#------------------------------------------------------------------------------
#$Date: 2025-08-21 23:13:44 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301852 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/02/7060207.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_7060207
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 H16 N2 O2'
_chemical_formula_sum            'C22 H16 N2 O2'
_chemical_formula_weight         340.37
_chemical_melting_point          420.0(10)
_chemical_name_common            NMeOMeCHO
_chemical_name_systematic
4-(4-methoxyphenylethynyl)-5-(4-formylphenylethynyl)-1-methylimidazole
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -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                97.151(2)
_cell_angle_beta                 114.1460(10)
_cell_angle_gamma                102.008(2)
_cell_formula_units_Z            2
_cell_length_a                   9.3320(4)
_cell_length_b                   9.8300(4)
_cell_length_c                   11.3679(5)
_cell_measurement_reflns_used    5537
_cell_measurement_temperature    273.(2)
_cell_measurement_theta_max      25.0492
_cell_measurement_theta_min      2.4064
_cell_volume                     904.73(7)
_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      273.(2)
_diffrn_detector_area_resol_mean 7.4074
_diffrn_measured_fraction_theta_full 0.942
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multilayered confocal mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8425
_diffrn_reflns_theta_full        25.06
_diffrn_reflns_theta_max         25.06
_diffrn_reflns_theta_min         2.41
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_crystal_colour            'fluorescent light yellow'
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             356
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane/Hexane'
_exptl_crystal_size_max          0.953
_exptl_crystal_size_mid          0.826
_exptl_crystal_size_min          0.197
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.142
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.396
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3031
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.396
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0482
_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] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1659
_refine_ls_wR_factor_ref         0.1766
_reflns_number_gt                2620
_reflns_number_total             3031
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0nj05323f2.cif
_cod_data_source_block           X190705KK_1e
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '419-421' was changed to
'420.0(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               7060207
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
O O1 -0.13902(15) 0.13005(15) 0.02523(11) 0.0800(4) Uani d . . . 1 . .
N N1 0.69459(15) 0.57444(13) 0.98267(12) 0.0534(4) Uani d . . . 1 . .
N N2 0.48397(16) 0.65786(14) 0.88278(14) 0.0635(4) Uani d . . . 1 . .
C C13 0.65954(17) 0.38668(15) 0.79833(14) 0.0533(4) Uani d . . . 1 . .
O O2 0.7147(2) -0.09897(16) 0.25714(15) 0.1028(5) Uani d . . . 1 . .
C C4 0.61180(17) 0.49499(14) 0.85472(14) 0.0474(4) Uani d . . . 1 . .
C C15 0.71204(17) 0.19858(15) 0.64797(15) 0.0515(4) Uani d . . . 1 . .
C C3 0.48111(17) 0.54764(15) 0.79380(15) 0.0509(4) Uani d . . . 1 . .
C C5 0.36142(18) 0.49563(16) 0.65979(16) 0.0565(4) Uani d . . . 1 . .
C C6 0.26799(18) 0.44058(16) 0.54566(16) 0.0580(4) Uani d . . . 1 . .
C C16 0.80819(18) 0.10853(15) 0.69315(14) 0.0547(4) Uani d . . . 1 . .
H H16 0.8597 0.1113 0.7832 0.066 Uiso calc U . R 1 . .
C C9 -0.11258(18) 0.24977(18) 0.23642(16) 0.0608(4) Uani d . . . 1 . .
H H9 -0.2255 0.2248 0.2068 0.073 Uiso calc U . R 1 . .
C C14 0.68729(18) 0.29860(16) 0.73612(15) 0.0570(4) Uani d . . . 1 . .
C C2 0.6132(2) 0.66921(17) 0.99294(17) 0.0629(5) Uani d . . . 1 . .
H H2 0.6455 0.7364 1.0708 0.076 Uiso calc U . R 1 . .
C C7 0.15924(18) 0.36763(15) 0.41112(15) 0.0537(4) Uani d . . . 1 . .
C C17 0.82672(19) 0.01448(16) 0.60297(15) 0.0569(4) Uani d . . . 1 . .
H H17 0.8915 -0.0459 0.6329 0.068 Uiso calc U . R 1 . .
C C8 -0.00891(18) 0.32814(17) 0.36408(16) 0.0605(5) Uani d . . . 1 . .
H H8 -0.0533 0.3551 0.42 0.073 Uiso calc U . R 1 . .
C C10 -0.04806(18) 0.20855(17) 0.15272(15) 0.0568(4) Uani d . . . 1 . .
C C18 0.75023(19) 0.00914(15) 0.46895(15) 0.0547(4) Uani d . . . 1 . .
C C19 0.6547(2) 0.10069(18) 0.42497(16) 0.0643(5) Uani d . . . 1 . .
H H19 0.6034 0.0983 0.335 0.077 Uiso calc U . R 1 . .
C C20 0.6361(2) 0.19371(18) 0.51329(16) 0.0638(5) Uani d . . . 1 . .
H H20 0.5719 0.2545 0.4832 0.077 Uiso calc U . R 1 . .
C C12 0.22202(19) 0.32782(19) 0.32438(16) 0.0636(5) Uani d . . . 1 . .
H H12 0.3348 0.3552 0.3532 0.076 Uiso calc U . R 1 . .
C C11 0.12052(19) 0.2488(2) 0.19717(16) 0.0646(5) Uani d . . . 1 . .
H H11 0.1646 0.2224 0.1409 0.077 Uiso calc U . R 1 . .
C C1 0.8430(2) 0.5606(2) 1.08671(18) 0.0787(6) Uani d . . . 1 . .
H H1A 0.9328 0.5894 1.0657 0.118 Uiso calc U . R 1 . .
H H1B 0.8276 0.4627 1.0935 0.118 Uiso calc U . R 1 . .
H H1C 0.8666 0.6204 1.1696 0.118 Uiso calc U . R 1 . .
C C22 0.7713(3) -0.09162(19) 0.3747(2) 0.0744(5) Uani d . . . 1 . .
H H22 0.8323 -0.1537 0.4078 0.089 Uiso calc U . R 1 . .
C C21 -0.3114(2) 0.0764(2) -0.0207(2) 0.0893(6) Uani d . . . 1 . .
H H21A -0.3325 0.0231 0.0387 0.134 Uiso calc U . R 1 . .
H H21B -0.3597 0.015 -0.1078 0.134 Uiso calc U . R 1 . .
H H21C -0.3582 0.1549 -0.0238 0.134 Uiso calc U . R 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
C10 O1 C21 . . 117.50(15) ?
C2 N1 C4 . . 106.45(13) ?
C2 N1 C1 . . 126.68(14) ?
C4 N1 C1 . . 126.86(13) ?
C2 N2 C3 . . 104.56(12) ?
C14 C13 C4 . . 171.75(15) ?
N1 C4 C3 . . 105.79(12) ?
N1 C4 C13 . . 125.66(12) ?
C3 C4 C13 . . 128.47(13) ?
C20 C15 C16 . . 119.82(13) ?
C20 C15 C14 . . 117.97(13) ?
C16 C15 C14 . . 122.22(14) ?
C4 C3 N2 . . 109.76(13) ?
C4 C3 C5 . . 125.08(13) ?
N2 C3 C5 . . 125.15(13) ?
C6 C5 C3 . . 173.11(15) ?
C5 C6 C7 . . 176.70(15) ?
C17 C16 C15 . . 119.31(14) ?
C17 C16 H16 . . 120.3 ?
C15 C16 H16 . . 120.3 ?
C10 C9 C8 . . 119.67(14) ?
C10 C9 H9 . . 120.2 ?
C8 C9 H9 . . 120.2 ?
C13 C14 C15 . . 173.44(16) ?
N2 C2 N1 . . 113.44(13) ?
N2 C2 H2 . . 123.3 ?
N1 C2 H2 . . 123.3 ?
C8 C7 C12 . . 117.86(14) ?
C8 C7 C6 . . 122.08(15) ?
C12 C7 C6 . . 119.98(13) ?
C16 C17 C18 . . 120.80(14) ?
C16 C17 H17 . . 119.6 ?
C18 C17 H17 . . 119.6 ?
C9 C8 C7 . . 121.67(15) ?
C9 C8 H8 . . 119.2 ?
C7 C8 H8 . . 119.2 ?
O1 C10 C9 . . 124.55(14) ?
O1 C10 C11 . . 115.76(15) ?
C9 C10 C11 . . 119.68(14) ?
C17 C18 C19 . . 119.30(14) ?
C17 C18 C22 . . 119.98(16) ?
C19 C18 C22 . . 120.71(16) ?
C20 C19 C18 . . 120.20(15) ?
C20 C19 H19 . . 119.9 ?
C18 C19 H19 . . 119.9 ?
C19 C20 C15 . . 120.57(14) ?
C19 C20 H20 . . 119.7 ?
C15 C20 H20 . . 119.7 ?
C11 C12 C7 . . 121.21(14) ?
C11 C12 H12 . . 119.4 ?
C7 C12 H12 . . 119.4 ?
C12 C11 C10 . . 119.88(15) ?
C12 C11 H11 . . 120.1 ?
C10 C11 H11 . . 120.1 ?
N1 C1 H1A . . 109.5 ?
N1 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
N1 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
O2 C22 C18 . . 124.2(2) ?
O2 C22 H22 . . 117.9 ?
C18 C22 H22 . . 117.9 ?
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 ?
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
O1 C10 . 1.3635(19) ?
O1 C21 . 1.425(2) ?
N1 C2 . 1.341(2) ?
N1 C4 . 1.3671(18) ?
N1 C1 . 1.454(2) ?
N2 C2 . 1.307(2) ?
N2 C3 . 1.3750(18) ?
C13 C14 . 1.1864(19) ?
C13 C4 . 1.4157(18) ?
O2 C22 . 1.205(2) ?
C4 C3 . 1.377(2) ?
C15 C20 . 1.389(2) ?
C15 C16 . 1.385(2) ?
C15 C14 . 1.4363(19) ?
C3 C5 . 1.416(2) ?
C5 C6 . 1.200(2) ?
C6 C7 . 1.427(2) ?
C16 C17 . 1.382(2) ?
C16 H16 . 0.93 ?
C9 C10 . 1.381(2) ?
C9 C8 . 1.378(2) ?
C9 H9 . 0.93 ?
C2 H2 . 0.93 ?
C7 C8 . 1.381(2) ?
C7 C12 . 1.393(2) ?
C17 C18 . 1.381(2) ?
C17 H17 . 0.93 ?
C8 H8 . 0.93 ?
C10 C11 . 1.388(2) ?
C18 C19 . 1.391(2) ?
C18 C22 . 1.469(2) ?
C19 C20 . 1.362(2) ?
C19 H19 . 0.93 ?
C20 H20 . 0.93 ?
C12 C11 . 1.373(2) ?
C12 H12 . 0.93 ?
C11 H11 . 0.93 ?
C1 H1A . 0.96 ?
C1 H1B . 0.96 ?
C1 H1C . 0.96 ?
C22 H22 . 0.93 ?
C21 H21A . 0.96 ?
C21 H21B . 0.96 ?
C21 H21C . 0.96 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168350029
