#------------------------------------------------------------------------------
#$Date: 2021-02-05 01:27:30 +0200 (Fri, 05 Feb 2021) $
#$Revision: 261739 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/02/7060205.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_7060205
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_sum            'C22 H15 F3 N2 O2'
_chemical_formula_weight         396.36
_chemical_melting_point          389(11)
_chemical_name_common            NMePhPh-TFA
_chemical_name_systematic
'4,5-bis(phenylethynyl)-1-methylimidazolium trifluoroacetate'
_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
;
2020-08-28 deposited with the CCDC.	2020-12-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.485(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.855(7)
_cell_length_b                   5.4499(15)
_cell_length_c                   16.896(5)
_cell_measurement_reflns_used    2472
_cell_measurement_temperature    273.(2)
_cell_measurement_theta_max      22.7318
_cell_measurement_theta_min      2.4183
_cell_volume                     2006.3(10)
_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 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0727
_diffrn_reflns_av_unetI/netI     0.0533
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17105
_diffrn_reflns_theta_full        24.12
_diffrn_reflns_theta_max         24.12
_diffrn_reflns_theta_min         2.42
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_crystal_colour            'lustrous pale white'
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             816
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane/dichloromethane'
_exptl_crystal_size_max          0.954
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.061
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.335
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3161
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.145
_refine_ls_R_factor_all          0.1298
_refine_ls_R_factor_gt           0.0744
_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+0.8840P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1948
_refine_ls_wR_factor_ref         0.2400
_reflns_number_gt                1797
_reflns_number_total             3161
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0nj05323f2.cif
_cod_data_source_block           X190703KK1aTFA
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '378-400' was changed to
'389(11)' -- 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               7060205
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 0.88444(13) 0.2190(6) 0.33205(18) 0.0625(9) Uani d . . . 1 . .
O O2 0.85473(13) -0.1315(6) 0.15343(19) 0.0952(10) Uani d . . . 1 . .
N N2 0.85124(14) 0.5036(6) 0.25027(19) 0.0679(9) Uani d . . . 1 . .
H H2 0.8511 0.6272 0.2186 0.081 Uiso calc U . R 1 . .
O O1 0.95400(13) -0.1239(7) 0.1901(2) 0.1013(11) Uani d . . . 1 . .
F F2 0.90561(18) -0.0079(8) 0.00982(19) 0.1486(14) Uani d . . . 1 . .
C C4 0.82080(16) 0.1985(7) 0.3230(2) 0.0607(10) Uani d . . . 1 . .
C C7 0.62451(17) 0.4751(8) 0.1856(2) 0.0646(10) Uani d . . . 1 . .
C C3 0.80051(16) 0.3776(7) 0.2710(2) 0.0613(10) Uani d . . . 1 . .
C C15 0.71811(17) -0.2992(7) 0.4305(2) 0.0636(10) Uani d . . . 1 . .
C C2 0.90032(17) 0.4024(8) 0.2874(2) 0.0665(11) Uani d . . . 1 . .
H H1 0.9405 0.4536 0.2827 0.08 Uiso calc U . R 1 . .
C C5 0.73993(19) 0.4275(8) 0.2407(2) 0.0685(11) Uani d . . . 1 . .
C C14 0.75565(18) -0.1213(8) 0.3950(2) 0.0699(11) Uani d . . . 1 . .
C C6 0.68762(18) 0.4517(8) 0.2161(2) 0.0701(11) Uani d . . . 1 . .
C C22 0.9088(2) -0.0668(8) 0.1478(3) 0.0718(11) Uani d . . . 1 . .
C C13 0.78721(19) 0.0221(8) 0.3625(2) 0.0691(11) Uani d . . . 1 . .
C C1 0.92571(19) 0.0543(8) 0.3784(2) 0.0785(12) Uani d . . . 1 . .
H H1A 0.9312 -0.0933 0.3488 0.118 Uiso calc U . R 1 . .
H H1B 0.9084 0.0145 0.4273 0.118 Uiso calc U . R 1 . .
H H1C 0.9647 0.1333 0.3897 0.118 Uiso calc U . R 1 . .
C C20 0.65813(19) -0.3348(8) 0.3999(2) 0.0774(12) Uani d . . . 1 . .
H H20 0.6421 -0.2386 0.3578 0.093 Uiso calc U . R 1 . .
F F1 0.8792(3) 0.2800(8) 0.0728(2) 0.188(2) Uani d . . . 1 . .
C C12 0.58160(19) 0.3082(9) 0.2083(2) 0.0787(12) Uani d . . . 1 . .
H H12 0.5934 0.1847 0.2443 0.094 Uiso calc U . R 1 . .
F F3 0.97206(19) 0.1862(10) 0.0763(2) 0.201(2) Uani d . . . 1 . .
C C10 0.5038(2) 0.5002(9) 0.1235(3) 0.0852(14) Uani d . . . 1 . .
H H10 0.4634 0.5076 0.1018 0.102 Uiso calc U . R 1 . .
C C8 0.6063(2) 0.6570(8) 0.1315(3) 0.0818(13) Uani d . . . 1 . .
H H8 0.6345 0.7716 0.1158 0.098 Uiso calc U . R 1 . .
C C16 0.7405(2) -0.4396(9) 0.4939(3) 0.0878(14) Uani d . . . 1 . .
H H16 0.7801 -0.4139 0.5166 0.105 Uiso calc U . R 1 . .
C C19 0.6224(2) -0.5094(10) 0.4309(3) 0.0876(14) Uani d . . . 1 . .
H H19 0.5821 -0.5309 0.4099 0.105 Uiso calc U . R 1 . .
C C9 0.5459(2) 0.6663(9) 0.1011(3) 0.0893(14) Uani d . . . 1 . .
H H9 0.5336 0.788 0.0646 0.107 Uiso calc U . R 1 . .
C C11 0.52100(19) 0.3246(9) 0.1775(3) 0.0883(14) Uani d . . . 1 . .
H H11 0.4921 0.2145 0.194 0.106 Uiso calc U . R 1 . .
C C21 0.9172(2) 0.0979(11) 0.0786(3) 0.0930(15) Uani d . . . 1 . .
C C18 0.6448(2) -0.6518(10) 0.4920(3) 0.0956(15) Uani d . . . 1 . .
H H18 0.6202 -0.7717 0.5124 0.115 Uiso calc U . R 1 . .
C C17 0.7039(3) -0.6195(10) 0.5238(3) 0.0994(16) Uani d . . . 1 . .
H H17 0.7194 -0.7184 0.5654 0.119 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'
F F 0.0171 0.0103 '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 . . 107.7(3) ?
C2 N1 C1 . . 126.6(3) ?
C4 N1 C1 . . 125.5(3) ?
C2 N2 C3 . . 108.2(3) ?
C2 N2 H2 . . 125.9 ?
C3 N2 H2 . . 125.9 ?
C3 C4 N1 . . 106.6(3) ?
C3 C4 C13 . . 129.6(3) ?
N1 C4 C13 . . 123.8(4) ?
C12 C7 C8 . . 119.2(4) ?
C12 C7 C6 . . 119.6(4) ?
C8 C7 C6 . . 121.2(4) ?
C4 C3 N2 . . 107.1(3) ?
C4 C3 C5 . . 128.4(4) ?
N2 C3 C5 . . 124.5(4) ?
C16 C15 C20 . . 118.8(4) ?
C16 C15 C14 . . 121.5(4) ?
C20 C15 C14 . . 119.7(4) ?
N1 C2 N2 . . 110.4(3) ?
N1 C2 H1 . . 124.8 ?
N2 C2 H1 . . 124.8 ?
C6 C5 C3 . . 175.0(5) ?
C13 C14 C15 . . 177.4(4) ?
C5 C6 C7 . . 178.6(4) ?
O1 C22 O2 . . 128.1(4) ?
O1 C22 C21 . . 118.0(4) ?
O2 C22 C21 . . 113.9(4) ?
C14 C13 C4 . . 176.4(4) ?
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 ?
C19 C20 C15 . . 120.6(4) ?
C19 C20 H20 . . 119.7 ?
C15 C20 H20 . . 119.7 ?
C7 C12 C11 . . 120.1(4) ?
C7 C12 H12 . . 119.9 ?
C11 C12 H12 . . 119.9 ?
C11 C10 C9 . . 119.8(4) ?
C11 C10 H10 . . 120.1 ?
C9 C10 H10 . . 120.1 ?
C9 C8 C7 . . 119.3(4) ?
C9 C8 H8 . . 120.4 ?
C7 C8 H8 . . 120.4 ?
C15 C16 C17 . . 119.7(4) ?
C15 C16 H16 . . 120.1 ?
C17 C16 H16 . . 120.1 ?
C18 C19 C20 . . 120.7(4) ?
C18 C19 H19 . . 119.7 ?
C20 C19 H19 . . 119.7 ?
C10 C9 C8 . . 121.2(4) ?
C10 C9 H9 . . 119.4 ?
C8 C9 H9 . . 119.4 ?
C10 C11 C12 . . 120.3(4) ?
C10 C11 H11 . . 119.8 ?
C12 C11 H11 . . 119.8 ?
F1 C21 F3 . . 107.6(5) ?
F1 C21 F2 . . 101.2(5) ?
F3 C21 F2 . . 104.7(4) ?
F1 C21 C22 . . 113.7(4) ?
F3 C21 C22 . . 114.6(5) ?
F2 C21 C22 . . 113.8(4) ?
C19 C18 C17 . . 120.0(5) ?
C19 C18 H18 . . 120.0 ?
C17 C18 H18 . . 120.0 ?
C18 C17 C16 . . 120.1(5) ?
C18 C17 H17 . . 119.9 ?
C16 C17 H17 . . 119.9 ?
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 . 1.315(5) ?
N1 C4 . 1.392(4) ?
N1 C1 . 1.457(5) ?
O2 C22 . 1.244(5) ?
N2 C2 . 1.320(5) ?
N2 C3 . 1.373(5) ?
N2 H2 . 0.86 ?
O1 C22 . 1.214(5) ?
F2 C21 . 1.304(5) ?
C4 C3 . 1.364(5) ?
C4 C13 . 1.409(6) ?
C7 C12 . 1.382(6) ?
C7 C8 . 1.385(6) ?
C7 C6 . 1.440(5) ?
C3 C5 . 1.408(5) ?
C15 C16 . 1.375(6) ?
C15 C20 . 1.384(5) ?
C15 C14 . 1.432(6) ?
C2 H1 . 0.93 ?
C5 C6 . 1.193(5) ?
C14 C13 . 1.203(5) ?
C22 C21 . 1.497(7) ?
C1 H1A . 0.96 ?
C1 H1B . 0.96 ?
C1 H1C . 0.96 ?
C20 C19 . 1.361(6) ?
C20 H20 . 0.93 ?
F1 C21 . 1.292(6) ?
C12 C11 . 1.387(5) ?
C12 H12 . 0.93 ?
F3 C21 . 1.296(5) ?
C10 C11 . 1.355(6) ?
C10 C9 . 1.366(7) ?
C10 H10 . 0.93 ?
C8 C9 . 1.379(6) ?
C8 H8 . 0.93 ?
C16 C17 . 1.386(7) ?
C16 H16 . 0.93 ?
C19 C18 . 1.352(6) ?
C19 H19 . 0.93 ?
C9 H9 . 0.93 ?
C11 H11 . 0.93 ?
C18 C17 . 1.370(7) ?
C18 H18 . 0.93 ?
C17 H17 . 0.93 ?
