 0.052 Uiso calc R 1 H
C4 0.1106(5) 0.8793(5) -0.0524(3) 0.0379(10) Uani d . 1 C
C5 0.2700(5) 1.1302(4) -0.0287(3) 0.0385(10) Uani d . 1 C
H5 0.1974 1.1386 -0.0844 0.046 Uiso calc R 1 H
C6 0.3968(6) 1.2436(5) 0.0226(3) 0.0441(11) Uani d . 1 C
H6 0.4095 1.3283 0.0017 0.053 Uiso calc R 1 H
C7 0.5086(5) 1.2350(4) 0.1064(3) 0.0426(11) Uani d . 1 C
H7 0.5958 1.3131 0.1409 0.051 Uiso calc R 1 H
C8 0.4886(5) 1.1103(4) 0.1373(3) 0.0366(9) Uani d . 1 C
H8 0.5623 1.1055 0.1937 0.044 Uiso calc R 1 H
C9 0.3585(5) 0.9889(4) 0.0855(3) 0.0325(9) Uani d . 1 C
C10 0.2452(5) 0.9993(4) 0.0003(3) 0.0331(9) Uani d . 1 C
C11 0.4573(5) 0.8514(4) 0.2083(3) 0.0389(10) Uani d . 1 C
H11A 0.5619 0.8471 0.1942 0.047 Uiso calc R 1 H
H11B 0.4729 0.9410 0.2590 0.047 Uiso calc R 1 H
C12 0.3467(5) 0.7321(4) 0.3195(3) 0.0397(10) Uani d . 1 C
H12 0.3197 0.8149 0.3539 0.048 Uiso calc R 1 H
C13 0.3805(6) 0.5097(5) 0.2723(4) 0.0503(12) Uani d . 1 C
H13 0.3803 0.4114 0.2685 0.060 Uiso calc R 1 H
C14 0.4341(7) 0.5857(5) 0.2149(4) 0.0563(13) Uani d . 1 C
H14 0.4780 0.5500 0.1643 0.068 Uiso calc R 1 H
C15 0.2605(7) 0.5651(5) 0.4142(3) 0.0538(13) Uani d . 1 C
H15A 0.1590 0.5975 0.4122 0.081 Uiso calc R 1 H
H15B 0.3381 0.6122 0.4764 0.081 Uiso calc R 1 H
H15C 0.2413 0.4608 0.4046 0.081 Uiso calc R 1 H
C16 -0.0105(5) 0.8845(5) -0.1442(3) 0.0447(11) Uani d . 1 C
H16A -0.1113 0.8138 -0.1562 0.054 Uiso calc R 1 H
H16B -0.0365 0.9811 -0.1356 0.054 Uiso calc R 1 H
C17 0.0822(5) 0.9400(5) -0.2834(3) 0.0378(10) Uani d . 1 C
H17 0.0648 1.0353 -0.2735 0.045 Uiso calc R 1 H
C18 0.1421(6) 0.7319(5) -0.3460(3) 0.0483(12) Uani d . 1 C
H18 0.1736 0.6590 -0.3870 0.058 Uiso calc R 1 H
C19 0.0927(5) 0.7207(4) -0.2677(3) 0.0412(10) Uani d . 1 C
H19 0.0848 0.6387 -0.2437 0.049 Uiso calc R 1 H
C20 0.1792(7) 0.9319(6) -0.4308(4) 0.0590(14) Uani d . 1 C
H20A 0.1790 1.0348 -0.4155 0.089 Uiso calc R 1 H
H20B 0.0996 0.8831 -0.4920 0.089 Uiso calc R 1 H
H20C 0.2863 0.9177 -0.4349 0.089 Uiso calc R 1 H
O1W 0.8353(9) 0.6125(7) 0.4395(4) 0.115(2) Uani d D 1 O
H1W 0.825(8) 0.619(8) 0.382(2) 0.10(2) Uiso d D 1 H
H2W 0.763(10) 0.651(12) 0.460(5) 0.22(6) Uiso d D 1 H
I1 0.65018(4) 0.84812(3) 0.59621(2) 0.05244(12) Uani d . 1 I
I2 0.88424(4) 0.64775(4) 0.20982(3) 0.05905(13) Uani d . 1 I
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'
I I -0.4742 1.8119 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C12 N1 C14 107.5(4) ?
C12 N1 C11 125.1(4) ?
C14 N1 C11 127.3(4) ?
C12 N2 C13 108.4(4) ?
C12 N2 C15 126.2(4) ?
C13 N2 C15 125.4(4) ?
C17 N3 C19 108.5(4) ?
C17 N3 C16 126.1(4) ?
C19 N3 C16 125.4(4) ?
C17 N4 C18 108.3(4) ?
C17 N4 C20 125.5(4) ?
C18 N4 C20 126.1(4) ?
C2 C1 C9 118.9(4) ?
C2 C1 C11 122.9(4) ?
C9 C1 C11 118.2(4) ?
C1 C2 C3 121.1(4) ?
C1 C2 H2 119.5 ?
C3 C2 H2 119.5 ?
C4 C3 C2 122.0(4) ?
C4 C3 H3 119.0 ?
C2 C3 H3 119.0 ?
C3 C4 C10 118.8(4) ?
C3 C4 C16 119.9(4) ?
C10 C4 C16 121.3(4) ?
C6 C5 C10 121.7(4) ?
C6 C5 H5 119.2 ?
C10 C5 H5 119.2 ?
C5 C6 C7 120.8(4) ?
C5 C6 H6 119.6 ?
C7 C6 H6 119.6 ?
C8 C7 C6 119.4(4) ?
C8 C7 H7 120.3 ?
C6 C7 H7 120.3 ?
C7 C8 C9 121.6(4) ?
C7 C8 H8 119.2 ?
C9 C8 H8 119.2 ?
C8 C9 C10 118.4(4) ?
C8 C9 C1 121.9(4) ?
C10 C9 C1 119.7(4) ?
C5 C10 C9 118.1(4) ?
C5 C10 C4 122.3(4) ?
C9 C10 C4 119.6(4) ?
N1 C11 C1 114.7(3) y
N1 C11 H11A 108.6 ?
C1 C11 H11A 108.6 ?
N1 C11 H11B 108.6 ?
C1 C11 H11B 108.6 ?
H11A C11 H11B 107.6 ?
N2 C12 N1 109.7(4) ?
N2 C12 H12 125.1 ?
N1 C12 H12 125.1 ?
C14 C13 N2 107.6(4) ?
C14 C13 H13 126.2 ?
N2 C13 H13 126.2 ?
C13 C14 N1 106.9(4) ?
C13 C14 H14 126.6 ?
N1 C14 H14 126.6 ?
N2 C15 H15A 109.5 ?
N2 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
N2 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
N3 C16 C4 111.6(3) y
N3 C16 H16A 109.3 ?
C4 C16 H16A 109.3 ?
N3 C16 H16B 109.3 ?
C4 C16 H16B 109.3 ?
H16A C16 H16B 108.0 ?
N3 C17 N4 108.7(4) ?
N3 C17 H17 125.6 ?
N4 C17 H17 125.6 ?
C19 C18 N4 106.9(4) ?
C19 C18 H18 126.5 ?
N4 C18 H18 126.5 ?
C18 C19 N3 107.5(4) ?
C18 C19 H19 126.2 ?
N3 C19 H19 126.2 ?
N4 C20 H20A 109.5 ?
N4 C20 H20B 109.5 ?
H20A C20 H20B 109.5 ?
N4 C20 H20C 109.5 ?
H20A C20 H20C 109.5 ?
H20B C20 H20C 109.5 ?
H1W O1W H2W 107(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C12 1.324(5) y
N1 C14 1.381(6) y
N1 C11 1.462(5) y
N2 C12 1.313(5) y
N2 C13 1.361(6) y
N2 C15 1.475(5) y
N3 C17 1.314(5) y
N3 C19 1.366(5) y
N3 C16 1.483(5) y
N4 C17 1.325(5) y
N4 C18 1.370(5) y
N4 C20 1.468(6) y
C1 C2 1.368(6) ?
C1 C9 1.439(5) ?
C1 C11 1.501(6) ?
C2 C3 1.413(6) ?
C2 H2 0.93 ?
C3 C4 1.368(6) ?
C3 H3 0.93 ?
C4 C10 1.431(6) ?
C4 C16 1.510(6) y
C5 C6 1.354(6) ?
C5 C10 1.415(5) ?
C5 H5 0.93 ?
C6 C7 1.396(6) ?
C6 H6 0.93 ?
C7 C8 1.371(6) ?
C7 H7 0.93 ?
C8 C9 1.415(6) ?
C8 H8 0.93 ?
C9 C10 1.424(6) ?
C11 H11A 0.97 ?
C11 H11B 0.97 ?
C12 H12 0.93 ?
C13 C14 1.345(7) ?
C13 H13 0.93 ?
C14 H14 0.93 ?
C15 H15A 0.96 ?
C15 H15B 0.96 ?
C15 H15C 0.96 ?
C16 H16A 0.97 ?
C16 H16B 0.97 ?
C17 H17 0.93 ?
C18 C19 1.335(6) ?
C18 H18 0.93 ?
C19 H19 0.93 ?
C20 H20A 0.96 ?
C20 H20B 0.96 ?
C20 H20C 0.96 ?
O1W H1W 0.85(4) ?
O1W H2W 0.85(9) ?
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
O1W H1W I2 . 0.85(4) 2.76(4) 3.578(6) 164(6)
O1W H2W I1 . 0.85(9) 2.87(9) 3.649(7) 154(6)
C17 H17 I2 2_675 0.93 2.90 3.799(5) 162
C18 H18 O1W 2_665 0.93 2.52 3.327(8) 145
C19 H19 I2 2_665 0.93 2.93 3.830(4) 163
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
C9 C1 C2 C3 0.0(6)
C11 C1 C2 C3 -179.3(4)
C1 C2 C3 C4 0.4(7)
C2 C3 C4 C10 -1.1(7)
C2 C3 C4 C16 179.0(4)
C10 C5 C6 C7 0.2(6)
C5 C6 C7 C8 -0.5(7)
C6 C7 C8 C9 1.0(6)
C7 C8 C9 C10 -1.1(6)
C7 C8 C9 C1 -178.8(4)
C2 C1 C9 C8 178.0(4)
C11 C1 C9 C8 -2.6(6)
C2 C1 C9 C10 0.3(6)
C11 C1 C9 C10 179.7(4)
C6 C5 C10 C9 -0.3(6)
C6 C5 C10 C4 179.1(4)
C8 C9 C10 C5 0.7(5)
C1 C9 C10 C5 178.5(4)
C8 C9 C10 C4 -178.8(4)
C1 C9 C10 C4 -1.0(6)
C3 C4 C10 C5 -178.1(4)
C16 C4 C10 C5 1.8(6)
C3 C4 C10 C9 1.4(6)
C16 C4 C10 C9 -178.8(4)
C12 N1 C11 C1 -100.2(5)
C14 N1 C11 C1 83.5(6)
C2 C1 C11 N1 -9.7(6)
C9 C1 C11 N1 170.9(4)
C13 N2 C12 N1 0.2(5)
C15 N2 C12 N1 179.0(4)
C14 N1 C12 N2 -0.3(5)
C11 N1 C12 N2 -177.3(4)
C12 N2 C13 C14 0.0(6)
C15 N2 C13 C14 -178.8(4)
N2 C13 C14 N1 -0.2(6)
C12 N1 C14 C13 0.3(6)
C11 N1 C14 C13 177.2(4)
C17 N3 C16 C4 -118.7(5)
C19 N3 C16 C4 64.8(5)
C3 C4 C16 N3 -100.6(5)
C10 C4 C16 N3 79.6(5)
C19 N3 C17 N4 -1.1(5)
C16 N3 C17 N4 -178.2(4)
C18 N4 C17 N3 1.7(5)
C20 N4 C17 N3 179.1(4)
C17 N4 C18 C19 -1.6(5)
C20 N4 C18 C19 -179.0(4)
N4 C18 C19 N3 0.9(5)
C17 N3 C19 C18 0.2(5)
C16 N3 C19 C18 177.2(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21126926
