# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_NMePhPh
_database_code_depnum_ccdc_archive 'CCDC 1950075'
loop_
_audit_author_name
_audit_author_address
'Youhei Miura'
;Keio University
Japan
;
_audit_update_record             
;
2019-08-29 deposited with the CCDC.	2020-12-03 downloaded from the CCDC.
;
_chemical_name_systematic        4,5-bisphenylethynyl-1methylimidazole
_chemical_name_common            NMePhPh
_chemical_formula_moiety         'C20 H14 N2'
_chemical_formula_sum            'C20 H14 N2'
_chemical_formula_iupac          ?
_chemical_formula_weight         282.33
_chemical_absolute_configuration ?

_chemical_melting_point          383-384

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   9.6262(10)
_cell_length_b                   12.6518(13)
_cell_length_c                   13.3053(14)
_cell_angle_alpha                87.690(4)
_cell_angle_beta                 81.189(4)
_cell_angle_gamma                80.098(4)
_cell_volume                     1577.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    636
_cell_measurement_theta_min      2.2877
_cell_measurement_theta_max      21.9521
_cell_measurement_temperature    300.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          1.260
_exptl_crystal_size_mid          0.474
_exptl_crystal_size_min          0.158
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592

_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.50
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      300.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayered confocal mirror'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.4074

_diffrn_reflns_number            14425
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_av_unetI/netI     0.0978
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measured_fraction_theta_full 0.952
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15

_refine_special_details          
;
;

_reflns_number_total             8200
_reflns_number_gt                6645
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0591
_refine_ls_wR_factor_gt          0.1521
_refine_ls_wR_factor_ref         0.1750
_refine_ls_goodness_of_fit_ref   0.790
_refine_ls_restrained_S_all      0.790
_refine_ls_number_reflns         8200
_refine_ls_number_parameters     797
_refine_ls_number_restraints     3
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.7308P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.137
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 2176 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -4.2(10)

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'

_computing_data_collection       ?
_computing_cell_refinement       'APEX3 v2016.1-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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 N4 0.7302(5) 0.5202(4) 0.0037(4) 0.0834(13) Uani d . . . 1 . .
N N7 1.0517(4) 0.9453(3) 0.3315(3) 0.0665(11) Uani d . . . 1 . .
N N8 1.1898(5) 0.9753(3) 0.1871(4) 0.0745(12) Uani d . . . 1 . .
C C64 1.1238(5) 0.8896(4) 0.1765(4) 0.0630(12) Uani d . . . 1 . .
N N5 0.3654(5) -0.2347(3) 0.3446(4) 0.0732(12) Uani d . . . 1 . .
C C28 1.0236(6) 0.3648(4) 0.0963(4) 0.0654(12) Uani d . . . 1 . .
C C36 0.6970(6) 0.1443(4) -0.0150(4) 0.0688(12) Uani d . . . 1 . .
N N1 0.8135(5) 0.3211(4) 0.7233(4) 0.0724(11) Uani d . . . 1 . .
N N2 0.6512(5) 0.4563(3) 0.6815(4) 0.0757(12) Uani d . . . 1 . .
C C27 0.9154(5) 0.3834(4) 0.0599(4) 0.0649(12) Uani d . . . 1 . .
C C29 1.1512(5) 0.3459(4) 0.1416(4) 0.0632(12) Uani d . . . 1 . .
C C37 0.6844(6) 0.0335(4) -0.0164(4) 0.0676(12) Uani d . . . 1 . .
C C65 1.0381(5) 0.8687(4) 0.2644(4) 0.0617(12) Uani d . . . 1 . .
C C68 1.1669(6) 0.7660(4) 0.0171(4) 0.0702(13) Uani d . . . 1 . .
C C55 0.4688(6) -0.0806(4) 0.3872(4) 0.0699(13) Uani d . . . 1 . .
N N3 0.5832(5) 0.4199(4) -0.0378(3) 0.0733(12) Uani d . . . 1 . .
N N6 0.2321(5) -0.2670(4) 0.4915(4) 0.0820(13) Uani d . . . 1 . .
C C24 0.7863(6) 0.4145(4) 0.0190(4) 0.0660(12) Uani d . . . 1 . .
C C77 0.7800(5) 0.6475(4) 0.3301(4) 0.0650(13) Uani d . . . 1 . .
C C63 1.1418(6) 1.0053(4) 0.2819(5) 0.0760(15) Uani d . . . 1 . .
H H63 1.1685 1.0628 0.3112 0.091 Uiso calc U . R 1 . .
C C67 1.1488(6) 0.8265(4) 0.0870(4) 0.0685(13) Uani d . . . 1 . .
C C47 0.2776(5) -0.1193(4) 0.5919(5) 0.0703(14) Uani d . . . 1 . .
C C81 0.6786(6) 0.5003(5) 0.2832(5) 0.0795(15) Uani d . . . 1 . .
H H81 0.6718 0.451 0.235 0.095 Uiso calc U . R 1 . .
C C76 0.8734(6) 0.7247(4) 0.3064(4) 0.0688(13) Uani d . . . 1 . .
C C7 0.4900(5) 0.3568(4) 0.6132(4) 0.0624(12) Uani d . . . 1 . .
C C15 0.7217(6) 0.1635(4) 0.6789(4) 0.0702(13) Uani d . . . 1 . .
C C49 0.2499(5) 0.0158(4) 0.7407(4) 0.0635(12) Uani d . . . 1 . .
C C48 0.2634(6) -0.0601(4) 0.6611(4) 0.0692(13) Uani d . . . 1 . .
C C16 0.7349(6) 0.0677(5) 0.6808(4) 0.0728(13) Uani d . . . 1 . .
C C35 0.7021(6) 0.2383(4) -0.0105(4) 0.0702(13) Uani d . . . 1 . .
C C17 0.7531(6) -0.0475(4) 0.6828(4) 0.0698(13) Uani d . . . 1 . .
C C75 0.9492(5) 0.7913(4) 0.2882(4) 0.0682(13) Uani d . . . 1 . .
C C11 0.0779(8) 0.2978(6) 0.4598(6) 0.105(2) Uani d . . . 1 . .
H H11 0.0458 0.2389 0.4372 0.126 Uiso calc U . R 1 . .
C C60 0.8126(6) 0.2150(5) 0.3015(5) 0.0825(16) Uani d . . . 1 . .
H H60 0.8724 0.2657 0.2864 0.099 Uiso calc U . R 1 . .
C C56 0.5436(6) -0.0136(5) 0.3677(4) 0.0732(14) Uani d . . . 1 . .
C C4 0.6137(5) 0.3598(4) 0.6585(4) 0.0622(11) Uani d . . . 1 . .
C C70 1.0926(6) 0.6161(4) -0.0575(4) 0.0742(14) Uani d . . . 1 . .
H H70 1.0238 0.6139 -0.0005 0.089 Uiso calc U . R 1 . .
C C8 0.3837(5) 0.3598(4) 0.5750(4) 0.0629(12) Uani d . . . 1 . .
C C62 0.6364(6) 0.1429(4) 0.4145(4) 0.0713(14) Uani d . . . 1 . .
H H62 0.5766 0.1452 0.4766 0.086 Uiso calc U . R 1 . .
C C80 0.5965(6) 0.5004(5) 0.3769(5) 0.0791(16) Uani d . . . 1 . .
H H80 0.5353 0.4507 0.3926 0.095 Uiso calc U . R 1 . .
C C3 0.7687(6) 0.4271(5) 0.7203(5) 0.0835(16) Uani d . . . 1 . .
H H3 0.8174 0.4761 0.744 0.1 Uiso calc U . R 1 . .
C C79 0.6051(6) 0.5733(5) 0.4462(5) 0.0799(16) Uani d . . . 1 . .
H H79 0.5487 0.5738 0.5095 0.096 Uiso calc U . R 1 . .
C C66 0.9780(7) 0.9580(5) 0.4355(5) 0.0857(17) Uani d . . . 1 . .
H H66A 1.0382 0.9835 0.477 0.129 Uiso calc U . R 1 . .
H H66B 0.9559 0.89 0.4617 0.129 Uiso calc U . R 1 . .
H H66C 0.8914 1.0087 0.4363 0.129 Uiso calc U . R 1 . .
C C54 0.1774(6) 0.0006(5) 0.8367(5) 0.0795(15) Uani d . . . 1 . .
H H54 0.1373 -0.0611 0.8517 0.095 Uiso calc U . R 1 . .
C C42 0.7969(7) -0.0451(5) -0.0059(7) 0.105(2) Uani d . . . 1 . .
H H42 0.8851 -0.0268 -0.0009 0.126 Uiso calc U . R 1 . .
C C14 0.1737(6) 0.4709(5) 0.5238(4) 0.0787(15) Uani d . . . 1 . .
H H14 0.2051 0.5306 0.5452 0.094 Uiso calc U . R 1 . .
C C45 0.3821(5) -0.1601(4) 0.4117(4) 0.0683(13) Uani d . . . 1 . .
C C25 0.6967(5) 0.3496(4) -0.0085(4) 0.0634(12) Uani d . . . 1 . .
C C61 0.7258(6) 0.2171(4) 0.3934(5) 0.0763(15) Uani d . . . 1 . .
H H61 0.7274 0.2684 0.4412 0.092 Uiso calc U . R 1 . .
C C69 1.1809(6) 0.6923(4) -0.0638(4) 0.0679(13) Uani d . . . 1 . .
C C30 1.2239(6) 0.2435(4) 0.1529(4) 0.0717(14) Uani d . . . 1 . .
H H30 1.1877 0.1854 0.1328 0.086 Uiso calc U . R 1 . .
C C10 0.2060(7) 0.2833(5) 0.4991(5) 0.0859(17) Uani d . . . 1 . .
H H10 0.2584 0.2147 0.5035 0.103 Uiso calc U . R 1 . .
C C9 0.2555(5) 0.3705(4) 0.5314(4) 0.0628(12) Uani d . . . 1 . .
C C82 0.7715(6) 0.5729(4) 0.2595(4) 0.0701(14) Uani d . . . 1 . .
H H82 0.8281 0.5713 0.1962 0.084 Uiso calc U . R 1 . .
C C71 1.1042(8) 0.5442(5) -0.1331(5) 0.0918(18) Uani d . . . 1 . .
H H71 1.0444 0.4931 -0.127 0.11 Uiso calc U . R 1 . .
C C58 0.7232(6) 0.0628(5) 0.2524(4) 0.0773(15) Uani d . . . 1 . .
H H58 0.7231 0.0108 0.2049 0.093 Uiso calc U . R 1 . .
C C57 0.6334(5) 0.0652(4) 0.3461(4) 0.0644(13) Uani d . . . 1 . .
C C12 0.0001(7) 0.3966(6) 0.4544(6) 0.102(2) Uani d . . . 1 . .
H H12 -0.0863 0.4053 0.4294 0.122 Uiso calc U . R 1 . .
C C53 0.1645(6) 0.0765(5) 0.9103(5) 0.0848(16) Uani d . . . 1 . .
H H53 0.1147 0.0661 0.9745 0.102 Uiso calc U . R 1 . .
C C43 0.2749(7) -0.2954(5) 0.3971(6) 0.0851(18) Uani d . . . 1 . .
H H43 0.2459 -0.3522 0.3683 0.102 Uiso calc U . R 1 . .
C C31 1.3496(6) 0.2257(5) 0.1937(5) 0.0827(16) Uani d . . . 1 . .
H H31 1.3971 0.156 0.2014 0.099 Uiso calc U . R 1 . .
C C72 1.2032(10) 0.5470(6) -0.2177(6) 0.104(2) Uani d . . . 1 . .
H H72 1.2107 0.4979 -0.2693 0.125 Uiso calc U . R 1 . .
C C78 0.6964(6) 0.6471(5) 0.4246(4) 0.0726(14) Uani d . . . 1 . .
H H78 0.7017 0.6964 0.4733 0.087 Uiso calc U . R 1 . .
C C46 0.4352(7) -0.2462(6) 0.2397(5) 0.094(2) Uani d . . . 1 . .
H H46A 0.536 -0.2679 0.2385 0.141 Uiso calc U . R 1 . .
H H46B 0.4174 -0.1788 0.2043 0.141 Uiso calc U . R 1 . .
H H46C 0.3982 -0.2995 0.2072 0.141 Uiso calc U . R 1 . .
C C26 0.4573(6) 0.3897(6) -0.0729(5) 0.0928(18) Uani d . . . 1 . .
H H26A 0.4004 0.3598 -0.017 0.139 Uiso calc U . R 1 . .
H H26B 0.488 0.3375 -0.1256 0.139 Uiso calc U . R 1 . .
H H26C 0.4017 0.4522 -0.099 0.139 Uiso calc U . R 1 . .
C C18 0.8819(8) -0.1053(5) 0.6999(6) 0.103(2) Uani d . . . 1 . .
H H18 0.9554 -0.0706 0.7116 0.124 Uiso calc U . R 1 . .
C C74 1.2819(7) 0.6961(5) -0.1509(5) 0.0899(18) Uani d . . . 1 . .
H H74 1.3413 0.7475 -0.1578 0.108 Uiso calc U . R 1 . .
C C51 0.2984(6) 0.1817(5) 0.7960(4) 0.0777(15) Uani d . . . 1 . .
H H51 0.3398 0.2429 0.7818 0.093 Uiso calc U . R 1 . .
C C50 0.3116(6) 0.1069(4) 0.7230(4) 0.0703(13) Uani d . . . 1 . .
H H50 0.3636 0.1173 0.6596 0.084 Uiso calc U . R 1 . .
C C59 0.8117(6) 0.1382(5) 0.2314(5) 0.0805(16) Uani d . . . 1 . .
H H59 0.8712 0.1372 0.1693 0.097 Uiso calc U . R 1 . .
C C52 0.2243(7) 0.1671(5) 0.8900(5) 0.0819(15) Uani d . . . 1 . .
H H52 0.2146 0.2183 0.9399 0.098 Uiso calc U . R 1 . .
C C5 0.7131(5) 0.2753(4) 0.6833(4) 0.0674(12) Uani d . . . 1 . .
C C34 1.2068(7) 0.4325(5) 0.1725(5) 0.0853(17) Uani d . . . 1 . .
H H34 1.1597 0.5024 0.1656 0.102 Uiso calc U . R 1 . .
C C6 0.9422(6) 0.2658(6) 0.7588(5) 0.0940(18) Uani d . . . 1 . .
H H6A 1.0191 0.2568 0.7029 0.141 Uiso calc U . R 1 . .
H H6B 0.9269 0.1967 0.7862 0.141 Uiso calc U . R 1 . .
H H6C 0.9659 0.3072 0.8106 0.141 Uiso calc U . R 1 . .
C C38 0.5561(7) 0.0031(6) -0.0199(7) 0.111(2) Uani d . . . 1 . .
H H38 0.4762 0.0553 -0.0241 0.134 Uiso calc U . R 1 . .
C C32 1.4040(7) 0.3103(6) 0.2227(5) 0.0934(19) Uani d . . . 1 . .
H H32 1.4897 0.2986 0.2489 0.112 Uiso calc U . R 1 . .
C C23 0.6103(7) 0.5189(5) -0.0293(5) 0.0857(16) Uani d . . . 1 . .
H H23 0.5496 0.5807 -0.0452 0.103 Uiso calc U . R 1 . .
C C22 0.6453(8) -0.1006(6) 0.6680(7) 0.108(2) Uani d . . . 1 . .
H H22 0.5589 -0.0614 0.6548 0.13 Uiso calc U . R 1 . .
C C13 0.0478(7) 0.4845(5) 0.4855(5) 0.0939(19) Uani d . . . 1 . .
H H13 -0.0053 0.5527 0.4806 0.113 Uiso calc U . R 1 . .
C C44 0.2987(6) -0.1815(4) 0.5014(4) 0.0693(14) Uani d . . . 1 . .
C C33 1.3322(7) 0.4127(6) 0.2134(6) 0.099(2) Uani d . . . 1 . .
H H33 1.3687 0.4699 0.2349 0.118 Uiso calc U . R 1 . .
C C73 1.2918(9) 0.6219(7) -0.2269(5) 0.106(2) Uani d . . . 1 . .
H H73 1.3595 0.6231 -0.2847 0.127 Uiso calc U . R 1 . .
C C39 0.5430(9) -0.1034(7) -0.0173(8) 0.132(3) Uani d . . . 1 . .
H H39 0.4547 -0.1227 -0.0199 0.158 Uiso calc U . R 1 . .
C C41 0.7817(9) -0.1507(6) -0.0025(9) 0.134(3) Uani d . . . 1 . .
H H41 0.8594 -0.2035 0.0057 0.161 Uiso calc U . R 1 . .
C C40 0.6560(11) -0.1790(6) -0.0111(7) 0.122(3) Uani d . . . 1 . .
H H40 0.648 -0.2511 -0.0126 0.146 Uiso calc U . R 1 . .
C C19 0.9002(13) -0.2152(8) 0.6994(8) 0.148(4) Uani d . . . 1 . .
H H19 0.9885 -0.2555 0.7065 0.177 Uiso calc U . R 1 . .
C C21 0.6620(12) -0.2089(8) 0.6722(8) 0.137(3) Uani d . . . 1 . .
H H21 0.5867 -0.2433 0.664 0.164 Uiso calc U . R 1 . .
C C20 0.7867(18) -0.2664(7) 0.6883(8) 0.153(4) Uani d . . . 1 . .
H H20 0.7977 -0.3409 0.692 0.184 Uiso calc U . R 1 . .


_geom_special_details            
;

All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
N4 C23 . 1.298(7) ?
N4 C24 . 1.372(7) ?
N7 C63 . 1.332(7) ?
N7 C65 . 1.379(6) ?
N7 C66 . 1.457(7) ?
N8 C63 . 1.323(7) ?
N8 C64 . 1.370(7) ?
C64 C65 . 1.368(7) ?
C64 C67 . 1.428(8) ?
N5 C43 . 1.355(8) ?
N5 C45 . 1.371(7) ?
N5 C46 . 1.454(8) ?
C28 C27 . 1.199(7) ?
C28 C29 . 1.429(7) ?
C36 C35 . 1.203(7) ?
C36 C37 . 1.429(7) ?
N1 C3 . 1.337(7) ?
N1 C5 . 1.389(7) ?
N1 C6 . 1.450(7) ?
N2 C3 . 1.305(7) ?
N2 C4 . 1.389(7) ?
C27 C24 . 1.420(7) ?
C29 C30 . 1.376(7) ?
C29 C34 . 1.400(8) ?
C37 C42 . 1.358(8) ?
C37 C38 . 1.363(8) ?
C65 C75 . 1.405(7) ?
C68 C67 . 1.200(8) ?
C68 C69 . 1.429(8) ?
C55 C56 . 1.199(7) ?
C55 C45 . 1.412(8) ?
N3 C23 . 1.336(7) ?
N3 C25 . 1.380(6) ?
N3 C26 . 1.476(7) ?
N6 C43 . 1.305(8) ?
N6 C44 . 1.369(7) ?
C24 C25 . 1.384(7) ?
C77 C82 . 1.378(8) ?
C77 C78 . 1.385(7) ?
C77 C76 . 1.433(7) ?
C63 H63 . 0.93 ?
C47 C48 . 1.188(8) ?
C47 C44 . 1.435(9) ?
C81 C80 . 1.369(8) ?
C81 C82 . 1.384(7) ?
C81 H81 . 0.93 ?
C76 C75 . 1.201(7) ?
C7 C8 . 1.205(7) ?
C7 C4 . 1.421(7) ?
C15 C16 . 1.196(7) ?
C15 C5 . 1.406(8) ?
C49 C50 . 1.381(7) ?
C49 C54 . 1.383(7) ?
C49 C48 . 1.434(8) ?
C16 C17 . 1.438(8) ?
C35 C25 . 1.401(7) ?
C17 C22 . 1.371(9) ?
C17 C18 . 1.373(8) ?
C11 C12 . 1.347(10) ?
C11 C10 . 1.393(9) ?
C11 H11 . 0.93 ?
C60 C61 . 1.370(9) ?
C60 C59 . 1.375(9) ?
C60 H60 . 0.93 ?
C56 C57 . 1.422(8) ?
C4 C5 . 1.373(7) ?
C70 C71 . 1.363(9) ?
C70 C69 . 1.383(8) ?
C70 H70 . 0.93 ?
C8 C9 . 1.426(7) ?
C62 C61 . 1.372(8) ?
C62 C57 . 1.373(8) ?
C62 H62 . 0.93 ?
C80 C79 . 1.351(9) ?
C80 H80 . 0.93 ?
C3 H3 . 0.93 ?
C79 C78 . 1.382(8) ?
C79 H79 . 0.93 ?
C66 H66A . 0.96 ?
C66 H66B . 0.96 ?
C66 H66C . 0.96 ?
C54 C53 . 1.376(9) ?
C54 H54 . 0.93 ?
C42 C41 . 1.368(10) ?
C42 H42 . 0.93 ?
C14 C13 . 1.367(8) ?
C14 C9 . 1.384(7) ?
C14 H14 . 0.93 ?
C45 C44 . 1.378(8) ?
C61 H61 . 0.93 ?
C69 C74 . 1.399(8) ?
C30 C31 . 1.382(8) ?
C30 H30 . 0.93 ?
C10 C9 . 1.383(8) ?
C10 H10 . 0.93 ?
C82 H82 . 0.93 ?
C71 C72 . 1.362(11) ?
C71 H71 . 0.93 ?
C58 C59 . 1.378(8) ?
C58 C57 . 1.402(8) ?
C58 H58 . 0.93 ?
C12 C13 . 1.375(10) ?
C12 H12 . 0.93 ?
C53 C52 . 1.368(8) ?
C53 H53 . 0.93 ?
C43 H43 . 0.93 ?
C31 C32 . 1.363(9) ?
C31 H31 . 0.93 ?
C72 C73 . 1.370(11) ?
C72 H72 . 0.93 ?
C78 H78 . 0.93 ?
C46 H46A . 0.96 ?
C46 H46B . 0.96 ?
C46 H46C . 0.96 ?
C26 H26A . 0.96 ?
C26 H26B . 0.96 ?
C26 H26C . 0.96 ?
C18 C19 . 1.370(12) ?
C18 H18 . 0.93 ?
C74 C73 . 1.388(10) ?
C74 H74 . 0.93 ?
C51 C50 . 1.360(8) ?
C51 C52 . 1.364(8) ?
C51 H51 . 0.93 ?
C50 H50 . 0.93 ?
C59 H59 . 0.93 ?
C52 H52 . 0.93 ?
C34 C33 . 1.379(9) ?
C34 H34 . 0.93 ?
C6 H6A . 0.96 ?
C6 H6B . 0.96 ?
C6 H6C . 0.96 ?
C38 C39 . 1.373(10) ?
C38 H38 . 0.93 ?
C32 C33 . 1.369(9) ?
C32 H32 . 0.93 ?
C23 H23 . 0.93 ?
C22 C21 . 1.351(11) ?
C22 H22 . 0.93 ?
C13 H13 . 0.93 ?
C33 H33 . 0.93 ?
C73 H73 . 0.93 ?
C39 C40 . 1.330(11) ?
C39 H39 . 0.93 ?
C41 C40 . 1.341(12) ?
C41 H41 . 0.93 ?
C40 H40 . 0.93 ?
C19 C20 . 1.392(16) ?
C19 H19 . 0.93 ?
C21 C20 . 1.334(15) ?
C21 H21 . 0.93 ?
C20 H20 . 0.93 ?

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
C23 N4 C24 . . 105.5(5) ?
C63 N7 C65 . . 106.8(4) ?
C63 N7 C66 . . 127.5(5) ?
C65 N7 C66 . . 125.7(5) ?
C63 N8 C64 . . 103.4(5) ?
C65 C64 N8 . . 111.4(5) ?
C65 C64 C67 . . 124.6(5) ?
N8 C64 C67 . . 123.9(5) ?
C43 N5 C45 . . 105.9(5) ?
C43 N5 C46 . . 128.1(6) ?
C45 N5 C46 . . 126.0(5) ?
C27 C28 C29 . . 178.1(6) ?
C35 C36 C37 . . 177.0(6) ?
C3 N1 C5 . . 105.8(4) ?
C3 N1 C6 . . 127.0(5) ?
C5 N1 C6 . . 127.2(5) ?
C3 N2 C4 . . 103.7(4) ?
C28 C27 C24 . . 175.3(5) ?
C30 C29 C34 . . 118.8(5) ?
C30 C29 C28 . . 121.2(5) ?
C34 C29 C28 . . 120.0(5) ?
C42 C37 C38 . . 117.6(5) ?
C42 C37 C36 . . 121.3(5) ?
C38 C37 C36 . . 121.0(5) ?
C64 C65 N7 . . 104.8(4) ?
C64 C65 C75 . . 131.4(5) ?
N7 C65 C75 . . 123.8(5) ?
C67 C68 C69 . . 176.7(6) ?
C56 C55 C45 . . 178.9(6) ?
C23 N3 C25 . . 107.0(4) ?
C23 N3 C26 . . 127.2(5) ?
C25 N3 C26 . . 125.9(5) ?
C43 N6 C44 . . 103.7(5) ?
N4 C24 C25 . . 109.5(5) ?
N4 C24 C27 . . 122.1(5) ?
C25 C24 C27 . . 128.3(5) ?
C82 C77 C78 . . 119.1(5) ?
C82 C77 C76 . . 120.7(5) ?
C78 C77 C76 . . 120.2(5) ?
N8 C63 N7 . . 113.6(5) ?
N8 C63 H63 . . 123.2 ?
N7 C63 H63 . . 123.2 ?
C68 C67 C64 . . 174.3(5) ?
C48 C47 C44 . . 173.9(6) ?
C80 C81 C82 . . 120.7(6) ?
C80 C81 H81 . . 119.6 ?
C82 C81 H81 . . 119.6 ?
C75 C76 C77 . . 178.2(6) ?
C8 C7 C4 . . 176.7(5) ?
C16 C15 C5 . . 175.2(6) ?
C50 C49 C54 . . 117.9(5) ?
C50 C49 C48 . . 120.1(5) ?
C54 C49 C48 . . 122.0(5) ?
C47 C48 C49 . . 176.6(6) ?
C15 C16 C17 . . 179.2(6) ?
C36 C35 C25 . . 175.0(6) ?
C22 C17 C18 . . 119.5(6) ?
C22 C17 C16 . . 121.6(5) ?
C18 C17 C16 . . 118.9(6) ?
C76 C75 C65 . . 178.6(6) ?
C12 C11 C10 . . 120.3(7) ?
C12 C11 H11 . . 119.8 ?
C10 C11 H11 . . 119.8 ?
C61 C60 C59 . . 120.3(6) ?
C61 C60 H60 . . 119.9 ?
C59 C60 H60 . . 119.9 ?
C55 C56 C57 . . 179.1(6) ?
C5 C4 N2 . . 110.3(4) ?
C5 C4 C7 . . 128.2(5) ?
N2 C4 C7 . . 121.5(4) ?
C71 C70 C69 . . 121.4(6) ?
C71 C70 H70 . . 119.3 ?
C69 C70 H70 . . 119.3 ?
C7 C8 C9 . . 176.3(5) ?
C61 C62 C57 . . 121.5(5) ?
C61 C62 H62 . . 119.3 ?
C57 C62 H62 . . 119.3 ?
C79 C80 C81 . . 119.5(5) ?
C79 C80 H80 . . 120.3 ?
C81 C80 H80 . . 120.3 ?
N2 C3 N1 . . 114.7(5) ?
N2 C3 H3 . . 122.6 ?
N1 C3 H3 . . 122.6 ?
C80 C79 C78 . . 121.2(5) ?
C80 C79 H79 . . 119.4 ?
C78 C79 H79 . . 119.4 ?
N7 C66 H66A . . 109.5 ?
N7 C66 H66B . . 109.5 ?
H66A C66 H66B . . 109.5 ?
N7 C66 H66C . . 109.5 ?
H66A C66 H66C . . 109.5 ?
H66B C66 H66C . . 109.5 ?
C53 C54 C49 . . 120.1(5) ?
C53 C54 H54 . . 119.9 ?
C49 C54 H54 . . 119.9 ?
C37 C42 C41 . . 120.7(6) ?
C37 C42 H42 . . 119.7 ?
C41 C42 H42 . . 119.7 ?
C13 C14 C9 . . 121.6(6) ?
C13 C14 H14 . . 119.2 ?
C9 C14 H14 . . 119.2 ?
N5 C45 C44 . . 105.3(5) ?
N5 C45 C55 . . 124.1(5) ?
C44 C45 C55 . . 130.6(5) ?
N3 C25 C24 . . 104.9(4) ?
N3 C25 C35 . . 121.2(5) ?
C24 C25 C35 . . 133.9(5) ?
C60 C61 C62 . . 119.5(6) ?
C60 C61 H61 . . 120.3 ?
C62 C61 H61 . . 120.3 ?
C70 C69 C74 . . 118.7(5) ?
C70 C69 C68 . . 120.0(5) ?
C74 C69 C68 . . 121.2(6) ?
C29 C30 C31 . . 121.0(5) ?
C29 C30 H30 . . 119.5 ?
C31 C30 H30 . . 119.5 ?
C9 C10 C11 . . 120.2(6) ?
C9 C10 H10 . . 119.9 ?
C11 C10 H10 . . 119.9 ?
C10 C9 C14 . . 117.9(5) ?
C10 C9 C8 . . 122.5(5) ?
C14 C9 C8 . . 119.6(5) ?
C77 C82 C81 . . 119.8(5) ?
C77 C82 H82 . . 120.1 ?
C81 C82 H82 . . 120.1 ?
C72 C71 C70 . . 120.1(7) ?
C72 C71 H71 . . 119.9 ?
C70 C71 H71 . . 119.9 ?
C59 C58 C57 . . 119.3(6) ?
C59 C58 H58 . . 120.4 ?
C57 C58 H58 . . 120.4 ?
C62 C57 C58 . . 118.9(5) ?
C62 C57 C56 . . 122.1(5) ?
C58 C57 C56 . . 119.0(5) ?
C11 C12 C13 . . 120.4(6) ?
C11 C12 H12 . . 119.8 ?
C13 C12 H12 . . 119.8 ?
C52 C53 C54 . . 120.7(6) ?
C52 C53 H53 . . 119.6 ?
C54 C53 H53 . . 119.6 ?
N6 C43 N5 . . 114.0(5) ?
N6 C43 H43 . . 123.0 ?
N5 C43 H43 . . 123.0 ?
C32 C31 C30 . . 119.9(6) ?
C32 C31 H31 . . 120.0 ?
C30 C31 H31 . . 120.0 ?
C71 C72 C73 . . 120.1(7) ?
C71 C72 H72 . . 119.9 ?
C73 C72 H72 . . 119.9 ?
C79 C78 C77 . . 119.8(5) ?
C79 C78 H78 . . 120.1 ?
C77 C78 H78 . . 120.1 ?
N5 C46 H46A . . 109.5 ?
N5 C46 H46B . . 109.5 ?
H46A C46 H46B . . 109.5 ?
N5 C46 H46C . . 109.5 ?
H46A C46 H46C . . 109.5 ?
H46B C46 H46C . . 109.5 ?
N3 C26 H26A . . 109.5 ?
N3 C26 H26B . . 109.5 ?
H26A C26 H26B . . 109.5 ?
N3 C26 H26C . . 109.5 ?
H26A C26 H26C . . 109.5 ?
H26B C26 H26C . . 109.5 ?
C19 C18 C17 . . 118.8(8) ?
C19 C18 H18 . . 120.6 ?
C17 C18 H18 . . 120.6 ?
C73 C74 C69 . . 118.8(7) ?
C73 C74 H74 . . 120.6 ?
C69 C74 H74 . . 120.6 ?
C50 C51 C52 . . 120.0(5) ?
C50 C51 H51 . . 120.0 ?
C52 C51 H51 . . 120.0 ?
C51 C50 C49 . . 121.7(5) ?
C51 C50 H50 . . 119.1 ?
C49 C50 H50 . . 119.1 ?
C60 C59 C58 . . 120.6(5) ?
C60 C59 H59 . . 119.7 ?
C58 C59 H59 . . 119.7 ?
C51 C52 C53 . . 119.6(6) ?
C51 C52 H52 . . 120.2 ?
C53 C52 H52 . . 120.2 ?
C4 C5 N1 . . 105.5(4) ?
C4 C5 C15 . . 132.5(5) ?
N1 C5 C15 . . 121.9(5) ?
C33 C34 C29 . . 119.1(6) ?
C33 C34 H34 . . 120.4 ?
C29 C34 H34 . . 120.4 ?
N1 C6 H6A . . 109.5 ?
N1 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
N1 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
C37 C38 C39 . . 120.9(7) ?
C37 C38 H38 . . 119.5 ?
C39 C38 H38 . . 119.5 ?
C31 C32 C33 . . 119.9(6) ?
C31 C32 H32 . . 120.1 ?
C33 C32 H32 . . 120.1 ?
N4 C23 N3 . . 113.1(5) ?
N4 C23 H23 . . 123.5 ?
N3 C23 H23 . . 123.5 ?
C21 C22 C17 . . 121.3(8) ?
C21 C22 H22 . . 119.3 ?
C17 C22 H22 . . 119.3 ?
C14 C13 C12 . . 119.5(6) ?
C14 C13 H13 . . 120.2 ?
C12 C13 H13 . . 120.2 ?
N6 C44 C45 . . 111.1(5) ?
N6 C44 C47 . . 124.1(5) ?
C45 C44 C47 . . 124.7(5) ?
C32 C33 C34 . . 121.2(6) ?
C32 C33 H33 . . 119.4 ?
C34 C33 H33 . . 119.4 ?
C72 C73 C74 . . 120.8(6) ?
C72 C73 H73 . . 119.6 ?
C74 C73 H73 . . 119.6 ?
C40 C39 C38 . . 120.3(7) ?
C40 C39 H39 . . 119.8 ?
C38 C39 H39 . . 119.8 ?
C40 C41 C42 . . 120.7(7) ?
C40 C41 H41 . . 119.6 ?
C42 C41 H41 . . 119.6 ?
C39 C40 C41 . . 119.6(7) ?
C39 C40 H40 . . 120.2 ?
C41 C40 H40 . . 120.2 ?
C18 C19 C20 . . 120.1(9) ?
C18 C19 H19 . . 119.9 ?
C20 C19 H19 . . 119.9 ?
C20 C21 C22 . . 120.0(10) ?
C20 C21 H21 . . 120.0 ?
C22 C21 H21 . . 120.0 ?
C21 C20 C19 . . 120.1(8) ?
C21 C20 H20 . . 119.9 ?
C19 C20 H20 . . 119.9 ?

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
C63 N8 C64 C65 . . . . -0.3(5) ?
C63 N8 C64 C67 . . . . -176.7(5) ?
N8 C64 C65 N7 . . . . 0.4(5) ?
C67 C64 C65 N7 . . . . 176.7(5) ?
N8 C64 C65 C75 . . . . 178.6(5) ?
C67 C64 C65 C75 . . . . -5.1(8) ?
C63 N7 C65 C64 . . . . -0.3(5) ?
C66 N7 C65 C64 . . . . 178.6(4) ?
C63 N7 C65 C75 . . . . -178.7(5) ?
C66 N7 C65 C75 . . . . 0.2(7) ?
C23 N4 C24 C25 . . . . 1.4(6) ?
C23 N4 C24 C27 . . . . -176.9(5) ?
C64 N8 C63 N7 . . . . 0.2(6) ?
C65 N7 C63 N8 . . . . 0.1(6) ?
C66 N7 C63 N8 . . . . -178.7(5) ?
C3 N2 C4 C5 . . . . -1.0(6) ?
C3 N2 C4 C7 . . . . -179.5(5) ?
C82 C81 C80 C79 . . . . 1.0(9) ?
C4 N2 C3 N1 . . . . 1.2(7) ?
C5 N1 C3 N2 . . . . -0.9(7) ?
C6 N1 C3 N2 . . . . 177.7(5) ?
C81 C80 C79 C78 . . . . -0.6(9) ?
C50 C49 C54 C53 . . . . 2.1(8) ?
C48 C49 C54 C53 . . . . -178.7(5) ?
C38 C37 C42 C41 . . . . 2.2(11) ?
C36 C37 C42 C41 . . . . 176.9(7) ?
C43 N5 C45 C44 . . . . -0.1(5) ?
C46 N5 C45 C44 . . . . -178.6(5) ?
C43 N5 C45 C55 . . . . 180.0(5) ?
C46 N5 C45 C55 . . . . 1.5(7) ?
C23 N3 C25 C24 . . . . 1.3(6) ?
C26 N3 C25 C24 . . . . -179.3(5) ?
C23 N3 C25 C35 . . . . -178.9(5) ?
C26 N3 C25 C35 . . . . 0.5(8) ?
N4 C24 C25 N3 . . . . -1.7(6) ?
C27 C24 C25 N3 . . . . 176.5(5) ?
N4 C24 C25 C35 . . . . 178.5(5) ?
C27 C24 C25 C35 . . . . -3.2(10) ?
C59 C60 C61 C62 . . . . -0.9(8) ?
C57 C62 C61 C60 . . . . 1.0(8) ?
C71 C70 C69 C74 . . . . 1.3(8) ?
C71 C70 C69 C68 . . . . -179.5(5) ?
C34 C29 C30 C31 . . . . -0.2(8) ?
C28 C29 C30 C31 . . . . 177.9(5) ?
C12 C11 C10 C9 . . . . -1.0(11) ?
C11 C10 C9 C14 . . . . 0.3(9) ?
C11 C10 C9 C8 . . . . 178.1(6) ?
C13 C14 C9 C10 . . . . 0.0(9) ?
C13 C14 C9 C8 . . . . -177.9(6) ?
C78 C77 C82 C81 . . . . 1.1(7) ?
C76 C77 C82 C81 . . . . -178.8(5) ?
C80 C81 C82 C77 . . . . -1.2(8) ?
C69 C70 C71 C72 . . . . -0.7(9) ?
C61 C62 C57 C58 . . . . -0.5(8) ?
C61 C62 C57 C56 . . . . 178.6(5) ?
C59 C58 C57 C62 . . . . -0.2(7) ?
C59 C58 C57 C56 . . . . -179.3(5) ?
C10 C11 C12 C13 . . . . 1.4(12) ?
C49 C54 C53 C52 . . . . -0.8(9) ?
C44 N6 C43 N5 . . . . 0.3(6) ?
C45 N5 C43 N6 . . . . -0.1(6) ?
C46 N5 C43 N6 . . . . 178.3(5) ?
C29 C30 C31 C32 . . . . -0.5(9) ?
C70 C71 C72 C73 . . . . 0.2(10) ?
C80 C79 C78 C77 . . . . 0.5(8) ?
C82 C77 C78 C79 . . . . -0.8(7) ?
C76 C77 C78 C79 . . . . 179.1(5) ?
C22 C17 C18 C19 . . . . 1.5(11) ?
C16 C17 C18 C19 . . . . -178.5(7) ?
C70 C69 C74 C73 . . . . -1.4(8) ?
C68 C69 C74 C73 . . . . 179.4(5) ?
C52 C51 C50 C49 . . . . 1.0(9) ?
C54 C49 C50 C51 . . . . -2.2(8) ?
C48 C49 C50 C51 . . . . 178.6(5) ?
C61 C60 C59 C58 . . . . 0.3(9) ?
C57 C58 C59 C60 . . . . 0.2(8) ?
C50 C51 C52 C53 . . . . 0.4(9) ?
C54 C53 C52 C51 . . . . -0.5(9) ?
N2 C4 C5 N1 . . . . 0.5(5) ?
C7 C4 C5 N1 . . . . 178.8(5) ?
N2 C4 C5 C15 . . . . 177.1(5) ?
C7 C4 C5 C15 . . . . -4.6(9) ?
C3 N1 C5 C4 . . . . 0.2(6) ?
C6 N1 C5 C4 . . . . -178.4(5) ?
C3 N1 C5 C15 . . . . -176.9(5) ?
C6 N1 C5 C15 . . . . 4.5(8) ?
C30 C29 C34 C33 . . . . 0.0(9) ?
C28 C29 C34 C33 . . . . -178.2(5) ?
C42 C37 C38 C39 . . . . -2.8(11) ?
C36 C37 C38 C39 . . . . -177.5(8) ?
C30 C31 C32 C33 . . . . 1.4(10) ?
C24 N4 C23 N3 . . . . -0.6(7) ?
C25 N3 C23 N4 . . . . -0.5(7) ?
C26 N3 C23 N4 . . . . -179.8(5) ?
C18 C17 C22 C21 . . . . 1.6(11) ?
C16 C17 C22 C21 . . . . -178.5(7) ?
C9 C14 C13 C12 . . . . 0.4(10) ?
C11 C12 C13 C14 . . . . -1.1(12) ?
C43 N6 C44 C45 . . . . -0.3(6) ?
C43 N6 C44 C47 . . . . 176.5(5) ?
N5 C45 C44 N6 . . . . 0.2(6) ?
C55 C45 C44 N6 . . . . -179.8(5) ?
N5 C45 C44 C47 . . . . -176.6(5) ?
C55 C45 C44 C47 . . . . 3.4(9) ?
C31 C32 C33 C34 . . . . -1.6(11) ?
C29 C34 C33 C32 . . . . 1.0(10) ?
C71 C72 C73 C74 . . . . -0.3(11) ?
C69 C74 C73 C72 . . . . 0.9(10) ?
C37 C38 C39 C40 . . . . 0.1(15) ?
C37 C42 C41 C40 . . . . 1.0(15) ?
C38 C39 C40 C41 . . . . 3.1(16) ?
C42 C41 C40 C39 . . . . -3.7(16) ?
C17 C18 C19 C20 . . . . -4.1(14) ?
C17 C22 C21 C20 . . . . -1.9(14) ?
C22 C21 C20 C19 . . . . -0.8(17) ?
C18 C19 C20 C21 . . . . 3.8(17) ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane/Hexane'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_X191029KK_NMePhCHO_TFA
_database_code_depnum_ccdc_archive 'CCDC 2025950'
loop_
_audit_author_name
_audit_author_address
'Youhei Miura'
;Keio University
Japan
;
_audit_update_record             
;
2020-08-28 deposited with the CCDC.	2020-12-03 downloaded from the CCDC.
;
_chemical_name_systematic        
'4-phenylethynyl-5-(4-formylphenylethynyl)-1-methylimidazolium trifluoroacetate'
_chemical_name_common            NMePhCHO_TFA
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H15 F3 N2 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         424.37
_chemical_absolute_configuration ?

_chemical_melting_point          428-430

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.5410(16)
_cell_length_b                   5.0337(9)
_cell_length_c                   21.921(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.137(5)
_cell_angle_gamma                90
_cell_volume                     1039.4(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2703
_cell_measurement_theta_min      2.4913
_cell_measurement_theta_max      23.2442
_cell_measurement_temperature    300.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear pale yellow'
_exptl_crystal_size_max          0.586
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_min          0.067
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             436

_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.73
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      300.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayered confocal mirror'

_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 7.4074

_diffrn_reflns_number            7930
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_av_unetI/netI     0.0568
_diffrn_reflns_theta_min         2.49
_diffrn_reflns_theta_max         23.37
_diffrn_reflns_theta_full        23.37
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24

_refine_special_details          
;
;

_reflns_number_total             2790
_reflns_number_gt                2109
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0573
_refine_ls_wR_factor_gt          0.1529
_refine_ls_wR_factor_ref         0.1783
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_restrained_S_all      0.997
_refine_ls_number_reflns         2790
_refine_ls_number_parameters     281
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.3732P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.256
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 692 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(9)

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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 O3 0.3732(4) 0.2767(11) 0.95022(19) 0.0786(14) Uani d . . . 1 . .
O O2 0.2546(4) 0.2488(11) 0.85435(19) 0.0767(13) Uani d . . . 1 . .
N N1 0.6031(5) 0.5953(11) 0.8838(2) 0.0592(13) Uani d . . . 1 . .
N N2 0.4395(5) 0.8658(11) 0.8444(2) 0.0637(14) Uani d . . . 1 . .
H H2 0.3778 0.9916 0.8412 0.076 Uiso calc U . R 1 . .
C C23 0.2714(6) 0.3155(13) 0.9099(3) 0.0616(16) Uani d . . . 1 . .
C C15 0.8030(6) -0.0108(12) 0.7454(3) 0.0560(15) Uani d . . . 1 . .
O O1 1.0074(6) -0.7211(13) 0.6259(3) 0.112(2) Uani d . . . 1 . .
F F1 0.1370(6) 0.4505(14) 0.9861(2) 0.152(3) Uani d . . . 1 . .
C C2 0.4735(6) 0.7151(13) 0.7961(3) 0.0614(16) Uani d . . . 1 . .
F F3 0.0260(5) 0.3997(17) 0.8988(3) 0.183(4) Uani d . . . 1 . .
C C14 0.7199(7) 0.1888(13) 0.7705(3) 0.0616(16) Uani d . . . 1 . .
C C3 0.5793(6) 0.5440(13) 0.8220(3) 0.0582(16) Uani d . . . 1 . .
C C13 0.6536(6) 0.3511(13) 0.7937(3) 0.0592(15) Uani d . . . 1 . .
C C18 0.9604(6) -0.3988(14) 0.6985(3) 0.0642(16) Uani d . . . 1 . .
C C1 0.5180(6) 0.7844(13) 0.8969(3) 0.0626(16) Uani d . . . 1 . .
H H1 0.5132 0.8505 0.9362 0.075 Uiso calc U . R 1 . .
F F2 0.1548(7) 0.7183(12) 0.9181(3) 0.160(2) Uani d . . . 1 . .
C C5 0.4136(6) 0.7377(16) 0.7338(3) 0.0709(18) Uani d . . . 1 . .
C C16 0.7556(6) -0.1201(13) 0.6884(3) 0.0628(16) Uani d . . . 1 . .
H H16 0.6706 -0.0614 0.6656 0.075 Uiso calc U . R 1 . .
C C22 0.1459(7) 0.4614(16) 0.9284(3) 0.0712(18) Uani d . . . 1 . .
C C6 0.3742(7) 0.7232(15) 0.6791(3) 0.0712(17) Uani d . . . 1 . .
C C19 1.0077(7) -0.2915(15) 0.7552(3) 0.0749(19) Uani d . . . 1 . .
H H19 1.0922 -0.3513 0.7781 0.09 Uiso calc U . R 1 . .
C C7 0.3320(7) 0.6919(15) 0.6141(3) 0.0714(18) Uani d . . . 1 . .
C C17 0.8322(7) -0.3153(13) 0.6644(3) 0.0665(17) Uani d . . . 1 . .
H H17 0.7989 -0.3902 0.6261 0.08 Uiso calc U . R 1 . .
C C20 0.9310(7) -0.0953(15) 0.7785(3) 0.077(2) Uani d . . . 1 . .
H H20 0.9652 -0.0191 0.8166 0.092 Uiso calc U . R 1 . .
C C4 0.7009(7) 0.4442(17) 0.9301(3) 0.082(2) Uani d . . . 1 . .
H H4A 0.7972 0.4843 0.9258 0.123 Uiso calc U . R 1 . .
H H4B 0.684 0.2574 0.9239 0.123 Uiso calc U . R 1 . .
H H4C 0.685 0.4926 0.9709 0.123 Uiso calc U . R 1 . .
C C21 1.0409(7) -0.6136(15) 0.6743(4) 0.081(2) Uani d . . . 1 . .
H H21 1.1244 -0.6693 0.6987 0.097 Uiso calc U . R 1 . .
C C12 0.4010(9) 0.5064(18) 0.5821(4) 0.095(2) Uani d . . . 1 . .
H H12 0.4755 0.4063 0.6031 0.114 Uiso calc U . R 1 . .
C C8 0.2190(8) 0.8326(18) 0.5817(3) 0.091(2) Uani d . . . 1 . .
H H8 0.1698 0.9541 0.6023 0.109 Uiso calc U . R 1 . .
C C9 0.1799(9) 0.793(2) 0.5196(4) 0.108(3) Uani d . . . 1 . .
H H9 0.1059 0.8925 0.4982 0.13 Uiso calc U . R 1 . .
C C10 0.2464(11) 0.613(2) 0.4889(4) 0.111(3) Uani d . . . 1 . .
H H10 0.2159 0.5851 0.4469 0.134 Uiso calc U . R 1 . .
C C11 0.3587(11) 0.471(2) 0.5190(4) 0.116(3) Uani d . . . 1 . .
H H11 0.4065 0.3511 0.4974 0.139 Uiso calc U . R 1 . .


_geom_special_details            
;

All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
O3 C23 . 1.221(7) ?
O2 C23 . 1.248(7) ?
N1 C1 . 1.313(8) ?
N1 C3 . 1.362(7) ?
N1 C4 . 1.476(8) ?
N2 C1 . 1.334(7) ?
N2 C2 . 1.383(8) ?
N2 H2 . 0.86 ?
C23 C22 . 1.514(9) ?
C15 C16 . 1.376(8) ?
C15 C20 . 1.384(9) ?
C15 C14 . 1.442(9) ?
O1 C21 . 1.188(8) ?
F1 C22 . 1.281(7) ?
C2 C3 . 1.379(8) ?
C2 C5 . 1.397(9) ?
F3 C22 . 1.261(8) ?
C14 C13 . 1.195(8) ?
C3 C13 . 1.404(9) ?
C18 C19 . 1.364(9) ?
C18 C17 . 1.393(8) ?
C18 C21 . 1.474(9) ?
C1 H1 . 0.93 ?
F2 C22 . 1.318(9) ?
C5 C6 . 1.202(9) ?
C16 C17 . 1.378(8) ?
C16 H16 . 0.93 ?
C6 C7 . 1.426(9) ?
C19 C20 . 1.375(9) ?
C19 H19 . 0.93 ?
C7 C8 . 1.387(9) ?
C7 C12 . 1.394(10) ?
C17 H17 . 0.93 ?
C20 H20 . 0.93 ?
C4 H4A . 0.96 ?
C4 H4B . 0.96 ?
C4 H4C . 0.96 ?
C21 H21 . 0.93 ?
C12 C11 . 1.389(10) ?
C12 H12 . 0.93 ?
C8 C9 . 1.368(9) ?
C8 H8 . 0.93 ?
C9 C10 . 1.347(13) ?
C9 H9 . 0.93 ?
C10 C11 . 1.368(12) ?
C10 H10 . 0.93 ?
C11 H11 . 0.93 ?

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
C1 N1 C3 . . 110.1(5) ?
C1 N1 C4 . . 124.6(5) ?
C3 N1 C4 . . 125.0(5) ?
C1 N2 C2 . . 109.0(5) ?
C1 N2 H2 . . 125.5 ?
C2 N2 H2 . . 125.5 ?
O3 C23 O2 . . 128.8(6) ?
O3 C23 C22 . . 117.1(6) ?
O2 C23 C22 . . 114.0(5) ?
C16 C15 C20 . . 119.2(5) ?
C16 C15 C14 . . 120.3(5) ?
C20 C15 C14 . . 120.5(6) ?
C3 C2 N2 . . 105.8(5) ?
C3 C2 C5 . . 127.8(6) ?
N2 C2 C5 . . 126.4(6) ?
C13 C14 C15 . . 177.3(7) ?
N1 C3 C2 . . 106.7(5) ?
N1 C3 C13 . . 123.7(6) ?
C2 C3 C13 . . 129.6(5) ?
C14 C13 C3 . . 178.3(7) ?
C19 C18 C17 . . 120.3(6) ?
C19 C18 C21 . . 120.2(6) ?
C17 C18 C21 . . 119.4(6) ?
N1 C1 N2 . . 108.4(5) ?
N1 C1 H1 . . 125.8 ?
N2 C1 H1 . . 125.8 ?
C6 C5 C2 . . 169.9(8) ?
C15 C16 C17 . . 120.9(6) ?
C15 C16 H16 . . 119.5 ?
C17 C16 H16 . . 119.5 ?
F3 C22 F1 . . 107.4(7) ?
F3 C22 F2 . . 103.4(8) ?
F1 C22 F2 . . 103.1(7) ?
F3 C22 C23 . . 115.7(6) ?
F1 C22 C23 . . 115.0(6) ?
F2 C22 C23 . . 110.8(7) ?
C5 C6 C7 . . 176.7(8) ?
C18 C19 C20 . . 120.3(6) ?
C18 C19 H19 . . 119.9 ?
C20 C19 H19 . . 119.9 ?
C8 C7 C12 . . 118.4(7) ?
C8 C7 C6 . . 121.8(6) ?
C12 C7 C6 . . 119.7(7) ?
C16 C17 C18 . . 119.0(6) ?
C16 C17 H17 . . 120.5 ?
C18 C17 H17 . . 120.5 ?
C19 C20 C15 . . 120.2(6) ?
C19 C20 H20 . . 119.9 ?
C15 C20 H20 . . 119.9 ?
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 ?
O1 C21 C18 . . 125.0(7) ?
O1 C21 H21 . . 117.5 ?
C18 C21 H21 . . 117.5 ?
C11 C12 C7 . . 120.0(8) ?
C11 C12 H12 . . 120.0 ?
C7 C12 H12 . . 120.0 ?
C9 C8 C7 . . 120.1(8) ?
C9 C8 H8 . . 120.0 ?
C7 C8 H8 . . 120.0 ?
C10 C9 C8 . . 121.4(8) ?
C10 C9 H9 . . 119.3 ?
C8 C9 H9 . . 119.3 ?
C9 C10 C11 . . 120.3(8) ?
C9 C10 H10 . . 119.8 ?
C11 C10 H10 . . 119.8 ?
C10 C11 C12 . . 119.7(8) ?
C10 C11 H11 . . 120.1 ?
C12 C11 H11 . . 120.1 ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane/dichloromethane'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_X191029KK_NMeOMeCHO_TFA
_database_code_depnum_ccdc_archive 'CCDC 2025952'
loop_
_audit_author_name
_audit_author_address
'Youhei Miura'
;Keio University
Japan
;
_audit_update_record             
;
2020-08-28 deposited with the CCDC.	2020-12-03 downloaded from the CCDC.
;
_chemical_name_systematic        
'4-(4-methoxyphenylethynyl)-5-(4-formylphenylethynyl)-1-methylimidazolium trifluoroacetate'
_chemical_name_common            NMeOMeCHO
_chemical_formula_moiety         ?
_chemical_formula_sum            'C50 H35 F9 N4 O10'
_chemical_formula_iupac          ?
_chemical_formula_weight         1022.82

_chemical_melting_point          406-408

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.8968(8)
_cell_length_b                   14.4328(9)
_cell_length_c                   14.7466(10)
_cell_angle_alpha                91.829(2)
_cell_angle_beta                 115.533(2)
_cell_angle_gamma                92.604(2)
_cell_volume                     2470.2(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2639
_cell_measurement_theta_min      2.2408
_cell_measurement_theta_max      21.0157
_cell_measurement_temperature    300.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear light yellow-colourless'
_exptl_crystal_size_max          0.704
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.022
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1048

_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_T_max  1.00

_exptl_special_details           
;
;

_diffrn_ambient_temperature      300.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayered confocal mirror'

_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 7.4074

_diffrn_reflns_number            21127
_diffrn_reflns_av_R_equivalents  0.0661
_diffrn_reflns_av_unetI/netI     0.0730
_diffrn_reflns_theta_min         2.24
_diffrn_reflns_theta_max         23.34
_diffrn_reflns_theta_full        23.34
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 0.965
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14

_refine_special_details          
;
;

_reflns_number_total             6930
_reflns_number_gt                3593
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1502
_refine_ls_R_factor_gt           0.0757
_refine_ls_wR_factor_gt          0.1972
_refine_ls_wR_factor_ref         0.2456
_refine_ls_goodness_of_fit_ref   1.224
_refine_ls_restrained_S_all      1.224
_refine_ls_number_reflns         6930
_refine_ls_number_parameters     662
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.0292P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.267
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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 O8 0.0290(3) 0.0415(3) 0.2947(3) 0.0838(10) Uani d . . . 1 . .
N N4 0.9739(3) 0.0926(2) 0.4349(3) 0.0636(10) Uani d . . . 1 . .
H H4 0.9918 0.077 0.3869 0.076 Uiso calc U . R 1 . .
N N3 0.9888(3) 0.1441(2) 0.5790(3) 0.0649(10) Uani d . . . 1 . .
O O5 0.2605(3) 0.5119(3) 0.2781(3) 0.0941(12) Uani d . . . 1 . .
O O4 0.2832(3) 0.2313(3) 0.6725(3) 0.0969(12) Uani d . . . 1 . .
N N1 0.5765(3) 0.6538(2) 0.5678(3) 0.0655(10) Uani d . . . 1 . .
O O2 1.3831(3) 0.7306(3) 0.6616(3) 0.1070(13) Uani d . . . 1 . .
N N2 0.4457(3) 0.5928(2) 0.4265(3) 0.0697(11) Uani d . . . 1 . .
H H2 0.3795 0.5741 0.3796 0.084 Uiso calc U . R 1 . .
O O3 0.2800(4) -0.1261(3) -0.0480(3) 0.1052(13) Uani d . . . 1 . .
O O7 0.1948(4) 0.1221(3) 0.3873(3) 0.1108(14) Uani d . . . 1 . .
O O1 0.6766(4) 0.3724(3) -0.0348(3) 0.1123(13) Uani d . . . 1 . .
F F1 0.1805(4) 0.6217(3) 0.3682(4) 0.1677(19) Uani d . . . 1 . .
O O6 0.0801(4) 0.4540(3) 0.1728(3) 0.1224(16) Uani d . . . 1 . .
F F5 0.1310(4) -0.0296(3) 0.1892(3) 0.1649(19) Uani d . . . 1 . .
C C40 0.4713(4) 0.2100(3) 0.6860(4) 0.0612(12) Uani d . . . 1 . .
F F4 0.2790(4) 0.0548(3) 0.2683(4) 0.1652(18) Uani d . . . 1 . .
C C37 0.6336(4) 0.1594(3) 0.6217(4) 0.0619(12) Uani d . . . 1 . .
C C2 0.5510(4) 0.5829(3) 0.4237(4) 0.0654(13) Uani d . . . 1 . .
C C25 0.8658(4) 0.0827(3) 0.4306(4) 0.0601(12) Uani d . . . 1 . .
F F3 0.0159(4) 0.5494(3) 0.2970(4) 0.171(2) Uani d . . . 1 . .
C C24 0.8750(4) 0.1158(3) 0.5226(4) 0.0606(12) Uani d . . . 1 . .
C C23 1.0453(4) 0.1291(3) 0.5225(4) 0.0633(12) Uani d . . . 1 . .
H H23 1.1236 0.1428 0.5429 0.076 Uiso calc U . R 1 . .
C C29 0.5801(4) -0.0191(3) 0.1901(4) 0.0655(13) Uani d . . . 1 . .
C C41 0.5866(4) 0.2272(3) 0.7474(4) 0.0684(13) Uani d . . . 1 . .
H H41 0.6099 0.256 0.811 0.082 Uiso calc U . R 1 . .
C C28 0.6832(5) 0.0159(3) 0.2735(4) 0.0664(13) Uani d . . . 1 . .
C C3 0.6336(4) 0.6216(3) 0.5123(4) 0.0649(13) Uani d . . . 1 . .
C C36 0.7187(4) 0.1381(3) 0.5858(4) 0.0679(13) Uani d . . . 1 . .
C C42 0.6681(4) 0.2025(3) 0.7160(4) 0.0712(13) Uani d . . . 1 . .
H H42 0.746 0.2147 0.7581 0.085 Uiso calc U . R 1 . .
C C18 1.2088(4) 0.7109(3) 0.6789(4) 0.0659(13) Uani d . . . 1 . .
C C1 0.4642(4) 0.6356(3) 0.5130(4) 0.0716(14) Uani d . . . 1 . .
H H1 0.4072 0.6507 0.5326 0.086 Uiso calc U . R 1 . .
F F6 0.1357(5) 0.1142(4) 0.1677(4) 0.215(3) Uani d . . . 1 . .
C C35 0.7892(4) 0.1261(3) 0.5561(4) 0.0674(13) Uani d . . . 1 . .
C C32 0.3748(5) -0.0880(4) 0.0322(4) 0.0735(14) Uani d . . . 1 . .
C C38 0.5176(4) 0.1395(3) 0.5607(4) 0.0726(14) Uani d . . . 1 . .
H H38 0.4942 0.1094 0.4976 0.087 Uiso calc U . R 1 . .
C C27 0.7675(5) 0.0455(3) 0.3449(4) 0.0669(13) Uani d . . . 1 . .
C C39 0.4364(4) 0.1642(3) 0.5932(4) 0.0728(14) Uani d . . . 1 . .
H H39 0.3585 0.1499 0.5526 0.087 Uiso calc U . R 1 . .
C C48 0.1283(5) 0.0756(4) 0.3135(4) 0.0761(14) Uani d . . . 1 . .
C C15 0.9766(4) 0.6641(3) 0.6135(4) 0.0685(13) Uani d . . . 1 . .
C C14 0.8553(5) 0.6451(3) 0.5777(4) 0.0726(14) Uani d . . . 1 . .
C C17 1.1441(5) 0.6680(4) 0.5849(4) 0.0839(16) Uani d . . . 1 . .
H H17 1.1794 0.6552 0.5431 0.101 Uiso calc U . R 1 . .
C C34 0.4749(4) 0.0065(3) 0.1827(4) 0.0750(14) Uani d . . . 1 . .
H H34 0.4727 0.0474 0.2318 0.09 Uiso calc U . R 1 . .
C C19 1.1565(4) 0.7281(3) 0.7398(4) 0.0728(14) Uani d . . . 1 . .
H H19 1.1997 0.7554 0.8041 0.087 Uiso calc U . R 1 . .
C C33 0.3736(5) -0.0274(4) 0.1044(4) 0.0776(14) Uani d . . . 1 . .
H H33 0.3038 -0.0088 0.1006 0.093 Uiso calc U . R 1 . .
C C13 0.7534(5) 0.6326(3) 0.5472(4) 0.0718(14) Uani d . . . 1 . .
C C7 0.6022(5) 0.4778(3) 0.1924(4) 0.0742(14) Uani d . . . 1 . .
C C30 0.5808(5) -0.0800(3) 0.1153(4) 0.0712(13) Uani d . . . 1 . .
H H30 0.6506 -0.0976 0.1181 0.085 Uiso calc U . R 1 . .
C C5 0.5618(4) 0.5433(3) 0.3402(4) 0.0726(14) Uani d . . . 1 . .
F F2 0.0646(5) 0.6445(4) 0.2189(4) 0.205(3) Uani d . . . 1 . .
C C44 0.3858(5) 0.2416(3) 0.7201(4) 0.0750(14) Uani d . . . 1 . .
H H44 0.4138 0.2719 0.7835 0.09 Uiso calc U . R 1 . .
C C6 0.5777(4) 0.5129(3) 0.2723(4) 0.0749(14) Uani d . . . 1 . .
C C10 0.6572(6) 0.4097(4) 0.0412(4) 0.0831(15) Uani d . . . 1 . .
C C22 1.3301(4) 0.7398(3) 0.7120(4) 0.0813(15) Uani d . . . 1 . .
H H22 1.37 0.7672 0.7767 0.098 Uiso calc U . R 1 . .
C C20 1.0406(5) 0.7057(3) 0.7079(4) 0.0752(14) Uani d . . . 1 . .
H H20 1.0058 0.7187 0.7501 0.09 Uiso calc U . R 1 . .
C C31 0.4803(5) -0.1141(3) 0.0380(4) 0.0768(15) Uani d . . . 1 . .
H H31 0.4819 -0.1551 -0.0112 0.092 Uiso calc U . R 1 . .
C C46 0.1558(6) 0.5070(4) 0.2417(5) 0.0924(17) Uani d . . . 1 . .
C C16 1.0297(5) 0.6439(3) 0.5517(4) 0.0802(15) Uani d . . . 1 . .
H H16 0.9877 0.6144 0.4883 0.096 Uiso calc U . R 1 . .
C C8 0.5238(5) 0.4188(3) 0.1137(4) 0.0809(15) Uani d . . . 1 . .
H H8 0.4519 0.4026 0.1111 0.097 Uiso calc U . R 1 . .
C C12 0.7063(5) 0.5028(4) 0.1917(4) 0.0902(16) Uani d . . . 1 . .
H H12 0.759 0.5434 0.2427 0.108 Uiso calc U . R 1 . .
C C9 0.5521(6) 0.3847(4) 0.0406(4) 0.0880(16) Uani d . . . 1 . .
H H9 0.4999 0.344 -0.0106 0.106 Uiso calc U . R 1 . .
C C47 0.1665(6) 0.0531(5) 0.2344(6) 0.1045(19) Uani d . . . 1 . .
O O9 0.1814(8) 0.3553(5) 0.0881(5) 0.210(4) Uani d . . . 1 . .
C C26 1.0407(5) 0.1822(4) 0.6839(4) 0.0894(17) Uani d . . . 1 . .
H H26A 1.0022 0.236 0.6891 0.134 Uiso calc U . R 1 . .
H H26B 1.1209 0.1992 0.7045 0.134 Uiso calc U . R 1 . .
H H26C 1.0331 0.1361 0.7265 0.134 Uiso calc U . R 1 . .
C C4 0.6335(5) 0.7006(4) 0.6677(4) 0.0933(17) Uani d . . . 1 . .
H H4A 0.577 0.7272 0.685 0.14 Uiso calc U . R 1 . .
H H4B 0.6873 0.7489 0.6679 0.14 Uiso calc U . R 1 . .
H H4C 0.6737 0.6566 0.7161 0.14 Uiso calc U . R 1 . .
C C45 0.1032(7) 0.5772(5) 0.2807(6) 0.112(2) Uani d . . . 1 . .
C C11 0.7339(5) 0.4689(4) 0.1165(5) 0.0911(17) Uani d . . . 1 . .
H H11 0.8046 0.4864 0.1173 0.109 Uiso calc U . R 1 . .
F F8 0.2789(7) 0.2096(5) 0.0523(6) 0.240(3) Uani d . . . 1 . .
F F7 0.2083(7) 0.2797(5) -0.0780(5) 0.251(4) Uani d . . . 1 . .
C C50 0.1364(11) 0.2976(8) 0.0365(9) 0.153(3) Uani d . . . 1 . .
F F9 0.1242(8) 0.1626(5) -0.0601(6) 0.278(4) Uani d . . . 1 . .
C C49 0.1809(15) 0.2391(8) -0.0164(9) 0.183(5) Uani d . . . 1 . .
C C43 0.1715(6) -0.1003(6) -0.0570(6) 0.153(3) Uani d . . . 1 . .
H H43A 0.1628 -0.1159 0.0022 0.229 Uiso calc U . R 1 . .
H H43B 0.1115 -0.1329 -0.115 0.229 Uiso calc U . R 1 . .
H H43C 0.1665 -0.0346 -0.0645 0.229 Uiso calc U . R 1 . .
O O10 0.0311(9) 0.2694(6) 0.0113(8) 0.263(5) Uani d . . . 1 . .
C C21 0.7865(7) 0.3937(6) -0.0347(6) 0.160(3) Uani d . . . 1 . .
H H21A 0.7938 0.4584 -0.0457 0.24 Uiso calc U . R 1 . .
H H21B 0.7925 0.3568 -0.0873 0.24 Uiso calc U . R 1 . .
H H21C 0.8467 0.3802 0.0291 0.24 Uiso calc U . R 1 . .


_geom_special_details            
;

All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
O8 C48 . 1.260(6) ?
N4 C23 . 1.296(5) ?
N4 C25 . 1.368(5) ?
N4 H4 . 0.86 ?
N3 C23 . 1.343(5) ?
N3 C24 . 1.373(5) ?
N3 C26 . 1.470(6) ?
O5 C46 . 1.217(7) ?
O4 C44 . 1.200(6) ?
N1 C1 . 1.328(6) ?
N1 C3 . 1.399(5) ?
N1 C4 . 1.457(6) ?
O2 C22 . 1.215(6) ?
N2 C1 . 1.319(6) ?
N2 C2 . 1.389(5) ?
N2 H2 . 0.86 ?
O3 C32 . 1.358(6) ?
O3 C43 . 1.416(7) ?
O7 C48 . 1.210(6) ?
O1 C10 . 1.351(6) ?
O1 C21 . 1.435(7) ?
F1 C45 . 1.361(8) ?
O6 C46 . 1.264(7) ?
F5 C47 . 1.310(7) ?
C40 C41 . 1.373(6) ?
C40 C39 . 1.377(6) ?
C40 C44 . 1.477(6) ?
F4 C47 . 1.314(7) ?
C37 C42 . 1.381(6) ?
C37 C38 . 1.383(6) ?
C37 C36 . 1.450(6) ?
C2 C3 . 1.361(6) ?
C2 C5 . 1.405(7) ?
C25 C24 . 1.378(6) ?
C25 C27 . 1.417(7) ?
F3 C45 . 1.298(7) ?
C24 C35 . 1.404(6) ?
C23 H23 . 0.93 ?
C29 C34 . 1.382(6) ?
C29 C30 . 1.392(6) ?
C29 C28 . 1.423(7) ?
C41 C42 . 1.374(6) ?
C41 H41 . 0.93 ?
C28 C27 . 1.189(6) ?
C3 C13 . 1.401(7) ?
C36 C35 . 1.183(6) ?
C42 H42 . 0.93 ?
C18 C19 . 1.358(6) ?
C18 C17 . 1.379(7) ?
C18 C22 . 1.459(7) ?
C1 H1 . 0.93 ?
F6 C47 . 1.286(7) ?
C32 C33 . 1.362(6) ?
C32 C31 . 1.395(7) ?
C38 C39 . 1.382(6) ?
C38 H38 . 0.93 ?
C39 H39 . 0.93 ?
C48 C47 . 1.482(8) ?
C15 C20 . 1.374(6) ?
C15 C16 . 1.387(6) ?
C15 C14 . 1.428(7) ?
C14 C13 . 1.195(6) ?
C17 C16 . 1.363(7) ?
C17 H17 . 0.93 ?
C34 C33 . 1.373(6) ?
C34 H34 . 0.93 ?
C19 C20 . 1.380(6) ?
C19 H19 . 0.93 ?
C33 H33 . 0.93 ?
C7 C12 . 1.379(7) ?
C7 C8 . 1.393(7) ?
C7 C6 . 1.429(7) ?
C30 C31 . 1.362(6) ?
C30 H30 . 0.93 ?
C5 C6 . 1.181(6) ?
F2 C45 . 1.316(7) ?
C44 H44 . 0.93 ?
C10 C11 . 1.362(7) ?
C10 C9 . 1.382(7) ?
C22 H22 . 0.93 ?
C20 H20 . 0.93 ?
C31 H31 . 0.93 ?
C46 C45 . 1.476(8) ?
C16 H16 . 0.93 ?
C8 C9 . 1.364(7) ?
C8 H8 . 0.93 ?
C12 C11 . 1.386(7) ?
C12 H12 . 0.93 ?
C9 H9 . 0.93 ?
O9 C50 . 1.070(12) ?
C26 H26A . 0.96 ?
C26 H26B . 0.96 ?
C26 H26C . 0.96 ?
C4 H4A . 0.96 ?
C4 H4B . 0.96 ?
C4 H4C . 0.96 ?
C11 H11 . 0.93 ?
F8 C49 . 1.333(13) ?
F7 C49 . 1.259(12) ?
C50 O10 . 1.286(12) ?
C50 C49 . 1.427(13) ?
F9 C49 . 1.283(13) ?
C43 H43A . 0.96 ?
C43 H43B . 0.96 ?
C43 H43C . 0.96 ?
C21 H21A . 0.96 ?
C21 H21B . 0.96 ?
C21 H21C . 0.96 ?

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
C23 N4 C25 . . 109.6(4) ?
C23 N4 H4 . . 125.2 ?
C25 N4 H4 . . 125.2 ?
C23 N3 C24 . . 108.0(4) ?
C23 N3 C26 . . 125.7(4) ?
C24 N3 C26 . . 126.2(4) ?
C1 N1 C3 . . 108.1(4) ?
C1 N1 C4 . . 127.4(4) ?
C3 N1 C4 . . 124.5(4) ?
C1 N2 C2 . . 108.8(4) ?
C1 N2 H2 . . 125.6 ?
C2 N2 H2 . . 125.6 ?
C32 O3 C43 . . 117.2(4) ?
C10 O1 C21 . . 118.1(5) ?
C41 C40 C39 . . 119.8(4) ?
C41 C40 C44 . . 119.5(5) ?
C39 C40 C44 . . 120.7(5) ?
C42 C37 C38 . . 119.8(4) ?
C42 C37 C36 . . 119.8(4) ?
C38 C37 C36 . . 120.4(4) ?
C3 C2 C5 . . 129.7(5) ?
C3 C2 N2 . . 106.8(4) ?
C5 C2 N2 . . 123.4(5) ?
N4 C25 C24 . . 106.5(4) ?
N4 C25 C27 . . 123.9(4) ?
C24 C25 C27 . . 129.5(4) ?
C25 C24 N3 . . 106.4(4) ?
C25 C24 C35 . . 129.9(5) ?
N3 C24 C35 . . 123.6(4) ?
N4 C23 N3 . . 109.5(4) ?
N4 C23 H23 . . 125.3 ?
N3 C23 H23 . . 125.3 ?
C34 C29 C30 . . 118.1(5) ?
C34 C29 C28 . . 119.7(4) ?
C30 C29 C28 . . 122.2(4) ?
C40 C41 C42 . . 120.9(5) ?
C40 C41 H41 . . 119.5 ?
C42 C41 H41 . . 119.5 ?
C27 C28 C29 . . 178.1(5) ?
C2 C3 N1 . . 106.6(4) ?
C2 C3 C13 . . 130.5(5) ?
N1 C3 C13 . . 122.9(5) ?
C35 C36 C37 . . 176.2(5) ?
C41 C42 C37 . . 119.6(5) ?
C41 C42 H42 . . 120.2 ?
C37 C42 H42 . . 120.2 ?
C19 C18 C17 . . 118.5(5) ?
C19 C18 C22 . . 120.2(5) ?
C17 C18 C22 . . 121.2(5) ?
N2 C1 N1 . . 109.7(4) ?
N2 C1 H1 . . 125.2 ?
N1 C1 H1 . . 125.2 ?
C36 C35 C24 . . 177.5(5) ?
O3 C32 C33 . . 125.2(5) ?
O3 C32 C31 . . 115.6(5) ?
C33 C32 C31 . . 119.2(5) ?
C37 C38 C39 . . 120.2(5) ?
C37 C38 H38 . . 119.9 ?
C39 C38 H38 . . 119.9 ?
C28 C27 C25 . . 178.2(5) ?
C40 C39 C38 . . 119.8(5) ?
C40 C39 H39 . . 120.1 ?
C38 C39 H39 . . 120.1 ?
O7 C48 O8 . . 128.3(5) ?
O7 C48 C47 . . 117.6(6) ?
O8 C48 C47 . . 114.1(6) ?
C20 C15 C16 . . 119.7(5) ?
C20 C15 C14 . . 120.2(5) ?
C16 C15 C14 . . 120.1(5) ?
C13 C14 C15 . . 177.6(5) ?
C16 C17 C18 . . 121.8(5) ?
C16 C17 H17 . . 119.1 ?
C18 C17 H17 . . 119.1 ?
C33 C34 C29 . . 121.3(5) ?
C33 C34 H34 . . 119.4 ?
C29 C34 H34 . . 119.4 ?
C18 C19 C20 . . 121.1(5) ?
C18 C19 H19 . . 119.4 ?
C20 C19 H19 . . 119.4 ?
C32 C33 C34 . . 120.3(5) ?
C32 C33 H33 . . 119.8 ?
C34 C33 H33 . . 119.8 ?
C14 C13 C3 . . 177.8(5) ?
C12 C7 C8 . . 118.1(5) ?
C12 C7 C6 . . 119.6(5) ?
C8 C7 C6 . . 122.3(5) ?
C31 C30 C29 . . 120.6(5) ?
C31 C30 H30 . . 119.7 ?
C29 C30 H30 . . 119.7 ?
C6 C5 C2 . . 175.7(6) ?
O4 C44 C40 . . 125.3(5) ?
O4 C44 H44 . . 117.4 ?
C40 C44 H44 . . 117.4 ?
C5 C6 C7 . . 177.5(6) ?
O1 C10 C11 . . 124.1(6) ?
O1 C10 C9 . . 116.4(6) ?
C11 C10 C9 . . 119.5(5) ?
O2 C22 C18 . . 125.0(5) ?
O2 C22 H22 . . 117.5 ?
C18 C22 H22 . . 117.5 ?
C15 C20 C19 . . 119.8(5) ?
C15 C20 H20 . . 120.1 ?
C19 C20 H20 . . 120.1 ?
C30 C31 C32 . . 120.5(5) ?
C30 C31 H31 . . 119.7 ?
C32 C31 H31 . . 119.7 ?
O5 C46 O6 . . 132.3(6) ?
O5 C46 C45 . . 116.2(7) ?
O6 C46 C45 . . 111.5(6) ?
C17 C16 C15 . . 119.1(5) ?
C17 C16 H16 . . 120.4 ?
C15 C16 H16 . . 120.4 ?
C9 C8 C7 . . 120.3(5) ?
C9 C8 H8 . . 119.8 ?
C7 C8 H8 . . 119.8 ?
C7 C12 C11 . . 121.3(5) ?
C7 C12 H12 . . 119.3 ?
C11 C12 H12 . . 119.3 ?
C8 C9 C10 . . 121.0(5) ?
C8 C9 H9 . . 119.5 ?
C10 C9 H9 . . 119.5 ?
F6 C47 F5 . . 108.9(7) ?
F6 C47 F4 . . 104.3(6) ?
F5 C47 F4 . . 103.9(5) ?
F6 C47 C48 . . 110.6(5) ?
F5 C47 C48 . . 115.0(6) ?
F4 C47 C48 . . 113.4(6) ?
N3 C26 H26A . . 109.5 ?
N3 C26 H26B . . 109.5 ?
H26A C26 H26B . . 109.5 ?
N3 C26 H26C . . 109.5 ?
H26A C26 H26C . . 109.5 ?
H26B C26 H26C . . 109.5 ?
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 ?
F3 C45 F2 . . 104.2(7) ?
F3 C45 F1 . . 106.0(6) ?
F2 C45 F1 . . 103.8(6) ?
F3 C45 C46 . . 117.5(6) ?
F2 C45 C46 . . 111.7(6) ?
F1 C45 C46 . . 112.4(7) ?
C10 C11 C12 . . 119.8(6) ?
C10 C11 H11 . . 120.1 ?
C12 C11 H11 . . 120.1 ?
O9 C50 O10 . . 124.9(13) ?
O9 C50 C49 . . 126.8(15) ?
O10 C50 C49 . . 108.2(13) ?
F7 C49 F9 . . 107.7(10) ?
F7 C49 F8 . . 105.2(14) ?
F9 C49 F8 . . 102.2(9) ?
F7 C49 C50 . . 114.6(10) ?
F9 C49 C50 . . 118.8(15) ?
F8 C49 C50 . . 106.6(10) ?
O3 C43 H43A . . 109.5 ?
O3 C43 H43B . . 109.5 ?
H43A C43 H43B . . 109.5 ?
O3 C43 H43C . . 109.5 ?
H43A C43 H43C . . 109.5 ?
H43B C43 H43C . . 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 ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane/dichloromethane'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_X190705KK_NMePhCHO
_database_code_depnum_ccdc_archive 'CCDC 1950078'
loop_
_audit_author_name
_audit_author_address
'Youhei Miura'
;Keio University
Japan
;
_audit_update_record             
;
2019-08-29 deposited with the CCDC.	2020-12-03 downloaded from the CCDC.
;
_chemical_name_systematic        
4-phenyl-5-(4-formylphenylethynyl)-1-methylimidazole
_chemical_name_common            ?
_chemical_formula_moiety         'C21 H14 N2 O'
_chemical_formula_sum            'C21 H14 N2 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         310.34

_chemical_melting_point          435-436

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   10.8306(3)
_cell_length_b                   16.0766(5)
_cell_length_c                   11.0441(3)
_cell_angle_alpha                90
_cell_angle_beta                 119.2370(10)
_cell_angle_gamma                90
_cell_volume                     1678.01(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7866
_cell_measurement_theta_min      2.4640
_cell_measurement_theta_max      25.0289
_cell_measurement_temperature    273.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear pale yellow'
_exptl_crystal_size_max          0.486
_exptl_crystal_size_mid          0.341
_exptl_crystal_size_min          0.124
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648

_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      273.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayered confocal mirror'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.4074

_diffrn_reflns_number            15906
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_theta_min         2.46
_diffrn_reflns_theta_max         25.07
_diffrn_reflns_theta_full        25.07
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13

_refine_special_details          
;
;

_reflns_number_total             2928
_reflns_number_gt                2420
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_gt          0.1214
_refine_ls_wR_factor_ref         0.1382
_refine_ls_goodness_of_fit_ref   0.779
_refine_ls_restrained_S_all      0.779
_refine_ls_number_reflns         2928
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.6550P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.206
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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 . .


_geom_special_details            
;

All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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_
_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 ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane/Hexane'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_X190703KK1aTFA
_database_code_depnum_ccdc_archive 'CCDC 2025951'
loop_
_audit_author_name
_audit_author_address
'Youhei Miura'
;Keio University
Japan
;
_audit_update_record             
;
2020-08-28 deposited with the CCDC.	2020-12-03 downloaded from the CCDC.
;
_chemical_name_systematic        
'4,5-bis(phenylethynyl)-1-methylimidazolium trifluoroacetate'
_chemical_name_common            NMePhPh-TFA
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H15 F3 N2 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         396.36

_chemical_melting_point          378-400

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   21.855(7)
_cell_length_b                   5.4499(15)
_cell_length_c                   16.896(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.485(10)
_cell_angle_gamma                90
_cell_volume                     2006.3(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2472
_cell_measurement_theta_min      2.4183
_cell_measurement_theta_max      22.7318
_cell_measurement_temperature    273.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            'lustrous pale white'
_exptl_crystal_size_max          0.954
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.061
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816

_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      273.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scan'

_diffrn_detector_area_resol_mean 7.4074

_diffrn_reflns_number            17105
_diffrn_reflns_av_R_equivalents  0.0727
_diffrn_reflns_av_unetI/netI     0.0533
_diffrn_reflns_theta_min         2.42
_diffrn_reflns_theta_max         24.12
_diffrn_reflns_theta_full        24.12
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19

_refine_special_details          
;
;

_reflns_number_total             3161
_reflns_number_gt                1797
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1298
_refine_ls_R_factor_gt           0.0744
_refine_ls_wR_factor_gt          0.1948
_refine_ls_wR_factor_ref         0.2400
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_restrained_S_all      1.145
_refine_ls_number_reflns         3161
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.8840P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.335
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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 . .


_geom_special_details            
;

All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 ?

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 ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane/dichloromethane'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_X200626KK_NMediCHO
_database_code_depnum_ccdc_archive 'CCDC 2025902'
loop_
_audit_author_name
_audit_author_address
'Youhei Miura'
;Keio University
Japan
;
_audit_update_record             
;
2020-08-28 deposited with the CCDC.	2020-12-03 downloaded from the CCDC.
;
_chemical_name_systematic        
4,5-bis(4-formylphenylethynyl)-1-methylimidazole
_chemical_name_common            NMeCHOCHO
_chemical_formula_moiety         'C22 H14 N2 O2'
_chemical_formula_sum            'C22 H14 N2 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         338.35

_chemical_melting_point          '203-206 C'

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   9.5584(3)
_cell_length_b                   22.8679(6)
_cell_length_c                   8.4503(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.7870(10)
_cell_angle_gamma                90
_cell_volume                     1768.36(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9887
_cell_measurement_theta_min      2.2255
_cell_measurement_theta_max      23.1918
_cell_measurement_temperature    273.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'clear pale yellow-orange'
_exptl_crystal_size_max          0.661
_exptl_crystal_size_mid          0.214
_exptl_crystal_size_min          0.164
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704

_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      273.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayered confocal mirror'

_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 7.4074

_diffrn_reflns_number            29380
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_theta_min         2.40
_diffrn_reflns_theta_max         23.27
_diffrn_reflns_theta_full        23.27
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9

_refine_special_details          
;
;

_reflns_number_total             2497
_reflns_number_gt                2201
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_gt          0.1514
_refine_ls_wR_factor_ref         0.1656
_refine_ls_goodness_of_fit_ref   1.454
_refine_ls_restrained_S_all      1.454
_refine_ls_number_reflns         2497
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.154
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 958)'
_computing_publication_material  ?

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 C1 1.01639(18) 0.29298(7) 0.2920(2) 0.0580(5) Uani d . . . 1 . .
H H1 1.061855 0.265633 0.241983 0.07 Uiso calc U . R 1 . .
N N1 0.99869(14) 0.34906(6) 0.24576(16) 0.0536(4) Uani d . . . 1 . .
O O1 0.4464(2) 0.43387(8) 1.2048(2) 0.1042(6) Uani d . . . 1 . .
C C2 0.90583(16) 0.33232(6) 0.44930(18) 0.0483(4) Uani d . . . 1 . .
N N2 0.96366(15) 0.28032(6) 0.41431(17) 0.0585(4) Uani d . . . 1 . .
O O2 0.66980(16) 0.75808(6) 0.2885(2) 0.0879(5) Uani d . . . 1 . .
C C3 0.92691(16) 0.37576(7) 0.34586(17) 0.0475(4) Uani d . . . 1 . .
C C4 1.0475(2) 0.37684(10) 0.1165(2) 0.0751(6) Uani d . . . 1 . .
H H4A 1.061656 0.347628 0.04096 0.113 Uiso calc U . R 1 . .
H H4B 1.137928 0.396904 0.164937 0.113 Uiso calc U . R 1 . .
H H4C 0.975015 0.404345 0.057993 0.113 Uiso calc U . R 1 . .
C C5 0.83430(18) 0.33871(7) 0.57360(19) 0.0546(5) Uani d . . . 1 . .
C C6 0.77358(18) 0.34638(7) 0.67703(19) 0.0566(5) Uani d . . . 1 . .
C C7 0.70452(16) 0.35716(7) 0.80389(18) 0.0516(5) Uani d . . . 1 . .
C C9 0.62980(18) 0.32456(8) 1.0363(2) 0.0588(5) Uani d . . . 1 . .
H H9 0.623462 0.295044 1.109603 0.071 Uiso calc U . R 1 . .
C C8 0.69254(17) 0.31288(7) 0.9128(2) 0.0569(5) Uani d . . . 1 . .
H H8 0.727012 0.275526 0.901632 0.068 Uiso calc U . R 1 . .
C C10 0.57603(16) 0.37938(8) 1.05329(19) 0.0564(5) Uani d . . . 1 . .
C C11 0.5881(2) 0.42341(8) 0.9450(2) 0.0634(5) Uani d . . . 1 . .
H H11 0.553247 0.460682 0.956406 0.076 Uiso calc U . R 1 . .
C C12 0.65066(18) 0.41241(7) 0.8220(2) 0.0605(5) Uani d . . . 1 . .
H H12 0.657333 0.442176 0.74954 0.073 Uiso calc U . R 1 . .
C C13 0.88427(17) 0.43489(7) 0.33685(19) 0.0530(5) Uani d . . . 1 . .
C C14 0.84248(17) 0.48411(7) 0.33636(19) 0.0567(5) Uani d . . . 1 . .
C C15 0.79238(17) 0.54262(7) 0.34204(18) 0.0521(5) Uani d . . . 1 . .
C C16 0.7242(2) 0.55860(8) 0.4593(2) 0.0633(5) Uani d . . . 1 . .
H H16 0.707869 0.530861 0.532531 0.076 Uiso calc U . R 1 . .
C C17 0.68027(19) 0.61578(8) 0.4676(2) 0.0636(5) Uani d . . . 1 . .
H H17 0.635796 0.626368 0.547805 0.076 Uiso calc U . R 1 . .
C C18 0.70145(17) 0.65740(7) 0.35869(19) 0.0545(5) Uani d . . . 1 . .
C C19 0.76776(19) 0.64128(8) 0.2394(2) 0.0615(5) Uani d . . . 1 . .
H H19 0.781771 0.66893 0.164712 0.074 Uiso calc U . R 1 . .
C C20 0.81249(19) 0.58505(8) 0.2312(2) 0.0619(5) Uani d . . . 1 . .
H H20 0.857011 0.574728 0.150852 0.074 Uiso calc U . R 1 . .
C C21 0.5088(2) 0.38998(10) 1.1860(2) 0.0753(6) Uani d . . . 1 . .
H H21 0.514991 0.360116 1.26244 0.09 Uiso calc U . R 1 . .
C C22 0.6544(2) 0.71772(9) 0.3725(2) 0.0692(5) Uani d . . . 1 . .
H H22 0.60862 0.72536 0.453573 0.083 Uiso calc U . R 1 . .


_geom_special_details            
;

All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
C1 N2 . 1.306(2) ?
C1 N1 . 1.337(2) ?
C1 H1 . 0.93 ?
N1 C3 . 1.376(2) ?
N1 C4 . 1.452(2) ?
O1 C21 . 1.201(3) ?
C2 C3 . 1.376(2) ?
C2 N2 . 1.379(2) ?
C2 C5 . 1.417(2) ?
O2 C22 . 1.199(2) ?
C3 C13 . 1.408(2) ?
C4 H4A . 0.96 ?
C4 H4B . 0.96 ?
C4 H4C . 0.96 ?
C5 C6 . 1.193(2) ?
C6 C7 . 1.433(2) ?
C7 C8 . 1.395(2) ?
C7 C12 . 1.389(2) ?
C9 C8 . 1.372(2) ?
C9 C10 . 1.378(2) ?
C9 H9 . 0.93 ?
C8 H8 . 0.93 ?
C10 C11 . 1.387(3) ?
C10 C21 . 1.465(2) ?
C11 C12 . 1.364(2) ?
C11 H11 . 0.93 ?
C12 H12 . 0.93 ?
C13 C14 . 1.194(2) ?
C14 C15 . 1.427(2) ?
C15 C16 . 1.384(2) ?
C15 C20 . 1.400(2) ?
C16 C17 . 1.381(3) ?
C16 H16 . 0.93 ?
C17 C18 . 1.379(2) ?
C17 H17 . 0.93 ?
C18 C19 . 1.387(2) ?
C18 C22 . 1.466(3) ?
C19 C20 . 1.363(2) ?
C19 H19 . 0.93 ?
C20 H20 . 0.93 ?
C21 H21 . 0.93 ?
C22 H22 . 0.93 ?

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
N2 C1 N1 . . 113.50(14) ?
N2 C1 H1 . . 123.2 ?
N1 C1 H1 . . 123.2 ?
C1 N1 C3 . . 106.82(13) ?
C1 N1 C4 . . 126.77(15) ?
C3 N1 C4 . . 126.41(16) ?
C3 C2 N2 . . 110.19(13) ?
C3 C2 C5 . . 125.96(14) ?
N2 C2 C5 . . 123.85(13) ?
C1 N2 C2 . . 104.39(13) ?
C2 C3 N1 . . 105.10(14) ?
C2 C3 C13 . . 129.38(14) ?
N1 C3 C13 . . 125.51(14) ?
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 ?
C6 C5 C2 . . 177.44(16) ?
C5 C6 C7 . . 177.92(18) ?
C8 C7 C12 . . 118.95(15) ?
C8 C7 C6 . . 120.77(15) ?
C12 C7 C6 . . 120.28(15) ?
C8 C9 C10 . . 120.98(16) ?
C8 C9 H9 . . 119.5 ?
C10 C9 H9 . . 119.5 ?
C9 C8 C7 . . 119.84(16) ?
C9 C8 H8 . . 120.1 ?
C7 C8 H8 . . 120.1 ?
C11 C10 C9 . . 119.14(15) ?
C11 C10 C21 . . 121.54(17) ?
C9 C10 C21 . . 119.32(16) ?
C10 C11 C12 . . 120.45(16) ?
C10 C11 H11 . . 119.8 ?
C12 C11 H11 . . 119.8 ?
C11 C12 C7 . . 120.64(16) ?
C11 C12 H12 . . 119.7 ?
C7 C12 H12 . . 119.7 ?
C14 C13 C3 . . 175.48(17) ?
C13 C14 C15 . . 177.84(17) ?
C16 C15 C20 . . 118.71(15) ?
C16 C15 C14 . . 120.27(14) ?
C20 C15 C14 . . 121.02(15) ?
C17 C16 C15 . . 119.95(15) ?
C17 C16 H16 . . 120.0 ?
C15 C16 H16 . . 120.0 ?
C16 C17 C18 . . 120.95(16) ?
C16 C17 H17 . . 119.5 ?
C18 C17 H17 . . 119.5 ?
C19 C18 C17 . . 119.20(16) ?
C19 C18 C22 . . 121.54(15) ?
C17 C18 C22 . . 119.26(16) ?
C20 C19 C18 . . 120.24(15) ?
C20 C19 H19 . . 119.9 ?
C18 C19 H19 . . 119.9 ?
C19 C20 C15 . . 120.95(16) ?
C19 C20 H20 . . 119.5 ?
C15 C20 H20 . . 119.5 ?
O1 C21 C10 . . 125.7(2) ?
O1 C21 H21 . . 117.1 ?
C10 C21 H21 . . 117.1 ?
O2 C22 C18 . . 125.76(19) ?
O2 C22 H22 . . 117.1 ?
C18 C22 H22 . . 117.1 ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_X190705KK_1e
_database_code_depnum_ccdc_archive 'CCDC 1950077'
loop_
_audit_author_name
_audit_author_address
'Youhei Miura'
;Keio University
Japan
;
_audit_update_record             
;
2019-08-29 deposited with the CCDC.	2020-12-03 downloaded from the CCDC.
;
_chemical_name_systematic        
4-(4-methoxyphenylethynyl)-5-(4-formylphenylethynyl)-1-methylimidazole
_chemical_name_common            NMeOMeCHO
_chemical_formula_moiety         'C22 H16 N2 O2'
_chemical_formula_sum            'C22 H16 N2 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         340.37

_chemical_melting_point          419-421

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3320(4)
_cell_length_b                   9.8300(4)
_cell_length_c                   11.3679(5)
_cell_angle_alpha                97.151(2)
_cell_angle_beta                 114.1460(10)
_cell_angle_gamma                102.008(2)
_cell_volume                     904.73(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5537
_cell_measurement_theta_min      2.4064
_cell_measurement_theta_max      25.0492
_cell_measurement_temperature    273.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            'fluorescent light yellow'
_exptl_crystal_size_max          0.953
_exptl_crystal_size_mid          0.826
_exptl_crystal_size_min          0.197
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             356

_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      273.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayered confocal mirror'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.4074

_diffrn_reflns_number            8425
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_theta_min         2.41
_diffrn_reflns_theta_max         25.06
_diffrn_reflns_theta_full        25.06
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measured_fraction_theta_full 0.942
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13

_refine_special_details          
;
;

_reflns_number_total             3031
_reflns_number_gt                2620
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_gt          0.1659
_refine_ls_wR_factor_ref         0.1766
_refine_ls_goodness_of_fit_ref   1.396
_refine_ls_restrained_S_all      1.396
_refine_ls_number_reflns         3031
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.142
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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 . .


_geom_special_details            
;

All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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_
_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 ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane/Hexane'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_MeImOMe2
_database_code_depnum_ccdc_archive 'CCDC 1950076'
loop_
_audit_author_name
_audit_author_address
'Youhei Miura'
;Keio University
Japan
;
_audit_update_record             
;
2019-08-29 deposited with the CCDC.	2020-12-03 downloaded from the CCDC.
;
_chemical_name_systematic        
4,5-bis(4-methoxyphenylethynyl)-1-methyl-imidazole
_chemical_name_common            ?
_chemical_formula_moiety         'C22 H18 N2 O2'
_chemical_formula_sum            'C22 H18 N2 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         342.38

_chemical_melting_point          375-377

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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'

_cell_length_a                   10.4483(9)
_cell_length_b                   7.9356(7)
_cell_length_c                   22.7149(18)
_cell_angle_alpha                90
_cell_angle_beta                 95.017(3)
_cell_angle_gamma                90
_cell_volume                     1876.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3717
_cell_measurement_theta_min      2.7200
_cell_measurement_theta_max      21.9067
_cell_measurement_temperature    300.(2)

_exptl_crystal_description       needle-like
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          1.100
_exptl_crystal_size_mid          0.229
_exptl_crystal_size_min          0.092
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720

_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.46
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      300.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayered confocal mirror'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.4074

_diffrn_reflns_number            15694
_diffrn_reflns_av_R_equivalents  0.2090
_diffrn_reflns_av_unetI/netI     0.0949
_diffrn_reflns_theta_min         2.08
_diffrn_reflns_theta_max         23.67
_diffrn_reflns_theta_full        23.67
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25

_refine_special_details          
;
;

_reflns_number_total             2804
_reflns_number_gt                1688
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1390
_refine_ls_R_factor_gt           0.0982
_refine_ls_wR_factor_gt          0.2446
_refine_ls_wR_factor_ref         0.2950
_refine_ls_goodness_of_fit_ref   1.438
_refine_ls_restrained_S_all      1.438
_refine_ls_number_reflns         2804
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.1252P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.592
_refine_diff_density_min         -0.484
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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 . .


_geom_special_details            
;

All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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_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_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) ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane/Hexane'
_exptl_crystal_preparation       Luminescent
