#------------------------------------------------------------------------------
#$Date: 2025-08-21 23:13:44 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301852 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/02/7060208.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_7060208
loop_
_publ_author_name
'Miura, Youhei'
'Kobayashi, Kotaro'
'Yoshioka, Naoki'
_publ_section_title
;
 V-shaped fluorophores with a 1-methyl-4,5-bis(arylethynyl)imidazole
 skeleton displaying solid-state fluorescence, acid responsiveness, and
 remarkable fluorescence solvatochromism
;
_journal_issue                   2
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              898
_journal_page_last               905
_journal_paper_doi               10.1039/D0NJ05323F
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         'C22 H18 N2 O2'
_chemical_formula_sum            'C22 H18 N2 O2'
_chemical_formula_weight         342.38
_chemical_melting_point          376.0(10)
_chemical_name_systematic
4,5-bis(4-methoxyphenylethynyl)-1-methyl-imidazole
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_update_record
;
2019-08-29 deposited with the CCDC.	2020-12-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.017(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4483(9)
_cell_length_b                   7.9356(7)
_cell_length_c                   22.7149(18)
_cell_measurement_reflns_used    3717
_cell_measurement_temperature    300.(2)
_cell_measurement_theta_max      21.9067
_cell_measurement_theta_min      2.7200
_cell_volume                     1876.2(3)
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      300.(2)
_diffrn_detector_area_resol_mean 7.4074
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multilayered confocal mirror'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2090
_diffrn_reflns_av_unetI/netI     0.0949
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            15694
_diffrn_reflns_theta_full        23.67
_diffrn_reflns_theta_max         23.67
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.46
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle-like
_exptl_crystal_F_000             720
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane/Hexane'
_exptl_crystal_size_max          1.100
_exptl_crystal_size_mid          0.229
_exptl_crystal_size_min          0.092
_refine_diff_density_max         0.592
_refine_diff_density_min         -0.484
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.438
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         2804
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.438
_refine_ls_R_factor_all          0.1390
_refine_ls_R_factor_gt           0.0982
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²+0.1252P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2446
_refine_ls_wR_factor_ref         0.2950
_reflns_number_gt                1688
_reflns_number_total             2804
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0nj05323f2.cif
_cod_data_source_block           MeImOMe2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '375-377' was changed to
'376.0(10)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7060201--7060208.cif.
;
_cod_database_code               7060208
loop_
_space_group_symop_operation_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_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C2 0.3405(4) 1.0384(5) 0.03257(18) 0.0827(11) Uani d . . . 1 . .
C C13 0.4217(4) 1.0418(5) 0.08566(19) 0.0859(12) Uani d . . . 1 . .
C C5 0.2221(4) 0.7679(6) 0.03625(19) 0.0910(12) Uani d . . . 1 . .
C C14 0.4882(4) 1.0511(5) 0.13092(19) 0.0859(12) Uani d . . . 1 . .
C C10 0.1406(4) 0.1962(5) 0.15747(19) 0.0876(12) Uani d . . . 1 . .
C C16 0.5206(4) 1.0166(6) 0.2383(2) 0.0974(13) Uani d . . . 1 . .
H H16 0.4346 0.9867 0.2386 0.117 Uiso calc U . R 1 . .
C C18 0.7250(5) 1.0616(5) 0.2906(2) 0.0960(13) Uani d . . . 1 . .
C C9 0.0807(4) 0.2159(5) 0.10145(19) 0.0870(12) Uani d . . . 1 . .
H H9 0.0267 0.1321 0.0848 0.104 Uiso calc U . R 1 . .
C C15 0.5688(4) 1.0583(5) 0.18547(19) 0.0853(12) Uani d . . . 1 . .
C C6 0.2013(4) 0.6388(6) 0.0615(2) 0.0894(12) Uani d . . . 1 . .
C C3 0.2527(4) 0.9239(5) 0.00942(19) 0.0853(11) Uani d . . . 1 . .
C C12 0.2372(4) 0.4658(6) 0.1514(2) 0.0925(13) Uani d . . . 1 . .
H H12 0.2894 0.5503 0.1688 0.111 Uiso calc U . R 1 . .
C C7 0.1787(4) 0.4886(5) 0.09393(19) 0.0829(11) Uani d . . . 1 . .
C C8 0.1014(4) 0.3611(5) 0.07026(18) 0.0901(12) Uani d . . . 1 . .
H H8 0.062 0.373 0.0322 0.108 Uiso calc U . R 1 . .
C C17 0.5978(5) 1.0186(6) 0.2899(2) 0.1061(14) Uani d . . . 1 . .
H H17 0.5637 0.9906 0.3251 0.127 Uiso calc U . R 1 . .
C C11 0.2186(4) 0.3229(6) 0.1818(2) 0.0948(13) Uani d . . . 1 . .
H H11 0.2591 0.3097 0.2196 0.114 Uiso calc U . R 1 . .
C C20 0.6961(5) 1.1058(6) 0.1868(2) 0.1035(14) Uani d . . . 1 . .
H H20 0.7299 1.1378 0.1519 0.124 Uiso calc U . R 1 . .
C C19 0.7735(5) 1.1064(6) 0.2386(2) 0.1076(15) Uani d . . . 1 . .
H H19 0.8593 1.1374 0.2385 0.129 Uiso calc U . R 1 . .
C C4 0.4146(5) 1.3204(5) -0.0032(2) 0.1169(16) Uani d . . . 1 . .
H H4A 0.4886 1.3058 -0.0249 0.175 Uiso calc U . R 1 . .
H H4B 0.4418 1.3427 0.0375 0.175 Uiso calc U . R 1 . .
H H4C 0.3644 1.4134 -0.0194 0.175 Uiso calc U . R 1 . .
C C1 0.2486(5) 1.1256(6) -0.0514(2) 0.1093(15) Uani d . . . 1 . .
H H1 0.2279 1.193 -0.0844 0.131 Uiso calc U . R 1 . .
C C22 0.9367(6) 1.0618(8) 0.3402(3) 0.145(2) Uani d . . . 1 . .
H H22A 0.9619 0.9774 0.3132 0.217 Uiso calc U . R 1 . .
H H22B 0.9793 1.0416 0.3787 0.217 Uiso calc U . R 1 . .
H H22C 0.9602 1.1712 0.3266 0.217 Uiso calc U . R 1 . .
C C21 0.0533(5) -0.0798(6) 0.1681(2) 0.1154(16) Uani d . . . 1 . .
H H21A -0.0324 -0.0432 0.1556 0.173 Uiso calc U . R 1 . .
H H21B 0.0502 -0.1668 0.1972 0.173 Uiso calc U . R 1 . .
H H21C 0.0932 -0.1228 0.1346 0.173 Uiso calc U . R 1 . .
N N1 0.3373(3) 1.1680(4) -0.00745(15) 0.0929(11) Uani d . . . 1 . .
N N2 0.1943(4) 0.9802(5) -0.04311(17) 0.1078(12) Uani d . . . 1 . .
O O1 0.1261(3) 0.0592(4) 0.19282(14) 0.1119(11) Uani d . . . 1 . .
O O2 0.7960(3) 1.0547(4) 0.34333(15) 0.1197(12) Uani d . . . 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'
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
C3 C2 N1 . . 105.5(4) ?
C3 C2 C13 . . 132.5(4) ?
N1 C2 C13 . . 122.0(3) ?
C14 C13 C2 . . 177.2(4) ?
C6 C5 C3 . . 176.2(4) ?
C13 C14 C15 . . 178.7(4) ?
O1 C10 C9 . . 124.6(3) ?
O1 C10 C11 . . 115.9(4) ?
C9 C10 C11 . . 119.5(4) ?
C17 C16 C15 . . 120.7(4) ?
C17 C16 H16 . . 119.6 ?
C15 C16 H16 . . 119.6 ?
O2 C18 C17 . . 117.0(5) ?
O2 C18 C19 . . 123.9(5) ?
C17 C18 C19 . . 119.0(4) ?
C10 C9 C8 . . 119.3(3) ?
C10 C9 H9 . . 120.3 ?
C8 C9 H9 . . 120.3 ?
C20 C15 C16 . . 118.1(4) ?
C20 C15 C14 . . 121.4(4) ?
C16 C15 C14 . . 120.6(4) ?
C5 C6 C7 . . 177.5(4) ?
C2 C3 N2 . . 110.7(4) ?
C2 C3 C5 . . 125.5(4) ?
N2 C3 C5 . . 123.8(3) ?
C11 C12 C7 . . 120.9(4) ?
C11 C12 H12 . . 119.6 ?
C7 C12 H12 . . 119.6 ?
C8 C7 C12 . . 117.5(4) ?
C8 C7 C6 . . 122.0(4) ?
C12 C7 C6 . . 120.5(3) ?
C7 C8 C9 . . 121.8(4) ?
C7 C8 H8 . . 119.1 ?
C9 C8 H8 . . 119.1 ?
C16 C17 C18 . . 120.8(4) ?
C16 C17 H17 . . 119.6 ?
C18 C17 H17 . . 119.6 ?
C12 C11 C10 . . 120.9(4) ?
C12 C11 H11 . . 119.5 ?
C10 C11 H11 . . 119.5 ?
C19 C20 C15 . . 121.1(4) ?
C19 C20 H20 . . 119.5 ?
C15 C20 H20 . . 119.5 ?
C20 C19 C18 . . 120.3(4) ?
C20 C19 H19 . . 119.8 ?
C18 C19 H19 . . 119.8 ?
N1 C4 H4A . . 109.5 ?
N1 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
N1 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
N2 C1 N1 . . 113.2(4) ?
N2 C1 H1 . . 123.4 ?
N1 C1 H1 . . 123.4 ?
O2 C22 H22A . . 109.5 ?
O2 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
O2 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
O1 C21 H21A . . 109.5 ?
O1 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
O1 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
C1 N1 C2 . . 106.2(3) ?
C1 N1 C4 . . 126.9(4) ?
C2 N1 C4 . . 126.8(3) ?
C1 N2 C3 . . 104.4(3) ?
C10 O1 C21 . . 117.8(3) ?
C18 O2 C22 . . 115.1(4) ?
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
C2 C3 . 1.363(5) ?
C2 N1 . 1.371(5) ?
C2 C13 . 1.413(5) ?
C13 C14 . 1.192(5) ?
C5 C6 . 1.203(6) ?
C5 C3 . 1.429(6) ?
C14 C15 . 1.437(6) ?
C10 O1 . 1.368(5) ?
C10 C9 . 1.377(5) ?
C10 C11 . 1.379(5) ?
C16 C17 . 1.363(6) ?
C16 C15 . 1.381(6) ?
C16 H16 . 0.93 ?
C18 O2 . 1.354(5) ?
C18 C17 . 1.372(7) ?
C18 C19 . 1.372(7) ?
C9 C8 . 1.380(5) ?
C9 H9 . 0.93 ?
C15 C20 . 1.380(6) ?
C6 C7 . 1.431(6) ?
C3 N2 . 1.367(5) ?
C12 C11 . 1.350(6) ?
C12 C7 . 1.404(5) ?
C12 H12 . 0.93 ?
C7 C8 . 1.375(5) ?
C8 H8 . 0.93 ?
C17 H17 . 0.93 ?
C11 H11 . 0.93 ?
C20 C19 . 1.367(6) ?
C20 H20 . 0.93 ?
C19 H19 . 0.93 ?
C4 N1 . 1.452(5) ?
C4 H4A . 0.96 ?
C4 H4B . 0.96 ?
C4 H4C . 0.96 ?
C1 N2 . 1.307(5) ?
C1 N1 . 1.344(5) ?
C1 H1 . 0.93 ?
C22 O2 . 1.479(7) ?
C22 H22A . 0.96 ?
C22 H22B . 0.96 ?
C22 H22C . 0.96 ?
C21 O1 . 1.427(5) ?
C21 H21A . 0.96 ?
C21 H21B . 0.96 ?
C21 H21C . 0.96 ?
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 C10 C9 C8 . . . . 179.1(4) ?
C11 C10 C9 C8 . . . . 1.0(6) ?
C17 C16 C15 C20 . . . . -1.5(6) ?
C17 C16 C15 C14 . . . . 178.1(4) ?
N1 C2 C3 N2 . . . . -0.9(5) ?
C13 C2 C3 N2 . . . . 178.0(4) ?
N1 C2 C3 C5 . . . . -179.4(4) ?
C13 C2 C3 C5 . . . . -0.5(8) ?
C11 C12 C7 C8 . . . . 0.6(6) ?
C11 C12 C7 C6 . . . . -178.5(4) ?
C12 C7 C8 C9 . . . . 0.4(6) ?
C6 C7 C8 C9 . . . . 179.5(4) ?
C10 C9 C8 C7 . . . . -1.2(6) ?
C15 C16 C17 C18 . . . . -0.3(7) ?
O2 C18 C17 C16 . . . . -177.7(4) ?
C19 C18 C17 C16 . . . . 1.5(7) ?
C7 C12 C11 C10 . . . . -0.8(7) ?
O1 C10 C11 C12 . . . . -178.3(4) ?
C9 C10 C11 C12 . . . . 0.0(6) ?
C16 C15 C20 C19 . . . . 2.0(7) ?
C14 C15 C20 C19 . . . . -177.6(4) ?
C15 C20 C19 C18 . . . . -0.8(7) ?
O2 C18 C19 C20 . . . . 178.2(4) ?
C17 C18 C19 C20 . . . . -1.0(7) ?
N2 C1 N1 C2 . . . . 0.1(6) ?
N2 C1 N1 C4 . . . . 180.0(5) ?
C3 C2 N1 C1 . . . . 0.5(5) ?
C13 C2 N1 C1 . . . . -178.5(4) ?
C3 C2 N1 C4 . . . . -179.4(4) ?
C13 C2 N1 C4 . . . . 1.5(6) ?
N1 C1 N2 C3 . . . . -0.6(6) ?
C2 C3 N2 C1 . . . . 0.9(6) ?
C5 C3 N2 C1 . . . . 179.5(4) ?
C9 C10 O1 C21 . . . . 6.1(6) ?
C11 C10 O1 C21 . . . . -175.8(4) ?
C17 C18 O2 C22 . . . . 166.1(4) ?
C19 C18 O2 C22 . . . . -13.1(6) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168350030
