#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/84/2008412.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_2008412
loop_
_publ_author_name
'Kovalainen, Jari T.'
'Wegelius, Elina'
'Christiaans, Johannes A. M.'
'Huuskonen, Juhani'
'Gynther, Jukka'
_publ_section_title
;
 4-[3-(4-Iodophenylmethoxy)propyl]-1H-imidazolium hydrogen
 maleate (iodoproxyfan hydrogen maleate)
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              IUC9900035
_journal_paper_doi               10.1107/S0108270199099564
_journal_volume                  55
_journal_year                    1999
_chemical_formula_moiety         'C13 H16 I N2 O 1+, C4 H3 O4 1-'
_chemical_formula_sum            'C17 H19 I N2 O5'
_chemical_formula_weight         458.28
_chemical_name_common
;
Iodoproxyfan
;
_chemical_name_systematic
;
3-(1H-imidazol-4-yl)propyl (4-iodophenyl)methyl ether hydrogen maleate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                97.26(2)
_cell_angle_beta                 93.40(2)
_cell_angle_gamma                92.60(3)
_cell_formula_units_Z            2
_cell_length_a                   5.493(2)
_cell_length_b                   10.104(2)
_cell_length_c                   16.288(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      10
_cell_volume                     893.9(4)
_computing_cell_refinement       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction
'XCAD4 (Harms & Wocadlo, 1996) and WINGX (Farrugia, 1998)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1993)'
_computing_publication_material  'SHELXL97 and WINGX'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a) and WINGX'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997b) and WINGX'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.014
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            3498
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.03
_diffrn_standards_decay_%        2
_diffrn_standards_interval_time  60
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    1.821
_exptl_absorpt_correction_T_max  0.772
_exptl_absorpt_correction_T_min  0.408
_exptl_absorpt_correction_type   '\y scan'
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.702
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.620
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.184
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3142
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.184
_refine_ls_R_factor_all          0.022
_refine_ls_R_factor_gt           0.021
_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)+(0.0294P)²+0.5981P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.057
_reflns_number_gt                3033
_reflns_number_total             3142
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            qb0075.cif
_cod_data_source_block           qb0075
_cod_database_code               2008412
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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
I1 0.21445(3) 0.924665(15) 0.575258(10) 0.03672(7) Uani d . 1 . . I
N1 0.6480(3) -0.18058(18) 0.85203(11) 0.0251(4) Uani d . 1 . . N
H1 0.7633 -0.2305 0.8320 0.030 Uiso calc R 1 . . H
C5 0.5959(4) -0.0565(2) 0.83014(13) 0.0238(4) Uani d . 1 . . C
C4 0.4078(4) -0.0158(2) 0.87536(14) 0.0276(5) Uani d . 1 . . C
H4 0.3297 0.0660 0.8744 0.033 Uiso calc R 1 . . H
N3 0.3507(3) -0.11445(19) 0.92301(12) 0.0267(4) Uani d . 1 . . N
H3 0.2345 -0.1123 0.9580 0.032 Uiso calc R 1 . . H
C2 0.4977(4) -0.2127(2) 0.90782(14) 0.0265(5) Uani d . 1 . . C
H2 0.4962 -0.2928 0.9327 0.032 Uiso calc R 1 . . H
C6 0.7355(4) 0.0086(2) 0.76913(14) 0.0282(5) Uani d . 1 . . C
H6A 0.7243 -0.0503 0.7155 0.034 Uiso calc R 1 . . H
H6B 0.9098 0.0205 0.7892 0.034 Uiso calc R 1 . . H
C7 0.6401(4) 0.1443(2) 0.75570(14) 0.0275(5) Uani d . 1 . . C
H7A 0.4663 0.1323 0.7350 0.033 Uiso calc R 1 . . H
H7B 0.6494 0.2028 0.8095 0.033 Uiso calc R 1 . . H
C8 0.7831(5) 0.2115(2) 0.69465(15) 0.0312(5) Uani d . 1 . . C
H8A 0.9567 0.2264 0.7151 0.037 Uiso calc R 1 . . H
H8B 0.7740 0.1548 0.6402 0.037 Uiso calc R 1 . . H
O9 0.6780(3) 0.33540(17) 0.68676(12) 0.0384(4) Uani d . 1 . . O
C10 0.8051(5) 0.4118(2) 0.63489(15) 0.0328(5) Uani d . 1 . . C
H10A 0.8226 0.3576 0.5807 0.039 Uiso calc R 1 . . H
H10B 0.9705 0.4393 0.6605 0.039 Uiso calc R 1 . . H
C11 0.6656(4) 0.5339(2) 0.62222(14) 0.0289(5) Uani d . 1 . . C
C12 0.7174(5) 0.6066(3) 0.55837(18) 0.0413(6) Uani d . 1 . . C
H12 0.8423 0.5792 0.5230 0.050 Uiso calc R 1 . . H
C13 0.5919(5) 0.7184(3) 0.54459(17) 0.0390(6) Uani d . 1 . . C
H13 0.6301 0.7676 0.5006 0.047 Uiso calc R 1 . . H
C14 0.4102(4) 0.7566(2) 0.59599(15) 0.0281(5) Uani d . 1 . . C
C15 0.3548(5) 0.6864(3) 0.65995(15) 0.0363(5) Uani d . 1 . . C
H15 0.2290 0.7136 0.6950 0.044 Uiso calc R 1 . . H
C16 0.4844(5) 0.5755(3) 0.67278(15) 0.0352(5) Uani d . 1 . . C
H16 0.4475 0.5273 0.7173 0.042 Uiso calc R 1 . . H
C17 0.9663(4) 0.5455(2) 0.85681(13) 0.0240(4) Uani d . 1 . . C
O1 1.0052(3) 0.63844(17) 0.81667(10) 0.0320(4) Uani d . 1 . . O
O2 0.7662(3) 0.53070(16) 0.89337(11) 0.0290(3) Uani d . 1 . . O
H2A 0.7737 0.4646 0.9198 0.043 Uiso calc PR 0.50 . . H
C18 1.1615(4) 0.4491(2) 0.86530(14) 0.0254(4) Uani d . 1 . . C
H18 1.3067 0.4689 0.8393 0.030 Uiso calc R 1 . . H
C19 1.1655(4) 0.3397(2) 0.90344(14) 0.0248(4) Uani d . 1 . . C
H19 1.3155 0.2965 0.9019 0.030 Uiso calc R 1 . . H
C20 0.9741(4) 0.2741(2) 0.94806(13) 0.0232(4) Uani d . 1 . . C
O3 1.0150(3) 0.16460(16) 0.97035(11) 0.0317(4) Uani d . 1 . . O
O4 0.7749(3) 0.33265(16) 0.96155(10) 0.0280(3) Uani d . 1 . . O
H4A 0.7717 0.4010 0.9371 0.042 Uiso calc PR 0.50 . . H
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
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
_geom_angle_publ_flag
C2 N1 C5 109.52(18) y
C4 C5 N1 105.68(19) y
C4 C5 C6 131.7(2) ?
N1 C5 C6 122.64(19) ?
C5 C4 N3 107.44(19) y
C2 N3 C4 109.06(19) y
N3 C2 N1 108.3(2) y
C5 C6 C7 112.10(19) ?
C8 C7 C6 112.28(19) ?
O9 C8 C7 107.31(19) ?
C10 O9 C8 112.82(18) ?
O9 C10 C11 109.25(19) ?
C16 C11 C12 118.2(2) ?
C16 C11 C10 121.6(2) ?
C12 C11 C10 120.2(2) ?
C11 C12 C13 121.7(2) ?
C14 C13 C12 118.5(2) ?
C15 C14 C13 121.1(2) ?
C15 C14 I1 119.75(18) ?
C13 C14 I1 119.16(17) ?
C14 C15 C16 119.2(2) ?
C11 C16 C15 121.2(2) ?
O1 C17 O2 122.3(2) ?
O1 C17 C18 118.30(19) ?
O2 C17 C18 119.34(19) ?
C19 C18 C17 130.6(2) ?
C18 C19 C20 130.8(2) ?
O3 C20 O4 122.8(2) ?
O3 C20 C19 117.89(19) ?
O4 C20 C19 119.33(19) ?
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
I1 C14 . 2.103(2) ?
N1 C2 . 1.323(3) y
N1 C5 . 1.383(3) y
C5 C4 . 1.353(3) y
C5 C6 . 1.490(3) ?
C4 N3 . 1.375(3) y
N3 C2 . 1.316(3) y
C6 C7 . 1.526(3) ?
C7 C8 . 1.510(3) ?
C8 O9 . 1.419(3) ?
O9 C10 . 1.408(3) ?
C10 C11 . 1.512(3) ?
C11 C16 . 1.376(3) ?
C11 C12 . 1.382(3) ?
C12 C13 . 1.385(4) ?
C13 C14 . 1.378(4) ?
C14 C15 . 1.373(3) ?
C15 C16 . 1.386(4) ?
C17 O1 . 1.228(3) ?
C17 O2 . 1.293(3) ?
C17 C18 . 1.492(3) ?
C18 C19 . 1.335(3) ?
C19 C20 . 1.491(3) ?
C20 O3 . 1.233(3) ?
C20 O4 . 1.284(3) ?
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
_geom_hbond_publ_flag
N1 H1 O1 1_545 0.88 1.92 2.778(3) 163.7 y
N3 H3 O3 2_657 0.88 1.95 2.802(3) 163.0 y
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
C2 N1 C5 C4 0.0(3)
C2 N1 C5 C6 179.2(2)
N1 C5 C4 N3 0.0(2)
C6 C5 C4 N3 -179.1(2)
C5 C4 N3 C2 0.0(3)
C4 N3 C2 N1 0.1(3)
C5 N1 C2 N3 -0.1(3)
C4 C5 C6 C7 -1.4(4)
N1 C5 C6 C7 179.6(2)
C5 C6 C7 C8 179.31(19)
C6 C7 C8 O9 179.65(19)
C7 C8 O9 C10 176.4(2)
C8 O9 C10 C11 173.7(2)
O9 C10 C11 C16 15.8(3)
O9 C10 C11 C12 -163.8(2)
C16 C11 C12 C13 -0.2(4)
C10 C11 C12 C13 179.5(3)
C11 C12 C13 C14 -0.4(4)
C12 C13 C14 C15 0.4(4)
C12 C13 C14 I1 -179.3(2)
C13 C14 C15 C16 0.1(4)
I1 C14 C15 C16 179.75(19)
C12 C11 C16 C15 0.6(4)
C10 C11 C16 C15 -179.0(2)
C14 C15 C16 C11 -0.6(4)
O1 C17 C18 C19 -178.6(2)
O2 C17 C18 C19 3.2(4)
C17 C18 C19 C20 2.3(4)
C18 C19 C20 O3 172.2(2)
C18 C19 C20 O4 -7.6(4)
