#------------------------------------------------------------------------------
#$Date: 2025-08-21 23:13:44 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301852 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/02/7060204.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_7060204
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         'C21 H14 N2 O'
_chemical_formula_sum            'C21 H14 N2 O'
_chemical_formula_weight         310.34
_chemical_melting_point          435.5(5)
_chemical_name_systematic
4-phenyl-5-(4-formylphenylethynyl)-1-methylimidazole
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 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                 119.2370(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8306(3)
_cell_length_b                   16.0766(5)
_cell_length_c                   11.0441(3)
_cell_measurement_reflns_used    7866
_cell_measurement_temperature    273.(2)
_cell_measurement_theta_max      25.0289
_cell_measurement_theta_min      2.4640
_cell_volume                     1678.01(9)
_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 0.985
_diffrn_measured_fraction_theta_max 0.985
_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  0.0446
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15906
_diffrn_reflns_theta_full        25.07
_diffrn_reflns_theta_max         25.07
_diffrn_reflns_theta_min         2.46
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_crystal_colour            'clear pale yellow'
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             648
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane/Hexane'
_exptl_crystal_size_max          0.486
_exptl_crystal_size_mid          0.341
_exptl_crystal_size_min          0.124
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.206
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.779
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2928
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.779
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0433
_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+0.6550P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1214
_refine_ls_wR_factor_ref         0.1382
_reflns_number_gt                2420
_reflns_number_total             2928
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0nj05323f2.cif
_cod_data_source_block           X190705KK_NMePhCHO
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '435-436' was changed to
'435.5(5)' -- 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_original_cell_volume        1678.01(8)
_cod_database_code               7060204
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
N N1 0.65585(14) 0.50323(8) 0.82147(13) 0.0525(3) Uani d . . . 1 . .
N N2 0.48335(14) 0.55962(9) 0.84776(13) 0.0553(4) Uani d . . . 1 . .
C C4 0.58662(15) 0.55756(9) 0.71272(14) 0.0446(3) Uani d . . . 1 . .
C C13 0.62173(15) 0.57150(10) 0.60754(15) 0.0479(4) Uani d . . . 1 . .
C C5 0.37707(16) 0.64879(10) 0.63975(16) 0.0521(4) Uani d . . . 1 . .
C C3 0.47964(15) 0.59138(9) 0.73070(14) 0.0467(4) Uani d . . . 1 . .
C C14 0.64734(15) 0.58568(10) 0.51543(15) 0.0508(4) Uani d . . . 1 . .
C C15 0.68308(15) 0.60307(10) 0.40992(14) 0.0482(4) Uani d . . . 1 . .
C C7 0.19372(15) 0.75372(10) 0.45873(15) 0.0498(4) Uani d . . . 1 . .
C C6 0.29205(16) 0.69582(10) 0.55697(16) 0.0539(4) Uani d . . . 1 . .
C C8 0.06121(16) 0.76607(11) 0.44717(17) 0.0564(4) Uani d . . . 1 . .
H H00B 0.0346 0.7355 0.5022 0.068 Uiso calc U . R 1 . .
C C16 0.79224(18) 0.55937(10) 0.40566(17) 0.0569(4) Uani d . . . 1 . .
H H00C 0.8396 0.5176 0.4701 0.068 Uiso calc U . R 1 . .
C C2 0.58958(18) 0.50739(11) 0.89769(16) 0.0575(4) Uani d . . . 1 . .
H H00D 0.6166 0.4763 0.9777 0.069 Uiso calc U . R 1 . .
C C20 0.61254(18) 0.66437(11) 0.31140(17) 0.0624(4) Uani d . . . 1 . .
H H00E 0.5388 0.6937 0.312 0.075 Uiso calc U . R 1 . .
C C17 0.8298(2) 0.57780(12) 0.30699(19) 0.0646(5) Uani d . . . 1 . .
H H00F 0.9031 0.5486 0.3055 0.077 Uiso calc U . R 1 . .
C C11 0.1393(2) 0.85726(12) 0.28403(19) 0.0696(5) Uani d . . . 1 . .
H H00G 0.1652 0.8881 0.2288 0.083 Uiso calc U . R 1 . .
C C10 0.00856(19) 0.86902(12) 0.27304(17) 0.0647(5) Uani d . . . 1 . .
H H00H -0.0536 0.9078 0.2106 0.078 Uiso calc U . R 1 . .
C C9 -0.03041(17) 0.82337(11) 0.35445(17) 0.0611(4) Uani d . . . 1 . .
H H00I -0.1191 0.8313 0.3467 0.073 Uiso calc U . R 1 . .
C C12 0.23164(18) 0.80030(11) 0.37611(18) 0.0631(5) Uani d . . . 1 . .
H H00J 0.3201 0.7928 0.3833 0.076 Uiso calc U . R 1 . .
C C18 0.7604(2) 0.63913(12) 0.20992(18) 0.0656(5) Uani d . . . 1 . .
O O1 0.8938(3) 0.62344(15) 0.0941(2) 0.1449(9) Uani d . . . 1 . .
C C1 0.7774(2) 0.45231(14) 0.8481(2) 0.0802(6) Uani d . . . 1 . .
H H00K 0.8007 0.4166 0.9261 0.12 Uiso calc U . R 1 . .
H H00L 0.8566 0.4876 0.8681 0.12 Uiso calc U . R 1 . .
H H00M 0.7552 0.4191 0.7678 0.12 Uiso calc U . R 1 . .
C C19 0.6518(2) 0.68188(13) 0.21246(18) 0.0723(5) Uani d . . . 1 . .
H H00N 0.6042 0.7231 0.1468 0.087 Uiso calc U . R 1 . .
C C21 0.8036(3) 0.65838(18) 0.1051(3) 0.1009(8) Uani d . . . 1 . .
H H00O 0.7563 0.7013 0.043 0.121 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
C2 N1 C4 . . 106.53(13) ?
C2 N1 C1 . . 127.40(14) ?
C4 N1 C1 . . 126.07(13) ?
C2 N2 C3 . . 104.53(12) ?
N1 C4 C3 . . 105.24(12) ?
N1 C4 C13 . . 124.84(13) ?
C3 C4 C13 . . 129.91(14) ?
C14 C13 C4 . . 177.36(17) ?
C6 C5 C3 . . 176.19(16) ?
N2 C3 C4 . . 110.42(13) ?
N2 C3 C5 . . 124.24(13) ?
C4 C3 C5 . . 125.31(13) ?
C13 C14 C15 . . 177.86(16) ?
C20 C15 C16 . . 118.81(14) ?
C20 C15 C14 . . 121.03(14) ?
C16 C15 C14 . . 120.15(14) ?
C12 C7 C8 . . 119.04(14) ?
C12 C7 C6 . . 119.96(13) ?
C8 C7 C6 . . 120.97(14) ?
C5 C6 C7 . . 178.30(17) ?
C9 C8 C7 . . 120.07(15) ?
C9 C8 H00B . . 120.0 ?
C7 C8 H00B . . 120.0 ?
C17 C16 C15 . . 120.27(16) ?
C17 C16 H00C . . 119.9 ?
C15 C16 H00C . . 119.9 ?
N2 C2 N1 . . 113.28(13) ?
N2 C2 H00D . . 123.4 ?
N1 C2 H00D . . 123.4 ?
C19 C20 C15 . . 120.04(16) ?
C19 C20 H00E . . 120.0 ?
C15 C20 H00E . . 120.0 ?
C16 C17 C18 . . 120.85(17) ?
C16 C17 H00F . . 119.6 ?
C18 C17 H00F . . 119.6 ?
C12 C11 C10 . . 120.30(16) ?
C12 C11 H00G . . 119.8 ?
C10 C11 H00G . . 119.8 ?
C11 C10 C9 . . 120.03(16) ?
C11 C10 H00H . . 120.0 ?
C9 C10 H00H . . 120.0 ?
C8 C9 C10 . . 120.24(15) ?
C8 C9 H00I . . 119.9 ?
C10 C9 H00I . . 119.9 ?
C11 C12 C7 . . 120.32(15) ?
C11 C12 H00J . . 119.8 ?
C7 C12 H00J . . 119.8 ?
C19 C18 C17 . . 119.26(15) ?
C19 C18 C21 . . 120.9(2) ?
C17 C18 C21 . . 119.9(2) ?
N1 C1 H00K . . 109.5 ?
N1 C1 H00L . . 109.5 ?
H00K C1 H00L . . 109.5 ?
N1 C1 H00M . . 109.5 ?
H00K C1 H00M . . 109.5 ?
H00L C1 H00M . . 109.5 ?
C18 C19 C20 . . 120.76(17) ?
C18 C19 H00N . . 119.6 ?
C20 C19 H00N . . 119.6 ?
O1 C21 C18 . . 125.0(3) ?
O1 C21 H00O . . 117.5 ?
C18 C21 H00O . . 117.5 ?
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
N1 C2 . 1.349(2) ?
N1 C4 . 1.3740(18) ?
N1 C1 . 1.453(2) ?
N2 C2 . 1.309(2) ?
N2 C3 . 1.3722(18) ?
C4 C3 . 1.379(2) ?
C4 C13 . 1.4056(19) ?
C13 C14 . 1.200(2) ?
C5 C6 . 1.197(2) ?
C5 C3 . 1.416(2) ?
C14 C15 . 1.424(2) ?
C15 C20 . 1.388(2) ?
C15 C16 . 1.396(2) ?
C7 C12 . 1.389(2) ?
C7 C8 . 1.392(2) ?
C7 C6 . 1.431(2) ?
C8 C9 . 1.374(2) ?
C8 H00B . 0.93 ?
C16 C17 . 1.369(2) ?
C16 H00C . 0.93 ?
C2 H00D . 0.93 ?
C20 C19 . 1.381(2) ?
C20 H00E . 0.93 ?
C17 C18 . 1.378(3) ?
C17 H00F . 0.93 ?
C11 C12 . 1.371(2) ?
C11 C10 . 1.374(3) ?
C11 H00G . 0.93 ?
C10 C9 . 1.377(2) ?
C10 H00H . 0.93 ?
C9 H00I . 0.93 ?
C12 H00J . 0.93 ?
C18 C19 . 1.375(3) ?
C18 C21 . 1.477(3) ?
O1 C21 . 1.183(3) ?
C1 H00K . 0.96 ?
C1 H00L . 0.96 ?
C1 H00M . 0.96 ?
C19 H00N . 0.93 ?
C21 H00O . 0.93 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168350027
