4,5-Bis(arylethynyl)-1,2,3-triazoles-A New Class of Fluorescent Labels: Synthesis and Applications.
Govdi, Anastasia I.; Tokareva, Polina V.; Rumyantsev, Andrey M.; Panov, Maxim S.; Stellmacher, Johannes; Alexiev, Ulrike; Danilkina, Natalia A.; Balova, Irina A.; Molecules (Basel, Switzerland) 27 (2022) 3191–; doi:10.3390/molecules27103191

data_1567075
_publ_section_title
;
 4,5-Bis(arylethynyl)-1,2,3-triazoles-A New Class of Fluorescent Labels:
 Synthesis and Applications.
;
_journal_issue                   10
_journal_name_full               'Molecules (Basel, Switzerland)'
_journal_page_first              3191
_journal_paper_doi               10.3390/molecules27103191
_journal_volume                  27
_journal_year                    2022
_chemical_formula_moiety         'C24 H21 Cl N4 O2'
_chemical_formula_sum            'C24 H21 Cl N4 O2'
_chemical_formula_weight         432.90
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-02-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                101.7710(10)
_cell_angle_beta                 103.6930(10)
_cell_angle_gamma                90.8430(10)
_cell_formula_units_Z            2
_cell_length_a                   8.72150(10)
_cell_length_b                   10.12750(10)
_cell_length_c                   12.82020(10)
_cell_measurement_reflns_used    15034
_cell_measurement_temperature    130.02(16)
_cell_measurement_theta_max      73.7900
_cell_measurement_theta_min      3.6230
_cell_volume                     1074.684(19)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      130.02(16)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -75.00 -24.00   0.50    0.20    --  -38.82 123.00  31.00  102
  2  \w    -64.00 -24.00   0.50    0.20    --  -38.82 148.00-164.00   80
  3  \w    -95.00 -69.00   0.50    0.20    --  -38.82 148.00-164.00   52
  4  \w     78.00 103.00   0.50    0.20    --   38.82-148.00 147.00   50
  5  \w     46.00  84.00   0.50    0.20    --   38.82-123.00 -48.00   76
  6  \w     92.00 118.00   0.50    0.20    --  107.00-123.00 -48.00   52
  7  \w    109.00 135.00   0.50    0.20    --  107.00 123.00  31.00   52
  8  \w     94.00 129.00   0.50    0.20    --  107.00-148.00 147.00   70
  9  \w    -62.00 -16.00   0.50    0.20    --  -38.82  65.00   0.00   92
 10  \w    -77.00 -30.00   0.50    0.20    --  -38.82 104.00-180.00   94
 11  \w    -52.00  27.00   0.50    0.20    --  -38.82  77.00  90.00  158
 12  \w     -7.00  26.00   0.50    0.20    --  -38.82  65.00   0.00   66
 13  \w   -111.00 -54.00   0.50    0.20    --  -38.82 -21.00 -90.00  114
 14  \w    -50.00 -24.00   0.50    0.20    --  -38.82 -21.00 -90.00   52
 15  \w    -57.00  11.00   0.50    0.20    --  -38.82  54.00 -60.00  136
 16  \w    -24.00  15.00   0.50    0.20    --  -38.82 104.00-180.00   78
 17  \w     27.00  58.00   0.50    0.20    --   38.82  54.00  60.00   62
 18  \w     -3.00  50.00   0.50    0.20    --   38.82 -32.00  60.00  106
 19  \w     19.00  46.00   0.50    0.20    --   38.82  77.00-150.00   54
 20  \w     -4.00  50.00   0.50    0.20    --   38.82 -32.00 120.00  108
 21  \w     20.00  93.00   0.50    0.20    --   38.82  54.00-180.00  146
 22  \w     59.00 105.00   0.50    0.20    --   38.82  77.00  30.00   92
 23  \w     35.00  73.00   0.50    0.20    --   38.82  32.00  90.00   76
 24  \w     36.00  89.00   0.50    0.20    --   38.82  32.00  60.00  106
 25  \w     26.00  51.00   0.50    0.20    --   38.82  43.00-180.00   50
 26  \w     36.00  62.00   0.50    0.20    --   38.82 -65.00 -90.00   52
 27  \w     16.00  42.00   0.50    0.20    --   38.82  77.00  30.00   52
 28  \w     72.00  97.00   0.50    0.20    --   38.82  77.00-150.00   50
 29  \w      3.00  28.00   0.50    0.20    --   38.82 -65.00 -90.00   50
 30  \w     82.00 108.00   0.50    0.20    --   38.82  32.00  90.00   52
 31  \w     88.00 143.00   0.50    0.20    --  107.00  22.00-120.00  110
 32  \w     58.00 128.00   0.50    0.20    --  107.00 -61.00 120.00  140
 33  \w     89.00 157.00   0.50    0.20    --  107.00  22.00  30.00  136
 34  \w    127.00 155.00   0.50    0.20    --  107.00  61.00 -30.00   56
 35  \w     38.00 114.00   0.50    0.20    --  107.00-111.00 120.00  152
 36  \w     43.00 120.00   0.50    0.20    --  107.00 -30.00  60.00  154
 37  \w     85.00 121.00   0.50    0.20    --  107.00  61.00 -30.00   72
 38  \w     40.00 130.00   0.50    0.20    --  107.00 -86.00 120.00  180
 39  \w     43.00  72.00   0.50    0.20    --  107.00 -45.00  90.00   58
 40  \w     45.00 113.00   0.50    0.20    --  107.00-111.00 -30.00  136
 41  \w     38.00 118.00   0.50    0.20    --  107.00 -30.00 -90.00  160
 42  \w     37.00 149.00   0.50    0.20    --  107.00 178.00 150.00  224
 43  \w    101.00 126.00   0.50    0.20    --  107.00  30.00 -30.00   50
 44  \w     94.00 120.00   0.50    0.20    --  107.00-133.00 -90.00   52
 45  \w     88.00 153.00   0.50    0.20    --  107.00  22.00 150.00  130
 46  \w     60.00 120.00   0.50    0.20    --  107.00 -61.00 -30.00  120
 47  \w     44.00 125.00   0.50    0.20    --  107.00 -45.00-180.00  162
 48  \w     80.00 143.00   0.50    0.20    --  107.00 111.00-120.00  126
 49  \w    126.00 152.00   0.50    0.20    --  107.00  69.00  90.00   52
 50  \w     91.00 155.00   0.50    0.20    --  107.00  45.00  60.00  128
 51  \w     94.00 130.00   0.50    0.20    --  107.00  37.00  90.00   72
 52  \w     49.00  78.00   0.50    0.20    --  107.00 -86.00 -90.00   58
 53  \w     92.00 119.00   0.50    0.20    --  107.00 -86.00 -90.00   54
 54  \w     56.00  84.00   0.50    0.20    --  107.00 -93.00-120.00   56
 55  \w     91.00 116.00   0.50    0.20    --  107.00  69.00  90.00   50
 56  \w     95.00 121.00   0.50    0.20    --  107.00  30.00-120.00   52
 57  \w     53.00  78.00   0.50    0.20    --  107.00-111.00-180.00   50
 58  \w     84.00 121.00   0.50    0.20    --  107.00 -45.00  90.00   74
 59  \w     43.00 129.00   0.50    0.20    --  107.00 -61.00 -90.00  172
 60  \w     84.00 109.00   0.50    0.20    --  107.00 148.00-164.00   50
 61  \w     35.00  60.00   0.50    0.20    --   38.82-148.00 147.00   50
 62  \w    -45.00 -20.00   0.50    0.20    --    8.00 129.00 155.20   50
 63  \w    -34.00  -9.00   0.50    0.20    --    8.00 111.00 -74.68   50
 64  \w     -4.00  21.00   0.50    0.20    --   28.00  91.00-153.72   50
 65  \w     -8.00  17.00   0.50    0.20    --   28.00 100.00  -2.28   50
 66  \w     -9.00  16.00   0.50    0.20    --   28.00 102.00-107.50   50
 67  \w     -6.00  19.00   0.50    0.20    --   28.00  97.00 102.70   50
 68  \w      6.00  31.00   0.50    0.20    --   36.00  87.00  92.69   50
 69  \w      5.00  30.00   0.50    0.20    --   36.00  89.00  46.19   50
 70  \w      4.00  29.00   0.50    0.20    --   36.00  90.00   4.20   50
 71  \w     21.00  54.00   0.50    0.20    --   38.82 -65.00 -30.00   66
 72  \w     10.00  35.00   0.50    0.20    --   38.82  84.00 -99.79   50
 73  \w     11.00  36.00   0.50    0.20    --   40.00  84.00 -23.38   50
 74  \w     11.00  37.00   0.50    0.20    --   40.00  84.00 121.01   52
 75  \w     16.00  41.00   0.50    0.20    --   44.00  82.00 -14.28   50
 76  \w     16.00  41.00   0.50    0.20    --   44.00  80.00 102.92   50
 77  \w     16.00  41.00   0.50    0.20    --   44.00  82.00  56.68   50
 78  \w     17.00  42.00   0.50    0.20    --   44.00  79.00  35.70   50
 79  \w     17.00  42.00   0.50    0.20    --   44.00  79.00 154.40   50
 80  \w     16.00  41.00   0.50    0.20    --   44.00  82.00 175.44   50
 81  \w     16.00  41.00   0.50    0.20    --   44.00  82.00 -70.53   50
 82  \w     27.00  53.00   0.50    0.20    --   52.00  77.00 -96.79   52
 83  \w     80.00 106.00   0.50    0.20    --   52.00  76.00  88.57   52
 84  \w     26.00  52.00   0.50    0.20    --   52.00  77.00-157.07   52
 85  \w     26.00  56.00   0.50    0.20    --   52.00  76.00  88.57   60
 86  \w     25.00  50.00   0.50    0.20    --   52.00  77.00 -47.33   50
 87  \w     33.00  59.00   0.50    0.20    --   56.00  73.00   0.50   52
 88  \w     31.00  57.00   0.50    0.20    --   56.00  77.00  44.45   52
 89  \w     34.00  59.00   0.50    0.20    --   60.00  74.00 134.05   50
 90  \w     35.00  61.00   0.50    0.20    --   60.00  75.00 -76.59   52
 91  \w     34.00  63.00   0.50    0.20    --   60.00  76.00-129.47   58
 92  \w     36.00  62.00   0.50    0.20    --   60.00  70.00 -22.08   52
 93  \w     42.00  67.00   0.50    0.20    --   64.00  61.00  87.42   50
 94  \w     39.00  65.00   0.50    0.20    --   64.00  72.00 173.86   52
 95  \w     47.00  88.00   0.50    0.20    --   68.00  73.00-159.23   82
 96  \w     46.00  72.00   0.50    0.20    --   68.00  69.00-112.98   52
 97  \w     43.00 116.00   0.50    0.20    --   68.00  71.00 138.62  146
 98  \w     50.00  89.00   0.50    0.20    --   72.00  71.00-172.22   78
 99  \w     48.00  74.00   0.50    0.20    --   72.00  77.00 -10.98   52
100  \w     50.00  75.00   0.50    0.20    --   72.00  60.00 -27.74   50
101  \w     93.00 138.00   0.50    0.20    --   72.00  71.00-172.22   90
102  \w     55.00  83.00   0.50    0.20    --   80.00  77.00   0.08   56
103  \w     55.00  92.00   0.50    0.20    --   80.00  72.00  75.71   74
104  \w     58.00  86.00   0.50    0.20    --   84.00  77.00  16.82   56
105  \w    113.00 148.00   0.50    0.20    --   84.00  76.00 -85.87   70
106  \w     58.00  83.00   0.50    0.20    --   84.00  76.00 -85.87   50
107  \w    123.00 149.00   0.50    0.20    --   84.00  73.00-109.44   52
108  \w     59.00 107.00   0.50    0.20    --   84.00  73.00-109.44   96
109  \w     70.00  95.00   0.50    0.20    --   88.00  54.00 -22.47   50
110  \w     98.00 124.00   0.50    0.20    --   88.00  54.00 -22.47   52
111  \w     63.00 108.00   0.50    0.20    --   88.00  71.00-119.33   90
112  \w     64.00 140.00   0.50    0.20    --   88.00  69.00  83.19  152
113  \w     66.00 104.00   0.50    0.20    --   92.00  75.00  49.60   76
114  \w     81.00 124.00   0.50    0.20    --  107.00  77.00   0.00   86
115  \w    129.00 157.00   0.50    0.20    --  107.00  77.00 -90.00   56
116  \w    132.00 157.00   0.50    0.20    --  107.00  77.00-120.00   50
117  \w     80.00 118.00   0.50    0.20    --  107.00  77.00 -90.00   76
118  \w    116.00 148.00   0.50    0.20    --  107.00  93.00  60.00   64
119  \w     81.00 107.00   0.50    0.20    --  107.00  93.00  60.00   52
120  \w    132.00 157.00   0.50    0.20    --  107.00  77.00  90.00   50
121  \w     80.00 124.00   0.50    0.20    --  107.00  77.00-120.00   88
122  \w     67.00 100.00   0.50    0.20    --  107.00 -37.00 -30.00   66
123  \w     80.00 106.00   0.50    0.20    --  107.00  77.00  90.00   52
124  \w    132.00 157.00   0.50    0.20    --  107.00  77.00 -30.00   50
125  \w     83.00 157.00   0.50    0.20    --  107.00  69.00-180.00  148
126  \w    125.00 154.00   0.50    0.20    --  107.00  61.00 150.00   58
127  \w     85.00 111.00   0.50    0.20    --  107.00  61.00 150.00   52
128  \w     80.00 115.00   0.50    0.20    --  107.00  77.00 -30.00   70
129  \w    112.00 138.00   0.50    0.20    --  107.00  61.00 120.00   52
130  \w     85.00 110.00   0.50    0.20    --  107.00  61.00 120.00   50
131  \w     80.00 149.00   0.50    0.20    --  107.00  77.00 150.00  138
132  \w     35.00  93.00   0.50    0.20    --  107.00 -22.00 150.00  116
133  \w    117.00 143.00   0.50    0.20    --  107.00  53.00-150.00   52
134  \w     87.00 112.00   0.50    0.20    --  107.00  53.00-150.00   50
135  \w     86.00 112.00   0.50    0.20    --  107.00  61.00   0.00   52
136  \w     85.00 111.00   0.50    0.20    --  107.00  69.00  60.00   52
137  \w    128.00 156.00   0.50    0.20    --  107.00  61.00 -60.00   56
138  \w     87.00 112.00   0.50    0.20    --  107.00  61.00 -60.00   50
139  \w    130.00 156.00   0.50    0.20    --  107.00  69.00  30.00   52
140  \w    131.00 157.00   0.50    0.20    --  107.00  77.00-150.00   52
141  \w     83.00 109.00   0.50    0.20    --  107.00  69.00  30.00   52
142  \w     81.00 110.00   0.50    0.20    --  107.00  77.00-150.00   58
143  \w     54.00  82.00   0.50    0.20    --  107.00 -30.00-120.00   56
144  \w    132.00 157.00   0.50    0.20    --  107.00  77.00 -60.00   50
145  \w    132.00 157.00   0.50    0.20    --  107.00  77.00 120.00   50
146  \w     82.00 110.00   0.50    0.20    --  107.00  77.00 -60.00   56
147  \w     80.00 106.00   0.50    0.20    --  107.00  77.00 120.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0690285000
_diffrn_orient_matrix_UB_12      0.0467517000
_diffrn_orient_matrix_UB_13      0.1248086000
_diffrn_orient_matrix_UB_21      0.1684308000
_diffrn_orient_matrix_UB_22      -0.0008783000
_diffrn_orient_matrix_UB_23      -0.0181401000
_diffrn_orient_matrix_UB_31      -0.0080759000
_diffrn_orient_matrix_UB_32      0.1485393000
_diffrn_orient_matrix_UB_33      -0.0110435000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20600
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.805
_diffrn_reflns_theta_min         3.632
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.807
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93421
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_F_000             452
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4326
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0365
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0537P)^2^+0.3622P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.0964
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4142
_reflns_number_total             4326
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            5d.cif
_cod_data_source_block           5699-11965_tok-101
_cod_database_code               1567075
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C28(H28A,H28B)
2.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C6(H6), C20(H20), C17(H17), C21(H21), C5(H5), C3(H3), C2(H2)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C23(H23A,H23B,H23C), C29(H29A,H29B,H29C)
;
_shelx_res_checksum              64044
_shelx_hkl_checksum              92532
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.218
_oxdiff_exptl_absorpt_empirical_full_min 0.881