#------------------------------------------------------------------------------
#$Date: 2021-01-04 00:55:08 +0200 (Mon, 04 Jan 2021) $
#$Revision: 260400 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/99/1559918.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_1559918
loop_
_publ_author_name
'Aouina, Aroua'
'Oloyede, Hammed Olawale'
'Akong, Raymond Akong'
'Abdelhak, Jawher'
'Görls, Helmar'
'Plass, Winfried'
'Eseola, Abiodun Omokehinde'
_publ_section_title
;
 Exploring Broad Molecular Derivatization as Tool in Selective Fluorescent
 Detection of Mercury(II) by a Series of Large Stokes Shift
 1,4-Bis(5-phenyl-1H-imidazol-4-yl)benzenes
;
_journal_issue                   52
_journal_name_full
'Industrial & Engineering Chemistry Research'
_journal_page_first              22398
_journal_page_last               22412
_journal_paper_doi               10.1021/acs.iecr.0c05087
_journal_volume                  59
_journal_year                    2020
_chemical_formula_moiety         'C40 H34 N4 O4, 2(C H4 O)'
_chemical_formula_sum            'C42 H42 N4 O6'
_chemical_formula_weight         698.79
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 96.354(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   29.7268(14)
_cell_length_b                   8.2380(5)
_cell_length_c                   14.9613(8)
_cell_measurement_reflns_used    9886
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      27.484
_cell_measurement_theta_min      2.567
_cell_volume                     3641.4(3)
_computing_cell_refinement       DENZO
_computing_data_collection       COLLECT
_computing_data_reduction        DENZO
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi + omega - scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9886
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.567
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6262
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1480
_exptl_crystal_size_max          0.112
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.098
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.201
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4123
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.201
_refine_ls_R_factor_all          0.1100
_refine_ls_R_factor_gt           0.0816
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0273P)²+9.9172P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1521
_refine_ls_wR_factor_ref         0.1650
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3199
_reflns_number_total             4123
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ie0c05087_si_002.cif
_cod_data_source_block           FO6710_L5.MeOH
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1559918
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.990
_shelx_estimated_absorpt_t_max   0.992
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.38271(6) 0.1580(3) 0.64097(14) 0.0359(5) Uani 1 1 d . . . . .
O2 O 0.47500(7) 0.6149(3) 0.63462(17) 0.0487(6) Uani 1 1 d . . . . .
N1 N 0.37559(7) 0.5248(3) 0.72549(14) 0.0257(5) Uani 1 1 d . . . . .
N2 N 0.36147(7) 0.5401(3) 0.57763(14) 0.0217(5) Uani 1 1 d . . . . .
C1 C 0.39006(8) 0.4850(3) 0.64756(17) 0.0237(5) Uani 1 1 d . . . . .
C2 C 0.32638(8) 0.6203(3) 0.61177(16) 0.0209(5) Uani 1 1 d . . . . .
C3 C 0.33567(8) 0.6088(3) 0.70366(16) 0.0230(5) Uani 1 1 d . . . . .
C4 C 0.30964(9) 0.6731(3) 0.77460(17) 0.0270(6) Uani 1 1 d . . . . .
C5 C 0.26271(10) 0.6552(4) 0.76859(19) 0.0328(7) Uani 1 1 d . . . . .
H5A H 0.247527 0.593030 0.720978 0.039 Uiso 1 1 calc R U . . .
C6 C 0.23809(12) 0.7267(4) 0.8309(2) 0.0458(9) Uani 1 1 d . . . . .
H6A H 0.206055 0.716989 0.825067 0.055 Uiso 1 1 calc R U . . .
C7 C 0.26005(16) 0.8115(4) 0.9010(2) 0.0575(11) Uani 1 1 d . . . . .
H7A H 0.242981 0.861448 0.943533 0.069 Uiso 1 1 calc R U . . .
C8 C 0.30641(17) 0.8261(4) 0.9113(2) 0.0575(11) Uani 1 1 d . . . . .
H8A H 0.321198 0.882712 0.961553 0.069 Uiso 1 1 calc R U . . .
C9 C 0.33188(13) 0.7569(4) 0.84709(19) 0.0421(8) Uani 1 1 d . . . . .
H9A H 0.363903 0.767325 0.853256 0.051 Uiso 1 1 calc R U . . .
C10 C 0.28836(8) 0.6898(3) 0.55355(16) 0.0198(5) Uani 1 1 d . . . . .
C11 C 0.26303(8) 0.8182(3) 0.58297(16) 0.0205(5) Uani 1 1 d . . . . .
H11A H 0.271911 0.865982 0.639996 0.025 Uiso 1 1 calc R U . . .
C12 C 0.22530(8) 0.8771(3) 0.53069(16) 0.0206(5) Uani 1 1 d . . . . .
H12A H 0.208511 0.964022 0.552375 0.025 Uiso 1 1 calc R U . . .
C13 C 0.42997(9) 0.3828(4) 0.63536(18) 0.0288(6) Uani 1 1 d . . . . .
C14 C 0.42485(9) 0.2145(4) 0.6308(2) 0.0327(7) Uani 1 1 d . . . . .
C15 C 0.46091(11) 0.1130(5) 0.6173(3) 0.0502(9) Uani 1 1 d . . . . .
H15A H 0.457197 -0.001423 0.614088 0.060 Uiso 1 1 calc R U . . .
C16 C 0.50226(12) 0.1841(5) 0.6086(3) 0.0638(12) Uani 1 1 d . . . . .
H16A H 0.527128 0.116483 0.598841 0.077 Uiso 1 1 calc R U . . .
C17 C 0.50877(11) 0.3494(5) 0.6137(3) 0.0586(11) Uani 1 1 d . . . . .
H17A H 0.537681 0.394681 0.607791 0.070 Uiso 1 1 calc R U . . .
C18 C 0.47233(9) 0.4496(4) 0.6277(2) 0.0398(8) Uani 1 1 d . . . . .
C19 C 0.37757(11) -0.0130(4) 0.6493(3) 0.0483(9) Uani 1 1 d . . . . .
H19A H 0.346776 -0.037455 0.662856 0.072 Uiso 1 1 calc R U . . .
H19B H 0.399412 -0.053499 0.698083 0.072 Uiso 1 1 calc R U . . .
H19C H 0.382970 -0.065737 0.592772 0.072 Uiso 1 1 calc R U . . .
C20 C 0.51921(11) 0.6857(5) 0.6356(3) 0.0647(12) Uani 1 1 d . . . . .
H20A H 0.517608 0.801847 0.649020 0.097 Uiso 1 1 calc R U . . .
H20B H 0.530086 0.670999 0.576641 0.097 Uiso 1 1 calc R U . . .
H20C H 0.540098 0.632507 0.681806 0.097 Uiso 1 1 calc R U . . .
O1M O 0.38014(6) 0.3917(3) 0.89801(13) 0.0322(5) Uani 1 1 d . . . . .
C1M C 0.36955(12) 0.2263(4) 0.8794(2) 0.0431(8) Uani 1 1 d . . . . .
H1M1 H 0.376126 0.162116 0.934405 0.065 Uiso 1 1 calc R U . . .
H1M2 H 0.387831 0.186190 0.833385 0.065 Uiso 1 1 calc R U . . .
H1M3 H 0.337361 0.216352 0.857400 0.065 Uiso 1 1 calc R U . . .
H1N2 H 0.3671(10) 0.539(4) 0.520(2) 0.040(9) Uiso 1 1 d . . . . .
H1OM H 0.3793(12) 0.444(5) 0.844(3) 0.060(11) 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'
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
C14 O1 C19 117.2(2) . . ?
C18 O2 C20 116.8(3) . . ?
C1 N1 C3 105.6(2) . . ?
C1 N2 C2 108.1(2) . . ?
C1 N2 H1N2 125(2) . . ?
C2 N2 H1N2 126(2) . . ?
N1 C1 N2 111.1(2) . . ?
N1 C1 C13 126.2(2) . . ?
N2 C1 C13 122.6(2) . . ?
C3 C2 N2 105.1(2) . . ?
C3 C2 C10 132.6(2) . . ?
N2 C2 C10 122.2(2) . . ?
C2 C3 N1 110.0(2) . . ?
C2 C3 C4 129.0(2) . . ?
N1 C3 C4 120.9(2) . . ?
C9 C4 C5 119.2(3) . . ?
C9 C4 C3 119.8(3) . . ?
C5 C4 C3 121.0(2) . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 H5A 119.6 . . ?
C4 C5 H5A 119.6 . . ?
C7 C6 C5 119.6(3) . . ?
C7 C6 H6A 120.2 . . ?
C5 C6 H6A 120.2 . . ?
C6 C7 C8 121.3(3) . . ?
C6 C7 H7A 119.4 . . ?
C8 C7 H7A 119.4 . . ?
C7 C8 C9 119.8(3) . . ?
C7 C8 H8A 120.1 . . ?
C9 C8 H8A 120.1 . . ?
C4 C9 C8 119.2(3) . . ?
C4 C9 H9A 120.4 . . ?
C8 C9 H9A 120.4 . . ?
C12 C10 C11 118.1(2) 7_566 . ?
C12 C10 C2 120.8(2) 7_566 . ?
C11 C10 C2 121.0(2) . . ?
C12 C11 C10 121.3(2) . . ?
C12 C11 H11A 119.4 . . ?
C10 C11 H11A 119.4 . . ?
C11 C12 C10 120.6(2) . 7_566 ?
C11 C12 H12A 119.7 . . ?
C10 C12 H12A 119.7 7_566 . ?
C18 C13 C14 118.9(3) . . ?
C18 C13 C1 122.0(3) . . ?
C14 C13 C1 119.1(2) . . ?
O1 C14 C15 123.0(3) . . ?
O1 C14 C13 115.5(2) . . ?
C15 C14 C13 121.5(3) . . ?
C16 C15 C14 117.8(3) . . ?
C16 C15 H15A 121.1 . . ?
C14 C15 H15A 121.1 . . ?
C17 C16 C15 122.4(3) . . ?
C17 C16 H16A 118.8 . . ?
C15 C16 H16A 118.8 . . ?
C16 C17 C18 119.1(3) . . ?
C16 C17 H17A 120.4 . . ?
C18 C17 H17A 120.4 . . ?
O2 C18 C13 115.7(3) . . ?
O2 C18 C17 124.1(3) . . ?
C13 C18 C17 120.2(3) . . ?
O1 C19 H19A 109.5 . . ?
O1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C1M O1M H1OM 107(2) . . ?
O1M C1M H1M1 109.5 . . ?
O1M C1M H1M2 109.5 . . ?
H1M1 C1M H1M2 109.5 . . ?
O1M C1M H1M3 109.5 . . ?
H1M1 C1M H1M3 109.5 . . ?
H1M2 C1M H1M3 109.5 . . ?
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
O1 C14 1.360(3) . ?
O1 C19 1.424(4) . ?
O2 C18 1.368(4) . ?
O2 C20 1.436(4) . ?
N1 C1 1.328(3) . ?
N1 C3 1.382(3) . ?
N2 C1 1.352(3) . ?
N2 C2 1.379(3) . ?
N2 H1N2 0.89(3) . ?
C1 C13 1.482(4) . ?
C2 C3 1.375(3) . ?
C2 C10 1.465(3) . ?
C3 C4 1.479(4) . ?
C4 C9 1.390(4) . ?
C4 C5 1.396(4) . ?
C5 C6 1.379(4) . ?
C5 H5A 0.9500 . ?
C6 C7 1.365(6) . ?
C6 H6A 0.9500 . ?
C7 C8 1.375(6) . ?
C7 H7A 0.9500 . ?
C8 C9 1.408(5) . ?
C8 H8A 0.9500 . ?
C9 H9A 0.9500 . ?
C10 C12 1.394(3) 7_566 ?
C10 C11 1.398(3) . ?
C11 C12 1.382(3) . ?
C11 H11A 0.9500 . ?
C12 H12A 0.9500 . ?
C13 C18 1.390(4) . ?
C13 C14 1.396(4) . ?
C14 C15 1.392(4) . ?
C15 C16 1.380(5) . ?
C15 H15A 0.9500 . ?
C16 C17 1.376(6) . ?
C16 H16A 0.9500 . ?
C17 C18 1.396(4) . ?
C17 H17A 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
O1M C1M 1.419(4) . ?
O1M H1OM 0.91(4) . ?
C1M H1M1 0.9800 . ?
C1M H1M2 0.9800 . ?
C1M H1M3 0.9800 . ?
